TEST BANK for Organic Chemistry 9th Edition by William H. Brown, Brent L. Iverson, Eric Anslyn, Chri by ACADEMIAMILL

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Chapter 01: Covalent Bonding and Shapes of Molecules 1. How many electrons can the shell with a principal quantum number of 1 hold? a. 1 b. 2 c. 4 d. 8 ANSWER: b 2. How many electrons can the shell with a principal quantum number of 6 hold? a. 1 b. 6 c. 36 d. 72 ANSWER: d 3. What is the ground-state electronic configuration of a nitrogen atom (nitrogen: atomic number 7)? a. 1s22s12p4 b. 1s22s22p3 c. 1s12s12p5 d. 1s22s22p2 ANSWER: b 4. What is the ground-state electronic configuration of a fluorine atom (fluorine: atomic number 9)? a. 1s12s12p7 b. 1s22s22p5 c. 1s22s22p6 d. 1s02s22p7 ANSWER: b 5. What is the ground-state electronic configuration of a fluoride anion (fluorine: atomic number 9)? a. 1s22s22p2 b. 1s22s22p5 c. 1s22s22p6 d. 1s22s22p7 ANSWER: c 6. What is the ground-state electronic configuration of a lithium cation (lithium: atomic number 3)? a. 1s22s1 b. 1s12s1 c. 1s2 d. 1s22s2 Copyright Cengage Learning. Powered by Cognero.

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Chapter 01: Covalent Bonding and Shapes of Molecules ANSWER: c 7. Which of the following species has an atom that has an unfilled valence shell of electrons? a. molecular iodine, I2 b. calcium cation, Ca2+ c. aluminum tribromide, AlBr3 d. water, H2O ANSWER: c 8. Which of the following species has an atom that has an unfilled valence shell of electrons? a. molecular bromine, Br2 b. fluoride anion, F− c. ammonia, NH3 d. aluminum trichloride, AlCl3 ANSWER: d 9. Which of the following species is charged? a. BH3 b. SO4 c. CO2 d. H2S ANSWER: b 10. Which of the following species possesses a formal charge? a. CCl4 b. SiCl4 c. AlCl4 d. PCl3 ANSWER: c 11. Which of the following compounds is an aldehyde? a. CH3CH2CH2COOH b. CH3CH2CHO c. CH3CH2CH2OH d. CH3CH2COCH3 ANSWER: b 12. Which of the following compounds is an alcohol? a. CH3CH2COOH Copyright Cengage Learning. Powered by Cognero.

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Chapter 01: Covalent Bonding and Shapes of Molecules b. CH3CH2OCH3 c. CH3CH2CH2OH d. CH3CH2CHO ANSWER: c 13. Which of the following compounds is a carboxylic acid? a. CH3CH2CH2COOH b. CH3CH2OCH3 c. CH3CH2CH2OH d. CH3CH2NH2 ANSWER: a 14. Which of the following compounds is a ketone? a. CH3CH2COOH b. CH3CH2CHO c. CH3CH2CH2OH d. CH3COCH3 ANSWER: d 15. Which of the following compounds is a ketone? a. CH3CH2COOH b. CH3CH2CHO c. CH3CH2CH2OH d. CH3COCH3 ANSWER: d 16. Which of the following compounds is a carboxylic ester? a. CH3CH2COOH b. CH3CH2OCH3 c. CH3CH2COOCH3 d. CH3CH2COCH3 ANSWER: c 17. Which of the following is a tertiary alcohol? a. CH3CH2OCH3 b. (CH3)3COH c. (CH3)2CHOH d. CH3CH2CH2OH Copyright Cengage Learning. Powered by Cognero.

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Chapter 01: Covalent Bonding and Shapes of Molecules ANSWER: b 18. Which of the following is a tertiary amine? a. CH3CH2N(CH3)2 b. (CH3)3CNH2 c. CH3CH2NHCH3 d. CH3CH2NHCH(CH3)2 ANSWER: a 19. Which of the following is a primary amine? a. CH3CH2NHCH3 b. CH3CH2NHCH(CH3)2 c. CH3CH2N(CH3)2 d. (CH3)3CNH2 ANSWER: d 20. Which of the following is trigonal planar? a. boron trifluoride, BF3 b. methyl anion, CH3− c. methane, CH4 d. ammonia, NH3 ANSWER: a 21. Which of the following molecules is not linear? a. H2O b. HCl c. HC≡CH d. Br2 ANSWER: a 22. What is the approximate value of the H−C−H bond angles in methane, CH4? a. 90° b. 109° c. 120° d. 180° ANSWER: b 23. What is the approximate C−C−C bond angle in propene, CH3CH=CH2? a. 90° b. 109° Copyright Cengage Learning. Powered by Cognero.

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Chapter 01: Covalent Bonding and Shapes of Molecules c. 120° d. 180° ANSWER: c 24. What is the approximate C−C−C bond angle in propyne, HC≡CCH3? a. 90° b. 109° c. 120° d. 180° ANSWER: d 25. What is the approximate H−C−O bond angle in formaldehyde, H2C=O? a. 90° b. 109° c. 120° d. 180° ANSWER: c 26. Which of the following elements has the highest electronegativity? a. N b. C c. O d. S ANSWER: c 27. Which of the following elements has the highest electronegativity? a. Rb b. Bi c. Ge d. Br ANSWER: d 28. Which of the following bonds is the most polar? a. F−F b. H−F c. C−H d. C−Si ANSWER: b 29. Which of the following bonds is the most polar? a. O−H b. C−H c. C−C Copyright Cengage Learning. Powered by Cognero.

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Chapter 01: Covalent Bonding and Shapes of Molecules d. H−H ANSWER: a 30. Which of the following bonds is a polar covalent bond? a. K−F b. C−H c. C−F d. Br−Br ANSWER: c 31. Which of the following bonds is a polar covalent bond? a. Na−Cl b. C−Cl c. C−H d. Cl−Cl ANSWER: b 32. Which of the following is an ionic bond? a. Br−Br b. C−Cl c. C−S d. Na−O ANSWER: d 33. Which of the following is an ionic bond? a. F−F b. C−H c. Li−O d. C−N ANSWER: c 34. Which of the following bonds has the smallest dipole moment? a. C−N b. C−O c. C−F d. O−H ANSWER: a 35. Which of the following bonds has the smallest dipole moment? a. Li−Cl b. C−H c. O−H d. H−Cl ANSWER: b Copyright Cengage Learning. Powered by Cognero.

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Chapter 01: Covalent Bonding and Shapes of Molecules 36. Which of the following molecules has a molecular dipole moment?

a. 1 b. 2 c. 3 d. 4 ANSWER: b 37. Which of the following molecules has a molecular dipole moment?

a. 1 b. 2 c. 3 d. 4 ANSWER: b 38. Which of the following molecules has a molecular dipole moment? a. CO2 b. BF3 c. NH3 d. CH4 ANSWER: c 39. Which of the following molecules has a molecular dipole moment? a. NBr3 b. CCl4 c. HC≡CH d. Cl2 ANSWER: a 40. Which of the following best represents the shape of the 2s atomic orbital of carbon?

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Chapter 01: Covalent Bonding and Shapes of Molecules

a. 1 b. 2 c. 3 d. 4 ANSWER: a 41. Which of the following best represents the shape of a 2p atomic orbital of carbon?

a. 1 b. 2 c. 3 d. 4 ANSWER: b 42. Which of the following best represents an sp2 hybridized atomic orbital of carbon which overlaps with the 1s atomic orbital of hydrogen to form a C−H σ bonding molecular orbital in ethene, H2C=CH2

a. 1 b. 2 c. 3 d. 4 ANSWER: c 43. Which of the following best represents an sp3 hybridized atomic orbital containing the lone pair of electrons of ammonia, NH3?

a. 1 b. 2 c. 3 Copyright Cengage Learning. Powered by Cognero.

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Chapter 01: Covalent Bonding and Shapes of Molecules d. 4 ANSWER: c 44. Which atomic orbitals overlap to form the C=O bond of acetone, (CH3)2C=O? a. C 2sp3 + O 2sp2 b. C 2sp2 + O 2p c. C 2sp2 + O 2sp2 d. C 2sp3 + O 2sp ANSWER: c 45. Which atomic orbitals overlap to form the C−N bond of dimethylamine, (CH3)2NH? a. C 2sp3 + N 2sp2 b. C 2sp2 + N 2p c. C 2sp2 + N 2sp2 d. C 2sp3 + N 2sp3 ANSWER: d 46. What is the approximate value of the length of the C=C bond in ethane, CH2=CH2? a. 121 pm b. 134 pm c. 142 pm d. 154 pm ANSWER: b 47. What is the approximate value of the length of the C≡C bond in ethyne, HC≡CH? a. 121 pm b. 134 pm c. 142 pm d. 154 pm ANSWER: a 48. Which of the following statements is not true regarding resonance structures? a. All resonance structures must have the same number of electrons b. Each atom in all of the resonance structures must have a complete shell of valence electrons c. All resonance structures must have the same arrangement of atoms d. All resonance structures must be valid Lewis structures ANSWER: b 49. Which of the following statements is not true regarding resonance structures? a. Each resonance structure is in rapid equilibrium with all of the other structures b. The resonance structures may have different energies Copyright Cengage Learning. Powered by Cognero.

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Chapter 01: Covalent Bonding and Shapes of Molecules c. All resonance structures must have the same arrangement of atoms d. All resonance structures must have the same number of electrons ANSWER: a 50. Which of the following statements is not true about the carbonate anion, CO32−? a. All of the oxygen atoms bear the same amount of charge b. All of the carbon-oxygen bonds are the same length c. One carbon-oxygen bond is different from the other two d. All the carbon-oxygen bonds lie in the same plane ANSWER: c 51. Which of the following statements is not true about the acetate anion, CH3CO2−? a. The oxygen atoms bear the same amount of charge b. The two carbon-oxygen bonds are the same length c. The carbon atom bears the negative charge d. It is basic ANSWER: c 52. Rank the following in order of decreasing importance as a contributing resonance structure to the molecular structure of acetone, CH3COCH3 (more important > less important)

a. 1 > 2 > 3 b. 1 > 3 > 2 c. 2 > 1 > 3 d. 3 > 1 > 2 ANSWER: b 53. Which of the following resonance structures is the least important contributor to the resonance hybrid of the acetate anion, CH3COO−?

a. 1 b. 2 c. 3 d. 4 Copyright Cengage Learning. Powered by Cognero.

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Chapter 01: Covalent Bonding and Shapes of Molecules ANSWER: c 54. How many electrons are there in the valence shell of the carbon atom of a methyl cation, CH3+? a. 4 b. 5 c. 6 d. 7 ANSWER: c 55. How many electrons are there in the valence shell of the carbon atom of the methyl anion, CH3−? a. 2 b. 4 c. 6 d. 8 ANSWER: d 56. How many electrons are there in the valence shell of the sulfur atom of sulfur hexafluoride? a. 2 b. 4 c. 8 d. 12 ANSWER: d 57. How many electrons are there in the valence shell of the nitrogen atom of ammonia? a. 4 b. 5 c. 6 d. 8 ANSWER: d 58. What is the approximate value of the H−O−C bond angles in a methanol, CH3OH? a. 90° b. 120° c. 109° d. 180° ANSWER: c 59. What is the approximate value of the H−C−H bond angles in a methyl anion, CH3−? a. 90° b. 109° c. 120° d. 180° ANSWER: b Copyright Cengage Learning. Powered by Cognero.

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Chapter 01: Covalent Bonding and Shapes of Molecules 60. Which atomic orbitals overlap to form the carbon-hydrogen σ bonding molecular orbitals of ethane, CH3CH3? a. C2p + H1s b. C2sp + H1s c. C2sp2 + H1s d. C2sp3 + H1s ANSWER: d 61. Which atomic orbitals overlap to form the carbon-hydrogen σ bonding molecular orbitals of ethene, H2C=CH2? a. C2p + H1s b. C2sp + H1s c. C2sp2 + H1s d. C2sp3 + H1s ANSWER: c 62. Which atomic orbitals overlap to form the carbon-carbon σ and π bonding molecular orbitals of ethene, H2C=CH2? a. C2sp3 + C2sp3, and C2p + C2p b. C2sp2 + C2sp2, and C2sp2 + C2sp2 c. C2sp2 + C2sp2, and C2p + C2p d. C2sp3 + C2sp3, and C2sp2 + C2sp2 ANSWER: c 63. Which atomic orbitals overlap to form the carbon-hydrogen σ bonding molecular orbitals of ethyne, HC≡CH? a. C2p + H1s b. C2sp + H1s c. C2sp2 + H1s d. C2sp3 + H1s ANSWER: b 64. Which atomic orbitals overlap to form the carbon-carbon σ molecular bonding orbital of ethyne, HC≡CH? a. C2p + C2p b. C2sp + C2sp c. C2sp2 + C2sp2 d. C2sp3 + C2sp3 ANSWER: b 65. Which of the following is a primary (1°) alcohol?

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Chapter 01: Covalent Bonding and Shapes of Molecules a. 1 b. 2 c. 3 d. 4 ANSWER: a 66. Which of the following is a tertiary (3°) alcohol?

a. 1 b. 2 c. 3 d. 4 ANSWER: c 67. Which of the following is a primary (1°) amine?

a. 1 b. 2 c. 3 d. 4 ANSWER: c 68. Which of the following is a secondary (2°) amine?

a. 1 b. 2 c. 3 d. 4 ANSWER: d 69. Which of the following is an carboxylic ester? Copyright Cengage Learning. Powered by Cognero.

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Chapter 01: Covalent Bonding and Shapes of Molecules

a. 1 b. 2 c. 3 d. 4 ANSWER: a 70. What is the approximate strength of the C−C bond of ethane? a. 376 kJ/mol (90 kcal./mol) b. 422 kJ/mol (101 kcal./mol) c. 556 kJ/mol (133 kcal./mol) d. 727 kJ/mol (174 kcal./mol) ANSWER: a 71. Which of the circled bonds is the strongest?

a. 1 b. 2 c. 3 d. 4 ANSWER: a 72. Which of the following resonance structures makes the largest contribution to the structure of [H2CCHO] −?

a. 1 b. 2 c. 3 d. 4 ANSWER: b 73. Which of the following shows curved arrows that correctly accounts for the differences between the two structures?

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Chapter 01: Covalent Bonding and Shapes of Molecules

a. 1 b. 2 c. 3 d. 4 ANSWER: c 74. Which of the following statements is not true? a. The sp3C−H bond of an alkane is weaker than the spC−H bond of an alkyne. b. The carbon-carbon triple bond of an alkyne is shorter than the carbon-carbon bond of alkenes. c. The carbon-carbon triple bond of an alkene is exactly three times as strong as a carbon-carbon single bond of an alkane. d. The sp3C−H bond of an alkane is longer than the spC−H bond of an alkyne. ANSWER: c 75. Which of the following is/are trigonal planar? 1. methane, CH4 2. methyl carbocation, CH3+ 3. trichloromethyl radical, CCl3. 4. chloroform, CHCl3 a. only 1 and 2 b. only 2 and 3 c. only 1 and 4 d. only 2 and 4 ANSWER: b 76. The following two structural formulas represent isomers. Copyright Cengage Learning. Powered by Cognero.

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Chapter 01: Covalent Bonding and Shapes of Molecules

a. True b. False ANSWER: False 77. Consider the following structural formula.

The following is a resonance structure.

a. True b. False ANSWER: False 78. Overlap of the two atomic orbitals as shown could result in the formation of a π bond.

a. True b. False ANSWER: True 79. Consider the following molecular model.

The condensed structural formula would be

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Chapter 01: Covalent Bonding and Shapes of Molecules a. True b. False ANSWER: True 80. The hybridization on the numbered carbon atoms in the following compound would be Carbon 1 sp3 and Carbon 2 sp2.

a. True b. False ANSWER: True 81. There are eight valence in a methyl anion, CH3−. a. True b. False ANSWER: True 82. The following species forms during an organic reaction.

The formal charge on the carbon atom indicated by the arrow is +1. a. True b. False ANSWER: True 83. In drawing the Lewis structure for an organic compound, the carbon atoms should always be shown with eight total electrons. a. True b. False ANSWER: True 84. Consider the structure of urea given below.

To complete the Lewis structure, six nonbonding electrons should be added, two to each of the nitrogen atoms and two to the oxygen atom. a. True Copyright Cengage Learning. Powered by Cognero.

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Chapter 01: Covalent Bonding and Shapes of Molecules b. False ANSWER: False 85. The curved arrows in the resonance structure for the acetate ion shown below

indicate the following alternative resonance structure for the acetate ion.

a. True b. False ANSWER: True 86. The maximum number of electrons that a molecular orbital can contain is four. a. True b. False ANSWER: False 87. The following molecules all contain the same functional group except 2.

CH3OH 1

CH3OCH3 2

CH3CH2OH 3

CH3CH(OH)CH3 4

a. True b. False ANSWER: True 88. The percent s character in an sp2 hybridized orbital is approximately 33%. a. True b. False ANSWER: True 89. The formal charges in the complex should below are 0 on each H, –1 on N, and +1 on B.

a. True b. False ANSWER: False Copyright Cengage Learning. Powered by Cognero.

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Chapter 01: Covalent Bonding and Shapes of Molecules 90. The most electronegative elements in the periodic table are generally found toward the right in a horizontal

row and toward the top in a column. a. True b. False ANSWER: True 91. Different compounds with the same molecular formula are called __________. ANSWER: isomers 92. The formal charge on carbon in carbon monoxide is______. ANSWER: minus one -1 93. The approximate H–C–H bond angle in methane is ______°. ANSWER: 109.5 109 94. The following molecule contains an _____________functional group.

ANSWER: aldehyde 95. The following molecule is classified as a __________amine.

ANSWER: secondary 2° 96. Provide a neatly drawn figure to show the atomic orbitals that overlap to form each of the bonds in water (H2O) and which contain the lone pair of electrons. Label each orbital with its hybridization. ANSWER:

97. Provide a neatly drawn figure to show the atomic orbitals that overlap to form each of the bonds in ammonia (NH3) and which contain the lone pair of electrons. Label each orbital with its hybridization.

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Chapter 01: Covalent Bonding and Shapes of Molecules ANSWER:

98. Provide a neatly drawn figure to show the atomic orbitals that overlap to form each of the bonds in ethene (ethylene, H2C=CH2). Label each bond (e.g., C–H σ bond) and indicate which atomic orbitals contribute to this bond (e.g., C 2sp3 + H 1s). ANSWER:

99. Provide a neatly drawn figure to show the atomic orbitals that overlap to form each of the bonds in ethyne (acetylene, HC≡CH). Label each bond (e.g., C–H σ bond) and indicate which atomic orbitals contribute to this bond (e.g., C 2sp3 + H 1s). ANSWER:

100. Draw bond-line structures of all of the alkanes that have the formula C5H12. ANSWER:

101. Draw bond-line structures of all of the alcohols that have the formula C4H10O. ANSWER:

102. Draw bond-line structures of all of the aldehydes that have the formula C5H10O. Copyright Cengage Learning. Powered by Cognero.

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Chapter 01: Covalent Bonding and Shapes of Molecules ANSWER:

103. Draw bond-line structures of all of the ketones that have the formula C5H10O. ANSWER:

104. Draw bond-line structures of all of the primary (1°) alcohols that have the formula C5H12O. ANSWER:

105. Draw bond-line structures of all of the tertiary (3°) alcohols that have the formula C6H14O. ANSWER:

106. Draw bond-line structures of all of the secondary (2°) amines that have the formula C4H9N. ANSWER:

107. Draw bond-line structures of all of the tertiary (3°) amines that have the formula C5H11N. ANSWER:

108. Circle all of the sp2 hybridized atoms in the following molecular structure.

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Chapter 01: Covalent Bonding and Shapes of Molecules ANSWER:

109. Circle all of the sp hybridized atoms in the following molecular structure.

ANSWER:

110. Convert the following structure into a bond-line drawing.

ANSWER:

111. Convert the following structure into a bond-line drawing.

ANSWER:

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Chapter 01: Covalent Bonding and Shapes of Molecules 112. What is the molecular formula of Ritalin, shown below?

ANSWER: C14H19NO2 113. What is the molecular formula of aspartame, shown below?

ANSWER: C14H18N2O5 114. Circle and name the functional groups in the following molecule.

ANSWER:

115. Circle and name the functional groups in the following molecule.

ANSWER:

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Chapter 01: Covalent Bonding and Shapes of Molecules Match the following compounds with their appropriate molecular geometry. a. Ethane b. Formaldehyde c. Thiocyanate (SCN ) d. Hydronium Ion e. Ozone 116. Linear ANSWER: c 117. Tetrahedral ANSWER: a 118. Bent ANSWER: e 119. Trigonal Planar ANSWER: b 120. Trigonal Pyramidal ANSWER: d Match the following compounds with their appropriate bond type. a. H3N→BF3 b. HCl c. KBr

d. CH4

121. Ionic Bond ANSWER: c 122. Dative Bond ANSWER: a 123. Covalent Bond ANSWER: d 124. Polar Covalent Bond ANSWER: b 125. In the given ion given, what is the formal charge of nitrogen, carbon, and sulfur, respectively?

a. -2, +1, and 0. b. 0, -2, and +1. c. -2, 0, and +1. d. +1, 0, and -2. Copyright Cengage Learning. Powered by Cognero.

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Chapter 01: Covalent Bonding and Shapes of Molecules ANSWER: c 126. How many resonating structures are shown by carbonate anion? a. 5 b. 4 c. 3 d. 2 ANSWER: c 127. Fill the appropriate electronic configuration in the blank. K (1s22s22p63s23p64s1) + Cl (1s22s22p63s23p5) → K+ _____ + Cl- (1s22s22p63s23p6) a. (1s22s22p63s23p64s2) b. (1s22s22p63s23p65s1) c. (1s22s22p63s23p6) d. (1s22s22p63s23p64s1) ANSWER: c 128. The energy released on the addition of an electron to an atom or a molecule is called _____. a. electron affinity b. ionization energy c. resonance energy d. delocalization ANSWER: a 129. Which of the 3 structures shown below has the shortest bond length? Justify your answer.

ANSWER: Structure 1 has the shortest bond length. It is an alkyne that possesses sp hybrid orbitals. As the percent scharacter of sp hybridized orbitals in alkynes is close to 50%, the bond length of the alkyne is the shortest. This is the reason the bonds are shorter and stronger.

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Chapter 02: Alkanes and Cycloalkanes 1. Approximately how long is a C−C single bond of an alkane? a. 111 pm b. 134 pm c. 142 pm d. 153 pm ANSWER: d 2. What is the approximate C−C−C bond angle in propane? a. 90° b. 109° c. 120° d. 180° ANSWER: b 3. What is the name of the linear hydrocarbon with the molecular formula C6H14? a. heptane b. hexane c. pentane d. nonane ANSWER: b 4. What is the name of the linear hydrocarbon with the molecular formula C11H24? a. heptane b. decane c. undecane d. eicosane ANSWER: c 5. How many hydrogen atoms are there in nonane, the linear hydrocarbon with nine carbon atoms? a. 16 b. 18 c. 20 d. 22 ANSWER: c 6. How many hydrogen atoms are there in heptadecane, the linear hydrocarbon with seventeen carbon atoms? a. 17 b. 25 c. 34 d. 36 ANSWER: d 7. How many constitutional isomers are there with the molecular formula C4H10? Copyright Cengage Learning. Powered by Cognero.

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Chapter 02: Alkanes and Cycloalkanes a. 2 b. 3 c. 4 d. 5 ANSWER: a 8. How many constitutional isomers are there with the molecular formula C5H12? a. 2 b. 3 c. 4 d. 5 ANSWER: b 9. How many constitutional isomers are there with the molecular formula C7H8? a. 8 b. 7 c. 9 d. 10 ANSWER: c 10. What is the IUPAC name of the following compound?

a. 3-propylpentane b. 1,1-diethylpropane c. 3-ethylhexane d. isooctane ANSWER: c 11. What is the IUPAC name of the following compound?

a. 2-ethyl-4-methylpentane b. 2,4-dimethylhexane c. 3,5-dimethylhexane d. 1,1,3-trimethylpentane ANSWER: b 12. What is the IUPAC name of the following compound? Copyright Cengage Learning. Powered by Cognero.

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Chapter 02: Alkanes and Cycloalkanes

a. 2,2-dimethyl-4-ethylheptane b. 4-ethyl-2,2-dimethyl-heptane c. 6,6-dimethyl-4-ethylheptane d. 4-ethyl-6,6-dimethyl-heptane ANSWER: b 13. What is the IUPAC name of the following compound?

a. 5,5-dimethyl-3-ethylheptane b. 5-ethyl-3,3-dimethyl-heptane c. 3,3-dimethyl-5-ethylheptane d. 3-ethyl-5,5-dimethyl-heptane ANSWER: d 14. What is the IUPAC name of the following compound?

a. 2-isopropyl-5-methylpentane b. 5-isopropyl-2-methylpentane c. 2,3,5-trimethylhexane d. 1,2-diisopropylpropane ANSWER: c 15. What is the IUPAC name of the following compound?

a. 2,4-dimethyl-3-isopropyl-pentane b. 3-isopropyl-1,5-dimethylpentane c. 3-isopropyl-2,4-dimethylpentane d. triisopropylmethane Copyright Cengage Learning. Powered by Cognero.

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Chapter 02: Alkanes and Cycloalkanes ANSWER: c 16. Which of the following compounds has 1°, 2°, 3° and 4° carbon atoms? a. hexane b. 2-methylhexane c. 2,2-dimethylhexane d. 2,2,3-trimethylhexane ANSWER: d 17. Which of the following compounds has only 1° and 2° carbon atoms? a. 2,2-dimethylpropane b. 2,2-dimethylpentane c. 2,2,3-trimethylpentane d. pentane ANSWER: d 18. What is the correct assignment of common names for the following molecules?

a. i = butane; ii = neopentane; iii = isopentane b. i = neobutane; ii = isobutane; iii = pentane c. i = butane; ii = isobutane; iii = isopentane d. i = butane; ii = isobutane; iii = neopentane ANSWER: d 19. What is the correct assignment of common names for the following molecules?

a. i = pentane; ii = isopentane; iii = neopentane b. i = neopentane; ii = isopentane; iii = pentane c. i = pentane; ii = neopentane; iii = isopentane d. i = neopentane; ii = pentane; iii = isopentane ANSWER: a 20. What is the IUPAC name of the following compound? Copyright Cengage Learning. Powered by Cognero.

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Chapter 02: Alkanes and Cycloalkanes

a. 1-isopropyl-4,6-dimethylcyclohexane b. 1-isopropyl-2,4-dimethylcyclohexane c. 4-isopropyl-1,3-dimethylcyclohexane d. 4-isopropyl-1,5-dimethylcyclohexane ANSWER: b 21. What is the IUPAC name of the following compound?

a. 1-methylbicyclo[2.2.1]heptane b. 2-methylbicyclo[2.2.1]heptane c. 3-methylbicyclo[2.2.1]heptane d. 4-methylbicyclo[2.2.1]heptane ANSWER: b 22. What is the IUPAC name of the following compound?

a. bicyclo[4.3]nonane b. bicyclo[4.3.0]nonane c. bicyclo[6.5]nonane d. bicyclo[6.5.0]nonane ANSWER: b 23. What is the IUPAC name for the following compound?

a. cycloheptane b. bicyclo[3.2.0]heptane c. bicyclo[5.4]heptane Copyright Cengage Learning. Powered by Cognero.

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Chapter 02: Alkanes and Cycloalkanes d. cyclobutylcyclopentane ANSWER: b 24. What is the IUPAC name for the following compound?

a. bicyclo[5.4.3]octane b. bicyclo[3.2.1]octane c. bicyclo[3.2.1]hexane d. bicyclo[2.2.1]octane ANSWER: b 25. Which of the following Newman projections does not represent 2-methylhexane?

a. 1 b. 2 c. 3 d. 4 ANSWER: c 26. Which of the following Newman projections represents 2,4-dimethylpentane?

a. 1 b. 2 c. 3 d. 4 ANSWER: a 27. Which of the following Newman projections represents the most stable conformation of 2,3-dimethylbutane? Copyright Cengage Learning. Powered by Cognero.

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Chapter 02: Alkanes and Cycloalkanes

a. 1 b. 2 c. 3 d. 4 ANSWER: c 28. Which of the following Newman projections represents the most stable conformation of 2-methylbutane?

a. 1 b. 2 c. 3 d. 4 ANSWER: a 29. Which of the following cycloalkanes has the most ring strain? a. cyclopropane b. cyclobutane c. cyclopentane d. cyclohexane ANSWER: a 30. Which of the following cycloalkanes has the least ring strain? a. cyclopropane b. cyclopentane c. cyclohexane d. cycloheptane ANSWER: c 31. Which of the following structures represents cis-1,3-dimethylcyclohexane with equatorial bonds?

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Chapter 02: Alkanes and Cycloalkanes

a. 2 b. 1 c. 4 d. 3 ANSWER: b 32. Which of the following structures represents trans-1,2-dimethylcyclohexane?

a. 1 b. 2 c. 3 d. 4 ANSWER: b 33. Which of the following is the most stable conformation of cis-1-isopropyl-3-methylcyclohexane?

a. 1 b. 2 c. 3 d. 4 ANSWER: c 34. Which of the following is the most stable conformation of trans-1-ethyl-3-methylcyclohexane?

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Chapter 02: Alkanes and Cycloalkanes a. 1 b. 2 c. 3 d. 4 ANSWER: d 35. Which of the following alkanes has the highest boiling point? a. Propane b. Butane c. 2-Methylpropane d. 2-Methylpentane ANSWER: d 36. Which of the following alkanes has the highest boiling point? a. 2,3-dimethylbutane b. 2-methylpentane c. 3-methylpentane d. hexane ANSWER: d 37. What is the IUPAC name of the following compound?

a. trans-1-isopropyl-4-methylcyclohexane b. cis-1-isopropyl-4-methylcyclohexane c. cis-2-isopropyl-5-methylcyclohexane d. cis-1-tert-butyl-4-methylcyclohexane ANSWER: b 38. What is the IUPAC name of the following compound?

a. trans-1-isopropyl-4-methylcyclopentane b. cis-1-tert-butyl-2-methylcyclopentane c. trans-1-tert-butyl-2-methylcyclopentane d. cis-1-isopropyl-2-methylcyclopentane ANSWER: c Copyright Cengage Learning. Powered by Cognero.

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Chapter 02: Alkanes and Cycloalkanes 39. Which one of the following structures represents a different compound from the other three?

a. 1 b. 2 c. 3 d. 4 ANSWER: d 40. Which one of the following structures represents a different compound from the other three?

a. 1 b. 2 c. 3 d. 4 ANSWER: c 41. In which of the following compounds are all of the carbon atoms in the same plane? a. cyclopropane b. cyclobutane c. cyclopentane d. cyclohexane ANSWER: a 42. Which of the following compounds can adopt a chair conformation in which there are no axial methyl groups? a. 1,1-dimethylcyclohexane b. cis-1,2-dimethylcyclohexane c. trans-1,2-dimethylcyclohexane d. cis-1,3-dimethylcyclohexane ANSWER: c 43. Which of the following compounds can adopt a chair conformation in which there are no axial methyl groups? Copyright Cengage Learning. Powered by Cognero.

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Chapter 02: Alkanes and Cycloalkanes a. cis-1,2-dimethylcyclohexane b. cis-1,3-dimethylcyclohexane c. trans-1,3-dimethylcyclohexane d. cis-1,4-dimethylcyclohexane ANSWER: b 44. Which of the following statements is not true regarding the conformation of substituted cyclohexanes? a. ring inversion of cyclohexane between two chair conformations takes place via a boat conformation b. substituted cyclohexanes are destabilized by 1,3-diaxial interactions c. the boat conformation of cyclohexane is usually more stable than the chair conformation d. the ratio of two conformations of substituted cyclohexanes at equilibrium can be determined from the difference in strain energy ANSWER: c 45. What is the approximate dihedral angle between the two chlorine atoms in cis-1,2-dichlorocyclohexane? a. 0° b. 60° c. 120° d. 180° ANSWER: b 46. What is the approximate dihedral angle between the two chlorine atoms in the diequatorial conformation of trans-1,2dichlorocyclohexane? a. 0° b. 60° c. 120° d. 180° ANSWER: b 47. What is the approximate dihedral angle between the two chlorine atoms in the diaxial conformation of trans-1,2dichlorocyclohexane? a. 0° b. 60° c. 120° d. 180° ANSWER: d 48. Which of the following is not true regarding the properties of alkanes? a. alkanes are nonpolar b. alkanes burn in air to give H2O and CO2 c. alkanes are highly miscible with water Copyright Cengage Learning. Powered by Cognero.

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Chapter 02: Alkanes and Cycloalkanes d. the strongest intermolecular force between alkane molecules is the van der Waals interaction ANSWER: c 49. Which of the following undergoes the most exothermic combustion? a. eicosane b. 2,3-dimethylheptane c. heptane d. 2,2-dimethylheptane ANSWER: a 50. How many moles of molecular oxygen (O2) are consumed in the complete combustion of one mole of decane (C10H22)? a. 15.5 b. 13 c. 14.5 d. 12.5 ANSWER: a 51. How many moles of molecular oxygen (O2) are consumed in the complete combustion of one mole of hexane (C6H14)? a. 6 b. 9.5 c. 12.5 d. 14 ANSWER: b 52. Which of the following statements is not true? a. Energy is released in a combustion reaction. b. Combustion is a form of reduction reaction. c. Strain energy is the difference between the predicted and actual heats of combustion. d. Heat of combustion can be measured in kcal/mol. ANSWER: b 53. Which of the following is the steroid nucleus?

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Chapter 02: Alkanes and Cycloalkanes

a. 1 b. 2 c. 3 d. 4 ANSWER: b 54. Which of the following cycloalkanes has the largest heat of combustion? a. cyclononane b. cyclopropane c. cycloheptane d. cyclotridecane ANSWER: d 55. Which of the following cycloalkanes has the largest heat of combustion per carbon atom? a. cyclopropane b. cyclohexane c. cyclononane d. cyclopentadecane ANSWER: a 56. Which of the following cycloalkanes has the smallest heat of combustion per carbon atom? a. cyclopropane b. cyclopentane c. cyclohexane d. cycloheptane ANSWER: c 57. Which of the following structures is different from the other three? Copyright Cengage Learning. Powered by Cognero.

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Chapter 02: Alkanes and Cycloalkanes

a. 1 b. 2 c. 3 d. 4 ANSWER: b 58. Which of the following structures is different from the other three?

a. 1 b. 2 c. 3 d. 4 Copyright Cengage Learning. Powered by Cognero.

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Chapter 02: Alkanes and Cycloalkanes ANSWER: a 59. Which of the following substituted cyclohexanes has the most negative value of ΔG° for ring flipping from the conformation in which the substituent is axial to the one where it is equatorial? a. methylcyclohexane b. chlorocyclohexane c. isopropylcyclohexane d. ethynylcyclohexane ANSWER: c 60. Which of the following substituted cyclohexanes has the most negative value of ΔG° for ring flipping from the conformation in which the substituent is axial to the one where it is equatorial? a. fluorocyclohexane b. methylcyclohexane c. ethylcyclohexane d. tert-butylcyclohexane ANSWER: d 61. The Newman projection of the gauche conformation of 1,2-dichloroethane is shown below.

a. True b. False ANSWER: True 62. The most stable conformation of an alkane occurs when carbon−carbon bonds are staggered and bulky groups are anti. a. True b. False ANSWER: True 63. The following pairs of Newman projections represent the same compound but in differing conformations.

a. True b. False ANSWER: False 64. There are four constitutional isomers for the molecular formula C6H14. Copyright Cengage Learning. Powered by Cognero.

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Chapter 02: Alkanes and Cycloalkanes a. True b. False ANSWER: False 65. The following Newman projection represents 2-methylhexane.

a. True b. False ANSWER: False 66. The following structures represent, from left to right, a cis and a trans isomer.

a. True b. False ANSWER: True 67. The following structures represent a pair of constitutional isomers.

a. True b. False ANSWER: False 68. 3-methylhexylcyclopentane represents a correct IUPAC name. a. True b. False ANSWER: False 69. In the following structure the positions labeled a and d are equatorial positions.

a. True Copyright Cengage Learning. Powered by Cognero.

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Chapter 02: Alkanes and Cycloalkanes b. False ANSWER: True 70. In the following conversion, the conformations are of equal stability.

a. True b. False ANSWER: True 71. The correct IUPAC name for the following compound is___________________________.

ANSWER: 3-methyl-5-(1-methylethyl)octane 3-methyl-5-isopropyloctane 72. The tertiary carbon atom in the following structure is indicated by the letter_____.

ANSWER: b B Match the Newman projection for the conformation of 2-methylbutane to the indicated position on the potential energy diagram.

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Chapter 02: Alkanes and Cycloalkanes

73. Conformation A is represented by Roman numeral ____. ANSWER: II 74. Conformation B is represented by Roman numeral ____. ANSWER: III 75. Conformation C is represented by Roman numeral ____. ANSWER: IV 76. Conformation D is represented by Roman numeral ____. ANSWER: I 77. What is the IUPAC name of the following compound?

ANSWER: 4-ethyl-2-methylhexane 78. What is the IUPAC name of the following compound?

ANSWER: 3-ethyl-2-methylhexane 79. What is the IUPAC name of the following compound?

ANSWER: 2,4,4-trimethylhexane 80. What is the IUPAC name of the following compound?

ANSWER: 2,2,4-trimethylhexane 81. What is the IUPAC name of the following compound? Copyright Cengage Learning. Powered by Cognero.

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Chapter 02: Alkanes and Cycloalkanes

ANSWER: bicyclo[4.2.0]octane 82. What is the IUPAC name of the following compound?

ANSWER: bicyclo[2.2.1]heptane 83. What is the IUPAC name of the following compound?

ANSWER: cis-1-tert-butyl-2-methylcyclohexane [ignoring absolute stereochemistry in Chap 2] 84. What is the IUPAC name of the following compound?

ANSWER: cis-1-isopropyl-3-methylcyclohexane [ignoring absolute stereochemistry in Chap 2] 85. How many hydrogen atoms are there in decane? ANSWER: 22 86. How many hydrogen atoms are there in octane? ANSWER: 18 87. What are the common and IUPAC names of the following compound?

ANSWER: common: neopentane IUPAC: 2,2-dimethylpropane 88. What are the common and IUPAC names of the following compound?

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Chapter 02: Alkanes and Cycloalkanes

ANSWER: common: isopentane IUPAC: 2-dimethylbutane 89. What is the IUPAC name of the following compound?

ANSWER: butanal 90. What is the IUPAC name of the following compound?

ANSWER: butanone 91. Provide a line-bond structure of hexanoic acid. ANSWER:

92. Provide a line-bond structure of pentanal. ANSWER:

93. Provide a Newman projection of the most stable conformation of 2-methylpentane, (CH3)2CHCH2CH2CH3, looking along the C2-C3 bond ANSWER:

94. Provide a Newman projection of the most stable conformation of 3-methylpentane, CH3CH2CH(CH3)CH2CH3 looking along the C2-C3 bond. ANSWER:

95. Provide a neatly drawn plot of energy versus dihedral angle for rotation around the C2-C3 bond of butane.

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Chapter 02: Alkanes and Cycloalkanes

ANSWER:

96. Provide a neatly drawn plot of energy versus dihedral angle for rotation around the C-C bond of ethane.

ANSWER:

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Chapter 02: Alkanes and Cycloalkanes 97. Identify the constitutional isomer with the molecular formula C7H16.

a. Only I b. Only I and II c. Only II d. I, II, and III ANSWER: c 98. The molecular formulae of neopentane and isobutane are ______ and _____ respectively. a. C6H12; C5H12 b. C5H10; C6H13 c. C7H12; C7H14 d. C5H12; C4H10 ANSWER: d 99. The total numbers of 2⁰ and 3⁰ carbon atoms in the following structure are _____ and _____, respectively.

a. 3; 7 b. 7; 4 c. 4; 6 d. 6; 4 ANSWER: b 100. What is “X” in the following reaction?

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Chapter 02: Alkanes and Cycloalkanes a.

b. c.

d. ANSWER: a 101. What is “X” in the following reaction?

c. d. ANSWER: a 102. What is “X” in the following reaction?

a. b. c.

d. ANSWER: d Match the structures with their IUPAC names.

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Chapter 02: Alkanes and Cycloalkanes a.

103. 3-ethyl-2-methylhexane ANSWER: a 104. 4-ethyl-2,2-dimethylhexane ANSWER: b 105. 4-ethyl-2-methylhexane ANSWER: c

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Chapter 03: Stereoisomerism and Chirality 1. Which of the following is the definition of a pair of enantiomers? a. A pair of structures that are superposable mirror images of one another b. A pair of stereoisomers that are non-superposable mirror images of one another c. A pair of stereoisomers that are not mirror images of one another d. A pair of stereoisomers that have equal specific rotations ANSWER: b 2. Which of the following is the definition of a pair of diastereomers? a. A pair of structures that are superposable mirror images of one another b. A pair of stereoisomers that are non-superposable mirror images of one another c. A pair of stereoisomers that are not mirror images of one another d. A pair of stereoisomers that have equal specific rotations ANSWER: c 3. Which of the following is the definition of chirality? a. The non-superposability of an object on its mirror image b. The superposability of an object on its mirror image c. A molecule that has a carbon atom with four different substituents d. A molecule with a mirror image ANSWER: a 4. Which of the following is the definition of a meso compound? a. A molecule with stereocenter centers which is chiral b. A molecule with stereocenter centers which is not chiral c. A diastereomer with no stereocenter centers d. A chiral compound with more than one stereocenter center ANSWER: b 5. Which of the following statements is not true regarding pairs of enantiomers? a. They have identical melting points b. They have identical boiling points c. They rotate plane-polarized light in opposite directions d. They react at identical rates with chiral reagents ANSWER: d 6. Which of the following statements is true? a. All mirror images are enantiomers b. All molecules that have stereocenter centers are chiral c. Isomers that are not superposable on their mirror images are enantiomers d. Superposable structural isomers are enantiomers ANSWER: c 7. Which of the following structures is different from the other three? Copyright Cengage Learning. Powered by Cognero.

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Chapter 03: Stereoisomerism and Chirality

a. 1 b. 2 c. 3 d. 4 ANSWER: d 8. Which of the following structures is different from the other three?

a. 1 b. 2 c. 3 d. 4 ANSWER: c 9. Which of the following compounds is/are chiral?

a. only 1 b. only 1 and 2 c. only 2 and 3 d. 1, 2 and 3 ANSWER: a 10. Which of the following compounds is/are chiral?

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Chapter 03: Stereoisomerism and Chirality

a. only 1 b. only 1 and 2 c. only 2 and 3 d. 1, 2 and 3 ANSWER: a 11. Which of the following have the S configuration?

a. only 1 b. only 2 c. only 1 and 2 d. 1, 2 and 3 ANSWER: c 12. Which of the following have the R configuration?

a. only 1 b. only 2 c. only 1 and 2 d. 1, 2 and 3 ANSWER: d 13. What is the configuration of the two chiral centers in the following molecule?

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Chapter 03: Stereoisomerism and Chirality

a. 3R,5R b. 3R,5S c. 3S,5R d. 3S,5S ANSWER: b 14. What is the configuration of the two chiral centers in the following molecule?

a. 3R,5R b. 3R,5S c. 3S,5R d. 3S,5S ANSWER: c 15. Which of the following Newman projections represents (2S,3S)-dibromobutane?

a. 2 and 4 b. 3 c. 1 d. None of the above ANSWER: a 16. Which of the following Newman projections represents meso-2,3-dibromobutane?

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Chapter 03: Stereoisomerism and Chirality

a. 1 b. 2 c. 3 d. 4 ANSWER: c 17. Which of the following structures represent the same stereoisomer?

a. only 1 and 2 b. only 1 and 3 c. only 2 and 3 d. 1, 2 and 3 ANSWER: c 18. Which of the following structures represent the same stereoisomer?

a. only 1 and 2 b. only 1 and 3 c. only 2 and 3 d. 1, 2 and 3 ANSWER: c 19. Which of the following structures represent the same stereoisomer?

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Chapter 03: Stereoisomerism and Chirality

a. only 1 and 2 b. only 1 and 3 c. only 2 and 3 d. 1, 2 and 3 ANSWER: a 20. Which of the following compounds is a meso compound? a. (2S,3S)-dibromobutane b. (2S,3R)-dibromobutane c. (2S,3R)-3-bromo-2-butanol d. (2S,3S)-3-chloro-2-butanol ANSWER: b 21. How many stereoisomers of 1,4-dichlorobutane-2,3-diol, CH2(Cl)CH(OH)CH(OH)CH2Cl, exist? a. 3 b. 4 c. 6 d. 5 ANSWER: a 22. How many stereoisomers of 3-chloro-2-methylbutane, (CH3)2CHCHClCH3, exist? a. 1 b. 2 c. 3 d. 4 ANSWER: b 23. How many stereoisomers of 2-bromo-3-chloro-1,4-butanedial, BrCH(CHO)CH(CHO)Cl, exist? a. 1 b. 2 c. 3 d. 4 ANSWER: d 24. How many stereoisomers of 2,3-butanediol, CH3CH(OH)CH(OH)CH3, exist? a. 1 b. 2 c. 3 Copyright Cengage Learning. Powered by Cognero.

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Chapter 03: Stereoisomerism and Chirality d. 4 ANSWER: c 25. How many stereoisomers of 1-chloro-2,4-dimethylpentane, CH3CH(CH2Cl)CH2CH(CH3)CH3 exist? a. 2 b. 3 c. 4 d. 1 ANSWER: a 26. How many stereoisomers of 2,3,4-trimethylpentane, (CH3)2CHCH(CH3)CH(CH3)2, exist? a. 2 b. 3 c. 4 d. 1 ANSWER: d 27. How many stereoisomers of 4-chloro-2-methylpentane (CH3)2CHCH2CHClCH3, exist? a. 1 b. 2 c. 3 d. 4 ANSWER: b 28. How many stereoisomers of 2,4-pentanediol, CH3CH(OH)CH2CH(OH)CH3, exist? a. 1 b. 2 c. 3 d. 4 ANSWER: c 29. How many isomers (constitutional and stereoisomers) exist for dimethylcyclobutane? a. 3 b. 4 c. 5 d. 6 ANSWER: d 30. How many isomers (constitutional and stereoisomers) exist for dimethylcyclohexane? a. 3 b. 5 c. 6 d. 9 Copyright Cengage Learning. Powered by Cognero.

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Chapter 03: Stereoisomerism and Chirality ANSWER: d 31. How many isomers (constitutional and stereoisomers) exist for dimethylcyclopentane? a. 3 b. 5 c. 7 d. 9 ANSWER: c 32. How many isomers (constitutional and stereoisomers) exist for dimethylpentane? a. 2 b. 3 c. 4 d. 5 ANSWER: c 33. Which of the following statements regarding optical rotation is not true? a. All (+) enantiomers rotate plane-polarized light in a clockwise direction. b. All S enantiomers are levorotatory. c. If the analyzing filter in a polarimeter must be turned to the right (clockwise), we say that the compound is dextror otatory. d. Specific rotation is the observed rotation measured in a cell 1 dm long and at a sample concentration of 1 g/mL. ANSWER: b 34. How much of the R enantiomer is present in 50 g of a mixture which has an enantiomeric excess of 15% of the S isomer? a. 29 g b. 42 g c. 21 g d. 7.5 g ANSWER: c 35. How much of the R enantiomer is present in 5 g of a mixture which has an enantiomeric excess of 67 % of the R isomer? a. 0.8 g b. 3.4 g c. 1.7 g d. 4.2 g ANSWER: d 36. A solution containing 0.7 g/mL of a pure R enantiomer in a 2.0 dm polarimeter rotates plane polarized light by +7.6°. What is the specific rotation of the R isomer? Copyright Cengage Learning. Powered by Cognero.

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Chapter 03: Stereoisomerism and Chirality a. -5.4° b. +5.4° c. +11° d. -11° ANSWER: b 37. A solution containing 0.04 g/mL of a pure S enantiomer in a 1 dm polarimeter rotates plane polarized light by +1.0°. What is the specific rotation of the R isomer? a. –25° b. +5.0° c. +35° d. +25° ANSWER: a 38. A solution containing 0.70 g/mL of a pure R enantiomer in a 1 dm polarimeter rotates plane polarized light by +4.8°. What is the rotation of a solution containing 1.9 g/mL of the R isomer in the same polarimeter? a. +1.8° b. +3.5° c. +26° d. +13° ANSWER: d 39. A solution of 0.40 g/mL of a pure R enantiomer in a 1 dm polarimeter rotates plane polarized light by +5.1°. What is the rotation observed on this solution in a 2 dm polarimeter? a. +2.6° b. +5.1° c. +16° d. +24° ANSWER: c 40. A pure sample of the R enantiomer of a compound has a specific rotation, [α], of +59°. A solution containing 0.80 g/mL of a mixture of enantiomers rotates plane polarized light by −4.0° in a 1 dm polarimeter. What is the enantiomeric excess (%ee) of the mixture? a. 38% R b. 38% S c. 8.5% S d. 8.5% R ANSWER: c 41. A pure sample of the R enantiomer of a compound has a specific rotation, [α], of −35°. A solution containing 0.10 g/mL of a mixture of enantiomers rotates plane polarized light by −3.0° in a 1.0 dm polarimeter. What is the enantiomeric excess (%ee) of the mixture? a. 86% R b. 86% S c. 14% R Copyright Cengage Learning. Powered by Cognero.

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Chapter 03: Stereoisomerism and Chirality d. 14% R ANSWER: a 42. Which of the following structures has a center of symmetry?

a. 1 b. 2 c. 3 d. 4 ANSWER: c 43. Which of the following structures has a center of symmetry (i.e., center of inversion)?

a. 1 b. 2 c. 3 d. 4 ANSWER: c 44. Which of the following structures have a plane of symmetry?

a. only 1 and 2 b. only 2 and 4 c. only 3 and 4 d. 1, 2, 3 and 4 Copyright Cengage Learning. Powered by Cognero.

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Chapter 03: Stereoisomerism and Chirality ANSWER: c 45. Which of the following structures does not have a plane of symmetry?

a. only 2 b. only 1 and 2 c. only 3 and 4 d. only 1, 2 and 4 ANSWER: a 46. How many chiral centers are there in the following molecule (the naturally occurring stereoisomer is the male hormone testosterone)?

a. Three b. Four c. Six d. Seven ANSWER: c 47. How many chiral centers are there in the following molecule (the naturally occurring stereoisomer is camphor, a pungent moth repellent)?

a. Two b. Three c. Four d. Five Copyright Cengage Learning. Powered by Cognero.

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Chapter 03: Stereoisomerism and Chirality ANSWER: a 48. Which of the following is the best definition of a pair of atropisomers? a. A pair of enantiomers which do not interconvert. b. A pair of enantiomers which lack chiral centers. c. A pair of enantiomeric structures which lack chiral centers and interconvert by rotation around carbon-carbon single bonds. d. A pair of enantiomers which lack chiral centers and do not interconvert because of hindered rotation around carbon-carbon single bonds. ANSWER: d 49. Which of the following structures is chiral?

a. 1 b. 2 c. 3 d. 4 ANSWER: c 50. Which of the following substituents has the highest priority according to the Cahn-Ingold-Prelog system used in assigning R and S configurations? a. -I b. -COOH c. -D d. -H ANSWER: a 51. Which of the following substituents has the lowest priority according to the Cahn-Ingold-Prelog system used in assigning R and S configurations? a. −CH2Br b. −CH2CH2COOH c. −CH2SH d. −CH2OH ANSWER: b Copyright Cengage Learning. Powered by Cognero.

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Chapter 03: Stereoisomerism and Chirality 52. What is the correct order of the Cahn-Ingold-Prelog ranking of the following substituents as used in assigning R and S configurations of chiral centers? (higher ranking > lower ranking) 1.

-CF3

-NH2

-OH

-CONH2

a. 4 > 1 > 2 > 3 b. 1 > 4 > 2 > 3 c. 3 > 2 > 1 > 4 d. 2 > 3 > 4 > 1 ANSWER: c 53. What is the correct order of the Cahn-Ingold-Prelog ranking of the following substituents as used in assigning R and S configurations of chiral centers? (higher ranking > lower ranking) 1.

−CH2OH

−CHO

−OCH3

−OCOCH3

a. 3 > 4 > 1 > 2 b. 4 > 3 > 1 > 2 c. 3 > 4 > 2 > 1 d. 4 > 3 > 2 > 1 ANSWER: d 54. What is the relationship between the following pair of structures?

a. They are enantiomers b. They are diastereomers c. The are constitutional isomers d. They are identical ANSWER: d 55. What is the relationship between the following pair of structures?

a. They are enantiomers b. They are diastereomers c. The are constitutional isomers d. They are identical Copyright Cengage Learning. Powered by Cognero.

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Chapter 03: Stereoisomerism and Chirality ANSWER: b 56. What is the relationship between the following pair of structures?

a. They are enantiomers b. They are diastereomers c. The are constitutional isomers d. They are identical ANSWER: a 57. Of the compounds listed below, only 2 has a chiral centers.

a. True b. False ANSWER: True 58. An unknown sample is tested with a polarimeter for optical activity. The results of the test required no

movement of the analyzer. This sample could be either a meso compound or a racemic mixture. a. True b. False ANSWER: True 59. The specific rotation of enantiomers have the same magnitude. a. True b. False ANSWER: True 60. The terms that best describe the relationship between (2R,3S)-2,3-butanediol and (2S,3S)-2,3-butanediol are

configurational and diastereomers. a. True b. False ANSWER: True 61. Of the following molecules, both 1 and 2 have a mirror plane of symmetry.

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Chapter 03: Stereoisomerism and Chirality

a. True b. False ANSWER: False 62. The following two compounds represent a pair of enantiomers.

a. True b. False ANSWER: False 63. A natural product having [α]D = +40.3° has been isolated and purified. This indicates that the natural product is dextrorotatory. a. True b. False ANSWER: True 64. A natural product having [α]D = +40.3° has been isolated and purified. Either of the following substances could be this natural product.

a. True b. False ANSWER: False 65. A work glove is chiral but disposable surgical gloves are not. a. True b. False ANSWER: True 66. In muscle tissue only (+)-lactic acid is found but in sour milk both (+)-lactic acid and (-)-lactic acid are present. This difference might be explained by the fact that the production of lactic acid in muscle tissue is catalyzed by biological Copyright Cengage Learning. Powered by Cognero.

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Chapter 03: Stereoisomerism and Chirality catalysts or enzymes. a. True b. False ANSWER: True 67. The process that separates enantiomers is called ______________. ANSWER: resolution 68. A mixture containing 0.50 mmol of each enantiomer is called a ___________mixture. ANSWER: racemic 69. For the compound shown below the number of chiral stereoisomers that can be drawn is_____.

CH3CHClCHBrCH3 ANSWER: 4 four 70. The number of chiral centers in progesterone (shown below) is ______.

ANSWER: 6 six 71. The following structures depicts (__)-3-ethyl-2,3-dimethylhexane.

ANSWER: R R 72. The absolute configurations around C-2 and C-3 in the following Fischer projection are, respectively,

____. (Enter the two configurations separated by a comma.)

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Chapter 03: Stereoisomerism and Chirality ANSWER: R,R R, R R,R R, R 73. ______________ are stereoisomers that are not mirror images. ANSWER: Diastereomers diastereomers 74. Complete the following diagram so that it represents (S)-2-butanol.

ANSWER:

75. Complete the following diagram so that it represents (S)-2-butanol.

ANSWER:

76. Complete the following diagram so that it represents (R)-2-bromobutane.

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Chapter 03: Stereoisomerism and Chirality

ANSWER:

77. Complete the following diagram so that it represents (R)-2-bromobutane.

ANSWER:

78. Complete the following Fischer diagram so that it represents (2R,3S)-butane-2,3-diol.

ANSWER:

79. Complete the following Fischer diagram so that it represents (2R,3R)-butane-2,3-diol. Copyright Cengage Learning. Powered by Cognero.

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Chapter 03: Stereoisomerism and Chirality

ANSWER:

80. Complete the following Fischer diagram so that it represents (2R,3R)-3-bromobutan-2-ol.

ANSWER:

81. Complete the following Fischer diagram so that it represents (2R,3S)-3-bromobutan-2-ol.

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Chapter 03: Stereoisomerism and Chirality ANSWER:

82. Complete the following zig-zag structure so that it represents (2R,3S)-3-chlorobutan-2-ol.

ANSWER:

83. Complete the following zig-zag structure so that it represents (2R,3R)-3-chlorobutan-2-ol.

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Chapter 03: Stereoisomerism and Chirality ANSWER:

84. Complete the following zig-zag structure so that it represents (2R,3S)-2,3-butanediol.

ANSWER:

85. Complete the following zig-zag structure so that it represents (2S,3R)-2,3-dibromobutane.

ANSWER:

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Chapter 03: Stereoisomerism and Chirality 86. Complete the following Newman projection so that it represents (2R,3R)-2,3-dibromobutane.

ANSWER:

87. Complete the following Newman projection so that it represents (2R,3S)-2,3-dibromobutane.

ANSWER:

88. Complete the following Newman projection so that it represents (2S,3S)-2,3-butanediol.

ANSWER:

89. Complete the following Newman projection so that it represents (2R,3S)-2,3-butanediol.

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Chapter 03: Stereoisomerism and Chirality

ANSWER:

90. What mass of (S)-(–)-mandelic acid is present in a 10 g sample which has an enantiomeric excess of 20% of the Senantiomer? ANSWER: 6 g 91. What mass of (S)-(–)-mandelic acid is present in a 10 g sample which has an enantiomeric excess of 30% of the Senantiomer? ANSWER: 6.5 g 92. The specific rotation of the S-enantiomer of a compound is -120º. What is the enantiomeric excess of a sample of the compound that has a measured specific rotation of -30º. ANSWER: ee = 25% of the S-enantiomer 93. The specific rotation of the S-enantiomer of a compound is -120º. A student determines that a sample of the compound has a specific rotation of +60º. What mass of the S-enantiomer is present in 10 g of the sample ANSWER: 2.5 g 94. How can enantiomers be separated using chromatography? ANSWER: Enantiomers can be separated using chromatography on a chiral substrate. The separation depends on the strength of the enantiomers to bind along the chiral stationary phase. Therefore, as the retention of one enantiomer is more than the other, it makes them pass down the column at different rates. 95. Which of the following is a use of atropisomers? a. Used for the kinetic resolution of tertiary alcohols b. Used for the kinetic resolution of secondary alcohols c. Used for the kinetic resolution of primary alcohols d. Used as a hydrogen bond catalyst in a single component domino reaction ANSWER: b 96. What is “X” in the following structure?

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Chapter 03: Stereoisomerism and Chirality

a. Inversion center b. Plane of symmetry c. Center of symmetry d. Point of symmetry ANSWER: b 97. How many stereocenters are present in trans-2-butene?

a. 1 b. 2 c. 3 d. 0 ANSWER: b 98. Structures I and II are the examples of a _____.

a. chiral resolving acid b. racemic resolving agent c. chiral resolving agent d. racemic resolving acid Copyright Cengage Learning. Powered by Cognero.

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Chapter 03: Stereoisomerism and Chirality ANSWER: c 99. When an object and its image are superposable, the object is _____. ANSWER: achiral Match the terms with the appropriate images. a.

100. Achiral Molecules ANSWER: d 101. Diastereomers ANSWER: b 102. Enantiomers ANSWER: a 103. Constitutional Isomers ANSWER: c

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Chapter 04: Acids and Bases 1. The pKa of HCl is −7. What is the value of the equilibrium constant, Keq, for the following equilibrium? [The concentration of water in a dilute aqueous solution is 55 M]

a. 1.8 × 105 b. 385 c. 1.8 × 10−5 d. −1.8 × 105 ANSWER: a 2. The pKa of acetic acid, CH3COOH, is 4.76. What is the value of the equilibrium constant Keq, for the following equilibrium? [The concentration of water in a dilute aqueous solution is 55 M]

a. 3.2 × 107 b. −3.2 × 10−7 c. −3.2 × 107 d. 3.2 × 10−7 ANSWER: d 3. Which of the following is the correct order of decreasing basicity (stronger base > weaker base)? a. NH3 > MeNH2 > H2O > HF b. NaOH > CH3COONa > H2O > CH3COOH c. NH3 > Me3N > H2O > MeOH d. CH3COONa > NaOH > NaOMe > NaNH2 ANSWER: b 4. Which of the following is the strongest acid? a. CH3CH3 b. CH3NH2 c. CH3OH d. CH3F ANSWER: c 5. Which of the following is the strongest acid? a. CH3COOH b. HNO3 c. CH3CH3 d. H3PO4 Copyright Cengage Learning. Powered by Cognero.

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Chapter 04: Acids and Bases ANSWER: b 6. Which of the following is easiest to deprotonate? a. CH≡CH b. PhNH2 c. CH2=CH2 d. PhOH ANSWER: d 7. Which of the following is the strongest acid? a. CH3OH b. CH3CHO c. CH3COCH3 d. CH3COOH ANSWER: d 8. Which of the following is the strongest acid? a. CH3NH2 b. CH3PH2 c. CH3OH d. CH3SH ANSWER: d 9. Which of the following compounds is the strongest acid? a. HF b. H2O c. NH3 d. CH4 ANSWER: a 10. Which of the following compounds is the strongest acid? a. CH3OCH3 b. CH3CH2OH c. CH3CHO d. HI ANSWER: d 11. Which of the following compounds is the strongest acid? a. (CH3)2CHCOOH b. (CH3)2CBrCOOH Copyright Cengage Learning. Powered by Cognero.

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Chapter 04: Acids and Bases c. (CH3)3COH d. BrCH2CH(CH3)COOH ANSWER: b 12. Which of the following compounds is the strongest acid? a. CH3COOH b. FCH2COOH c. ClCH2COOH d. BrCH2COOH ANSWER: b 13. Which of the following compounds is the strongest acid? a. CH4 b. CH3CH2CH2CH3 c. CH3CH2CH2CH=CH2 d. CH3CH2CH2C≡CH ANSWER: d 14. Which of the following compounds is the strongest acid? a. CF3OH b. CF3CH2 CH2OH c. CF3CH2 CH2 CH2OH d. CF3CH2 CH2 CH2CH2OH ANSWER: a 15. Which of the following compounds is the strongest acid? a. CH3CH2CH2COOH b. CH3CH2CHClCOOH c. CH3CHClCH2COOH d. ClCH2CH2CH2COOH ANSWER: b 16. Which of the following is the strongest base? a. NH3 b. H2O c. NaHCO3 d. CH3OH ANSWER: a Copyright Cengage Learning. Powered by Cognero.

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Chapter 04: Acids and Bases 17. Which of the following is the strongest base? a. iodide anion, I− b. fluoride anion, F− c. bromide anion, Br− d. chloride anion, Cl− ANSWER: b 18. Which of the following anions is the strongest base? a. CH3COO− b. HO− c. NH2− d. Cl− ANSWER: c 19. Which of the following anions is the strongest base? a. NH2− b. NH3 c. CH3CH=N− d. CH3C≡N ANSWER: a 20. Which of the following compounds has the highest pKa? a. SiH4 b. H2S c. PH3 d. HCl ANSWER: a 21. Which of the following compounds has the highest pKa? a. NH3 b. H2O c. HCl d. CH4 ANSWER: d 22. Which of the following compounds has the lowest pKa? a. H2O b. HBr Copyright Cengage Learning. Powered by Cognero.

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Chapter 04: Acids and Bases c. NH3 d. CH4 ANSWER: b 23. Which of the following compounds has the lowest pKa? a. HF b. HCl c. HBr d. HI ANSWER: d 24. Which of the following is present in the highest concentration upon dissolution of NaOH in water? a. NaOH b. H+ only c. Na+ and OHd. HO− only ANSWER: c 25. Which of the following is present in the highest concentration upon dissolution of benzoic acid in water? a. OH− b. H3O+ c. C6H5COOH d. C6H5COOANSWER: c 26. Which of the following terms describes the reactivity of boron tribromide, BBr3? a. Lewis acid and Arrhenius acid b. Bronsted-Lowry acid and not a Lewis acid c. Lewis acid and not a Bronsted-Lowry acid d. Lewis acid and Bronsted-Lowry acid ANSWER: c 27. Which of the following terms describes the reactivity of aluminum chloride, AlCl3? a. Arrhenius acid b. Only Lewis acid c. Lewis acid and Bronsted-Lowry acid d. Only Lewis base ANSWER: b 28. Which set of curved arrows accounts for the deprotonation of an acid (A-H) by a base (:B)? Copyright Cengage Learning. Powered by Cognero.

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Chapter 04: Acids and Bases

a. 1 b. 2 c. 3 d. 4 ANSWER: b 29. Which sets of curved arrows accounts for the protonation of propene with HI?

a. 1 b. 2 c. 3 d. 4 ANSWER: d 30. Which of the following terms describes the role of ethene in the acid-base reaction shown?

a. Brønsted-Lowry acid b. Brønsted-Lowry base c. Lewis acid d. Lewis base ANSWER: b 31. Which of the following terms describes the role of ethanol in the acid-base reaction shown?

a. Brønsted-Lowry acid b. Brønsted-Lowry base c. Lewis acid Copyright Cengage Learning. Powered by Cognero.

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Chapter 04: Acids and Bases d. Lewis base ANSWER: b 32. Which of the following terms describes the role of ethanol in the acid-base reaction shown?

a. Brønsted-Lowry acid b. Brønsted-Lowry base c. Lewis acid d. Lewis base ANSWER: a 33. Which of the following terms describes the role of ethyne in the acid-base reaction shown?

a. Brønsted-Lowry acid b. Brønsted-Lowry base c. Lewis acid d. Lewis base ANSWER: a 34. Which species is the conjugate acid in the following acid-base reaction?

a. 1 b. 2 c. 3 d. 4 ANSWER: d 35. Which species is the conjugate acid in the following acid-base reaction?

a. 1 b. 2 c. 3 d. 4 Copyright Cengage Learning. Powered by Cognero.

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Chapter 04: Acids and Bases ANSWER: d 36. What is the value of the equilibrium constant, Keq, for the following reaction?

a. 1013 b. 10−13 c. 13 d. 1/13 ANSWER: a 37. What is the value of the equilibrium constant, Keq, for the following reaction?

a. 109 b. 10−9 c. 9 d. 1/9 ANSWER: b 38. Which of the following is a Lewis acid but not a Brønsted-Lowry acid? a. CH3COOH b. BCl3 c. H2O d. CH3OH ANSWER: b 39. Which of the following is a feature of a Lewis acid? a. proton donor b. proton acceptor c. electron pair donor d. electron pair acceptor ANSWER: d 40. Which of the following is a feature of a Lewis base? a. proton donor b. proton acceptor Copyright Cengage Learning. Powered by Cognero.

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Chapter 04: Acids and Bases c. electron pair donor d. electron pair acceptor ANSWER: c 41. Which of the following is a feature of a Brønsted-Lowry acid? a. proton donor b. proton acceptor c. electron pair donor d. electron pair acceptor ANSWER: a 42. Which of the following is a feature of a Brønsted-Lowry base? a. proton donor b. proton acceptor c. electron pair donor d. electron pair acceptor ANSWER: b 43. Which of the following has the highest bond dissociation energy? a. HF b. HCl c. HBr d. HI ANSWER: a 44. Which of the following concepts can be used to rationalize the observation that acetic acid is a stronger acid than methanol? a. electronegativity b. resonance c. valence shell electron pair repulsion theory d. Pauli exclusion principle ANSWER: b 45. Which atom in the following structure is preferentially protonated by a strong acid?

a. i b. ii c. iii d. iv Copyright Cengage Learning. Powered by Cognero.

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Chapter 04: Acids and Bases ANSWER: a 46. What is the approximate pKa value of HCl? a. −7 b. 5 c. 16 d. 51 ANSWER: a 47. What is the approximate pKa value of acetic acid? a. −7 b. 5 c. 16 d. 51 ANSWER: b 48. Which of the following has a pKa value of 15.7? a. HBr b. CH3COOH c. H2O d. HC≡CH ANSWER: c 49. Which of the following has a pKa value of approximately 25? a. HI b. CH2=CH2 c. CH≡CH d. CH3CH2OH ANSWER: c 50. Which of the following statements is not true? a. Heat is absorbed in an endothermic reaction. b. The Gibbs free energy of the products of an exergonic reaction is equal to that of the reactants. c. The equilibrium constant of a reaction for which ΔG° = 0 is 1. d. ΔG° = ΔH° − TΔS° ANSWER: b 51. Which of the following equations is correct? a. ΔG° = ΔH° − TΔS° b. ΔH° = ΔG° − TΔS° c. ΔG° = ΔH° − ΔS° d. ΔG° = ΔH° − ΔS°/T Copyright Cengage Learning. Powered by Cognero.

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Chapter 04: Acids and Bases ANSWER: a 52. Which of the following energy diagrams represents the fastest reaction?

a. 1 b. 2 c. 3 d. 4 ANSWER: b 53. Which of the following energy diagrams represents the slowest reaction?

a. 1 b. 2 c. 3 d. 4 ANSWER: d 54. Which of the following is a definition of the rate-determining step of a reaction mechanism? a. the first step b. the last step c. the step that crosses the highest energy barrier d. the most exothermic step ANSWER: c 55. Which of the following is a definition of the enthalpy change? a. The difference in total bond strengths and solvation between various points under comparison on a reaction coordi nate diagram. b. The measure of disorder change in the system. Copyright Cengage Learning. Powered by Cognero.

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Chapter 04: Acids and Bases c. The difference in total bond strengths between various points under comparison on a reaction coordinate diagram. d. The energy contained within chemical bonds. ANSWER: a 56. Under which of the following conditions will a reaction be spontaneous when TΔS° < 0? a. ΔH° = 0 b. ΔH° <TΔSo c. ΔH° > 0 d. ΔG° = 0 ANSWER: b 57. Which of the following energy diagrams best represents the changes in energy during addition of HBr to an alkene?

a. 1 b. 2 c. 3 d. 4 ANSWER: a 58. An acid with a low pKa is a strong acid and has a weak conjugate base. a. True b. False ANSWER: True 59. In the following list, there are four Lewis acids, CH3OH, HCl, BCl3 and FeBr3.

a. True b. False ANSWER: True 60. In the following list, there are two organic Lewis bases. Copyright Cengage Learning. Powered by Cognero.

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Chapter 04: Acids and Bases

a. True b. False ANSWER: False 61. The following correctly shows the electron flow for the given reaction.

a. True b. False ANSWER: True 62. Indole is pleasant smelling in highly dilute solutions and has been used in perfumery.

When indole is placed in the presence of a strong base the nitrogen atom will be deprotonated. a. True b. False ANSWER: True 63. Indole is pleasant smelling in highly dilute solutions and has been used in perfumery.

Indole can be classified as a Brønsted-Lowry base but not as a Lewis base.. a. True b. False ANSWER: False 64. The following is generic depiction of a reaction using the curve arrow formalism. Copyright Cengage Learning. Powered by Cognero.

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Chapter 04: Acids and Bases

In this reaction electrons move from C to B and A will have a positive charge in the product. a. True b. False ANSWER: False 65. The structure of the alkaloid ephedrine is shown below. When ephedrine is placed in the presence of an acid, the — OH group will be protonated.

a. True b. False ANSWER: False 66. Consider the following reaction coordinate diagram.

This reaction is endergonic. a. True b. False ANSWER: False 67. Consider the following reaction coordinate diagram.

The transition state is represented by the letter B. a. True b. False ANSWER: True Copyright Cengage Learning. Powered by Cognero.

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Chapter 04: Acids and Bases 68. Consider the following reaction coordinate diagram.

The free energy of activation is represented by the letter C. a. True b. False ANSWER: False Consider the acidity constants below to answer the following question(s). ACID

STRUCTURE

phenol

pKa

10.00

ethanol

CH3CH2OH

16.00

water

HOH

15.74

69. Which acid will be almost completely deprotonated by NaOH? ANSWER: phenol 70. Which acid has the strongest conjugate base? ANSWER: ethanol 71. Which acid has the smallest Ka? ANSWER: ethanol Consider the following terms. Use these as appropriate to complete the following statements. transition state endergonic exergonic free energy of activation Gibbs free energy changes reaction intermediate 72. A species that lies at an energy maximum during an individual step in a reaction is termed ____________________. ANSWER: transition state Copyright Cengage Learning. Powered by Cognero.

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Chapter 04: Acids and Bases 73. The energy needed by reactants to reach the transition state is the____________________, ANSWER: free energy of activation 74. A reaction where ΔG° is positive is _____________. ANSWER: endergonic 75. ____________________ is defined by the following equation. ΔG° = −RT ln Keq ANSWER: Gibbs free energy change 76. A reaction in which the free energy of the products is greater than the reactants is termed____________________ . ANSWER: endergonic 77. Use curved arrows to show the movement of pairs of electrons in the following acid-base reaction and show the structures of the conjugate acid and conjugate base.

ANSWER:

78. Use curved arrows to show the movement of pairs of electrons in the following acid-base reaction and show the structures of the conjugate acid and conjugate base.

ANSWER:

79. Complete the equation below for the protonation of 2-butene with HBr. Show the movement of pairs of electrons with curved arrows and provide the structures of the conjugate acid and conjugate base.

ANSWER:

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Chapter 04: Acids and Bases 80. Complete the equation below for the protonation of cyclohexene with HCl. Show the movement of pairs of electrons with curved arrows and provide the structures of the conjugate acid and conjugate base.

ANSWER:

81. Provide the equation for the equilibrium constant, Keq, for the following equilibrium.

ANSWER:

82. Provide the equation for the acid dissociate constant, Ka,for the following equilibrium. ANSWER:

83. Provide the equation that relates the equilibrium constant, Keq, to the acid dissociation constant, Ka, for the following equilibrium. ANSWER: Ka = [H2O] Keq 84. Provide the equation that relates the acid dissociation constant, Ka, to the pKa of an acid. ANSWER: pKa = –log10Ka 85. What is the value of the equilibrium constant for the following equilibrium?

ANSWER: log10Keq = pKa(acid) – pKa(conjugate acid) = -8 – (-1.74) = -6.26 Keq = 10-6.26 = 5.5 x 10-7 86. What is the value of the equilibrium constant for the following equilibrium?

ANSWER: log10Keq = pKa(acid) – pKa(conjugate acid) = -4.76 – (-1.74) = -3.02

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Chapter 04: Acids and Bases Keq = 10-3.02 = 9.5 x 10-4 87. What is the value of the equilibrium constant for the following equilibrium?

ANSWER: log10Keq = pKa(acid) – pKa(conjugate acid) = 25 – 15.7 = 9.3 Keq = 109.3 = 2.0 x 109 88. What is the value of the equilibrium constant for the following equilibrium?

ANSWER: log10Keq = pKa(acid) – pKa(conjugate acid) = 25 – 38 = 13 Keq = 1013 89. Provide a brief explanation, based on features of the molecules, for the following trend in pKa values? CH3OH > CH3NH2 > CH3CH3 16 38 51 ANSWER: This trend is best understood in terms of the stability of the conjugate base that would be formed upon deprotonation of each of these acids. The methoxide anion (CH3O-), the conjugate base of methanol, has a negative charge on a highly electronegative oxygen atom. The oxygen atom accommodates the negative charge better than the nitrogen atom or carbon in the conjugate bases of methylamine and ethane (CH3NHand CH3CH2-, respectively). 90. Provide a brief explanation, based on features of the molecules, for the following trend in pKa values? CH3CH2OH > CH3COOH 15.9 4.76 ANSWER: This trend is best understood in terms of the stability of the conjugate base that would be formed upon deprotonation of each of these acids. One explanation is that the negative charge of the acetate anion (CH3CO2-), the conjugate base of acetic acid, is delocalized over the two oxygen atoms by resonance. In contrast, in the ethoxide anion (CH3CH2O-), the conjugate base of ethanol, the negative charge is localized on a single oxygen atom. 91. Provide a brief explanation, based on features of the molecules, for the following trend in pKa values? CH3CH2OH > CF3CH2OH ethanol 2,2,2-trifluoromethanol 15.9 12.4 ANSWER: This trend is best understood in terms of the stability of the conjugate base that would be formed upon deprotonation of each of these acids. The highly electronegative fluorine atoms of the 2,2,2-trifluoroethoxide anion (CF3CH2O-), the conjugate base of 2,2,2-trifluoroethanol, withdraw electron density from the oxygen Copyright Cengage Learning. Powered by Cognero.

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Chapter 04: Acids and Bases atom and thereby stabilize the anion relative to the ethoxide anion (CH3CH2O-), the conjugate base of ethanol. 92. Provide a brief explanation, based on features of the molecules, for the following trend in pKa values? CH3CH3 ethane

CH2=CH2 > HCCH ethene ethyne (ethylene) (acetylene) 51 44 25 ANSWER: This trend is best understood in terms of the stability of the conjugate base that would be formed upon deprotonation of each of these acids. The lone pair of electrons of the acetylide anion (HCC-) are in a lowerenergy atomic orbital (an sp orbital), and more tightly held, than the lone pair of electrons in the conjugate bases of ethylene (H2C=CH-, sp2 hybridized) and ethane (CH3CH2-, sp3 hybridized), respectively. 93. Use curved arrows to show the movement of pairs of electrons in the following reaction between a Lewis acid and a Lewis base, and show the structure of the product.

ANSWER:

94. Use curved arrows to show the movement of pairs of electrons in the following reaction between a Lewis acid and a Lewis base, and show the structure of the product.

ANSWER:

Match the types of reactions with the most appropriate relationships. a. Exergonic Reaction b. Endergonic Reaction c. Exothermic Reaction d. Endothermic Reaction 95. ΔHproduct < ΔHreactant ANSWER: c 96. ΔGproduct < ΔGreactant ANSWER: a 97. ΔHproduct > ΔHreactant ANSWER: d 98. ΔGproduct > ΔGreactant Copyright Cengage Learning. Powered by Cognero.

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Chapter 04: Acids and Bases ANSWER: b 99. Gaseous HCl when dissolved in water is a _____. a. strong acid b. weak acid c. proton acceptor d. neutral substance ANSWER: a 100. Calculate the ΔGo for an imaginary reaction with a Keq of 3.3 x 102 at 1300 K. a. –14.98 kcal/mol b. −1200 kcal/mol c. −4600.80 kcal/mol d. −1300 kcal/mol ANSWER: a Match the organic acids with the most appropriate pKa values. a. Methane b. Ethane c. Benzene d. Ethyne 101. 42 ANSWER: c 102. 60 ANSWER: a 103. 25 ANSWER: d 104. 51 ANSWER: b 105. Place the following compounds in the order of their decreasing basicity: Cyclohexylamine, Diphenylamine, Aniline a. Cyclohexylamine > Aniline > Diphenylamine b. Cyclohexylamine > Diphenylamine > Aniline c. Diphenylamine > Cyclohexylamine > Aniline d. Aniline > Cyclohexylamine > Diphenylamine ANSWER: a 106. Explain the highly basic nature of guanidine. ANSWER: Guanidine is highly basic in nature because of the resonance stabilization of protonated guanidine. The resonance stabilization of a guanidine base is small because of the large charge separation. However, the conjugate acid of guanidine is highly stabilized due to charge delocalization. This makes guanidine highly basic. Copyright Cengage Learning. Powered by Cognero.

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Chapter 04: Acids and Bases 107. Why are phenols more acidic than alcohols? ANSWER: Phenols are more acidic than alcohols because the phenoxide ion formed by the loss of a proton is resonance stabilized. This resonance stabilization makes it easy to remove an H+ ion.

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Chapter 05: Alkenes: Bonding, Nomenclature, and Properties 1. What is the approximate value of the C−C−C bond angle in propene? a. 90° b. 109° c. 120° d. 180° ANSWER: c 2. What is the approximate value of the H−C−H bonds angle in ethene? a. 90° b. 109° c. 120° d. 180° ANSWER: c 3. What is the approximate value of the length of the carbon-carbon bond in ethene? a. 121 pm b. 134 pm c. 142 pm d. 154 pm ANSWER: b 4. What type of molecular orbital is formed by the overlap of atomic orbitals shown?

a. σ bonding b. σ antibonding c. π bonding d. π antibonding ANSWER: c 5. What type of molecular orbital is formed by the overlap of atomic orbitals shown?

a. σ bonding b. σ antibonding c. π bonding d. π antibonding ANSWER: a 6. What type of molecular orbital is formed by the overlap of atomic orbitals shown? a. σ bonding Copyright Cengage Learning. Powered by Cognero.

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Chapter 05: Alkenes: Bonding, Nomenclature, and Properties b. σ antibonding c. π bonding d. π antibonding ANSWER: a 7. What is the hybridization of carbon atoms labeled i − iii in the following structure?

a. i = sp; ii = sp; iii = sp b. i = sp2; ii = p; iii = sp2 c. i = sp2; ii = sp; iii = sp2 d. i = sp2; ii = sp2; iii = sp2 ANSWER: c 8. What is the hybridization of carbon atoms labeled i − iii in the following structure?

a. i = sp2; ii = sp2; iii = sp2 b. i = sp; ii = sp; iii = sp3 c. i = sp2; ii = sp; iii = sp3 d. i = sp2; ii = sp2; iii = sp3 ANSWER: d 9. What is the index of hydrogen deficiency of a compound with a molecular formula of C5H8? a. 4 b. 2 c. 1 d. 3 ANSWER: b 10. What is the index of hydrogen deficiency of a compound with a molecular formula of C10H22? a. 3 b. 2 c. 1 d. 0 ANSWER: d 11. What is the index of hydrogen deficiency of a compound with a molecular formula of C4H5F? Copyright Cengage Learning. Powered by Cognero.

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Chapter 05: Alkenes: Bonding, Nomenclature, and Properties a. 3 b. 2 c. 4 d. 0 ANSWER: b 12. What is the index of hydrogen deficiency of a compound with a molecular formula of C8H16Br2? a. 1 b. 2 c. 4 d. 0 ANSWER: d 13. What is the index of hydrogen deficiency of a compound with a molecular formula of C7H16N2? a. 1 b. 2 c. 3 d. 0 ANSWER: a 14. What is the index of hydrogen deficiency of a compound with a molecular formula of C10H16N2? a. 2 b. 3 c. 4 d. 5 ANSWER: c 15. Which of the following molecular formulae corresponds to a compound with a hydrogen deficiency of 3? a. C5H6O b. C5H8O2 c. C6H15N d. C6H11Br ANSWER: a 16. Which of the following molecular formulae corresponds to a compound with a hydrogen deficiency of 1? a. C5H8N2 b. C5H11N c. C6H11N d. C5H13NO2 ANSWER: b Copyright Cengage Learning. Powered by Cognero.

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Chapter 05: Alkenes: Bonding, Nomenclature, and Properties 17. Which of the following compounds has a hydrogen deficiency of 3?

a. only 1 b. only 2 c. only 3 and 4 d. only 1,3 and 4 ANSWER: d 18. Which of the following compounds does not have a hydrogen deficiency of 5?

a. 1 b. 2 c. 3 d. 4 ANSWER: d 19. Which of the following does not correspond to a molecular formula of a neutral compound? a. C5H5Br b. C7H9Cl2 c. C5H5Br3 d. C5H8Cl4 ANSWER: b 20. Which of the following does not correspond to a molecular formula of a neutral compound? a. C5H5NO b. C8H9NO2 c. C7H13O2 d. C8H8N2 Copyright Cengage Learning. Powered by Cognero.

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Chapter 05: Alkenes: Bonding, Nomenclature, and Properties ANSWER: c 21. Which of the following does not correspond to a molecular formula of a neutral compound? a. C4H8BrNO b. C5H9ClN2O c. C15H30BrO3 d. C10H18ClN ANSWER: c 22. What is the IUPAC name of the following compound?

a. 2-methylenepentane b. 2-methyl-1-pentene c. 2-vinylpentane d. 2-propyl-1-propene ANSWER: b 23. What is the IUPAC name of the following compound?

a. 1,3-dimethylhexene b. 2,4-dimethyl-2-hexene c. 2,4-dimethyl-1-hexene d. 3,5-dimethyl-4-hexene ANSWER: b 24. Which of the following substituents has the highest priority according to the Cahn-Ingold-Prelog system used in assigning E and Z configurations of carbon-carbon double bonds? a. −CH(CH3)2 b. −CH2OCH3 c. −CH2CH3 d. −CH2Br ANSWER: d 25. Which of the following substituents has the highest priority according to the Cahn-Ingold-Prelog system used in assigning E and Z configurations of carbon-carbon double bonds? a. −F b. −H Copyright Cengage Learning. Powered by Cognero.

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Chapter 05: Alkenes: Bonding, Nomenclature, and Properties c. −OH d. −SH ANSWER: d 26. What is the IUPAC name of the following compound?

a. (E)-3-methyl-4-hexene b. (Z)-3-methyl-4-hexene c. (E)-4-methyl-2-hexene d. (Z)-4-methyl-2-hexene ANSWER: c 27. What is the IUPAC name of the following compound?

a. (E)-3-methyl-3-pentene b. (Z)-3-methyl-3-pentene c. (E)-3-methyl-2-pentene d. (Z)-3-methyl-2-pentene ANSWER: d 28. What is the IUPAC name of the following compound?

a. 2-methyl-4-vinyl-2-pentene b. 3,5-dimethyl-1,4-hexadiene c. 2,4-dimethyl-3,5-hexadiene d. 1,1,3-trimethyl-1,4-pentadiene ANSWER: b 29. What is the IUPAC name of the following compound?

a. (Z)-3-ethyl-5-methyl-1,4-heptadiene Copyright Cengage Learning. Powered by Cognero.

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Chapter 05: Alkenes: Bonding, Nomenclature, and Properties b. (E)-3-ethyl-5-methyl-1,4-heptadiene c. (E)-3-methyl-5-vinyl-3-heptene d. (Z)-1,3-diethyl-1-methyl-1,4-pentadiene ANSWER: b 30. What is the IUPAC name of the following compound?

a. 1,2-dimethylcyclohexene b. 2,3-dimethyl-1-cyclohexene c. 1,2-dimethyl-2-cyclohexene d. 1,6-dimethylcyclohexene ANSWER: d 31. What is the IUPAC name of the following compound?

a. 1,3-dimethylcyclopentene b. 1,4-dimethylcyclopentene c. 2,4-dimethylcyclopentene d. 1,3-dimethyl-5-cyclopentene ANSWER: b 32. What is the name of the following compound?

a. cis-4-methyl-1-allylcyclohexane b. cis-4-allyl-1-methylcyclohexane c. trans-4-allyl-1-methylcyclohexane d. cis-4-methyl-1-vinylcyclohexane ANSWER: d 33. What is the name of the following compound?

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Chapter 05: Alkenes: Bonding, Nomenclature, and Properties

a. vinylcyclohexane b. allylcyclohexane c. methylenecyclohexane d. propargylcyclohexane ANSWER: b 34. What is the IUPAC name of the following compound?

a. bicyclo[6.2]oct-2-ene b. bicyclo[4.4.4]oct-2-ene c. bicyclo[2.2.2]-2-octene d. bicyclo[2.2]-2-octene ANSWER: c 35. What is the IUPAC name of the following compound?

a. bicyclo[5.4.3]-2-octene b. bicyclo[5.4.3]-3-octene c. bicyclo[3.2.1]-2-octene d. 2,6-methyleno-1-cyclooctene ANSWER: c 36. Which is the correct assignment of the common names of the following compounds?

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Chapter 05: Alkenes: Bonding, Nomenclature, and Properties a. 1 = ethylene; 2 = isobutylene; 3 = isoprene b. 1 = acetylene; 2 = isoprene; 3 = isobutylene c. 1 = ethylene; 2 = isoprene; 3 = isobutylene d. 1 = acetylene; 2 = isobutylene; 3 = isoprene ANSWER: b 37. Which is the correct assignment of the names of the following groups?

a. 1 = methylene; 2 = vinyl; 3 = phenyl b. 1 = vinyl; 2 = propargyl; 3 = benzyl c. 1 = allyl; 2 = vinyl; 3 = benzyl d. 1 = vinyl; 2 = allyl; 3 = phenyl ANSWER: d 38. Which is the correct assignment of the names of the following groups?

a. 1 = vinyl; 2 = benzyl; 3 = allyl b. 1 = allyl; 2 = phenyl; 3 = vinyl c. 1 = methylene; 2 = phenyl; 3 = vinyl d. 1 = methylene; 2 = benzyl; 3 = allyl ANSWER: c 39. How many alkenes (excluding cis,trans isomers) have the formula C5H10? a. 3 b. 4 c. 5 d. 6 ANSWER: c 40. How many constitutional isomeric alkenes are there with the formula C6H12, that contains four carbons in the principal chain? a. 5 b. 4 c. 4 d. 2 Copyright Cengage Learning. Powered by Cognero.

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Chapter 05: Alkenes: Bonding, Nomenclature, and Properties ANSWER: c 41. How many isomers of 1,6-heptadiene exist? a. 1 b. 2 c. 3 d. 4 ANSWER: a 42. How many isomers of 1,3-heptadiene exist? a. 1 b. 2 c. 3 d. 4 ANSWER: b 43. How many isomers of 2,4-heptadiene exist? a. 1 b. 2 c. 3 d. 4 ANSWER: d 44. How many isomers of 1,3,5-heptatriene exist? a. 1 b. 2 c. 4 d. 8 ANSWER: c 45. What is the smallest trans cycloalkene that is stable at room temperature? a. (E)-cyclohexene b. (E)-cycloheptene c. (E)-cyclooctene d. (E)-cyclodecene ANSWER: c 46. What types of units make up terpenes? a. isoprene b. propene c. vitamin A d. pentadiene ANSWER: a Copyright Cengage Learning. Powered by Cognero.

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Chapter 05: Alkenes: Bonding, Nomenclature, and Properties 47. Which of the following is a terpene?

a. 1 b. 2 c. 3 d. 4 ANSWER: b 48. Which of the following is not a terpene?

a. 1 b. 2 c. 3 d. 4 ANSWER: a 49. Which of the following is not true regarding alkenes? a. Cis, trans isomerism is possible in alkenes. b. The rotation about carbon-carbon double bonds in alkenes is restricted at room temperature. c. Cis, trans isomerism is not possible in alkenes. d. Alkenes are soluble in ethanol. ANSWER: c 50. Which of the following compounds is most reactive (least stable)? a. (Z)-cyclohexene b. (E)-cyclohexene c. (Z)-cycloheptene d. (E)-cycloheptene Copyright Cengage Learning. Powered by Cognero.

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Chapter 05: Alkenes: Bonding, Nomenclature, and Properties ANSWER: b 51. 2-methyl-2-hexene can exhibit cis/trans isomerism. a. True b. False ANSWER: False 52. The structure for 2,3-dimethyl-2-pentene is shown below.

a. True b. False ANSWER: False 53. The following compound contains an allyl group.

a. True b. False ANSWER: False 54. The following compound contains a carbon-carbon double bond with Z stereochemistry.

a. True b. False ANSWER: True 55. The following molecular formula could represent an alkene.

C27H56 a. True b. False ANSWER: False 56. In the carbon-carbon bond of an alkene, a π bond is considerably weaker than a σ bond. a. True b. False ANSWER: True 57. The presence of both rings and pi bonds contribute to the index of hydrogen deficiency in a compound. a. True Copyright Cengage Learning. Powered by Cognero.

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Chapter 05: Alkenes: Bonding, Nomenclature, and Properties b. False ANSWER: True 58. In the calculation of the index of hydrogen deficiency, when the elements of Group 6 are found in a formula no correction to the number of hydrogen atoms is needed. a. True b. False ANSWER: True 59. (3E)-3,7-dimethyl-1,3,6-octatriene can be represented by either of the following two formulas.

a. True b. False ANSWER: True 60. Consider the following two structures.

The structure on the left represents the more stable form of this compound. a. True b. False ANSWER: False 61. The following could be named as either trans-2-methylhex-3-ene or (Z)-2-methylhex-3-ene .

a. True b. False ANSWER: False 62. The following substance contains ______ terpene units.

ANSWER: two Copyright Cengage Learning. Powered by Cognero.

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Chapter 05: Alkenes: Bonding, Nomenclature, and Properties 2 Consider the compounds named below. Use the letter of the substance to answer the following questions. Some letters may be used more than once. Some questions may have more than one correct answer. In the latter case, only one letter need be given. a. propene b. 1-butene c. 2-butene d. 1-pentene e. 2-pentene 63. The compound with the lowest boiling point is represented by the letter ______. ANSWER: a 64. A compound likely to be a liquid at room temperature is represented by the letter ______. ANSWER: d e 65. A compound that can exhibit cis-trans isomerism is represented by the letter ______. ANSWER: e 66. A compound with the following molecular formula contains two double bonds. The correct subscript for H in the formula is ________. C10H?ClN2O ANSWER: 19 nineteen 67. Using the EZ system, the following would designated as the ____isomer.

ANSWER: E E 68. What is the value of the index of hydrogen deficiency of a molecule with the formula C8H12? ANSWER: three 69. What is the value of the index of hydrogen deficiency of a molecule with the formula C9H10? ANSWER: five 70. What is the value of the index of hydrogen deficiency of a molecule with the formula C7H15N? ANSWER: one Copyright Cengage Learning. Powered by Cognero.

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Chapter 05: Alkenes: Bonding, Nomenclature, and Properties 71. What is the value of the index of hydrogen deficiency of a molecule with the formula C8H19N? ANSWER: zero 72. What is the value of the index of hydrogen deficiency of Ritalin, shown below?

ANSWER: six 73. What is the value of the index of hydrogen deficiency of aspartame, shown below?

ANSWER: seven 74. What is the IUPAC name of the following compound?

ANSWER: (E)-3-methyl-2-hexene 75. What is the IUPAC name of the following compound?

ANSWER: (Z)-5-methyl-2-hexene 76. What is the IUPAC name of the following compound?

ANSWER: (Z)-3-chloro-4-methyl-2-pentene Copyright Cengage Learning. Powered by Cognero.

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Chapter 05: Alkenes: Bonding, Nomenclature, and Properties 77. What is the IUPAC name of the following compound?

ANSWER: (E)-4-chloro-3-methyl-2-pentene 78. What is the IUPAC name of the following compound?

ANSWER: 1,6-dimethylcyclohexene 79. What is the IUPAC name of the following compound?

ANSWER: 1,4-dimethylcyclohexene 80. What is the IUPAC name of the following compound?

ANSWER: 3,4-dimethylcyclopentene 81. What is the IUPAC name of the following compound?

ANSWER: 3,5-dimethylcyclopentene 82. What is the IUPAC name of the following compound?

ANSWER: (2Z,5Z)-2,5-octadiene

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Chapter 05: Alkenes: Bonding, Nomenclature, and Properties 83. What is the IUPAC name of the following compound?

ANSWER: (2E,4Z)-2,4-octadiene 84. Provide the bond-line structure of (2E,5E)-2,5-octadiene. ANSWER: 85. Provide the bond-line structure of (2Z,6E)-octa-2,6-diene. ANSWER:

86. Provide the bond-line structure of (Z)-4,5-dichloro-2-pentene. ANSWER:

87. Provide the bond-line structure of (E)-3-chloro-3-hexene. ANSWER:

88. Identify the gaseous form(s) of alkenes.

a. Only II and III b. Only I c. I, II, and III d. Only III ANSWER: a Match the alkenes with the IUPAC names. a. b.

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Chapter 05: Alkenes: Bonding, Nomenclature, and Properties c.

89. 2-methyl-1,3-butadiene ANSWER: a 90. 3-methyl-2,6-octadiene ANSWER: b 91. 3-ethyl-1-methylcyclohexene ANSWER: c 92. 1-ethyl-4-methyl-1,3-cyclohexadiene ANSWER: d 93. Which of the following structure(s) have cis geometry?

a. Only I b. Only II c. Only III d. I, II, and III ANSWER: a 94. An example of a terpene with eight isoprene units is _____. a. vitamin A b. camphor c. lycopene d. menthol ANSWER: c 95. The decreasing order of melting points of the following alkenes is _____.

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Chapter 05: Alkenes: Bonding, Nomenclature, and Properties

a. I>II>III>IV b. III<I<II<IV c. II<III<I<IV d. IV>I>II>III ANSWER: d Match the index of hydrogen deficiency with their structures. a. 4 b. 3 c. 4 d. 2 e. 1

96. ANSWER: a

97. ANSWER: b

98. ANSWER: c

99. ANSWER: d 100. ANSWER: e 101. “X” is a naturally occurring unsaturated hydrocarbon with the molecular formula C10H18O. It is a monoterpene and is one of the components of the rose flower. Identify “X”, and find its index of hydrogen deficienc y. a. X is geraniol, and the index of hydrogen deficiency is 3. Copyright Cengage Learning. Powered by Cognero.

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Chapter 05: Alkenes: Bonding, Nomenclature, and Properties b. X is menthol, and the index of hydrogen deficiency is 3. c. X is geraniol, and the index of hydrogen deficiency is 2 d. X is menthol, and the index of hydrogen deficiency is 2. ANSWER: c

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Chapter 06: Reactions of Alkenes 1. What type of carbocation is shown?

a. primary b. secondary c. tertiary d. quaternary ANSWER: b 2. What type of carbocation is shown?

a. primary b. secondary c. tertiary d. quaternary ANSWER: c 3. Which of the following concepts explains why tertiary carbocations are more stable than primary and secondary carbocations? a. electronegativity b. resonance c. hyperconjugation d. the octet rule ANSWER: c 4. What type of orbitals overlap to provide stability to the tert-butyl carbocation by hyperconjugation? a. 3° C 2p atomic orbital + 3° C sp2 atomic orbital b. 3° C 2p atomic orbital + methyl C−H σ molecular orbital c. 3° C sp2 atomic orbital + methyl C−H σ molecular orbital d. 3° C 2p atomic orbital + methyl C 2s atomic orbital ANSWER: b 5. Which of the following concepts explains Markovnikov's rule as applied to the addition of HBr to propene? a. the relative stability of carbocations b. the nucleophilicity of bromide anion c. the acidity of HBr d. the aufbau principle ANSWER: a

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Chapter 06: Reactions of Alkenes 6. What is the correct order of stability of the following carbocations (more stable > less stable)?

a. 1 > 2 > 3 b. 1 > 3 > 2 c. 3 > 1 > 2 d. 3 > 2 > 1 ANSWER: d 7. What is the correct order of stability of the following carbocations (more stable > less stable)?

a. 1 > 2 > 3 b. 2 > 1 > 3 c. 2 > 3 > 1 d. 3 > 2 > 1 ANSWER: c 8. What is the major organic product obtained from the following reaction?

a. 1 b. 2 c. 3 d. 4 ANSWER: b 9. What is the major organic product obtained from the following reaction?

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Chapter 06: Reactions of Alkenes

a. 1 b. 2 c. 3 d. 4 ANSWER: b 10. What is the major organic product obtained from the following reaction?

a. 1 b. 2 c. 3 d. 4 ANSWER: c 11. What is the major organic product obtained from the following reaction?

a. 1 b. 2 c. 3 d. 4 ANSWER: c 12. Which of the following alkenes is most likely to undergo rearrangement upon acid-catalyzed hydration (treatment with aqueous H2SO4)?

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Chapter 06: Reactions of Alkenes

a. 1 b. 2 c. 3 d. 4 ANSWER: b 13. Which of the following alkenes is most likely to undergo rearrangement upon acid-catalyzed hydration (treatment with aqueous H2SO4)?

a. 1 b. 2 c. 3 d. 4 ANSWER: b 14. What is the major organic product obtained from the following reaction?

a. 1 b. 2 c. 3 d. 4 ANSWER: c 15. What is the major organic product obtained from the following reaction?

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Chapter 06: Reactions of Alkenes a. 1 b. 2 c. 3 d. 4 ANSWER: c 16. What is the major organic product obtained from the following reaction?

a. 1 b. 2 c. 3 d. 4 ANSWER: b 17. What is the major organic product obtained from the following reaction?

a. 1 b. 2 c. 3 d. 4 ANSWER: b 18. What is the major organic product obtained from the following reaction?

a. 1 b. 2 Copyright Cengage Learning. Powered by Cognero.

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Chapter 06: Reactions of Alkenes c. 3 d. 4 ANSWER: b 19. What is the major organic product obtained from the following reaction?

a. 1 b. 2 c. 3 d. 4 ANSWER: c 20. What is the major organic product obtained from the following reaction?

a. 1 b. 2 c. 3 d. 4 ANSWER: b 21. What is the major organic product obtained from the following reaction?

a. 1 b. 2 c. 3 d. 4 Copyright Cengage Learning. Powered by Cognero.

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Chapter 06: Reactions of Alkenes ANSWER: b 22. What is the major organic product obtained from the following reaction?

a. 1 b. 2 c. 3 d. 4 ANSWER: c 23. What is the major organic product obtained from the following reaction?

a. 1 b. 2 c. 3 d. 4 ANSWER: b 24. What is the major organic product obtained from the following reaction?

a. 1 b. 2 c. 3 d. 4 ANSWER: c Copyright Cengage Learning. Powered by Cognero.

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Chapter 06: Reactions of Alkenes 25. What is the major organic product obtained from the following reaction?

a. 1 b. 2 c. 3 d. 4 ANSWER: d 26. What is the major product obtained upon addition of Cl2 to (R)-4-isobutylcyclohexene? a. (1R,2R,4S)-1,2-dichloro-4-isobutylcyclohexane b. (1S,2R,4R)-1,2-dichloro-4-isobutylcyclohexane c. (1S,2S,4R)-1,2-dichloro-4-isobutylcyclohexane d. (1S,2S,4S)-1,2-dichloro-4-isobutylcyclohexane ANSWER: c 27. What is (are) the major organic product(s) obtained from the following reaction?

1. 2. 3.

(2R,3R)-dibromobutane (2S,3S)-dibromobutane meso-2,3-dibromobutane

a. only 1 b. only 2 c. only 3 d. only 1 and 2 ANSWER: c 28. What is (are) the major organic product(s) obtained from the following reaction?

1. 2. 3.

(2R,3R)-dibromobutane (2S,3S)-dibromobutane meso-2,3-dibromobutane a. only 1

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Chapter 06: Reactions of Alkenes b. only 2 c. only 3 d. only 1 and 2 ANSWER: d 29. What is the major organic product obtained from the following reaction?

a. 1 b. 2 c. 3 d. 4 ANSWER: b 30. What is the major organic product obtained from the following reaction?

a. 1 b. 2 c. 3 d. 4 ANSWER: a 31. What is the major organic product obtained from the following reaction?

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Chapter 06: Reactions of Alkenes

a. 1 b. 2 c. 3 d. 4 ANSWER: d 32. What is (are) the major organic product(s) obtained from the following reaction?

1. 2. 3.

(2R,3R)-butanediol (2S,3S)-butanediol meso-2,3-butanediol

a. only 1 b. only 2 c. only 3 d. only 1 and 2 ANSWER: d 33. What is (are) the major organic product(s) obtained from the following reaction?

1. 2. 3.

(2R,3R)-butanediol (2S,3S)-butanediol meso-2,3-butanediol

a. only 1 b. only 2 c. only 3 d. only 1 and 2 ANSWER: c Copyright Cengage Learning. Powered by Cognero.

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Chapter 06: Reactions of Alkenes 34. What is (are) the major organic product(s) obtained from the following reaction?

a. only 1 b. only 2 c. only 3 d. only 2 and 3 ANSWER: a 35. What is the best choice of reagent(s) to perform the following transformation?

a. H2O, H2SO4 b. Hg(OAc)2 and H2O; followed by NaBH4 c. BH3; followed by H2O2 d. OsO4; followed by H2S ANSWER: d 36. What is the best choice of reagent to perform the following transformation?

a. Br2 b. HBr c. Br2, H2O d. N-bromosuccinimide ANSWER: c 37. What is the best choice of reagent(s) to perform the following transformation?

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Chapter 06: Reactions of Alkenes

a. NaOH, H2O b. Hg(OAc)2 and H2O ; followed by NaBH4 c. B2H6; followed by H2O2, NaOH d. O3; followed by (CH3)2S ANSWER: c 38. What is the best choice of reagent(s) to perform the following transformation?

a. hot concentrated KMnO4 b. Hg(OAc)2 and H2O; followed by NaBH4 c. BH3; followed by H2O2, NaOH d. a peroxyacid followed by acidic solution in presence of Pd ANSWER: a 39. What is the best choice of reagent(s) to perform the following transformation?

a. H2O, H2SO4 b. Hg(OAc)2 and H2O; followed by NaBH4 c. BH3; followed by H2O2, NaOH d. OsO4; followed by NaHSO3 ANSWER: b 40. What type of reactive intermediate is formed in the reaction of an alkene with Br2 to give a dibromoalkane? a. cyclic bromonium ion b. carbanion c. radical Copyright Cengage Learning. Powered by Cognero.

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Chapter 06: Reactions of Alkenes d. carbocation ANSWER: a 41. What type of reactive intermediate is formed in the reaction of an alkene with Br2 and hydrogen peroxide to give a bromoalkane? a. carbocation b. carbanion c. cyclic bromonium ion d. radical ANSWER: d 42. What type of reactive intermediate is formed in the reaction of an alkene with HI to give an iodoalkane? a. carbocation b. carbanion c. radical d. carbene ANSWER: a 43. What type of reaction mechanism accounts for the reaction of an alkene with aqueous acid to give an alcohol? a. nucleophilic addition b. electrophilic addition c. radical addition d. elimination ANSWER: b 44. What type of reaction mechanism accounts for the reaction of an alkene with HBr to give an alkyl bromide? a. nucleophilic addition b. electrophilic addition c. radical addition d. elimination ANSWER: b 45. Which of the following alkenes undergoes the most exothermic hydrogenation upon treatment with H2/Pd?

a. 1 b. 2 c. 3 d. 4 ANSWER: d Copyright Cengage Learning. Powered by Cognero.

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Chapter 06: Reactions of Alkenes 46. Which of the following alkenes undergoes the least exothermic hydrogenation upon treatment with H2/Pd?

a. 1 b. 2 c. 3 d. 4 ANSWER: c 47. What is the correct order of exothermicity for hydrogenation of the following butenes upon treatment with H2/Pd (more exothermic > less exothermic)?

a. 1 > 2 > 3 b. 1 > 3 > 2 c. 3 > 2 > 1 d. 2 > 3 > 1 ANSWER: a 48. What is (are) the major organic product(s) obtained from the following reaction?

1. 2. 3.

(R)-2-bromo-3-methylbutane (S)-2-bromo-3-methylbutane 2-bromo-2-methylbutane

a. only 1 b. only 2 c. only 3 d. only 1 and 2 ANSWER: c 49. What is (are) the major organic product(s) obtained from the following reaction?

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Chapter 06: Reactions of Alkenes

1. 2. 3.

(R)-3-methyl-2-butanol (S)-3-methyl-2-butanol 2-methyl-2-butanol

a. only 1 b. only 2 c. only 3 d. only 1 and 2 ANSWER: d 50. Which of the following reactions of alkenes is not stereospecific? a. dishydroxylation (treatment with OsO4 followed by NaHSO3) b. hydrogenation (treatment with H2/Pt) c. cleavage with permanganate (treatment with hot concentrated KMnO4) d. bromohydrin formation (treatment with Br2/H2O) ANSWER: c 51. Which of the following reactions of alkenes is stereospecific? a. addition of HCl (treatment with HCl) b. dihydroxylation (treatment with OsO4 followed by NaHSO3) c. addition of HBr (treatment with HBr) d. oxymercuration-demercuration (treatment with aqueous Hg2+ followed by NaBH4) ANSWER: b 52. Which of the following reactions of alkenes takes place with anti stereospecificity? a. hydroboration-oxidation (treatment with BH3 followed by H2O2) b. hydrogenation (treatment with H2/Pt) c. addition of HBr (treatment with HBr) d. addition of bromine (treatment with Br2) ANSWER: d 53. Which of the following reactions of alkenes takes place with syn stereospecificity? a. ozonolysis (treatment with O3) b. hydroboration-oxidation (treatment with BH3 followed by H2O2) c. addition of HBr (treatment with HBr) d. acid-catalyzed hydration (treatment with aqueous H2SO4) ANSWER: b Copyright Cengage Learning. Powered by Cognero.

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Chapter 06: Reactions of Alkenes 54. The reagents that could effect the following conversion are H2 and Ni.

a. True b. False ANSWER: True 55. The reagents that could effect the following conversion are: BH3, then H2O2 and NaOH.

a. True b. False ANSWER: False 56. Consider the following reaction.

The product would be

a. True b. False ANSWER: False 57. The products obtained by the acid-catalyzed hydration of 1-methylcyclohexene and methylenecyclohexene

are identical. a. True b. False ANSWER: True 58. Consider the following reaction sequence.

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Chapter 06: Reactions of Alkenes The product of this sequence is

a. True b. False ANSWER: False 59. Markovnikov addition of HCl to propene involves the formation of a secondary carbocation. a. True b. False ANSWER: True 60. Br2 in CCl4 can be used to distinguish cyclohexene from cyclohexane. a. True b. False ANSWER: True 61. Consider the following reaction.

The mechanism for this reaction is shown below.

a. True b. False ANSWER: True 62. If the following compound were dissolved in ether and treated with HCl, the product of the reaction would a mixture of 3-bromoheptane and 2-bromoheptane.

a. True Copyright Cengage Learning. Powered by Cognero.

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Chapter 06: Reactions of Alkenes b. False ANSWER: True 63. _____________is the starting material required to produce 3-methyl-1-butanol using the hydroboration-

oxidation reaction. (Enter an IUPAC name.) ANSWER: 3-methyl-1-butene 64. Upon ozonolysis, _____________ will produce only acetone, (CH3)2C=O. (Enter an IUPAC name.) ANSWER: 2,3-dimethyl-2-butene 65. ____________________ predicts that the more stable carbocation intermediate is formed in electrophilic additions to alkenes. ANSWER: Markovnikov's rule 66. Consider the following reactions.

Pathway ___ involves a 1,2-shift. ANSWER: b B The reaction of methylpropene with HBr in ether gives one of the two products below as the major product. Answer the following question(s) about this reaction.

67. Product _____would be the major product. ANSWER: B 68. Product _____would be formed via a primary carbocation. ANSWER: A 69. Product _____ would have a higher energy transition state for the formation of the intermediate leading to it. ANSWER: A Copyright Cengage Learning. Powered by Cognero.

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Chapter 06: Reactions of Alkenes 70. Product _____ is the non-Markovnikov product. ANSWER: A 71. Product _____ would be formed by a carbocation experiencing the greatest degree of hyperconjugation stabilization. ANSWER: B 72. Product _____ would have the lowest activation energy required to form the intermediate in the mechanism. ANSWER: B 73. What is the major organic product obtained from the following reaction?

ANSWER:

74. What is the major organic product obtained from the following reaction?

ANSWER:

75. What is the major organic product obtained from the following reaction?

ANSWER:

76. What is the major organic product obtained from the following reaction?

ANSWER:

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Chapter 06: Reactions of Alkenes 77. What is the major organic product obtained from the following reaction?

ANSWER:

78. What is the major organic product obtained from the following reaction?

ANSWER:

79. What is the major organic product obtained from the following reaction?

ANSWER:

80. What is the major organic product obtained from the following reaction?

ANSWER:

81. What is the major organic product obtained from the following reaction?

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Chapter 06: Reactions of Alkenes

ANSWER: 2 equivalents of

82. What is the major organic product obtained from the following reaction?

ANSWER:

83. What is the major organic product obtained from the following reaction?

ANSWER:

84. What is the best choice of reagent(s) to perform the following transformation?

ANSWER: (i) BH3; (ii) H2O2, NaOH 85. What is the best choice of reagent(s) to perform the following transformation?

ANSWER: H2O, H2SO4 or (i) Hg(OAc)2, H2O; (ii) NaBH4 Copyright Cengage Learning. Powered by Cognero.

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Chapter 06: Reactions of Alkenes 86. What is the best choice of reagent(s) to perform the following transformation?

ANSWER: (i) OsO4; (ii) NaHSO3, H2O 87. What is the best choice of reagent(s) to perform the following transformation?

ANSWER: H2, transition metal catalyst (e.g., Pt, Pd) 88. What is the best choice of reagent(s) to perform the following transformation?

ANSWER: Br2 89. What is the best choice of reagent(s) to perform the following transformation?

ANSWER: Br2, H2O 90. What is the best choice of reagent(s) to perform the following transformation?

ANSWER: HBr 91. What is the best choice of reagent(s) to perform the following transformation?

ANSWER: (i) O3 (ii) (CH3)2S 92. Provide the structure of the key intermediate in the following reaction? Copyright Cengage Learning. Powered by Cognero.

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Chapter 06: Reactions of Alkenes

ANSWER:

93. Provide the structure of the key intermediate in the following reaction?

ANSWER:

94. Provide the structure of the key intermediate in the following reaction?

ANSWER:

95. Provide a neatly drawn mechanism for the following reaction, including curved arrows to show the movement of pairs of electrons and the structure of reactive intermediates.

ANSWER: The reaction proceeds in two steps: 1. Protonation of propene to form the 2-propyl cation 2. Nucleophilic addition of bromide anion to the 2-propyl cation

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Chapter 06: Reactions of Alkenes

96. Provide a neatly drawn mechanism for the following reaction, including curved arrows to show the movement of pairs of electrons and the structure of reactive intermediates.

ANSWER: The reaction proceeds in three steps: 1. Protonation of propene to form the 2-propyl cation 2. Nucleophilic addition of bromine to the 2-propyl cation 3. Deprotonation of the oxygen

97. Provide a neatly drawn mechanism for the following reaction, including curved arrows to show the movement of pairs of electrons and the structure of reactive intermediates.

ANSWER: The reaction proceeds in two steps: 1. Addition of bromine to propene to afford a cyclic bromonium ion 2. Nucleophilic ring-opening addition of bromide anion Copyright Cengage Learning. Powered by Cognero.

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Chapter 06: Reactions of Alkenes

98. Provide a neatly drawn mechanism for the following reaction, including curved arrows to show the movement of pairs of electrons and the structure of reactive intermediates.

ANSWER: The reaction proceeds in three steps: 1. Addition of bromine to propene to afford a cyclic bromonium ion 2. Nucleophilic ring-opening addition of water 3. Deprotonation of oxygen

99. Identify the correct statement for the given reaction given.

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Chapter 06: Reactions of Alkenes

a. II and III are electrophiles. b. Only IV is a nucleophile. c. I and II are electrophiles. d. Only IV is an electrophile. ANSWER: a 100. Identify “X” and “Y” in the following reaction.

a. X is 1-methylcyclopentene, and Y is Br2/H2O in DMSO. b. X is cyclopentene, and Y is Pd/H2. c. X is cyclopentadiene, and Y is H2O. d. X is 2-methylcyclopentadiene, and Y is Br2 in DMSO. ANSWER: a Match the reactants with their products. a.

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Chapter 06: Reactions of Alkenes

101. ANSWER: a

102. ANSWER: b

103. ANSWER: c 104. “X” is a naturally occurring terpenoid with the molecular formula C10H18O. It is isolated from geranium oil. “X” reacts with (S)-BINAP-RuCl3 and (R)-BINAP-RuCl3 to form A and B, respectively. Identify “X”.

a. Naproxen b. Geraniol c. Cannabinoid d. Curcuminoid ANSWER: b 105. The reduction of an alkene to an alkane by hydrogen in the presence of a catalyst is known as _____. ANSWER: catalytic hydrogenation 106. Identify the given structure given.

a. Tetraphenyl phosphate b. BINOL c. BINAP Copyright Cengage Learning. Powered by Cognero.

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Chapter 06: Reactions of Alkenes d. Binaphthyl ANSWER: c 107. Identify “X” and “Y” in the following reaction.

a. X is 1-methyl-3-cyclohexene, and Y is OsO4. b. X is 1-methylcyclopentene, and Y is H2SO4/H2O. c. X is 1-methylcyclohexene, and Y is O3/(CH3)2S. d. X is cyclopentane, and Y is OsO4. ANSWER: c

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Chapter 07: Alkynes 1. Approximately how long is a carbon-carbon bond length in ethane ? a. 142 pm b. 153 pm c. 121 pm d. 134 pm ANSWER: b 2. What is the approximate C−C−C bond angle in propene? a. 98° b. 108° c. 180o d. 120o ANSWER: d 3. How many alkynes are there with the molecular formula C5H8? a. 4 b. 5 c. 6 d. 3 ANSWER: d 4. How many terminal alkynes are there with the molecular formula C5H8? a. 1 b. 3 c. 2 d. 4 ANSWER: c 5. Which atomic orbitals overlap to form the carbon-hydrogen acetylenic bond? a. 2s + 1s b. sp + sp3 c. sp + 1s d. sp3 + 1s ANSWER: c 6. Which atomic orbitals overlap to form the carbon-carbon single bond of 1-propyne? a. 2s + sp b. sp + sp2 c. sp + sp3 d. sp2 + sp3 ANSWER: c Copyright Cengage Learning. Powered by Cognero.

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Chapter 07: Alkynes 7. What is the smallest cycloalkyne that is stable at room temperature? a. cyclohexyne b. cyclononyne c. cyclododecyne d. cycloeicosyne ANSWER: b 8. What is the IUPAC name of the following compound? CH3CH(CH3)C≡CH a. 2-isopropyl-1-ethyne b. 3-methyl-1-butyne c. 4-methyl-1-pentyne d. isopropyl ethyne ANSWER: b 9. What is the IUPAC name of the following compound? CH(CH3)2C≡CCH(CH3)2 a. 2,5-dimethyl-3-hexyne b. 2,5-dimethyl-4-hexyne c. 2,2,5,5-tetramethyl-2-butyne d. 4-octyne ANSWER: a 10. What is the IUPAC name of the following compound?

a. 3,4-dimethyl-1-hexen-5-yne b. 4-ethynyl-2-vinylbutane c. 3-methyl-4-vinyl-1-pentyne d. 4-ethynyl-3-methyl-1-pentyne ANSWER: a 11. What is the IUPAC name of the following compound

a. vinylcyclohexane b. allylcyclohexane Copyright Cengage Learning. Powered by Cognero.

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Chapter 07: Alkynes c. ethynylcyclohexane d. acetylcyclohexane ANSWER: c 12. What is the IUPAC name of the following compound?

a. (R)-4-methyl-2-hexyne b. (S)-4-methyl-2-hexyne c. (R)-3-methyl-4-hexyne d. (S)-3-methyl-4-hexyne ANSWER: b 13. What is the IUPAC name for the following compound?

a. (R)-3-methyl-1-penten-4-yne b. (S)-3-methyl-1-penten-4-yne c. (R)-4-methyl-4-penten-1-yne d. (S)-4-methyl-4-penten-1-yne ANSWER: a 14. Which of the following is the strongest acid? a. butane b. cyclobutane c. 1-butene d. 1-butyne ANSWER: d 15. Which of the following has the lowest pKa? a. 3-methylpentane b. pentene c. 3-methyl-1-pentyne d. methylcyclopentane ANSWER: c 16. What is the correct assignment of the acid, base, conjugate acid and conjugate base in the following equilibrium? Copyright Cengage Learning. Powered by Cognero.

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Chapter 07: Alkynes

a. 1 = acid; 2 = base; 3 = conjugate acid; 4 = conjugate base b. 1 = acid; 2 = base; 3 = conjugate base; 4 = conjugate acid c. 1 = base; 2 = acid; 3 = conjugate acid; 4 = conjugate base d. 1 = base; 2 = acid; 3 = conjugate base; 4 = conjugate acid ANSWER: b 17. What is the major organic product obtained from the following reaction?

a. cyclohexyne b. 1,3-cyclohexadiene c. cyclohexene d. 1,2-diaminocyclohexane ANSWER: b 18. What is the major organic product obtained from the following reaction?

a. (E) 2-butene b. (Z) 2-butene c. 2-butyne d. 1-butyne ANSWER: c 19. Which sequence of reactions can be used to convert 1,2-dibromopentane to 2-pentanone? a. Treatment with NaNH2; followed by treatment with (sia)2BH b. Treatment with NaNH2; followed by treatment with HgSO4 in concentrated H2SO4 c. Treatment with (sia)2BH; followed by treatment with alkaline peroxide d. Treatment with H2 in the presence of Lindlar catalyst; followed by treatment with HgSO4 in concentrated H2SO4 ANSWER: b 20. Which sequence of reactions can be used to convert (E) 2-pentene to 2-pentyne? a. Treatment with Cl2; followed by treatment with NaNH2 Copyright Cengage Learning. Powered by Cognero.

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Chapter 07: Alkynes b. Treatment with Cl2, H2O; followed by treatment with NaOH c. Treatment with Cl2; followed by treatment with H2SO4 d. Treatment with HCl; followed by treatment with NaOH ANSWER: a 21. What is the major organic product obtained from the following reaction?

a. 2-methyl-3-hexene b. 2-methyl-3-heptyne c. 2-bromo-3-methylbutane d. 2-methyl-2-butene ANSWER: b 22. What is the major organic product obtained from the following reaction?

a. 1-methyl-4-nonyne b. 2-methyl-4-nonyne c. 2-methyl-3-nonyne d. 3-methyl-4-nonyne ANSWER: d 23. What is the major organic product obtained from the following reaction?

a. (E) 1,2-dibromobutene b. (Z) 1,2-dibromobutene c. (E) 2,3-dibromobutene d. (Z) 2,3-dibromobutene ANSWER: c 24. What is the major organic product obtained from the following reaction?

a. (E) 3,4-dibromohexene Copyright Cengage Learning. Powered by Cognero.

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Chapter 07: Alkynes b. (Z) 3,4-dibromohexene c. (E) 2,3-dibromohexene d. (Z) 2,3-dibromobutene ANSWER: a 25. What is the major organic product obtained from the following reaction?

a. 2,3-dibromobutane b. 2,2,3,3-tetrabromobutane c. 2,3-dibromobutene d. 2,2-dibromobutane ANSWER: b 26. What is the major organic product obtained from the following reaction?

a. 3,4-dibromohexane b. 3,3-dibromohexane c. (Z) 3,4-dibromohexene d. 3,3,4,4-tetrabromohexane ANSWER: d 27. What is the major organic product obtained from the following reaction?

a. 2,3-dibromobutane b. 2,2,3,3-tetrabromobutane c. 2,3-dibromobutene d. 2,2-dibromobutane ANSWER: d 28. What is the major organic product obtained from the following reaction?

a. 3,4-dibromohexane b. 3,3-dibromohexane c. (E) 3,4-dibromohexene d. 3,3,4,4-tetrabromohexane ANSWER: b Copyright Cengage Learning. Powered by Cognero.

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Chapter 07: Alkynes 29. What is the major organic product obtained from the following reaction?

a. butanal b. cis-2-butene c. 2-butanol d. butanone ANSWER: a 30. What is the major organic product obtained from the following reaction?

a. 2-hexanone b. hexanal c. 2-hexanol d. cis-2-hexene ANSWER: b 31. What is the major organic product obtained from the following reaction?

a. butanal b. cis-2-butene c. 2-butanol d. butanone ANSWER: a 32. What is the major organic product obtained from the following reaction?

a. 2-hexanone b. hexanal c. 2-hexanol d. cis-2-hexene ANSWER: b 33. What is the major organic product obtained from the following reaction? Copyright Cengage Learning. Powered by Cognero.

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Chapter 07: Alkynes

a. 1 b. 2 c. 3 d. 4 ANSWER: a 34. What is the major organic product obtained from the following reaction?

a. 1 b. 2 c. 3 d. 4 ANSWER: d 35. What is the major organic product obtained from the following reaction?

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Chapter 07: Alkynes

a. 1 b. 2 c. 3 d. 4 ANSWER: d 36. What is the major organic product obtained from the following reaction?

a. 1 b. 2 c. 3 d. 4 ANSWER: d 37. What is the major organic product obtained from the following reaction?

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Chapter 07: Alkynes a. 1 b. 2 c. 3 d. 4 ANSWER: b 38. What type of intermediate is formed in the addition of bromine to alkynes? a. bromine gas b. bridged bromonium ion c. bromide ion d. bromine water ANSWER: b 39. What is the major organic product obtained from the following reaction?

a. 1 b. 2 c. 3 d. 4 ANSWER: c 40. What is the major organic product obtained from the following reaction?

a. 1 b. 2 c. 3 d. 4 Copyright Cengage Learning. Powered by Cognero.

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Chapter 07: Alkynes ANSWER: d 41. What is the major organic product obtained from the following reaction?

a. butane b. 1-butene c. cis-2-butene d. trans-2-butene ANSWER: d 42. What is the major organic product obtained from the following reaction?

a. 1 b. 2 c. 3 d. 4 ANSWER: b 43. What is the major organic product obtained from the following reaction?

a. butane b. 1-butene c. cis-2-butene d. trans-2-butene ANSWER: c 44. What is the major organic product obtained from the following reaction?

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Chapter 07: Alkynes

a. 1 b. 2 c. 3 d. 4 ANSWER: a 45. What is the major organic product obtained from the following reaction?

a. butane b. 1-butene c. cis-2-butene d. trans-2-butene ANSWER: c 46. What is the major organic product obtained from the following reaction?

a. 1 b. 2 c. 3 d. 4 ANSWER: a Copyright Cengage Learning. Powered by Cognero.

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Chapter 07: Alkynes 47. What is the best choice of reagent(s) to perform the following transformation?

a. 1 mol of Br2 b. 2 mol of Br2 c. 1 mol of HBr d. 2 mol of HBr ANSWER: d 48. What is the best choice of reagent(s) to perform the following transformation?

a. 1 mol of Br2 b. 2 mol of Br2 c. 1 mol of HBr d. 2 mol of HBr ANSWER: a 49. What is the best choice of reagent(s) to perform the following transformation?

a. H2O; H2SO4 b. 1.) 3 mol of NaNH2; 2.) H3O+ c. KMnO4, NaOH, H2O d. Zn ANSWER: b 50. What is the best choice of reagent(s) to perform the following transformation?

a. H2/Pt Copyright Cengage Learning. Powered by Cognero.

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Chapter 07: Alkynes b. H2/Lindlar catalyst c. Na/NH3 d. BH3; followed by H2O2, NaOH ANSWER: c 51. What is the best choice of reagent(s) to perform the following transformation?

a. H2/Pt b. H2/Lindlar catalyst c. Na/NH3 d. BH3; followed by H2O2, NaOH ANSWER: b 52. What is the best choice of reagent(s) to perform the following transformation?

a. H2/Lindlar catalyst b. Na/NH3 c. (sia)2BH; followed by H2O2, NaOH d. BH3; followed by H2O2, NaOH ANSWER: c 53. What is the best choice of reagent(s) to perform the following transformation?

a. H2/Lindlar catalyst b. Na/NH3 c. (sia)2BH; followed by H2O2, NaOH d. BH3; followed by H2O2, NaOH ANSWER: d 54. What is the major organic product obtained from the following series of reactions? Copyright Cengage Learning. Powered by Cognero.

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Chapter 07: Alkynes

a. 1 b. 2 c. 3 d. 4 ANSWER: a 55. What is the major organic product obtained from the following series of reactions?

a. propanal, CH3CH2CHO b. 1-propanol, CH3CH2CH2OH c. butanal, CH3CH2CH2CHO d. butanone, CH3COCH2CH3 ANSWER: d 56. What is the major organic product obtained from the following series of reactions?

a. (E)-5-phenyl-2-pentene b. 6-phenyl-1-hexene c. (Z)-6-phenyl-2-hexene d. (E)-6-methyl-3-heptene ANSWER: c 57. What is the major organic product obtained from the following series of reactions? Copyright Cengage Learning. Powered by Cognero.

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Chapter 07: Alkynes

a. (Z)-2-heptene b. (Z)-1,5-heptene c. 1-heptene d. heptane ANSWER: d 58. What is the major organic product obtained from the following series of reactions?

a. (Z)-2-heptene b. (E)-2-heptene c. 1-heptene d. heptane ANSWER: b 59. Which of the following reagents react with 2-butyne to form (Z)-2-butene? 1. 2. 3.

H2/Lindlar catalyst (sia)2BH followed by CH3COOH Na/NH3

a. only 1 b. only 2 c. only 3 d. only 1 and 2 ANSWER: d 60. Which of the following reagents react with 2-butyne to form 2-butanone? a. H2 gas b. Hg(II) salt with sulphuric acid c. CH3COOH d. NH3 ANSWER: b 61. The IUPAC name for the following compound is 2,5-dimethyl-4-ethyl-3-hexene.

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Chapter 07: Alkynes a. True b. False ANSWER: False 62. The triple bond in ethyne is made up of two π bonds, each formed by lateral overlap of two p orbitals, and a

σ bond formed by end-on overlap of two sp hybrid orbitals. a. True b. False ANSWER: True 63. Acetylene (ethyne) is more acidic and has a shorter carbon to carbon bond than either ethane or ethene. a. True b. False ANSWER: True 64. Consider the following,

the product formed is shown below.

a. True b. False ANSWER: True 65. H2 and Ni would be the required reagents for the following conversion.

a. True b. False ANSWER: True 66. The following deuteration reaction correctly shows the stereochemistry of the product.

a. True b. False ANSWER: True 67. The product of the following reaction would be an aldehyde. Copyright Cengage Learning. Powered by Cognero.

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Chapter 07: Alkynes

a. True b. False ANSWER: False 68. The key intermediate in the following reaction would be a vinylic carbocation.

a. True b. False ANSWER: True 69. 2-hexyne will produce a single product upon mercury(II)-catalyzed hydration. a. True b. False ANSWER: False 70. The product of the reaction when the following substance is treated with BH3 in THF followed by H2O2 would be a ketone.

a. True b. False ANSWER: False 71. Addition of H2 to 2-pentyne in the presence of the Lindlar's catalyst will produce ___-2-pentene. ANSWER: cis cis 72. The name of the final product after adding 1 mole of each reactant in the following sequence is

______________________.

ANSWER: 2-bromo-2-chloropropane 73. Consider an unknown with the molecular formula C4H6. The number of possible alkyne isomers is _____. Copyright Cengage Learning. Powered by Cognero.

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Chapter 07: Alkynes ANSWER: 2 two 74. Consider an unknown with the molecular formula C4H6. The index of hydrogen deficiency of this compound is _____. ANSWER: 2 two 75. The following species is referred to as a(an)_________________.

ANSWER: acetylide anion acetylide ion 76. The following species is the conjugate base of _________________.

ANSWER: acetylene ethyne 77. The name of the product of the reaction of the following substance with bromoethane would be ________________.

ANSWER: 1-butyne but-1-yne 78. ____________________refers to a synthesis developed by examining the structure of the desired product. ANSWER: retrosynthetic analysis retrosynthesis Select the best reagent or sequence of reagents from the list provided which would best accomplish each transformation below. Place the letter corresponding to the reagent(s) in the blank to the left of each reaction. Each transformation requires only one answer. a. b.

H2SO4, HgSO4 H2, Lindlar

1. Br2,CH2Cl2 2. 2 NaNH2, NH3(l) Page 19

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Chapter 07: Alkynes c. d.

1. 2. 1. 2.

BH3, THF H2O2, NaOH NaNH2, NH3(l) CH3CH2I

f. g. h.

1. HCl 2. NaNH2, NH3(l) Li, NH3(l) 1. NaNH2, NH3(l) 2. CH3CH2CH2I

79. _____

ANSWER: g 80. _____

ANSWER: a 81. _____

ANSWER: e 82. _____

ANSWER: h 83. What is IUPAC name of the following compound?

ANSWER: (R)-4-chloro-2-pentyne 84. What is IUPAC name of the following compound? Copyright Cengage Learning. Powered by Cognero.

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Chapter 07: Alkynes

ANSWER: (S)-2-chloro-3-hexyne 85. What is IUPAC name of the following compound?

ANSWER: 1,5-heptadiyne 86. What is IUPAC name of the following compound?

ANSWER: 2,5-octadiyne 87. What is the major organic product obtained from the following reaction?

ANSWER:

88. What is the major organic product obtained from the following reaction?

ANSWER:

89. What is the major organic product obtained from the following reaction?

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Chapter 07: Alkynes ANSWER:

90. What is the major organic product obtained from the following reaction?

ANSWER:

91. What is the major organic product obtained from the following reaction?

ANSWER:

92. What is the major organic product obtained from the following reaction?

ANSWER: 93. What is the major organic product obtained from the following reaction?

ANSWER:

94. What is the major organic product obtained from the following reaction?

ANSWER: 95. What is the major organic product obtained from the following reaction?

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Chapter 07: Alkynes

ANSWER:

96. What is the major organic product obtained from the following reaction?

ANSWER:

97. What is the major organic product obtained from the following reaction?

ANSWER:

98. Outline how one might achieve the following transformation, showing reagents and the isolated intermediates in the synthetic scheme. ANSWER:

99. Outline how one might achieve the following transformation, showing reagents and the isolated intermediates in the synthetic scheme.

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Chapter 07: Alkynes ANSWER:

100. Outline how one might achieve the following transformation, showing reagents and the isolated intermediates in the synthetic scheme.

ANSWER:

101. Outline how one might achieve the following transformation, showing reagents and the isolated intermediates in the synthetic scheme.

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Chapter 07: Alkynes ANSWER:

102. Outline how one might achieve the following transformation, showing reagents and the isolated intermediates in the synthetic scheme.

ANSWER:

103. The compound shown below is a natural pesticide found in carrots. What is the IUPAC name of the compound?

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Chapter 07: Alkynes

a. (3R, 9Z)-heptadeca-1,9-diene-4,6-diyn-3-ol b. (3S, 9E)-heptadeca-1,9-diene-4,6-diyn-3-ol c. 3-hydroxy-heptadeca-1,9-diene-4,6-diyn d. 8,16-heptadecadiene-11,13-diyn-15-ol ANSWER: a 104. What is the common name of the following compound? (Note: The grey balls indicate carbon atoms while the white ones indicate hydrogen atoms.)

a. Isopropyl acetylene b. Ethyl methyl acetylene c. 3-methyl-1-butyne d. 3-methyl hexyne ANSWER: b 105. _____ is a commonly used sterically hindered disubstituted borane to prevent the second hydroboration step, in terminal alkyne hydroboration. ANSWER: Di-sec-isoamylborane 106. Write a brief note about the following reaction.

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Chapter 07: Alkynes

ANSWER: The given reaction is an example of an acid-catalyzed reaction. Alkynes, in the presence of concentrated sulfuric acid and Hg(II) salts as catalysts, undergo the addition of water. In terminal alkynes, the addition follows Markovnikov’s rule. According to the rule, the negative part of the addendum (hydroxyl group) is added to the part of the carbon atom that is more alkylated. 107. What is the product obtained from the following organic reaction?

c. d. ANSWER: a 108. What is the product obtained from the following organic reaction?

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Chapter 07: Alkynes

a. 1-cyclooctyl-trans-1-propene b. 1-cyclooctyl-cis-1-propene c. 1-cyclooctyl-1-propanone d. 1-cyclooctyl-1-propanal ANSWER: a Match the organic compounds with their respective IUPAC names. a. b.

109. 1-cyclooctyl-1-propyne ANSWER: b 110. 1-cyclooctyl-1-ethyne ANSWER: a 111. 2,2,7,7-tetramethyl-3,5-octadiyne ANSWER: c 112. 2,2,8,8-tetramethyl-3,6-nonadiyne ANSWER: d

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Chapter 08: Haloalkanes, Halogenation, and Radical Reactions 1. What is the IUPAC name of the following compound?

a. (R)-1-chloro-3-methyl-2-cyclohexene b. (S)-1-chloro-3-methyl-2-cyclohexene c. (R)-3-chloro-1-methylcyclohexene d. (S)-3-chloro-1-methylcyclohexene ANSWER: c 2. What is the IUPAC name of the following compound?

a. (R)-2-bromo-2-vinylpentane b. (S)-2-bromo-2-vinylpentane c. (S)-3-bromo-3-propyl-1-butene d. (R)-3-bromo-3-methyl-1-hexene ANSWER: d 3. What is the IUPAC name of the following compound?

a. (E)-1-chloro-1,2,3-trimethyl-1-butene b. (Z)-1-chloro-1,2,3-trimethyl-1-butene c. (E)-2-chloro-3,4-dimethyl-2-pentene d. (Z)-2-chloro-3,4-dimethyl-2-pentene ANSWER: d 4. What is the correct assignment of the names of the following compounds? 1. 2. 3.

C2Cl4 C3F8 C2Cl6 a. 1 = perchloroethylene; 2 = perfluoroethane; 3 = perchloropropane

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Chapter 08: Haloalkanes, Halogenation, and Radical Reactions b. 1 = trichlor; 2 = perfluoroethane; 3 = perchloropropane c. 1 = perchloroethylene; 2 = perfluoropropane; 3 = perchloroethane d. 1 = perchloroethane; 2 = perfluoropropane; 3 = trichlor ANSWER: c 5. Which of the following has the list of compounds in the correct order of increasing boiling point (lower boiling point < higher boiling point)? a. 1-chloroethane < 1-chloromethane < 2-chloropropane < 2-chloro-2-methylpropane b. 1-chloromethane < 1-chloroethane < 2-chloropropane < 2-chloro-2-methylpropane c. 2-chloropropane < 2-chloro-2-methylpropane < 1-chloroethane <1-chloromethane d. 2-chloro-2-methylpropane < 1-chloroethane < 1-chloromethane < 2-chloropropane ANSWER: b 6. Which of the following has the list of compounds in the correct order of increasing boiling point (lower boiling point > higher boiling point)? a. 3-iodopentane < 3-bromopentane < 3-chloropentane < 3-fluoropentane b. 3-bromopentane < 3-iodopentane < 3-fluoropentane < 3-chloropentane c. 3-chloropentane < 3-fluoropentane < 3-iodopentane < 3-bromopentane d. 3-fluoropentane < 3-chloropentane < 3-bromopentane < 3-iodopentane ANSWER: d 7. Which of the following has the list of compounds in the correct order of decreasing density (higher density > lower density)? a. CBr4 > CI4 > CCl4 b. CCl4 > CBr4 > CI4 c. CI4 > CBr4 > CCl4 d. CCl4 > CI4> CBr4 ANSWER: c 8. Which of the following has the list of compounds in the correct order of increasing polarity (less polar < more polar)? a. CH2Cl2 < CH2Br2 < CH2I2 b. CH2I2 < CH2Br2 < CH2Cl2 c. CH2Cl2 < CH2I2 < CH2Br2 d. CH2Br2 < CH2Cl2 < CH2I2 ANSWER: b 9. Which of the following has the list of compounds in the correct order of increasing molecular polarity (less polarity < more polarity)? a. CHF3 < CHI3 < CHBr3 < CHCl3 b. CHCl3 < CHBr3 < CHI3 < CHF3 c. CHI3 < CHBr3 < CHCl3 < CHF3 Copyright Cengage Learning. Powered by Cognero.

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Chapter 08: Haloalkanes, Halogenation, and Radical Reactions d. CHCl3 < CHBr3 < CHF3 < CHI3 ANSWER: c 10. Which of the following bonds has the highest bond dissociation enthalpy? a. C−Cl b. C−I c. C−Br d. C−H ANSWER: d 11. Which of the following statements is not true? a. Homolytic cleavage of a bond in a neutral molecule gives two radicals. b. Radicals have one or more unpaired electrons. c. Movement of single electrons is depicted using a fishhook arrow. d. The C−F bond is the weakest bond between carbon atom and a halogen. ANSWER: d 12. Which halogen is most useful in the regioselective radical halogenation of alkenes?? a. fluorine b. chlorine c. bromine d. iodine ANSWER: c 13. What is the major organic product obtained from the following reaction?

a. 1 b. 2 c. 3 d. 4 ANSWER: b 14. What is the major organic product obtained from the following reaction?

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Chapter 08: Haloalkanes, Halogenation, and Radical Reactions

a. 1 b. 2 c. 3 d. 4 ANSWER: b 15. What is the major organic product obtained from the following reaction?

a. 1 b. 2 c. 3 d. 4 ANSWER: a 16. What are the major organic products obtained from the following reaction?

a. 1 and 2 b. 3 and 4 c. 1 and 3 d. 2 and 4 ANSWER: c 17. What is the correct order of stability of the following radicals (more stable > less stable)?

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Chapter 08: Haloalkanes, Halogenation, and Radical Reactions

a. 1 > 2 > 3 b. 1 > 3 > 2 c. 3 > 1 > 2 d. 3 > 2 > 1 ANSWER: d 18. What is the correct order of stability of the following radicals (more stable > less stable)?

a. 1 > 2 > 3 b. 2 > 1 > 3 c. 2 > 3 > 1 d. 3 > 2 > 1 ANSWER: c 19. What is the characteristic of a radical chain initiation step? a. Radicals are formed. b. Substitution products are formed. c. A radical reacts with a molecule to give a new radical and a new molecule. d. Two radicals combine to give a molecule. ANSWER: a 20. What is the characteristic of a radical chain propagation step? a. Radicals are formed. b. Byproducts are formed. c. A radical reacts with a molecule to give a new radical and a new molecule. d. Two radicals combine to give a molecule. ANSWER: c 21. What is the characteristic of a radical chain termination step? a. Radicals are formed. b. Substitution products are formed. c. A radical reacts with a molecule to give a new radical and a new molecule. d. Two radicals combine to give a molecule. Copyright Cengage Learning. Powered by Cognero.

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Chapter 08: Haloalkanes, Halogenation, and Radical Reactions ANSWER: d 22. What type of reactive intermediate is formed in the reaction of propene with N-bromosuccinimide to give 3-bromo-1propene? a. allylic carbocation b. allylic carbanion c. allylic radical d. cyclic bromonium ion ANSWER: c 23. What type of reactive intermediate is formed upon irradiation of a solution of toluene (Ph-CH3) and bromine? a. benzylic carbocation b. benzylic carbanion c. benzylic radical d. cyclic bromonium ion ANSWER: c 24. Which of the following alkanes does not undergo monobromination to form a single bromoalkane as the major product?

a. 1 b. 2 c. 3 d. 4 ANSWER: d 25. Which of the following alkenes undergoes allylic bromination to form a single monobrominated product?

a. 1 b. 2 c. 3 d. 4 Copyright Cengage Learning. Powered by Cognero.

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Chapter 08: Haloalkanes, Halogenation, and Radical Reactions ANSWER: a 26. What is the major product formed upon radical bromination of butane? a. (S)-2-bromobutane b. (R)-2-bromobutane c. a mixture of (R)- and (S)-2-bromobutane d. 1-bromobutane ANSWER: c 27. What is the geometry of the central carbon atom of a tert-butyl radical? a. tetrahedral b. trigonal planar c. trigonal pyramidal d. square planar ANSWER: b 28. Which of the following statements is true about the allyl radical? a. The eight atoms of the allyl radical do not lie in a single plane. b. Each atom in an allyl radical is sp2 hybridized. c. An allyl radical is less stable than a tertiary alkyl radical. d. Radical reactivity occurs at carbon 2. ANSWER: b 29. How many electrons does the allyl radical have in p orbitals a. 1 b. 2 c. 3 d. 4 ANSWER: c 30. How many π-bonding, non-bonding, and antibonding orbitals does the allyl radical possess? a. one bonding, one nonbonding, and one antibonding b. two bonding, no nonbonding, and no antibonding c. two bonding, one nonbonding, and no antibonding d. three bonding, no nonbonding, and no antibonding ANSWER: a 31. What type of orbitals overlap to provide stability to the tert-butyl radical by hyperconjugation? a. 3° C 2p atomic orbital + 3° C sp2 atomic orbital b. 3° C 2p atomic orbital + methyl C−H σ molecular orbital c. 3° C sp2 atomic orbital + methyl C−H σ molecular orbital d. 3° C 2p atomic orbital + methyl C 2s atomic orbital ANSWER: b Copyright Cengage Learning. Powered by Cognero.

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Chapter 08: Haloalkanes, Halogenation, and Radical Reactions 32. What type of orbital contains the unpaired electron of the tert-butyl radical? a. s b. p c. sp3 d. σ ANSWER: b 33. Which of the following is an accurate statement of Hammond's postulate? a. The transition state of an exothermic reaction will resemble the starting materials (reactants) more than the product. b. The transition state of an exothermic reaction will resemble the products more than the starting materials (reactants). c. The transition state of an endothermic reaction will resemble the starting materials (reactants) more than the product. d. the difference in energy between the starting materials (reactants) and transition state controls the rate of a reaction. ANSWER: a 34. Which of the following statements is not true regarding the halogenation of alkanes upon treatment with halogen and light? a. It is possible to prepare chloromethane or tetrachloromethane in a relatively pure form by this reaction. b. The radicals are formed from nonradical compounds in the initiation step of the reaction. c. On summing the chain propagation steps, the observed stoichiometry of the reaction can be obtained. d. Halogenation reactions are most commonly carried out with fluorine and iodine. ANSWER: d 35. What type of reactive intermediate is formed in the reaction of 2-methyl-1-propene with hydrogen bromide in the absence of peroxides to give 2-bromo-2-methylpropane? a. 2° radical b. allylic carbocation c. 2° carbocation d. 3° carbocation ANSWER: d 36. What is the major product obtained from the reaction of 2-methyl-1-propene with hydrogen bromide in the presence of peroxides? a. 2-bromo-2-methylpropane b. 1-bromo-2-methylpropane c. 1,2-dibromo-2-methylpropane d. no reaction occurs ANSWER: b 37. Which of the following statements is not true? a. HBr reacts with alkenes in the presence of a peroxide, via a free radical chain mechanism. Copyright Cengage Learning. Powered by Cognero.

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Chapter 08: Haloalkanes, Halogenation, and Radical Reactions b. Addition of HBr to alkenes in the presence of peroxides occur via a carbocation intermediate. c. The combination of two bromine radicals occurs in the chain termination step of the free radical addition of HBr to alkenes. d. Free radical addition of HX to alkenes is possible only with HBr. ANSWER: b 38. Which of the following compounds is most susceptible to autoxidation? a. 1,3,5-hexatriene b. 1,5-octadiene c. 2,5-dimethyl-1,4-hexadiene d. 1,3-pentadiene ANSWER: c 39. What is the reactive intermediate in the autooxidation of cyclohexene? a. an allylic radical b. a 2° carbocation c. a carbocation d. a diene ANSWER: a 40. What is the major product of autooxidation of cyclohexene?

a. 1 b. 2 c. 3 d. 4 ANSWER: c 41. What is the major organic product obtained from the following reaction?

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Chapter 08: Haloalkanes, Halogenation, and Radical Reactions

a. 1 b. 2 c. 3 d. 4 ANSWER: c 42. What is the major organic product obtained from the following reaction?

a. 1 b. 2 c. 3 d. 4 ANSWER: c 43. What is the major organic product obtained from the following reaction?

a. 1 b. 2 c. 3 d. 4 ANSWER: a 44. What are the major products formed upon treatment of (E)-3-methyl-2-hexene with HBr in the presence of peroxides? 1. 2. 3.

(S,S)-2-bromo-3-methylhexane (S,R)-2-bromo-2-methylhexane (R,S)-2-bromo-2-methylhexane

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Chapter 08: Haloalkanes, Halogenation, and Radical Reactions 4.

(R,R)-2-bromo-2-methylhexane

a. only 1 and 2 b. only 1 and 4 c. only 2 and 3 d. a mixture of 1, 2, 3, and 4 ANSWER: d 45. What are the major products formed upon treatment of (E)-3-methyl-2-hexene with Br2 in the presence of peroxides? 1. 2. 3.

(S)-3-bromo-3-methylhexane (R)-3-bromo-3-methylhexane 2-bromo-3-methylhexane

a. only 1 b. only 2 c. a mixture of 3 and 2 d. none of the mentioned ANSWER: d 46. Which of the following accounts for the anti-Markovnikov regiochemistry of the reaction of an alkene with HBr in the presence of peroxides? a. The alkene reacts with HBr to give a carbocation. b. The alkene reacts with a bromine atom to give a radical. c. The alkene reacts with a hydrogen atom to give a radical. d. The alkene reacts with peroxide to five an allylic radical. ANSWER: b 47. The IUPAC name for the following substance is 6-methyl-2-bromoheptane.

a. True b. False ANSWER: False 48. The IUPAC name for the following substance is trans-1-bromo-4-methylcyclohexane.

a. True b. False ANSWER: True Copyright Cengage Learning. Powered by Cognero.

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Chapter 08: Haloalkanes, Halogenation, and Radical Reactions 49. The boiling points of alkanes increase as the length of the carbon chain increases but decrease as the amount

of branching increases. a. True b. False ANSWER: True 50. In the chlorination of methane, the propagation steps involve forming methyl, chlorine, and hydrogen

radicals. a. True b. False ANSWER: False 51. Consider the following reaction.

In the absence of peroxides, the major product of the reaction is shown below.

a. True b. False ANSWER: False 52. Consider the following reaction.

In the presence of peroxides, the major product of the reaction is shown below.

a. True b. False ANSWER: True 53. The structure of (S)-2-bromobutane is given below.

a. True b. False Copyright Cengage Learning. Powered by Cognero.

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Chapter 08: Haloalkanes, Halogenation, and Radical Reactions ANSWER: True 54. The products of the addition of HBr to an alkene in the presence of peroxides is accounted for by a polar reaction mechanism. a. True b. False ANSWER: False 55. Homolytic cleavage of CH3CH2CH2—O—O—CH2CH3 would produce two identical radicals. a. True b. False ANSWER: False 56. Autoxidation occurs by a radical chain mechanism that requires oxygen and an initiator. a. True b. False ANSWER: False 57. The number of possible monobromination products, including cis-trans isomers, of methylcyclopentane is

______. ANSWER: 6 six 58. The number of possible dibromination products of 2-methylpropane is______. ANSWER: three 3 59. The number of possible monobromination products of cyclopentane is______. ANSWER: one 1 Consider the reaction below to answer the following question(s).

60. The number of allylic positions in compound A is ______. ANSWER: 2 two 61. The name of one of the minor products of this reaction is____________________. ANSWER: 1-bromo-2-hexene 1-bromohex-2-ene 2-bromo1-hexene 2-bromohex-1-ene Copyright Cengage Learning. Powered by Cognero.

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Chapter 08: Haloalkanes, Halogenation, and Radical Reactions 62. The major products of the reaction would be formed from the radical intermediate numbered _____ as shown below. 1.

2. ANSWER: 1 one 1. 63. During bromination using NBS, the addition product is not observed because the rate of addition is _______than the rate of the chain propagation steps. ANSWER: less slower 64. During bromination using NBS, the concentration of bromine remains ________throughout the course of the reaction. ANSWER: low small 65. Provide the IUPAC name of the following compound.

ANSWER: (S)-4-bromo-2-methylhexane 66. Provide the IUPAC name of the following compound.

ANSWER: (S)-2-chloro-4-methylpentane 67. Provide the IUPAC name of the following compound (shown as a Fischer projection).

ANSWER: (S)-2-fluorobutane 68. Provide the IUPAC name of the following compound (shown as a Fischer projection).

ANSWER: (S)-2-iodopentane Copyright Cengage Learning. Powered by Cognero.

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Chapter 08: Haloalkanes, Halogenation, and Radical Reactions 69. What is the structure of all of the monobrominated products, including regioismers and stereoisomers, obtained from the following reaction?

ANSWER:

70. What is the structure of all of the monobrominated products, including regioismers and stereoisomers, obtained from the following reaction?

ANSWER:

71. What is the major organic product obtained from the following reaction?

ANSWER:

72. What is the major organic product obtained from the following reaction?

ANSWER:

73. What is the major organic product obtained from the following reaction?

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Chapter 08: Haloalkanes, Halogenation, and Radical Reactions ANSWER:

74. What is the major organic product obtained from the following reaction?

ANSWER:

75. Provide neatly drawn resonance structures of the key intermediate in the following reaction.

ANSWER:

76. What is the structure of the key intermediate in the following reaction?

ANSWER:

77. What is the IUPAC name of the following compound?

a. 1,3-dichloro-3-methylhexane b. 3-methyl-1,3-dichlorohexane Copyright Cengage Learning. Powered by Cognero.

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Chapter 08: Haloalkanes, Halogenation, and Radical Reactions c. 2-chloro-2-(1-chloroethyl)-hexane d. 2,4-dichloro-2-(n-propyl)butane ANSWER: a 78. What is the major product in the following reaction?

a. Only I b. Only II c. Only III d. I, II, and III in equal amounts ANSWER: b Match the haloforms with their structures. a. trichlor c. chloroform

b. methyl chloroform d. methylene chloride

79. ANSWER: a 80. ANSWER: b 81. ANSWER: c 82. ANSWER: d 83. Identify the step of the given free radical reaction mechanism.

a. Chain propagation Copyright Cengage Learning. Powered by Cognero.

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Chapter 08: Haloalkanes, Halogenation, and Radical Reactions b. Chain termination c. Chain initiation d. Chain extension ANSWER: c Match the haloalkanes with the electronegativity of halogens. a. b.

84. 3 ANSWER: a 85. 2.5 ANSWER: b 86. 2.8 ANSWER: c 87. 4 ANSWER: d 88. Identify the correct statement for the given reactions given.

a. Reaction A is an allylic halogenation reaction, and reaction B is an electrophilic addition reaction. b. Reaction A is an electrophilic addition reaction, and reaction B is an allylic substitution reaction. c. Reactions A and B are allylic substitution reactions. d. Reaction A is a displacement reaction, and reaction B is an allylic halogenation reaction. ANSWER: a 89. Why does the presence of bromine not facilitate the electrophilic addition of bromine to the carbon–carbon double bonds in allylic halogenation reactions of alkenes? ANSWER: In allylic halogenation reactions of alkenes, the presence of bromine does not facilitate the electrophilic Copyright Cengage Learning. Powered by Cognero.

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Chapter 08: Haloalkanes, Halogenation, and Radical Reactions addition of bromine to the carbon–carbon double bonds because of the following reasons: 1. The rate of chain propagation step is faster in allylic substitution than the rate of electrophilic addition of bromine to the alkene when radicals are present. 2. The concentration of bromine is low during the course of the reaction.

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Chapter 09: Nucleophilic Substitution and b-Elimination 1. Which of the following reactions corresponds to a substitution? a. 1-pentene → 1,2-dichloropentane b. 2-chloro-3-methylbutane → 2-methylbut-2-ene c. ethene → ethane d. 1-bromopropane → ethoxypropane ANSWER: d 2. Which of the following reactions corresponds to a substitution? a. iodoethane → diethyl ether b. tert-butanol → 2-methylpropene c. 3,3-dimethyl-2-butanol → 2,3-dimethyl-2-butene d. 1-butene → 1,2-dichlorobutane ANSWER: a 3. Which of the following statements related to SN1 reactions is not true? a. The heterolysis of a bond between atoms which do not bear formal charges always produces a cation and an anion b. The carbocation intermediate is one electron shy from an octet c. Carbocations are Lewis acids d. Nucleophiles seek centers of low electron density ANSWER: b 4. Which of the following statements related to SN1 reactions is not true? a. These reactions lead to the formation of a racemic mixture b. Carbocations are electrophilic c. These reactions are accelerated in a polar protic solvent d. The attack of the nucleophile is the rate determining step ANSWER: d 5. What is the equation for the rate of formation of tert-butyl alcohol from the reaction of tert-butyl bromide (t-BuBr) with water by an SN1 mechanism? a. Rate = k [t-BuBr] b. Rate = k [t-BuBr][H2O] c. Rate = k [H2O] d. Rate = k [t-BuBr]2 ANSWER: a 6. What is the equation for the rate of formation of 1-iodobutane from the reaction of 1-chlorobutane (BuCl) with NaI by an SN2 mechanism? a. Rate = k [BuCl] b. Rate = k [BuCl][NaI] c. Rate = k [NaI] Copyright Cengage Learning. Powered by Cognero.

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Chapter 09: Nucleophilic Substitution and b-Elimination d. Rate = k [BuCl]2 ANSWER: b 7. What is the equation for the rate of formation of 2-methoxybutane, (CH3CH2CH(OCH3)CH3), from the reaction of 2bromobutane (sec-BuBr) with potassium methoxide (KOCH3)? a. Rate = k [sec-BuBr] b. Rate = k [sec-BuBr]2 c. Rate = k [KOCH3] d. Rate = k [sec-BuBr][KOCH3] ANSWER: d 8. What is the equation for the rate of formation of 2-methoxybutane, (CH3CH(OCH3)CH2CH3), from the reaction of 2bromobutane (sec-BuBr) with methanol? a. Rate = k [sec-BuBr] b. Rate = k [sec-BuBr]2 c. Rate = k [CH3OH] d. Rate = k [sec-BuBr][CH3OH] ANSWER: a 9. The reaction of methyl iodide with sodium azide, NaN3, proceeds by an SN2 mechanism. What is the effect of doubling the concentration of NaN3 on the rate of the reaction? a. the rate remains the same b. the rate decreases by a factor of 2 c. the rate increases by a factor of 2 d. the rate increases by a factor of 4 ANSWER: c 10. The reaction of 1-bromopropane with sodium iodide gives 1-iodopropane. What is the effect of increasing by four times the concentration of NaI on the rate of the reaction? a. the rate remains the same b. the rate decreases by a factor of 4 c. the rate increases by a factor of 4 d. the rate increases by a factor of 8 ANSWER: c 11. The reaction of tert-butyl bromide, (CH3)3CBr, with methanol in an inert solvent proceeds by an SN1 mechanism to give tert-butyl methyl ether, (CH3)3COCH3. What is the effect of doubling the concentration of methanol on the rate of the reaction? a. the rate remains the same b. the rate decreases by a factor of 2 c. the rate increases by a factor of 2 Copyright Cengage Learning. Powered by Cognero.

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Chapter 09: Nucleophilic Substitution and b-Elimination d. the rate increases by a factor of 4 ANSWER: a 12. The reaction of tert-butyl chloride, (CH3)3CCl, with water in an inert solvent gives tert-butyl alcohol, (CH3)3COH. What is the effect of decreasing in three times the concentration of alkyl halide on the rate of the reaction? a. the rate decreases by a factor of 3 b. the rate increases by a factor of 3 c. the rate increases by a factor of 6 d. the rate decreases by a factor of 6 ANSWER: a 13. Which of the following alkyl halides undergoes the fastest SN2 reaction with sodium azide, NaOCH3? a. 1-fluoropentane b. 1-chloropentane c. 1-bromopentane d. 1-iodopentane ANSWER: d 14. Which of the following alkyl halides undergoes the fastest SN2 reaction with sodium cyanide, NaCN? a. ethyl bromide b. 1-bromopropane c. 2-bromopropane d. tert-butyl bromide ANSWER: a 15. Which of the following alkyl halides undergoes the fastest SN2 reaction with sodium methylthiolate, NaSMe? a. methyl iodide b. ethyl iodide c. 2-bromopropane d. tert-butyl chloride ANSWER: a 16. Which of the following alkyl halides undergoes the fastest solvolysis reaction with formic acid, HCOOH? a. tert-butyl fluoride b. tert-butyl chloride c. tert-butyl bromide d. tert-butyl iodide ANSWER: d 17. Which of the following alkyl halides undergoes the fastest solvolysis reaction with methanol, CH3OH? a. methyl chloride b. ethyl chloride c. 2-chloropropane Copyright Cengage Learning. Powered by Cognero.

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Chapter 09: Nucleophilic Substitution and b-Elimination d. tert-butyl chloride ANSWER: d 18. Which of the following alkyl halides undergoes the fastest solvolysis reaction with ethanol, CH3CH2OH? a. methyl fluoride b. ethyl bromide c. 2-chloropropane d. tert-butyl bromide ANSWER: d 19. Which of the following is best set of conditions for the preparation of tert-butanol? a. tert-butyl fluoride in water b. tert-butyl bromide in water c. tert-butyl fluoride and NaOH in DMSO d. tert-butyl bromide and NaOH in DMSO ANSWER: b 20. Which of the following is the best set of conditions for the preparation of tert-butyl ethyl ether? a. tert-butyl flluoride and NaOCH2CH3 in ethanol b. ethanol and sodium tert-butoxide in tert-butanol c. fluoroethane and sodium tert-butoxide in tert-butanol d. tert-butyl bromide and CH3CH2OH ANSWER: d 21. What is the major product formed upon treatment of (S) 1-chloro-5-methylheptane with sodium iodide? a. (S) 1-iodo-5-methylheptane b. (R) 1-iodo-5-methylheptane c. (S) 5-methyl-1-heptene d. (R) 5-methyl-1-heptene ANSWER: a 22. What is the major product formed upon treatment of (R) 2-bromohexane with sodium cyanide? a. (R) 2-cyanohexane b. (S) 2-cyanohexane c. 1-hexene d. 2-hexene ANSWER: b 23. What is the major organic product obtained from the following reaction?

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Chapter 09: Nucleophilic Substitution and b-Elimination

a. 1 b. 2 c. 3 d. 4 ANSWER: b 24. What is the major organic product obtained from the following reaction?

a. 1 b. 2 c. 3 d. 4 ANSWER: a 25. What is the major organic product obtained from the following reaction?

a. 1 b. 2 c. 3 d. 4 ANSWER: a 26. What is the major organic product obtained from the following reaction?

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Chapter 09: Nucleophilic Substitution and b-Elimination

a. 1 b. 2 c. 3 d. 4 ANSWER: b 27. What is the major organic product obtained from the following reaction?

a. 1 b. 2 c. 3 d. 4 ANSWER: c 28. What is the major organic product(s) obtained from the following reaction?

a. 1-hexyne b. 2-hexyne c. propene + propyne d. propane + propyne ANSWER: b 29. What is the major organic product(s) obtained from the following reaction?

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Chapter 09: Nucleophilic Substitution and b-Elimination

a. 3-methyl-1-pentyne b. 3-methyl-2-pentyne c. 1-propene + propyne d. 4-methyl-2-pentene ANSWER: c 30. What is(are) the major organic product(s) obtained from the following substitution reaction?

a. only 1 b. only 2 c. only 3 d. a mixture of 1 and 2 ANSWER: a 31. What is(are) the major organic product(s) obtained from the following substitution reaction?

a. only 1 b. only 2 c. only 3 d. a mixture of 1 and 2 ANSWER: d 32. What is(are) the major organic product(s) obtained from the following substitution reaction?

a. only 1 b. only 2 c. only 1 and 2 d. 1, 2 and 3 Copyright Cengage Learning. Powered by Cognero.

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Chapter 09: Nucleophilic Substitution and b-Elimination ANSWER: d 33. What is(are) the major organic product(s) obtained from the following substitution reaction?

a. only 1 b. only 2 c. only 1 and 2 d. 1, 2 and 3 ANSWER: d 34. In which of the following solvents would the reaction of 1-bromobutane with sodium azide, NaN3, proceed the fastest? a. acetic acid b. formic acid c. water d. acetone ANSWER: d 35. Which of the following solvents is the best choice for the reaction of 1-chlorohexane with sodium bromide? a. dimethylsulfoxide b. water c. hexane d. toluene, PhCH3 ANSWER: a 36. Which of the following solvents is the best choice for the reaction of 1-chlorohexane with sodium bromide? a. water b. N,N-dimethylformamide c. hexane d. toluene, PhCH3 ANSWER: b 37. Which of the following anions is the most nucleophilic in polar protic solvents? a. F− b. Cl− Copyright Cengage Learning. Powered by Cognero.

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Chapter 09: Nucleophilic Substitution and b-Elimination c. Br− d. I− ANSWER: d 38. Which of the following anions is the most nucleophilic in polar aprotic solvents? a. F− b. Cl− c. Br− d. I− ANSWER: a 39. Which of the following compounds is the most nucleophilic in polar protic solvents? a. H2O b. NH3 c. H2S d. PH3 ANSWER: d 40. Which of the following is the most nucleophilic? a. sodium methoxide b. acetic acid c. propanoic acid d. water ANSWER: a 41. Which of the following anions is the best leaving group in an SN1 reaction? a. F− b. HO− c. CH3O− d. I− ANSWER: d 42. Which of the following is the best leaving group in an SN2 reaction? a. F− b. H3C− c. CH3O2SO− d. HO− ANSWER: c Copyright Cengage Learning. Powered by Cognero.

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Chapter 09: Nucleophilic Substitution and b-Elimination 43. Which of the following statements is true regarding the reactivity of 1 and 2 with potassium tert-butoxide?

a. 1 reacts faster than 2 b. 1 and 2 give different dehydrochlorinated products c. 2 reacts by elimination whereas 1 reacts by substitution d. 1 reacts by elimination whereas 2 reacts by substitution ANSWER: a 44. What is the major elimination product obtained from the following reaction?

a. 1 b. 2 c. 3 d. 4 ANSWER: b 45. What is the major organic product obtained from the following reaction?

a. 1 b. 2 c. 3 d. 4 ANSWER: a 46. Which of the following alkyl bromides reacts the slowest with NaSCH3 in DMF?

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Chapter 09: Nucleophilic Substitution and b-Elimination a. 1 b. 2 c. 3 d. 4 ANSWER: a 47. Which of the following is most likely to undergo rearrangement during reaction with methanol?

a. 1 b. 2 c. 3 d. 4 ANSWER: b 48. Which of the following compounds undergoes the most rapid hydrolysis reaction?

a. 1 b. 2 c. 3 d. 4 ANSWER: b 49. Which of the following statements is not true regarding the SN2 reaction of (R)-2-bromobutane with sodium cyanide? a. the reaction proceeds with inversion of configuration b. the rate is proportional to the concentration of sodium cyanide c. the rate is proportional to the concentration of (R)-2-bromobutane d. the rate of the reaction is independent of the identity of the solvent ANSWER: d 50. Which of the following statements is true regarding the reaction of tert-butyl bromide with water? a. the rate is proportional to the concentration of tert-butyl bromide b. the rate is proportional to the concentration of water c. the rate is independent of the identity of the solvent d. the rate of the reaction is independent of the temperature ANSWER: a 51. Which of the following is not a characteristic of SN2 reactions? Copyright Cengage Learning. Powered by Cognero.

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Chapter 09: Nucleophilic Substitution and b-Elimination a. the electrophilic carbon undergoes inversion of stereochemistry b. the rate is proportional to the concentration of substrate c. the rate is proportional to the concentration of nucleophile d. the rate is independent of the solvent ANSWER: d 52. Which of the following is not a characteristic of SN1 reactions? a. the electrophilic carbon undergoes inversion of stereochemistry b. the rate is proportional to the concentration of substrate c. the reaction proceeds faster in a more polar solvent d. the rate is independent of the concentration of nucleophile ANSWER: a 53. What is the role of tetrabutylammonium chloride as a phase transfer catalyst in the reaction of 1-bromopentane and potassium azide in a mixture of water and CH2Cl2? a. it transfers 1-bromopentane into the aqueous phase b. it transfers azide anion into the organic phase c. it makes water and dichloromethane miscible d. it transfers the potassium cation into the organic phase ANSWER: b 54. Which of the following statements is not true regarding SN2 reactions? a. At the transition state, the intermediate has a trigonal planar geometry. b. Such reactions are accelarated by small nucleophiles. c. The rate of these reactions depends on the concentration of both the substrate and the attacking nucleophile. d. The stereochemical outcome is inversion at the carbon bearing the leaving group. ANSWER: a 55. Which of the following statements is not true regarding SN1 reactions? a. The rate-determining step is the carbocation formation. b. The mechanism has only one step. c. Polar protic solvents are good choices for SN1 reactions. d. The stereochemical outcome is racemization at the carbon bearing the leaving group. ANSWER: b 56. Which of the following energy diagrams represents the course of an exothermic SN1 reaction?

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Chapter 09: Nucleophilic Substitution and b-Elimination

a. 1 b. 2 c. 3 d. 4 ANSWER: a 57. Which of the following energy diagrams represents the course of an exothermic SN2 reaction?

a. 1 b. 2 c. 3 d. 4 ANSWER: c 58. Which of the following energy diagrams represents the course of an exothermic E2 reaction?

a. 1 b. 2 c. 3 d. 4 ANSWER: c Copyright Cengage Learning. Powered by Cognero.

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Chapter 09: Nucleophilic Substitution and b-Elimination 59. Which of the following energy diagrams represents the course of an exothermic E1 reaction?

a. 1 b. 2 c. 3 d. 4 ANSWER: a 60. Which of the following represents the transition state of the rate-determining step in the SN1 reaction between tertbutyl chloride and water?

a. 1 b. 2 c. 3 d. 4 ANSWER: b 61. Which of the following represents the transition state of the rate-determining step in the reaction between tert-butyl bromide and methanol?

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Chapter 09: Nucleophilic Substitution and b-Elimination

a. 1 b. 2 c. 3 d. 4 ANSWER: a 62. Which of the following represents the transition state of the reaction between methyl iodide and ammonia?

a. 1 b. 2 c. 3 d. 4 ANSWER: c 63. Which of the following represents the transition state of the reaction between methyl bromide and sodium methylthiolate, NaSCH3?

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Chapter 09: Nucleophilic Substitution and b-Elimination

a. 1 b. 2 c. 3 d. 4 ANSWER: d 64. Which of the following represents the transition state of the rate-determining step in the reaction between 2bromopropane and sodium methoxide leading to elimination?

a. 1 b. 2 c. 3 d. 4 ANSWER: a 65. Which of the following represents the transition state of the rate-determining step in the reaction between 2chloropropane and sodium amide leading to elimination?

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Chapter 09: Nucleophilic Substitution and b-Elimination

a. 1 b. 2 c. 3 d. 4 ANSWER: c 66. Which of the following represents the transition state of the rate-determining step in the reaction between tert-butyl bromide and methanol leading to elimination?

a. 1 b. 2 c. 3 d. 4 ANSWER: b 67. Which of the following represents the transition state of the rate-determining step in the reaction between tert-butyl iodide and water leading to elimination?

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Chapter 09: Nucleophilic Substitution and b-Elimination

a. 1 b. 2 c. 3 d. 4 ANSWER: a 68. Which of the following sets consists of only polar aprotic solvents? a. water, hexane, methanol b. acetic acid, DMF, toluene c. DMSO, ethanol, acetonitrile d. DMF, acetonitrile, DMSO ANSWER: d 69. Which of the following sets consists of only polar protic solvents? a. water, DMF, DMSO b. acetic acid, isopropanol, water c. DMSO, ethanol, acetonitrile d. DMF, diethyl ether, DMSO ANSWER: b 70. Which of the following most favors elimination rather substitution in a reaction with 2-chloropentane? a. potassium ethoxide b. sodium methoxide c. potassium methoxide d. sodium acetylide ANSWER: d 71. Which of the following most favors elimination rather substitution in a reaction with sodium methoxide? a. bromomethane b. bromoethane c. 1-bromopropane d. 2-bromopropane Copyright Cengage Learning. Powered by Cognero.

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Chapter 09: Nucleophilic Substitution and b-Elimination ANSWER: d 72. What is the best choice of reagent to perform the following transformation?

a. H2SO4 b. H2O c. NaOCH3 d. KOtBu ANSWER: d 73. What is the best choice of reagent to perform the following transformation?

a. H2SO4 b. H2O c. NaOCH3 d. KOtBu ANSWER: a 74. The following reaction would be classified as an elimination.

a. True b. False ANSWER: False 75. HCl is the electrophile in the following reaction.

a. True b. False ANSWER: True Copyright Cengage Learning. Powered by Cognero.

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Chapter 09: Nucleophilic Substitution and b-Elimination 76. In the following reaction the cyanide ion is both a nucleophile and a Lewis acid.

a. True b. False ANSWER: False 77. The following energy diagram could represent an SN2 reaction.

a. True b. False ANSWER: True 78. The rate law for the following reaction would be of the form Rate = k[A][B].

a. True b. False ANSWER: False 79. The first step in the mechanism for the following reaction would be the formation of a secondary carbocation.

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Chapter 09: Nucleophilic Substitution and b-Elimination a. True b. False ANSWER: False 80. The following reaction would have a faster rate in a higher polarity solvent than one of low polarity.

a. True b. False ANSWER: True 81. Consider the reaction below to answer the following question:

The product of this reaction is

a. True b. False ANSWER: True 82. Consider the reaction below to answer the following question:

This reaction proceeds by an E1 mechanism. a. True b. False ANSWER: False Consider the pair of reactions below to answer the following question(s).

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Chapter 09: Nucleophilic Substitution and b-Elimination a. or b. 83. Reaction ____ will be faster. ANSWER: b b. 84. These reactions are classified as ________________reactions. ANSWER: substitution 85. The mechanism for these reactions is _______. ANSWER: SN2 Sn2 SN2 Sn2 86. In the reactions a and b if concentration of OH– and SH–, respectively, were doubled, the rate of the reactions would ___________. ANSWER: double increase by a factor of two Consider the pair of reactions below to answer the following question(s). a. or b. 87. The solvent in these reactions would be classified as ______ ________. ANSWER: polar aprotic aprotic polar 88. The nucleophile is these reactions is________. ANSWER: iodide iodide ion I– 89. Reaction ____ is faster. ANSWER: b Copyright Cengage Learning. Powered by Cognero.

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Chapter 09: Nucleophilic Substitution and b-Elimination b. Consider the reaction below to answer the following question(s).

90. Compound B by is formed by an _____ mechanism. ANSWER: SN1 Sn1 SN1 Sn1 91. Compound C is formed by an _____ mechanism. ANSWER: E1 For each substrate below, choose which reaction type is favored. Place the letter of the reaction type in the blank to the left of the substrate. a. SN1 b. SN2 c. E1 d. E2 92. ______ ANSWER: b

93. _____ ANSWER: d Classify each of the following species as a. an electrophile. b. a nucleophile. c. either an electrophile or a nucleophile. Place the letter of the choice in the blank to the left of the formula. 94. ________

ANSWER: c 95. ________ Copyright Cengage Learning. Powered by Cognero.

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Chapter 09: Nucleophilic Substitution and b-Elimination

ANSWER: a 96. ________

ANSWER: b 97. Draw all of the chloroalkanes that undergo base-promoted dehydrochlorination to form the following alkene?

ANSWER:

98. Draw all of the chloroalkanes that undergo base-promoted dehydrochlorination to form the following alkene?

ANSWER:

99. Draw all of the chloroalkanes that undergo base-promoted dehydrochlorination to form the following alkene?

ANSWER:

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Chapter 09: Nucleophilic Substitution and b-Elimination 100. Draw all of the chloroalkanes that undergo base-promoted dehydrochlorination to form the following alkene?

ANSWER:

101. What is the major organic product obtained from the following reaction?

ANSWER:

102. What is the major organic product obtained from the following reaction?

ANSWER:

103. What is the major organic product obtained from the following reaction?

ANSWER:

104. What is the major organic product obtained from the following reaction?

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Chapter 09: Nucleophilic Substitution and b-Elimination

ANSWER:

105. What is the major organic product obtained from the following reaction?

ANSWER:

106. What is the major organic product obtained from the following reaction?

ANSWER: ANS 107. What is the major organic product obtained from the following reaction?

ANSWER:

108. What is the major organic product obtained from the following reaction?

ANSWER:

109. What is the major organic product obtained from the following reaction?

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Chapter 09: Nucleophilic Substitution and b-Elimination ANSWER:

110. What is the major organic product obtained from the following reaction?

ANSWER:

111. Provide a neatly drawn mechanism for the following reaction, including curved arrows to show the movement of pairs of electrons and the structure of reactive intermediates.

ANSWER: The reaction proceeds in three steps: 1. Dissociation by cleavage of the carbon-chlorine bond to afford a tertiary carbocation 2. Nucleophilic addition of water to the carbocation 3. Deprotonation of oxygen

112. Provide a neatly drawn mechanism for the following reaction, including curved arrows to show the movement of pairs of electrons and the structure of reactive intermediates.

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Chapter 09: Nucleophilic Substitution and b-Elimination ANSWER: The reaction proceeds in a single step: Concerted nucleophilic attack on the electrophilic carbon atom with departure of bromide anion as the leaving group.

113. Arrange the following in decreasing order of their nucleophilicity. CH3CH2SH, CH3CH2NH2, CH3CH2COO-, CH3CH2OH a. CH3CH2COO- > CH3CH2SH > CH3CH2NH2 > CH3CH2OH b. CH3CH2SH > CH3CH2NH2 > CH3CH2OH > CH3CH2COOc. CH3CH2COO- > CH3CH2OH > CH3CH2NH2 > CH3CH2SH d. CH3CH2OH > CH3CH2NH2 > CH3CH2SH > CH3CH2COOANSWER: a 114. Why is cyclohexylamine more reactive than aniline when the former reacts with methyl bromide? ANSWER: -NH2 is a poor leaving group, but it is a good nucleophile because of the presence of lone pairs. The reaction between cyclohexylamine or aniline and methyl bromide helps in the formation of N-methylamines via an SN2 mechanism. However, in the case of anilines, the resonance of N lone pairs with its adjacent π system decreases the availability of the lone pair. This makes aniline a poorer nucleophile and therefore, less reactive. 115. Identify the major product of the following reaction.

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Chapter 09: Nucleophilic Substitution and b-Elimination c.

ANSWER: a 116. Explain Walden inversion. ANSWER: During an aliphatic nucleophilic substitution by SN2 mechanism, a complete inversion in stereochemistry of a particular structure takes place. This stereochemical outcome is called Walden inversion. One such example is the conversion of L-malic acid into D-chlorosuccinic acid. 117. Identify the major product of the following reaction.

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Chapter 09: Nucleophilic Substitution and b-Elimination a.

ANSWER: a 118. In the case of a unimolecular nucleophilic substitution reaction, the reaction rate completely depends on the concentration of the _____. ANSWER: substrate Match the organic structures with the appropriate dielectric constants. a. b.

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Chapter 09: Nucleophilic Substitution and b-Elimination c.

119. 4.30 ANSWER: b 120. 37.5 ANSWER: a 121. 6.15 ANSWER: d 122. 48.9 ANSWER: c

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Chapter 10: Alcohols 1. What is the approximate C−O−H bond angle of an alcohol? a. 90° b. 109.5° c. 120° d. 180° ANSWER: b 2. What is the approximate C−C−O bond angle of ethanol? a. 90° b. 109.5° c. 120° d. 180° ANSWER: b 3. Which of the following is/are tertiary (3°) alcohols?

a. only 4 b. only 2 c. only 1 d. 1, 2, 3 and 4 ANSWER: c 4. Which of the following is/are secondary (2°) alcohols?

a. only 1 b. only 1 and 2 c. only 1 and 3 d. only 2, 3, and 4 ANSWER: b 5. What is the IUPAC name of the following compound?

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Chapter 10: Alcohols a. 4−methyl-4-penten-1-ol b. 2-methyl-1-penten-5-ol c. 5-hydroxy-2-methyl-1-pentene d. 4-methyl-5-penten-1-ol ANSWER: a 6. What is the IUPAC name of the following compound?

a. 3-methyl-1-penten-4-ol b. 3-methyl-4-penten-2-ol c. 1,2-dimethyl-2-propan-1-ol d. 2,3-dimethyl-1-propan-3-ol ANSWER: b 7. What is the IUPAC name of the following compound?

a. cyclohexen-3-ol b. cyclohexen-2-ol c. 2-cyclohexenol d. 3-cyclohexenol ANSWER: c 8. What is the IUPAC name of the following compound?

a. 2-cyclopentenol b. 3-cyclopentenol c. cyclopenten-3-ol d. cyclopenten-2-ol ANSWER: a 9. What is the IUPAC name of the following compound?

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Chapter 10: Alcohols

a. cis-4-ethylcyclohexanol b. trans-4-ethylcyclohexanol c. cis-4-hydroxy-1-ethylcyclohexane d. trans-4-hydroxy-1-ethylcyclohexane ANSWER: a 10. What is the IUPAC name of the following compound?

a. cis-4-isopropylcyclohexanol b. trans-4-isopropylcyclohexanol c. cis-4-hydroxy-1-isopropylcyclohexane d. trans-4-hydroxy-1-isopropylcyclohexane ANSWER: b 11. What is the IUPAC name of the following compound?

a. (R)-2-methyl-4-pentanol b. (S)-2-methyl-4-pentanol c. (R)-4-methyl-2-pentanol d. (S)-4-methyl-2-pentanol ANSWER: c 12. What is the IUPAC name of the following compound?

a. (R)-2,2-dimethyl-3-pentanol b. (S)-2,2-dimethyl-3-pentanol c. 1-tert-butyl-1-propanol d. (S)-4,4-dimethyl-3-pentanol ANSWER: b 13. What is the IUPAC name of the following compound?

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Chapter 10: Alcohols

a. (E)-2-methyl-3-penten-2-ol b. (Z)-2-methyl-3-penten-2-ol c. (E)-4-methyl-2-penten-4-ol d. (Z)-2-methyl-4-penten-2-ol ANSWER: a 14. What is the IUPAC name of the following compound?

a. (E)-5-methyl-2-hexen-5-ol b. (Z)-5-methyl-2-hexen-5-ol c. (E)-2-methyl-4-hexen-2-ol d. (Z)-2-methyl-4-hexen-2-ol ANSWER: d 15. Which of the following has the highest boiling point? a. 1-ethanol b. 1-propanol c. 1-butanol d. 1-pentanol ANSWER: d 16. Which of the following has the highest boiling point? a. pentane-2,3-diol b. 2-hexanol c. 2-methylpentane-2,3,4-triol d. hexane-2,3,4-triol ANSWER: d 17. What is the approximate pKa value of ethanol? a. −5 b. 5 c. 16 d. 25 ANSWER: c 18. Which of the following best describes the reaction of hydrogen bromide with 1-butanol to give 1-bromobutane? Copyright Cengage Learning. Powered by Cognero.

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Chapter 10: Alcohols a. Lewis acid-base b. Brønsted-Lowry acid-base c. oxidation-reduction d. nucleophilic substitution ANSWER: d 19. What is the major organic product obtained from the reaction of 1-hexanol with aqueous HBr at reflux?? a. 1-bromohexane b. 2-bromohexane c. 2-bromo-1-hexanol d. 1-hexene ANSWER: a 20. What is the major organic product obtained from the reaction of 2,2-dimethyl-1-pentanol with aqueous HBr at reflux? a. 2-bromo-2,2-dimethylpentane b. 1-bromo-2-methylhexane c. 2-bromo-2-methylhexane d. 3-bromo-2-methylhexane ANSWER: c 21. What is the major organic product obtained from the following reaction?

a. 1 b. 2 c. 3 d. 4 ANSWER: d 22. What is the major organic product obtained from the following reaction?

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Chapter 10: Alcohols

a. 1 b. 2 c. 3 d. 4 ANSWER: b 23. Which of the following alcohols reacts fastest with HBr to give the corresponding alkyl bromide? a. cyclohexylmethanol b. 1-cyclohexanol c. cyclopentylmethanol d. 1-methylcyclohexanol ANSWER: d 24. Which of the following alcohols reacts fastest with HBr to give the corresponding alkyl bromide?

a. 1 b. 2 c. 3 d. 4 ANSWER: c 25. What type of reactive intermediate is formed in the reaction of 2-methyl-2-hexanol with HBr to give 2-bromo-2methylhexane? a. an alkoxide b. a tertiary cation c. a tertiary radical d. a tertiary anion ANSWER: b Copyright Cengage Learning. Powered by Cognero.

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Chapter 10: Alcohols 26. What is the major organic product obtained from the following reaction?

a. 1 b. 2 c. 3 d. 4 ANSWER: b 27. What is the major organic product obtained from the following reaction?

a. 1 b. 2 c. 3 d. 4 ANSWER: c 28. What is the major organic product obtained from the following reaction?

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Chapter 10: Alcohols

a. 1 b. 2 c. 3 d. 4 ANSWER: d 29. What is the major organic product obtained from the following reaction?

a. 1 b. 2 c. 3 d. 4 ANSWER: d 30. What is the major organic product obtained from the following reaction?

a. 1 b. 2 Copyright Cengage Learning. Powered by Cognero.

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Chapter 10: Alcohols c. 3 d. 4 ANSWER: d 31. What is the major organic product obtained from the following reaction?

a. 1 b. 2 c. 3 d. 4 ANSWER: a 32. What is the major organic product obtained upon heating a mixture of cyclopentylmethanol and 85% H3PO4? a. 1-methylcyclopentene b. methylenecyclopentane c. 1-methyl-2-cyclopentene d. 1-methyl-3-cyclopentene ANSWER: a 33. What is the major organic product obtained upon heating a mixture of 2,2-dimethylcyclohexanol, (CH3)2C6H9(OH), with sulfuric acid? a. 3,3-dimethylcyclohexene b. 2,3-dimethylcyclohexene c. 1,2-dimethylcyclohexene d. 1,3-dimethylcyclohexene ANSWER: c 34. What is the major organic product obtained upon heating a mixture of 4-heptanol and 85% H3PO4? a. 1-heptene b. cis-4-heptene c. trans-4-heptene d. 2-methyl-2-hexene ANSWER: c Copyright Cengage Learning. Powered by Cognero.

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Chapter 10: Alcohols 35. Which of the following alcohols undergoes the least rapid dehydration upon treatment with H2SO4 to give an alkene? a. cyclopentanol b. 3-methylcyclopentanol c. 1-methylcyclopentanol d. cyclopentylmethanol ANSWER: d 36. Which of the following alcohols undergoes the least rapid dehydration upon treatment with H2SO4 to give an alkene?

a. 3 b. 2 c. 1 d. 4 ANSWER: c 37. What is the major organic product obtained from the following reaction?

a. 1 b. 2 c. 3 d. 4 ANSWER: b 38. What is the major organic product obtained from the following reaction?

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Chapter 10: Alcohols

a. 1 b. 2 c. 3 d. 4 ANSWER: b 39. What is the major organic product obtained from the following reaction?

a. 1 b. 2 c. 3 d. 4 ANSWER: b 40. What is the major organic product obtained from the following reaction?

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Chapter 10: Alcohols

a. 1 b. 2 c. 3 d. 4 ANSWER: c 41. What is the major organic product obtained from the following reaction?

a. 1-butene, CH3CH2CH=CH2 b. butanal, CH3CH2CH2CHO c. butanone, CH3CH2COCH3 d. butanoic acid, CH3CH2CH2COOH ANSWER: c 42. What is the major organic product obtained from the following reaction?

a. 1-butene, CH3CH2CH=CH2 b. butanal, CH3CH2CH2CHO c. butanone, CH3CH2COCH3 d. butanoic acid, CH3CH2CH2COOH ANSWER: d 43. What is the major organic product obtained from the following reaction?

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Chapter 10: Alcohols

a. 1 b. 2 c. 3 d. 4 ANSWER: c 44. What is the major organic product obtained from the following reaction?

a. 1 b. 2 c. 3 d. 4 ANSWER: b 45. What is the major organic product obtained from the following reaction?

a. 1,6-hexanediol, HO(CH2)6OH b. hexanedial, OHC(CH2)4CHO c. hexanedioic acid, HO2C(CH2)4COOH d. cyclohexene Copyright Cengage Learning. Powered by Cognero.

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Chapter 10: Alcohols ANSWER: b 46. What is the major organic product obtained from the following reaction?

a. trans-2-butene, (E) CH3CH=CHCH3 b. butanedione, CH3COCOCH3 c. acetaldehyde, CH3CHO d. acetic acid, CH3COOH ANSWER: c 47. What type of reactive intermediate is formed in the reaction of tert-butyl alcohol with HCl to give tert-butyl chloride? a. tert-butyl radical b. tert-butyl anion c. tert-butyl cation d. tert-butoxide ANSWER: c 48. What type of reactive intermediate is formed in the reaction of 2-methyl-2-butanol with H2SO4 to give 2-methyl-2butene? a. a tertiary cation b. a tertiary anion c. a tertiary radical d. butoxide ANSWER: a 49. What is the best choice of reagent to achieve the following transformation?

a. HCl b. Cl2, light c. SOCl2, pyridine d. HOCl, H2O ANSWER: c 50. What is the best choice of reagent to perform the following transformation? Copyright Cengage Learning. Powered by Cognero.

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Chapter 10: Alcohols

a. HCl b. NaOH c. H2SO4 d. KMnO4 ANSWER: c 51. What is the best choice of reagent to perform the following transformation?

a. PCC b. HIO4 c. CrO3 d. NaOH ANSWER: b 52. What is the best choice of reagent to achieve the following transformation?

a. CrO3 b. NaOH c. PCC d. HIO4 ANSWER: a 53. What is the best choice of reagent to perform the following transformation?

a. HCl b. NaOH c. HIO4 Copyright Cengage Learning. Powered by Cognero.

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Chapter 10: Alcohols d. PCC ANSWER: d 54. What is the major organic product obtained from the following sequence of reactions?

a. 3-methyl-1-butene b. 2-iodo-2-methylbutane c. 1-iodo-3-methylbutane d. 1-chloro-3-methylbutane ANSWER: c 55. What is the major organic product obtained from the following sequence of reactions?

a. (±)-2-azidopentane b. (R)-2-azidopentane c. (S)-2-azidopentane d. (S)-2-pentyl tosylate ANSWER: b 56. What is the correct assignment of the names of the following functional groups?

a. 1 = thiol; 2 = sulfone; 3 = sulfoxide b. 1 = thiol; 2 = sulfoxide; 3 = sulfone c. 1 = thiol; 2 = sulfinic acid; 3 = sulfonic acid d. 1 = sulfonic acid; 2 = sulfone; 3 = sulfinic acid ANSWER: c 57. The following substance would be named as 3-pentyn-1-ol.

a. True b. False ANSWER: True Copyright Cengage Learning. Powered by Cognero.

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Chapter 10: Alcohols 58. Consider following structures.

Only structure III represents a secondary alcohol. a. True b. False ANSWER: True 59. The following substance would be correctly name as 2-pentanthiol.

a. True b. False ANSWER: True 60. (CH3)3CO– Na+ would be formed by the reaction of sodium metal and 1-butanol. a. True b. False ANSWER: False 61. Of the following compounds, 3 would have the highest boiling point.

a. True b. False ANSWER: False 62. (CH3)3COH would react faster than (CH3)2CHCH2OH under SN1 conditions. a. True b. False ANSWER: True 63. The rate-determining step in the following reaction is protonation of the alcohol.

a. True b. False Copyright Cengage Learning. Powered by Cognero.

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Chapter 10: Alcohols ANSWER: False 64. The rate-determining step in the following reaction is displacement of water from the protonated alcohol by

the bromide ion.

a. True b. False ANSWER: True 65. When a secondary (2°) alcohol is treated with Jones reagent the product of the reaction is a ketone. a. True b. False ANSWER: True 66. Reaction with Na, NaH, or NaOH can be used to irreversibly accomplish the following reaction.

a. True b. False ANSWER: False –17

67. If the Ka of isopropyl alcohol is 1.0 × 10 ANSWER: 17

, the pKa of isopropyl alcohol______.

68. Including stereoisomers, the number alkene isomers produced by the acid-catalyzed dehydration of 3-

methyl-3-hexanol is _____. ANSWER: 5 five

Consider the following reagents. 1. H2CrO4 2. PCC 3. PCl3 4. SOCl2 Choose the correct reagent to carry out the following conversions by placing the appropriate number in the blank provided to the left of the statement. If more than one number applies, enter the numbers separated by commas. 69. _______Oxidation of a secondary alcohol to a ketone. ANSWER: 1,2 2,1 70. _______Oxidation of a primary alcohol to a carboxylic acid. ANSWER: 1 Copyright Cengage Learning. Powered by Cognero.

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Chapter 10: Alcohols To answer the following question, consider the reaction below:

71. Provide the complete IUPAC name for the starting material in this reaction. ANSWER: (R)-2-heptanol (R)-heptan-2-ol 72. The starting material would be classified as a __________ alcohol. ANSWER: secondary 2° 73. The mechanism of this reaction would be classified as ______. ANSWER: SN2 SN2 Sn 2 74. Consider the following species. This substance is a _______conjugate base than the substance shown below.

ANSWER: weaker 75. The pKa of CH3CH2CH2OH is _______than that of CH3CH2CH2SH. ANSWER: less smaller 76. Consider the following structures.

Structure(s)____could be used to produce an aldehyde by reaction with PCC. Enter the number of the appropriate structure. If more than one structure is correct, enter the appropriate numbers separated by commas. ANSWER: I,II II,I 77. What is the IUPAC name of the following compound? Copyright Cengage Learning. Powered by Cognero.

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Chapter 10: Alcohols

ANSWER: (R)-4-methylpent-4-en-2-ol 78. What is the IUPAC name of the following compound?

ANSWER: (R)-2-methylhex-5-en-3-ol 79. What is the IUPAC name of the following compound (shown as a Fischer projection)?

ANSWER: (S)-butan-2-ol 80. What is the IUPAC name of the following compound (shown as a Fischer projection)?

ANSWER: (R)-pentan-2-ol 81. What is the major organic product obtained from the following reaction?

ANSWER:

82. What is the major organic product obtained from the following reaction?

ANSWER:

83. What is the major organic product obtained from the following reaction? Copyright Cengage Learning. Powered by Cognero.

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Chapter 10: Alcohols

ANSWER: 84. What is the major organic product obtained from the following reaction?

ANSWER:

85. What is the major organic product obtained from the following reaction?

ANSWER:

86. What is the major organic product obtained from the following reaction?

ANSWER:

87. What is the major organic product obtained from the following reaction?

ANSWER:

88. What is the major organic product obtained from the following reaction?

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Chapter 10: Alcohols

ANSWER:

89. What is the major organic product obtained from the following reaction?

ANSWER: 90. What is the major organic product obtained from the following reaction?

ANSWER: 91. What is the major organic product obtained from the following reaction?

ANSWER:

92. What is the major organic product obtained from the following reaction?

ANSWER:

93. What is the major organic product obtained from the following reaction?

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Chapter 10: Alcohols

ANSWER:

94. What is the major organic product obtained from the following reaction?

ANSWER:

95. What is the major organic product obtained from the following reaction?

ANSWER:

96. What is the major organic product obtained from the following reaction?

ANSWER:

97. What is the IUPAC name of the following compound (shown as a Fischer projection)? Copyright Cengage Learning. Powered by Cognero.

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Chapter 10: Alcohols

ANSWER: (1S,3S)-3-methylcyclohexanol 98. What is the IUPAC name of the following compound (shown as a Fischer projection)?

ANSWER: (1R,2R)-2-methylcyclohexanol 99. A solution of chromic acid in aqueous sulfuric acid is known as the _____ reagent. ANSWER: Jones 100. Why can’t tertiary alcohols be oxidized to ketones or aldehydes? ANSWER: The prerequisite for the oxidation of alcohol to a ketone or an aldehyde is the presence of a free hydrogen atom on the carbon-bearing hydroxyl group. In tertiary alcohols, the carbon bearing the hydroxyl group is bonded with three more carbon atoms but not to the hydrogen atoms. Hence, tertiary alcohols are resistant to oxidation as they cannot form any additional carbon–oxygen bond. 101. The oxidation states of iodine in periodic acid and iodic acid are _____ and _____, respectively.

a. 7; 5 b. 5; 7 c. 7; 7 d. 6; 5 ANSWER: a 102. Identify “X” and “Y” in the following reaction.

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Chapter 10: Alcohols a. X is 3-methylbutan-1-al, and Y is H2CrO4/H2O/acetone. b. X is 2-methylbutan-1-ol, and Y is H2CrO4/H2O/acetone. c. X is 3-methylbutan-1-ol, and Y is H2CrO4/H2O/acetone. d. X is 2-methylbutan-1-al, and Y is H2CrO4/H2O/acetone. ANSWER: b 103. Identify “X” and “Y” in the following reaction.

a. X is 4-methylpentane-3,4-diol, and Y is HIO4. b. X is 3-methylpentane-2,3-diol, and Y is HIO3. c. X is 2-methylpentane-2,3-diol, and Y is HIO4. d. X is 2-methylpentane-2,3-diol, and Y is HIO3. ANSWER: c Match the structures with their IUPAC names. a. b.

104. 3-methyl-2-butanethiol ANSWER: a 105. 2-methylcyclohexanol ANSWER: b 106. 3-sulfanylpropan-1-ol ANSWER: c 107. 2-pentene-1-thiol ANSWER: d Copyright Cengage Learning. Powered by Cognero.

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Chapter 10: Alcohols 108. Oxidation of methanol by chromic acid produces methanoic acid, which is commonly known as formic acid. In the c ourse of the reaction, methanol is first converted to formaldehyde. Then, hydration of formaldehyde produces “X”, which bears two hydroxyl groups. “X” reacts with the chromic acid in the presence of an acid catalyst to form “Y”. A base reacts with “Y” to produce formic acid. Identify “X” and “Y”. a. X is ethanal hydrate, and Y is methyl chromate ester. b. X is propionaldehyde hydrate, and Y is methyl chromate ester. c. X is formaldehyde hydrate, and Y is ethyl chromate ester. d. X is formaldehyde hydrate, and Y is methyl chromate ester. ANSWER: d

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Chapter 11: Ethers, Epoxides, and Sulﬁdes 1. Which of the following are ethers?

a. only 1 and 2 b. only 1 and 4 c. only 1, 2 and 3 d. 1, 2, 3 and 4 ANSWER: d 2. Which of the following are epoxides?

a. only 2 and 3 b. only 3 and 4 c. only 2, 3 and 4 d. 1, 2, 3 and 4 ANSWER: b 3. What is the correct assignment of the names of the following ethers?

a. 1 = oxirane; 2 = oxetane; 3= oxolane b. 1 = oxetane; 2 = oxirane; 3= oxane c. 1 = oxane; 2 = oxetane; 3= dioxane d. 1 = oxirane; 2 = oxolane; 3= oxetane ANSWER: a 4. What is the correct assignment of the names of the following ethers?

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Chapter 11: Ethers, Epoxides, and Sulﬁdes a. 1 = oxirane; 2 = oxetane; 3 = oxane b. 1 = oxirane; 2 = oxitane; 3 = oxane c. 1 = oxane; 2 = dioxane; 3 = oxetane d. 1 = oxirane; 2 = oxolane; 3 = oxane ANSWER: d 5. Which of the following are thiols?

a. only 1 b. only 1 and 4 c. only 2 and 3 d. 1, 2, 3 and 4 ANSWER: a 6. Which of the following statements are true? 1. 2. 3.

Ethers associate by weak dipole-dipole interactions and dispersion forces. Alcohols have lower boiling points that ethers. Common ethers are highly volatile and flammable.

a. only 1 b. only 1 and 2 c. 1, 2 and 3 d. only 1 and 3 ANSWER: d 7. What is the IUPAC name of the following compound?

a. cis-1,4-anisole b. cis-4-methoxyanisole c. cis-1,4-dimethoxycyclohexane d. para-dianisole Copyright Cengage Learning. Powered by Cognero.

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Chapter 11: Ethers, Epoxides, and Sulﬁdes ANSWER: c 8. What is the IUPAC name of the following compound?

a. ethyl isopropyl thiol b. 2-ethylsulfanylpropane c. ethyl isopropyl disulfide d. isopropylsufanylethane ANSWER: b 9. What is the major organic product obtained from the following reaction?

a. 1 b. 2 c. 3 d. 4 ANSWER: b 10. What is the major organic product obtained from the following reaction?

a. 1 b. 2 c. 3 Copyright Cengage Learning. Powered by Cognero.

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Chapter 11: Ethers, Epoxides, and Sulﬁdes d. 4 ANSWER: c 11. What is the major organic product obtained from the following reaction?

a. 1 b. 2 c. 3 d. 4 ANSWER: a 12. Which of the following reactions provides diethylether in a high yield? a. ethyl bromide + ethyl bromide b. ethanol + sodium ethoxide c. acid catalysed dehydration of ethanol d. ethane + sodium ethoxide ANSWER: c 13. Which of the following reactions provides 2-methoxypropane in a high yield? a. methyl bromide + sodium isopropoxide b. propyl bromide + sodium methoxide c. methanol + propanol in the presence of KOH d. iodomethane + propyl bromide in the presence of KOH ANSWER: a 14. Which of the following ethers cannot be prepared by a Williamson ether synthesis? a. di-tert-butyl ether b. isopropyl methyl ether c. anisole d. tert-butyl methyl ether ANSWER: a 15. What is the major organic product obtained from the following reaction?

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Chapter 11: Ethers, Epoxides, and Sulﬁdes

a. 1 b. 2 c. 3 d. 4 ANSWER: b 16. What is the major organic product obtained from the following reaction?

a. 1 b. 2 c. 3 d. 4 ANSWER: d 17. What is the major organic product obtained from the following reaction?

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Chapter 11: Ethers, Epoxides, and Sulﬁdes

a. 1 b. 2 c. 3 d. 4 ANSWER: b 18. What type of reactive intermediate is formed in the reaction of 2-ethoxy-2-methylbutane with HBr to give 2-ethoxy-2methylbutyl bromide? a. 2-methylbutyl anion b. 2-methylbutoxide c. 2-methylbutyl radical d. 2-methylbutyl cation ANSWER: d 19. What type of mechanism accounts for the cleavage of di-tert-butyl ether upon treatment with HBr to give two moles of tert-butyl bromide? a. SN2 b. SN1 c. E1 d. E2 ANSWER: b 20. What type of mechanism accounts for the cleavage of tret-butyl methyl ether upon treatment with HBr? a. SN1 b. SN2 c. E1 d. E2 ANSWER: a 21. What are the major products obtained upon treatment of di-tert-butyl ether, (CH3)3COC(CH3)3, with excess HBr? a. 2 moles of butyl bromide b. tert-butyl bromide and tert-butyl alcohol Copyright Cengage Learning. Powered by Cognero.

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Chapter 11: Ethers, Epoxides, and Sulﬁdes c. 2 moles of tert-butyl bromide d. 2 moles of tert-butyl alcohol ANSWER: c 22. What are the major products obtained upon treatment of ethylpentyl ether with excess HBr? a. ethanol and pentanol b. bromoethane and pentanol c. ethanol and 1,1-dibromopentane d. bromoethane and bromopentane ANSWER: d 23. What type of reactive intermediate is formed in the reaction of 2-methyl-2-butene with methanol in the presence of an acid catalyst to give 2-methoxy-2-methylbutane? a. 2-methylbutyl carbocation b. 2-methylbutyl radical c. 2-methylbutyl anion d. 2-methylbutyl butoxide ANSWER: a 24. What is the major organic product obtained from the following reaction?

a. only 1 b. only 2 c. only 3 d. both 2 and 3 ANSWER: c 25. What is the major organic product obtained from the following reaction?

a. 1 b. 2 c. 3 d. 4 Copyright Cengage Learning. Powered by Cognero.

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Chapter 11: Ethers, Epoxides, and Sulﬁdes ANSWER: a 26. What is the major organic product obtained from the following reaction?

a. 1 b. 2 c. 3 d. 4 ANSWER: a 27. What is the major organic product obtained from the following reaction?

a. 1 b. 2 c. 3 d. 4 ANSWER: a 28. What is the best choice of reagent(s) to perform the following transformation?

a. H2O b. H2SO4, H2O c. LiAlH4 followed by H3O+ d. KMnO4 Copyright Cengage Learning. Powered by Cognero.

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Chapter 11: Ethers, Epoxides, and Sulﬁdes ANSWER: c 29. What is the best choice of reagent(s) to perform the following transformation?

a. meta-Chloroperoxybenzoic acid b. LiAlH4 followed by H3O+ c. OsO4; followed by NaHSO3 d. H2O, H2SO4 ANSWER: a 30. What is the major organic product obtained from the following sequence of reactions?

a. 1 b. 2 c. 3 d. 4 ANSWER: d 31. What is the major organic product obtained from the following sequence of reactions?

a. 1 Copyright Cengage Learning. Powered by Cognero.

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Chapter 11: Ethers, Epoxides, and Sulﬁdes b. 2 c. 3 d. 4 ANSWER: c 32. What is the major organic product obtained from the following sequence of reactions?

a. 1 b. 2 c. 3 d. 4 ANSWER: a 33. What is the major organic product obtained from the following sequence of reactions?

a. 1 b. 2 c. 3 d. 4 ANSWER: b 34. What is the major organic product obtained from the following reaction?

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Chapter 11: Ethers, Epoxides, and Sulﬁdes

a. only 1 b. only 2 c. only 3 d. both 2 and 3 ANSWER: b 35. What is the major organic product obtained from the following reaction?

a. 1 b. 2 c. 3 d. 4 ANSWER: b 36. What is the major organic product obtained from the following reaction?

a. 1 b. 2 c. 3 d. 4 ANSWER: c 37. What is the major organic product obtained from the following reaction? Copyright Cengage Learning. Powered by Cognero.

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Chapter 11: Ethers, Epoxides, and Sulﬁdes

a. 1 b. 2 c. 3 d. 4 ANSWER: d 38. What is the best choice of reagent(s) to perform the following transformation?

a. CH3MgBr; followed by H3O+ b. H2O, NaOH c. LiAlH4 followed by H3O+ d. KMnO4 ANSWER: c 39. What is the best choice of reagent(s) to perform the following transformation?

a. O3 b. Cl2 in water followed by NaOH and H2O c. OsO4; followed by NaHSO3 d. H2O, H2SO4 ANSWER: b 40. What is the major organic product obtained from the following sequence of reactions?

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Chapter 11: Ethers, Epoxides, and Sulﬁdes

a. 1 b. 2 c. 3 d. 4 ANSWER: a 41. What is the major organic product obtained from the following sequence of reactions?

a. 1 b. 2 c. 3 d. 4 ANSWER: c 42. What is the major organic product obtained from the following sequence of reactions?

a. 1 b. 2 c. 3 Copyright Cengage Learning. Powered by Cognero.

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Chapter 11: Ethers, Epoxides, and Sulﬁdes d. 4 ANSWER: c 43. What is the major organic product obtained from the following sequence of reactions?

a. 1 b. 2 c. 3 d. 4 ANSWER: a 44. Which of the following general structures can be made by sequential reaction of epichlorohydrin with appropriate nucleophiles?

a. 1 b. 2 c. 3 d. 4 ANSWER: c 45. What is the major organic product obtained from the following reaction?

a. 1 Copyright Cengage Learning. Powered by Cognero.

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Chapter 11: Ethers, Epoxides, and Sulﬁdes b. 2 c. 3 d. 4 ANSWER: c 46. What is the name of the following compound?

a. 6-crown-12 b. 12-crown-6 c. 18-crown-12 d. 18-crown-6 ANSWER: b 47. Which of the following ions forms the strongest complex with 18-Crown-6? a. Li+ b. Mg2+ c. Na+ d. Cs+ ANSWER: c 48. Which of the following statements is not true? a. Crown ethers form complexes with alkali metal ions by donation of lone pairs from the oxygen atoms to the metal cation. b. Metal ion complexes of crown ethers dissolve in nonpolar aprotic organic solvents. c. Addition of 18-crown-6 to a solution of benzyl bromide and potassium cyanide in a nonpolar solvent increases the rate of nucleophilic substitution. d. The cavity of a crown ether is hydrocarbon-like. ANSWER: d 49. Which of the following synthetic routes is used in industry to provide epichlorohydrin?

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Chapter 11: Ethers, Epoxides, and Sulﬁdes

a. 1 b. 2 c. 3 d. 4 ANSWER: d 50. What is the major organic product obtained from the following reaction?

a. 1 b. 2 c. 3 d. 4 ANSWER: c 51. What is the major organic product obtained from the following reaction?

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Chapter 11: Ethers, Epoxides, and Sulﬁdes a. 1 b. 2 c. 3 d. 4 ANSWER: b 52. What is the major organic product obtained from the following reaction?

a. 1 b. 2 c. 3 d. 4 ANSWER: b 53. What is the major organic product obtained from the following reaction?

a. 1 b. 2 c. 3 d. 4 ANSWER: a 54. What is the major organic product obtained from the following reaction?

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Chapter 11: Ethers, Epoxides, and Sulﬁdes

a. 1 b. 2 c. 3 d. 4 ANSWER: c 55. What would be the best choice of reagent(s) to perform the following transformation?

a. H3O+ b. H2O, NaOH c. LiAlH4 followed by H3O+ d. O2/NO2 ANSWER: d 56. What would be the best choice of reagent(s) to perform the following transformation?

a. H2O b. NaIO4 c. H2O, NaOH d. H2SO4 ANSWER: b 57. What would be the best choice of reagent(s) to perform the following transformation?

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Chapter 11: Ethers, Epoxides, and Sulﬁdes a. CH3OH, H2SO4 b. H2SO4, followed by CH3OH c. NaOH with CH3I d. CH3OCH3 ANSWER: c 58. What would be the best choice of reagent(s) to perform the following transformation?

a. CH3S-Na+ b. CH3SH, H2SO4 c. CH3OH, Na2S d. CH3I, H2SO4 ANSWER: a 59. The correct structure for dibenzyl ether is shown below.

a. True b. False ANSWER: False 60. The structure shown below can be named as either ethylene oxide or oxirane.

a. True b. False ANSWER: True 61. The correct name for the following substance is cis-1,2-dimethyloxirane.

a. True b. False ANSWER: False 62. The correct name for the following compound is 12-crown-4. Copyright Cengage Learning. Powered by Cognero.

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Chapter 11: Ethers, Epoxides, and Sulﬁdes

a. True b. False ANSWER: True 63. The synthesis of dipropyl ether can be accomplished by reacting 1-propanol with H2SO4 at 140°C. a. True b. False ANSWER: True 64. The first step in the mechanism of acid catalyzed ring opening of oxirane is protonation of the oxygen in the

oxirane. a. True b. False ANSWER: True 65. Adding Br2 in H2O will distinguish between ethyl phenyl ether and allyl phenyl ether. a. True b. False ANSWER: True 66. The correct name for the following compound is cyclopropyl ethyl thiol.

a. True b. False ANSWER: False 67. Consider the following reaction.

The major organic product obtained from the reaction is

a. True b. False ANSWER: False Copyright Cengage Learning. Powered by Cognero.

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Chapter 11: Ethers, Epoxides, and Sulﬁdes 68. The following reaction is a valid means of preparing the given product.

a. True b. False ANSWER: True 69. A protecting group changes the reactivity of a functional group to one that is inert to reaction conditions without becoming a permanent part of the molecule. a. True b. False ANSWER: True 70. The first step in the following conversion should be the addition of (CH3)3SiCl, (CH3CH2)3N.

a. True b. False ANSWER: True 71. Consider the cleavage of the following ether with H2O and H+.

Cleavage of the following ether will be a slower process.

a. True b. False ANSWER: False 72. A crown ether named 18-crown-6 has a total of ANSWER: 18, 6 Copyright Cengage Learning. Powered by Cognero.

carbons and

oxygens . Page 21

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Chapter 11: Ethers, Epoxides, and Sulﬁdes eighteen, six 73. The name of the alkene that reacts with methanol in an acid catalyzed reaction to produce t-butyl methyl ether is

________________. ANSWER: 2-methylpropene 74. The following reaction would be best accomplished by the addition of _______________. (Assume that CH3CO2H

is also produced.)

ANSWER: peroxyacetic acid

CH3CO3H peracetic acid Consider the reaction below to answer the following questions.

75. The reaction shown here is an example of a ______________ ________synthesis ANSWER: Williamson ether 76. The reaction shown here proceeds by a(n) _______ mechanism. ANSWER: SN2 SN2 Sn2 Sn2 77. The name of the product of the reaction is _______________________. ANSWER: cylcopentyl methyl ether 78. The following reaction would result in the formation of a ____________group.

ANSWER: protecting 79. Consider the following reaction.

The name of the aromatic product is __________________. ANSWER: phenol Copyright Cengage Learning. Powered by Cognero.

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Chapter 11: Ethers, Epoxides, and Sulﬁdes 80. When cyclopentene is treated with peroxyacetic acid, the product that forms is _________________. ANSWER: cyclopentene oxide 1,2-epoxycyclopentane 81. What is the IUPAC name of the following compound? ANSWER: 2-ethoxyethanol 82. What is the IUPAC name of the following compound? ANSWER: 1,2-diethoxyethane 83. What is the IUPAC name of the following compound?

ANSWER: 1-methoxycyclohex-1-ene 84. What is the IUPAC name of the following compound?

ANSWER: dicyclopentyl ether (oxadicyclopentane) 85. Provide the structures of the sodium alkoxide and the alkyl iodide that would be the best starting materials for the preparation of the following compound by a Williamson ether synthesis.

ANSWER:

86. Provide the structures of the sodium alkoxide and the alkyl iodide that would be the best starting materials for the preparation of the following compound by a Williamson ether synthesis.

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Chapter 11: Ethers, Epoxides, and Sulﬁdes

ANSWER:

87. What is the major organic product obtained from the following reaction?

ANSWER:

88. What is the major organic product obtained from the following reaction?

ANSWER: 89. What is the major organic product obtained from the following reaction?

ANSWER:

90. What is the major organic product obtained from the following reaction?

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Chapter 11: Ethers, Epoxides, and Sulﬁdes

ANSWER:

91. What is the major organic product obtained from the following reaction?

ANSWER:

92. What is the major organic product obtained from the following reaction?

ANSWER:

93. What is the major organic product obtained from the following reaction?

ANSWER:

Match the organic compounds in the with their boiling points. a. Dimethyl ether b. Diphenyl ether Copyright Cengage Learning. Powered by Cognero.

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Chapter 11: Ethers, Epoxides, and Sulﬁdes c. Butyl methyl ether

d. Diethyl ether

94. 259oC ANSWER: b 95. −24oC ANSWER: a 96. 35oC ANSWER: d 97. 71oC ANSWER: c 98. What is the IUPAC name of the following compound?

a. 1,2-Epoxycyclohexane b. 1,6-Epoxycyclohexane c. 1,2-Oxocyclohexane d. 1,6-Oxocyclohexane ANSWER: a 99. What is the IUPAC name of the following compound?

a. trans-2-butyl-3-phenyloxirane b. cis-2-butyl-3-phenyloxirane c. trans-3-butyl-2-phenyloxirane d. cis-3-butyl-2-phenyloxirane ANSWER: a 100. What is the major product obtained from the following organic reaction? Copyright Cengage Learning. Powered by Cognero.

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Chapter 11: Ethers, Epoxides, and Sulﬁdes

ANSWER: a 101. Identify the major product of the following reaction.

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Chapter 11: Ethers, Epoxides, and Sulﬁdes a.

ANSWER: a 102. Identify the major product of the following reaction.

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Chapter 11: Ethers, Epoxides, and Sulﬁdes d.

ANSWER: a 103. An oxirane reacts with methylamine to give a product “A”. Then, “A” reacts with an oxirane to give “B”, which further reacts with SOCl2 to give a product “C”. Identify product “C”. a.

ANSWER: a

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Chapter 12: Infrared Spectroscopy 1. Which of the following regions in the electromagnetic spectrum corresponds to the radiation with the lowest energy? a. ultraviolet b. radio waves c. infrared d. visible ANSWER: b 2. Which of the following regions in the electromagnetic spectrum corresponds to the radiation with the shortest wavelength? a. ultraviolet b. radio waves c. infrared d. visible ANSWER: a 3. What range of wavelengths corresponds to the ultraviolet region of the electromagnetic spectrum? a. 400-700 nm b. 0.01-10 cm c. 100-400 nm d. 0.01-1 nm ANSWER: c 4. Which of the following processes takes place upon absorption of infrared radiation? a. bond vibration b. electron excitation c. nuclear spin flip d. electron spin flip ANSWER: a 5. What are the units of wavenumber, , in infrared spectroscopy? a. cm b. cm−1 c. J⋅mol−1 d. none, wavenumber is a dimensionless quantity ANSWER: b 6. Which of the following relationships is not valid as applied to infrared spectroscopy? a. wavenumber = 1/λ (in cm) b. ΔE = h ν c. λ = 4.12 (K/µ) d. ν = c/λ ANSWER: c 7. Which of the following laws relates the frequency of a stretching vibration to the masses and spring constant of a Copyright Cengage Learning. Powered by Cognero.

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Chapter 12: Infrared Spectroscopy simple harmonic oscillator? a. Pan's law b. Hooke's law c. Peter's law d. Barrie's law ANSWER: b 8. What is required for a bond to give an infrared absorption? a. a change in bond length during vibration b. a change in bond angle during vibration c. a change in bond dipole during vibration d. a change in reduced mass during vibration ANSWER: c 9. Which of the following bonds (circled) gives a very weak or no stretching absorption in the infrared spectrum?

a. 1 b. 2 c. 3 d. 4 ANSWER: a 10. Which of the following bonds gives the weakest peak in the infrared spectrum for a stretching vibration?

a. 1 b. 2 c. 3 d. 4 ANSWER: b 11. Which of the following bonds undergoes stretching at the highest frequency (estimate without doing the calculation)? a. C≡C b. C−C c. C=C d. C−O ANSWER: a 12. Which of the following bonds undergoes stretching at the highest frequency (estimate without doing the calculation)? Copyright Cengage Learning. Powered by Cognero.

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Chapter 12: Infrared Spectroscopy a. C−H b. C−C c. C=O d. C≡C ANSWER: a 13. Which of the following carbon-nitrogen bonds undergoes stretching at the highest frequency? a. sp3 C − sp3 N b. primary imine sp2 C − sp2 N c. secondary imine sp2 C − sp2 N d. C≡N ANSWER: d 14. Which of the following bonds (circled) vibrates at the highest frequency?

a. 1 b. 2 c. 3 d. 4 ANSWER: d 15. Which of the following bonds (circled) gives the weakest absorbance in the infrared spectrum?

a. 1 b. 2 c. 3 d. 4 ANSWER: b 16. Which of the following bonds gives rise to a strong absorbance at approximately 1630-1820 cm−1 in the infrared spectrum? a. C=O b. C−O c. C=C d. C≡C ANSWER: a Copyright Cengage Learning. Powered by Cognero.

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Chapter 12: Infrared Spectroscopy 17. Which of the following bonds gives rise to an absorbance at approximately 2700-3300 cm−1 in the infrared spectrum? a. C≡C b. C=O c. C=C d. C−H ANSWER: d 18. Which of the following bonds gives rise to a strong,broad absorbance at approximately 3200-3650 cm−1 in the infrared spectrum? a. C=O b. O−H c. C=C d. C−H ANSWER: b 19. Which of the following bonds gives rise to a strong absorbance at approximately 1700-1725 cm−1 in the infrared spectrum? a. O−H b. C−C c. C=O (carboxylic acid) d. C≡N ANSWER: c 20. Which of the following functional groups is likely to be present in a molecule that has peaks in the infrared spectrum at 1630-1680 cm−1 (strong) and 3200-3400 cm−1 (one peak, medium)? a. alcohol b. amine c. primary amide d. secondary amide ANSWER: d 21. Which of the following functional groups is likely to be present in a molecule that has peaks in the infrared spectrum at 1700-1725 cm−1 (strong, broad), and a very broad peak between 2500-3300 cm−1? a. alcohol b. carboxylic acid c. ether d. ketone ANSWER: b 22. Which of the following functional groups is likely to be present in a molecule that has peaks in the infrared spectrum at 3200-3650 cm−1 (strong), has peak at 1000-1250 but does not have peak at 16301820 cm−1? Copyright Cengage Learning. Powered by Cognero.

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Chapter 12: Infrared Spectroscopy a. alcohol b. aldehyde or ketone c. ether d. ester ANSWER: a 23. Which of the following functional groups is likely to be present in a molecule that has peaks in the infrared spectrum 1630-1820 cm−1 (strong) and 2720 cm−1 (weak), but does not have peaks at 22002250 cm−1 ? a. ketone b. ether c. aldehyde d. ester ANSWER: c 24. Which of the following compounds gives an infrared spectrum with peaks in the ranges of 3200-3650 (strong, broad) and 1600-1640 cm−1 (medium); but does not have peaks at 1630-1820 (strong)?

a. 1 b. 2 c. 3 d. 4 ANSWER: c 25. Which of the following compounds gives an infrared spectrum with a peak in the range of 1630-1820 cm−1 (strong peak), but does not have peaks at 3200-3650 or 1000-1250 cm−1?

a. 1 b. 2 c. 3 d. 4 ANSWER: b Copyright Cengage Learning. Powered by Cognero.

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Chapter 12: Infrared Spectroscopy 26. Which of the following compounds gives an infrared spectrum with peaks at 1000-1250 cm−1 (strong), but does not have peaks at 3200-3650 or 1630-1820 cm−1 (sharp, weak peak)?

a. 1 b. 2 c. 3 d. 4 ANSWER: a 27. Which of the following compounds gives an infrared spectrum with peaks in the ranges of 3200-3650 (strong, broad), but does not have peaks at 1630-1820 (strong) or 1600-1640 cm−1 (medium)?

a. 1 b. 2 c. 3 d. 4 ANSWER: d 28. Which of the following compounds gives an infrared spectrum with absorbances at 3000-3100 cm−1 (weak) and 16001680 cm−1(weak)?

a. 3 b. 1 c. 2 d. 4 ANSWER: a 29. Which of the following compounds gives an infrared spectrum with no significant peaks at ∼3300 cm−1 or 1600-1680 Copyright Cengage Learning. Powered by Cognero.

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Chapter 12: Infrared Spectroscopy cm−1?

a. 1 b. 2 c. 3 d. 4 ANSWER: b 30. Which of the following compounds gives an infrared spectrum with peaks at 2500-3300 cm−1 and ~ 1700-1725 cm−1?

a. 1 b. 2 c. 3 d. 4 ANSWER: c 31. Which of the following compounds gives an infrared spectrum with a peak at ∼1750 cm−1, but no significant peaks at 3000-3500 cm−1 or 1050-1250 cm−1?

a. 1 b. 2 c. 3 d. 4 ANSWER: b 32. Which of the following compounds does not give an infrared spectrum with peak at 3000-3500 cm−1?

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Chapter 12: Infrared Spectroscopy a. 1, 2 and 3 b. 4 c. none of the above d. all of the above ANSWER: a 33. Which of the following compounds gives a carbonyl bond absorption at the highest frequency?

a. 1 b. 2 c. 3 d. 4 ANSWER: a 34. Which of the following compounds gives a carbonyl bond absorption at the highest frequency?

a. 1 b. 2 c. 3 d. 4 ANSWER: c 35. Which of the following compounds gives a carbonyl bond absorption at the lowest frequency?

a. 1 b. 2 Copyright Cengage Learning. Powered by Cognero.

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Chapter 12: Infrared Spectroscopy c. 3 d. 4 ANSWER: b 36. Cyclohexene and 2-hexyne both have the molecular formula C6H10. Any of the following regions of an IR spectrum could be used to distinguish these two compounds. 3020-3100 cm−1 2100-2260 cm−1 1650-1670 cm−1 a. True b. False ANSWER: True 37. Assume you are carrying out the conversion of 1-bromobutane to 1-butanol. How could you use IR spectroscopy to determine when the reaction is complete?

As the reaction progress the 3400−3640 cm−1 IR band should increase in intensity. a. True b. False ANSWER: True 38. The region of the IR spectrum between 1500 - 400 cm-1 would be significantly different for the following two substances?

a. True b. False ANSWER: True 39. The area in the infrared spectrum between 1400 and 400 cm–1 is called the functional group region. a. True b. False ANSWER: False 40. An IR spectrum of an unknown organic molecule having the formula which contains carbon, hydrogen, and

oxygen reveals a strong absorption at 1715–1725 cm–1. This molecule is most likely an ether. a. True b. False ANSWER: False Copyright Cengage Learning. Powered by Cognero.

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Chapter 12: Infrared Spectroscopy 41. Examining the infrared spectrum of a compound allows us to determine the nature of the conjugated pi electron system in the compound. a. True b. False ANSWER: False 42. A C=O bond undergoes stretching at a lower frequency than C=C. a. True b. False ANSWER: False 43. The vertical axis on an IR spectrum represents the percent transmission and the horizontal axis measures frequency (wavenumber). a. True b. False ANSWER: True 44. he amount of energy in infrared light corresponds to the amount of energy needed to increase certain molecular motions, such as bond vibrations, in organic molecules. a. True b. False ANSWER: True 45. In terms of the electromagnetic spectrum, 2870 cm−1 represents lower energy than 2.91 × 1016 Hz. a. True b. False ANSWER: True 46. The radio wave region of the electromagnetic spectrum would have sufficient energy to produce the following energy transition.

a. True b. False ANSWER: False MATCH each of the following groups of bond-types to the region of the infrared spectrum in which their absorptions occur. Place the letter of the region in the blank to the left of the bond-type. a.

4000 to 2500 cm−1

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Chapter 12: Infrared Spectroscopy b. c. d.

2500 to 2000 cm−1 2000 to 1500 cm−1 below 1500 cm−1

47. _____ C−C, C−O, C−N, and C−X single-bond vibrations. ANSWER: d 48. _____ C=O, C=N, and C=C bond absorptions. ANSWER: c 49. _____ N−H, C−H, and O−H stretching and bending motions. ANSWER: a 50. _____ triple bond stretching vibrations. ANSWER: b MATCH a structure from the list below to the following IR spectra. Place the letter of the structure in the blank provided.

51. _____

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Chapter 12: Infrared Spectroscopy Spectrum obtained from: SDBSWeb: http://www.aist.go.jp/RIODB/SDBS/ ANSWER: F 52. _____

Spectrum obtained from: SDBSWeb: http://www.aist.go.jp/RIODB/SDBS/ ANSWER: D 53. _____

Spectrum obtained from: SDBSWeb: http://www.aist.go.jp/RIODB/SDBS/ ANSWER: A

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Chapter 12: Infrared Spectroscopy MATCH each of the following molecules to the region of the infrared spectrum in which they may show a significant absorption. Place the letter of the region in the blank to the left of the bond-type. a. b. c. d.

4000 to 2500 cm−1 2500 to 2000 cm−1 2000 to 1500 cm−1 below 1500 cm−1

54. _______ ANSWER: b 55. _______ CH3CH2OCH(CH3) ANSWER: d 56. _______

ANSWER: a 57. Provide the structure of three compounds with the molecular formula C4H8O that give an absorption peak at 16001640 cm-1 in the infrared spectrum, but no significant peaks at 3000-3600 cm-1 or at 1650-1750 cm-1. ANSWER: Any three of the following:

58. Provide the structure of four compounds with the molecular formula C5H10O which give a strong absorption peak at 1700-1740 cm-1 in the infrared spectrum, but no significant peaks at 1600-1640 cm-1 . ANSWER: Any four of the following:

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Chapter 12: Infrared Spectroscopy 59. Provide a brief explanation to account for the observation that 1-butyne gives a significantly stronger peak at ∼1250 cm-1 in the infrared spectrum than 2-butyne.. ANSWER: 2-Butyne is a symmetrical molecule and stretching of the triple bond does not give rise to a change in the bond dipole moment. 60. Provide a brief explanation to account for the observation that the frequency of the C=O stretching absorption in the infrared spectrum of 2-butanone is higher than that of 3-buten-2-one. ANSWER: The C=O bond of 3-buten-2-one is weaker in 2-butanone by virtue of the existence of an additional resonance structure with a C–O single bond.

61. Provide a brief explanation to account for the observation that the frequency of the C=O stretching absorption in the infrared spectrum of N,N-dimethylacetamide, CH3CON(CH3)2, is higher than that of methyl acetate, CH3CO2CH3. ANSWER: The C=O bond of the amide is weaker than that of the ester. Nitrogen is less electronegative than oxygen, and therefore a better electron pair donor. Accordingly, the resonance contributor in which the nitrogen has donated a pair of electrons to the carbonyl carbon atom is an important contributor to the structure.

62. How could you distinguish between 1-hexyne and 2-hexyne by infrared spectroscopy?

ANSWER: 1-Hexyne, a terminal alkyne, has a stronger peak for the C≡C stretching vibration than 2-hexyne, an internal alkynes. 63. How could you distinguish between 1-butanol and diethyl ether by infrared spectroscopy? Copyright Cengage Learning. Powered by Cognero.

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Chapter 12: Infrared Spectroscopy

ANSWER: The infrared spectrum of 1-butanol has a strong and broad peak at 3500-3000 cm-1 for the O–H bond. This peak is absent in the spectrum of ethers. 64. How could you distinguish between methyl butanoate and pentanoic acid by infrared spectroscopy?

ANSWER: The infrared spectrum of pentanoic acid has a very broad peak at 3300-2500 cm-1 for the O–H bond. This peak is absent in the spectrum of esters. 65. Label three peaks in the following spectrum with the bond that gives rise to them, and identify the functional group that is present in the compound (the compound has a formula of C6H14O)?

ANSWER: O-H: ∼3300 cm-1 C-H: ∼2900 cm-1 C-O: ∼1060 cm-1 Functional group: alcohol 66. Label three peaks in the following spectrum with the bond that gives rise to them, and identify the functional group that is present in the compound (the compound has a formula of C5H10O2)?

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Chapter 12: Infrared Spectroscopy

ANSWER: O-H: 3000-3600 cm-1 C-H: ∼2900 cm-1 C-O: ∼1700 cm-1 Functional group: carboxylic acid 67. Label three peaks in the following spectrum with the bond that gives rise to them, and identify the functional group that is present in the compound (the compound has a formula of C4H9NO)?

ANSWER: N-H: ∼3500 cm-1 C-H: ∼2900 cm-1 C=O: ∼1680 cm-1 Functional group: amide 68. What is the frequency of a radiation with a wavelength of 7.8 × 10−5 m? (Speed of light = 3.0 × 108 m/s) a. b. c. d. ANSWER: a 69. What is the energy of a photon moving with a frequency of 1.2× 1010 s−1? (Planck’s constant = 6.626 × 10−34 J s) a. b. Copyright Cengage Learning. Powered by Cognero.

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Chapter 12: Infrared Spectroscopy c. d. ANSWER: a 70. What is the wavenumber of a radiation with a wavelength of 7.0 × 10−5 m? a. cm−1 b.

cm−1

ANSWER: a 71. Why KBr and NaCl are used for sample preparation in the infrared spectroscopic analysis of compounds? ANSWER: KBr and NaCl are used for sample preparation in the infrared spectroscopic analysis of compounds because they are ionic solids and therefore do not absorb infrared radiation. 72. The “n” values for propanol and xenon difluoride are given below. The total numbers of fundamental vibrations observed in propanol and xenon difluoride are _____ and _____, respectively. Molecule n

C3H8O 12

XeF2 3

a. 30; 3 b. 30; 4 c. 31; 4 d. 31; 3 ANSWER: b 73. The given molecule shows two absorption peaks, each at 1760 cm−1 and 1810 cm−1. The peaks are due to the _____.

a. symmetric and unsymmetric bending vibrations of the entire anhydride group b. symmetric stretching vibration of only one carbonyl group c. unsymmetric stretching vibrations of the carbonyl groups d. symmetric and unsymmetric stretching vibrations of the entire anhydride group ANSWER: d 74. The given molecule shows a stretching absorption peak at 2200–2250 cm−1 due to the presence of a _____.

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Chapter 12: Infrared Spectroscopy a. nitrile functional group b. hydroxyl functional group c. carbon–carbon double bond d. carbon–carbon single bond ANSWER: a

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Chapter 13: Nuclear Magnetic Resonance Spectroscopy 1. Which feature in the 1H NMR spectrum provides information about the number of types of different protons in a compound? a. number of signals b. integral c. splitting d. chemical shift ANSWER: a 2. Which feature in the 1H NMR spectrum provides information about the relative number of each type of proton in a compound? a. number of signals b. integral c. splitting d. chemical shift ANSWER: b 3. Which feature in the 1H NMR spectrum provides information about the electronic environment of the protons in a compound? a. number of signals b. integral c. splitting d. chemical shift ANSWER: d 4. Which feature in the 1H NMR spectrum provides information about the number of neighboring protons of each proton in the compound? a. number of signals b. integral c. multiplicity d. chemical shift ANSWER: c 5. Which of the following is not true regarding 1H NMR spectroscopy? a. "shielding" leads to peaks at lower values of δ b. a "downfield" peak appears at a higher value of δ c. in the presence of an applied magnetic field, the nuclei with positive spin quantum number value are aligned oppos ite to the applied field. d. on a 300 MHz instrument, a proton that adsorbs irradiation at a frequency 1200 Hz higher than the adsorption of TMS appears at δ 4 ppm. ANSWER: c 6. Which of the following is not true regarding 1H NMR spectroscopy? Copyright Cengage Learning. Powered by Cognero.

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Chapter 13: Nuclear Magnetic Resonance Spectroscopy a. the reference compound used for 1H-NMR spectroscopy is trimethylsilane (TMS) b. on a 300 MHz instrument, a proton that adsorbs irradiation at a frequency 900 Hz higher than the adsorption of TMS appears at δ 3 ppm. c. δ for a particular proton is independent of the magnetic field strength of the instrument used. d. "deshielding" leads to peaks at higher values of δ ANSWER: a 7. How many sets of equivalent protons are there in hexane? a. 2 b. 3 c. 6 d. 7 ANSWER: b 8. How many sets of equivalent protons are there in 2,3-dimethylbutane? a. 4 b. 3 c. 2 d. 1 ANSWER: c 9. How many sets of equivalent protons are there in 3-methylhexane? a. 2 b. 3 c. 6 d. 7 ANSWER: d 10. What is the splitting of the signal in the 1H NMR spectrum for the methyl protons of isobutane? a. doublet b. singlet c. triplet d. quartet ANSWER: a 11. What is the splitting of the signal in the 1H NMR spectrum for the methyl protons of 2,3-dimethylbutane? a. triplet b. singlet c. doublet d. quartet ANSWER: c 12. What is the splitting of the signal in the 1H NMR spectrum for the methyl protons of 3,3-dichloro-2,4Copyright Cengage Learning. Powered by Cognero.

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Chapter 13: Nuclear Magnetic Resonance Spectroscopy dimethylpentane? a. triplet b. doublet c. singlet d. nontet ANSWER: b 13. Which of the following combinations of peaks appears in the 1H NMR spectrum of diethyl ether, CH3CH2OCH2CH3? a. a triplet b. a quartet c. a doublet and a quartet d. a triplet and a quartet ANSWER: d 14. Which of the following combinations of peaks appears in the 1H NMR spectrum of 2,2-dichloropropane? a. a triplet and a doublet b. a singlet c. a triplet and a septet d. two singlets ANSWER: b 15. Which of the following combinations of peaks appears in the 1H NMR spectrum of 3-pentanone? a. a triplet and a quartet b. a doublet and a triplet c. a singlet and two quartets d. a quartet and an octet ANSWER: a 16. Which of the following combinations of peaks appears in the 1H NMR spectrum of 3-methyl-2-butanone? a. a singlet, a septet and a doublet b. a singlet and a quartet c. a singlet and two triplets d. a doublet and a triplet ANSWER: a 17. Which of the following combinations of peaks appears in the 1H NMR spectrum of 2,2-dimethylbutane, (CH3)3CCH2CH3? a. a quartet b. a doublet, a triplet c. a quartet, a singlet, a triplet d. a singlet, a quartet ANSWER: c Copyright Cengage Learning. Powered by Cognero.

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Chapter 13: Nuclear Magnetic Resonance Spectroscopy 18. Which of the following combinations of peaks appears in the 1H NMR spectrum of 2-methylpropane? a. two singlets b. a singlet and a nonet c. a singlet and a decet d. a doublet and a decet ANSWER: d 19. What is the appearance of the signal corresponding to the CH2 protons in the 1H NMR spectrum of 1-bromo-3chloropropane, BrCH2CH2CH2Cl? a. two quintets b. a triplet and a quartet c. a triplet and a quintet d. two triplets ANSWER: c 20. Which C4H9Br compound gives a triplet at approximately 3.5 ppm in the 1H NMR spectrum?

a. 1 b. 2 c. 3 d. 4 ANSWER: a 21. Which C4H9Br compound gives a sextet at approximately 4 ppm in the 1H NMR spectrum?

a. 3 b. 4 c. 2 d. 1 ANSWER: c 22. What is the relative area of the three peaks in a triplet in an 1H NMR spectrum? a. 1:3:1 b. 1:4:1 Copyright Cengage Learning. Powered by Cognero.

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Chapter 13: Nuclear Magnetic Resonance Spectroscopy c. 1:2:1 d. 2:4:2 ANSWER: c 23. What is the relative area of the seven peaks in a septet in an 1H NMR spectrum? a. 1:2:3:4:3:2:1 b. 1:3:6:12:6:3:1 c. 1:6:15:30:15:6:1 d. 1:6:15:20:15:6:1 ANSWER: d 24. How many signals appear in proton-decoupled 13C NMR spectrum of benzene? a. 4 b. 1 c. 3 d. 2 ANSWER: b 25. How many signals appear in proton-decoupled 13C NMR spectrum of 2-pentanone? a. 5 b. 4 c. 1 d. 6 ANSWER: a 26. Which of the protons in the following molecule appear furthest downfield in the 1H NMR spectrum?

a. i b. ii c. iii d. iv ANSWER: d 27. Which of the protons in the following molecule appear furthest downfield in the 1H NMR spectrum?

a. i b. ii Copyright Cengage Learning. Powered by Cognero.

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Chapter 13: Nuclear Magnetic Resonance Spectroscopy c. iii d. iv ANSWER: c 28. Which of the protons in the following molecule appear furthest downfield in the 1H NMR spectrum?

a. i b. ii c. iii d. iv ANSWER: d 29. Which of the protons in the following molecule appear at the highest δ-value in the 1H NMR spectrum?

a. i b. ii c. iii d. iv ANSWER: d 30. Which of the protons in the following molecule appear at the highest δ-value in the 1H NMR spectrum?

a. i b. ii c. iii d. iv ANSWER: a 31. Which of the protons in the following molecule appear at the highest δ-value in the 1H NMR spectrum?

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Chapter 13: Nuclear Magnetic Resonance Spectroscopy a. i b. ii c. iii d. iv ANSWER: c 32. How many signals appear in the proton-decoupled 13C NMR spectrum of 1,4-dibromobenzene? a. 1 b. 2 c. 3 d. 4 ANSWER: b 33. How many signals appear in the proton-decoupled 13C NMR spectrum of 1,3-dibromobenzene? a. 1 b. 2 c. 3 d. 4 ANSWER: d 34. How many signals appear in the proton-decoupled 13C NMR spectrum of 1,2-dibromobenzene? a. 1 b. 2 c. 3 d. 4 ANSWER: c 35. How many signals appear in the proton-decoupled 13C NMR spectrum of 1,3,5-trimethylbenzene? a. 2 b. 5 c. 3 d. 4 ANSWER: c 36. How many signals appear in the proton-decoupled 13C NMR spectrum of 2-bromotoluene? a. 3 b. 4 c. 5 d. 7 ANSWER: d 37. How many signals appear in the proton-decoupled 13C NMR spectrum of 2-bromotoluene? Copyright Cengage Learning. Powered by Cognero.

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Chapter 13: Nuclear Magnetic Resonance Spectroscopy a. 3 b. 4 c. 5 d. 7 ANSWER: d 38. Which C4H9Br compound(s) gives a 13C NMR spectrum consisting of three signals?

a. only 1 b. only 3 c. only 2 and 3 d. 1, 2, 3 and 4 ANSWER: b 39. Which C4H9Br compound(s) gives a 13C NMR spectrum consisting of two signals?

a. only 1 b. only 2 c. only 2 and 3 d. 1, 2, 3 and 4 ANSWER: b 40. Which of the following compounds gives a 1H NMR spectrum consisting of two singlets and a 13C NMR consisting of consisting of three signals?

a. only i b. only iii c. only ii and iii Copyright Cengage Learning. Powered by Cognero.

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Chapter 13: Nuclear Magnetic Resonance Spectroscopy d. only ii, iii and iv ANSWER: c 41. Which of the following compounds would give a 1H NMR spectrum consisting of three signals and a 13C NMR consisting of consisting of four signals?

a. only iv b. only iii c. only i and iii d. only i ANSWER: d 42. How many signals appear in the proton-decoupled 13C NMR spectrum of the following compound?

a. 7 b. 8 c. 9 d. 11 ANSWER: c 43. How many signals appear in the proton-decoupled 13C NMR spectrum of the following compound?

a. 6 b. 7 c. 8 d. 11 ANSWER: b 44. Which of the carbon atoms in the following molecule appears furthest downfield in the 13C NMR spectrum?

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Chapter 13: Nuclear Magnetic Resonance Spectroscopy

a. i b. ii c. iii d. iv ANSWER: c 45. Which of the carbon atoms in the molecule appears furthest downfield in the 13C NMR spectrum?

a. i b. ii c. iii d. iv ANSWER: d 46. The chemical shift of the protons of one equivalent set of hydrogens in cis-but-2-ene, C4H8, is 5.2 ppm when the spectrum is obtained at 250 MHz. What is the chemical shift of these protons when the spectrum is acquired at 500 MHz? a. 2.6 ppm b. 5.2 ppm c. 10.4 ppm d. 20.8 ppm ANSWER: b 47. The coupling constant, J, between the protons of chloroethane belonging to the hydrogens attached to the same carbon is 12.8 Hz when the spectrum is obtained at 250 MHz. What is the coupling constant between these protons when the spectrum is acquired at 500 MHz? a. 6.4 Hz b. 12.8 Hz c. 25.6 Hz d. 38.4 Hz ANSWER: b 48. What is the hydrogen deficiency index for a compound with a molecular formula of C7H14S? a. 3 b. 2 c. 1 d. 0 Copyright Cengage Learning. Powered by Cognero.

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Chapter 13: Nuclear Magnetic Resonance Spectroscopy ANSWER: c 49. What is the hydrogen deficiency index for a compound with a molecular formula of C12H16O? a. 2 b. 4 c. 5 d. 6 ANSWER: c 50. What is the hydrogen deficiency index for a compound with a molecular formula of C3H7N? a. 2 b. 1 c. 3 d. 4 ANSWER: b 51. What is the hydrogen deficiency index for a compound with a molecular formula of C5H10O? a. 3 b. 2 c. 1 d. 4 ANSWER: c 52. Which of the following compounds gives a 1H NMR spectrum consisting of only a singlet? a. 1,1-dibromopropane b. 1,2-dibromopropane c. 1,3-dibromopropane d. 2,2-dibromopropane ANSWER: d 53. Which of the following compounds gives a 1H NMR spectrum consisting of only one singlet? a. CH3OCH2CH2OCH2CH3 b. CH3OCH2CH2CH2CH2OH c. CH3OCH3 d. CH3OCH2CH(CH3)OCH3 ANSWER: c 54. Which of the following compounds gives a 1H NMR spectrum consisting of only a singlet, a triplet, and two quintets? a. CH3CH(OCH3)2 b. CH3OCH2CH2CH2CH2CH2OCH3 c. CH3OCH2CH2OCH3 Copyright Cengage Learning. Powered by Cognero.

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Chapter 13: Nuclear Magnetic Resonance Spectroscopy d. CH3OCH2CH(OH)CH3 ANSWER: b 55. Which of the following compounds gives a 1H NMR spectrum consisting of a doublet and a quartet? a. CH3OCH2CH2CH2CH2OH b. CH3OCH2CH2OCH2CH3 c. CH3CH=CHCH3 d. CH3OCH2CH(CH3)OCH3 ANSWER: c 56. Which of the protons in the following molecule appear at the highest δ-value in the 1H NMR spectrum?

a. i b. ii c. iii d. iv ANSWER: d 57. Which of the following compounds have homotopic protons? 1. 2. 3.

propane butane 2-methylpropane

a. only 1 b. only 2 c. only 1 and 2 d. 1, 2 and 3 ANSWER: d 58. Which of the following compounds have enantiotopic protons? 1. 2. 3.

propane butane 2-methylpropane

a. only 1 b. only 2 c. only 1 and 2 d. 1, 2 and 3 ANSWER: b Copyright Cengage Learning. Powered by Cognero.

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Chapter 13: Nuclear Magnetic Resonance Spectroscopy 59. Which of the following is true for pair of homotropic protons? 1. 2.

They will appear at the same chemical shift in an achiral (i.e., nonchiral) environment They will appear at the same chemical shifts in a chiral environment

a. only 1 b. only 2 c. neither 1 nor 2 d. both 1 and 2 ANSWER: d 60. Which of the following is true for pair of enantiotopic protons? 1. 2.

They will appear at the same chemical shift in an achiral (i.e., nonchiral environment) They will appear at the same chemical shifts in a chiral environment

a. only 1 b. only 2 c. neither 1 nor 2 d. both 1 and 2 ANSWER: a 61. Which of the following is true for pair of diastereotopic protons? 1. 2.

They will appear at the same chemical shift in an achiral (i.e., nonchiral environment) They will appear at the same chemical shifts in a chiral environment

a. only 1 b. only 2 c. neither 1 nor 2 d. both 1 and 2 ANSWER: c 62. Which C9H10O compound gives the following 1H NMR spectrum?

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Chapter 13: Nuclear Magnetic Resonance Spectroscopy

a. 1 b. 2 c. 3 d. 4 ANSWER: b 63. Which C9H10O compound gives the following 1H NMR spectrum?

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Chapter 13: Nuclear Magnetic Resonance Spectroscopy

a. 1 b. 2 c. 3 d. 4 ANSWER: a 64. Which C6H12O2 compound gives the following 1H NMR spectrum?

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Chapter 13: Nuclear Magnetic Resonance Spectroscopy

a. 1 b. 2 c. 3 d. 4 ANSWER: b 65. Which C6H12O2 compound gives the following 1H NMR spectrum?

a. 1 b. 2 Copyright Cengage Learning. Powered by Cognero.

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Chapter 13: Nuclear Magnetic Resonance Spectroscopy c. 3 d. 4 ANSWER: c 66. Which C8H10 compound gives the following 1H NMR spectrum?

a. 1 b. 2 c. 3 d. 4 ANSWER: a 67. Which C8H10 compound gives the following 1H NMR spectrum?

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Chapter 13: Nuclear Magnetic Resonance Spectroscopy

a. 1 b. 2 c. 3 d. 4 ANSWER: c 68. Nuclear magnetic resonance spectroscopy provides information about a molecule's carbon-hydrogen framework. a. True b. False ANSWER: True 69. All of the following would produce nuclear magnetic resonance: 2H, 14N, 16O, and 19F. a. True b. False ANSWER: False 70. All of the following compound produce only singlets in a 1H NMR spectrum.

a. True b. False Copyright Cengage Learning. Powered by Cognero.

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Chapter 13: Nuclear Magnetic Resonance Spectroscopy ANSWER: True 71. The splitting of signals in the 1H NMR spectrum provides information about the number of neighboring protons of each proton in the compound. a. True b. False ANSWER: True 72. Consider the following structure.

If the proton attached to C2 in 1,1,2-tribromopropane is coupled with the protons on C1 (J = 3.6 Hz) and C3 (J = 6.8), the tree diagram of the C2 proton is shown below.

a. True b. False ANSWER: True 73. The following compound will have a 1H NMR spectrum that consists of:

two triplets and a singlet, area ratio 3:3:4. a. True b. False ANSWER: False 74. Consider the compound shown below.

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Chapter 13: Nuclear Magnetic Resonance Spectroscopy The above compound would produce a signal further downfield in a 13C NMR spectrum than

a. True b. False ANSWER: True For each of the compounds below tell how many signals you would expect the molecule to have in its normal, broadband hydrogen-decoupled 13C NMR spectra. Enter the numerical value in the blank provided to the left of the structure. 75. _______

ANSWER: 3 three 76. _______

ANSWER: 5 five 77. _______

ANSWER: 6 six 78. _______

ANSWER: 5 five 79. _______ Copyright Cengage Learning. Powered by Cognero.

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Chapter 13: Nuclear Magnetic Resonance Spectroscopy

ANSWER: 5 five Predict the splitting of each of the numbered hydrogen atoms in the structure below in a 1H NMR spectrum. Identify as singlet, doublet, triplet, quartet, quintet, sextet, septet, .... Place the correct splitting in the blank to the left of the number.

80. ______ 1 ANSWER: singlet 81. ______ 1 ANSWER: quartet 82. ______ 1 ANSWER: triplet 83. Identify the ratio of peak areas upon integration of the 1H NMR spectrum for A, B, and C respectively. Enter the numbers separated by colons.

ANSWER: 3:1:6 Consider the following structure. Answer the following questions by placing the appropriate number in the blank to the left.

84. _____The number of nonequivalent hydrogen atoms in this compound. ANSWER: 3 three 85. _____The number of signals in the hydrogen-decoupled 13C NMR of this compound. ANSWER: 3 three 86. _____The number of nonsinglet splitting patterns in the 1H NMR of this compound. Copyright Cengage Learning. Powered by Cognero.

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Chapter 13: Nuclear Magnetic Resonance Spectroscopy ANSWER: 0 zero The following questions pertain to the display of NMR spectra. Match a term to each description below. a. TMS b. high-field or upfield side c. MHz d. delta (δ) e. low-field or downfield side f. chemical shift g. intensity 87. When looking at a NMR spectrum the right-hand part of the chart is the _____. ANSWER: b 88. The exact place on the spectrum at which a nucleus absorbs is called its _____. ANSWER: f 89. The calibration standard for 1H and 13C NMR is _____. ANSWER: a 90. NMR spectrum are calibrated using an arbitrary scale that is divided into _____ units. ANSWER: d 91. The vertical axis of spectrum displays the _____ of the signal. ANSWER: g 92. Identify the compound (C4H6O2) that gives the following 1H NMR spectrum.

ANSWER: methyl propionate, CH3CH2CO2CH3 93. Identify the compound (C4H8O2) that gives the following 1H NMR spectrum.

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Chapter 13: Nuclear Magnetic Resonance Spectroscopy

ANSWER: ethyl acetate, CH3CO2CH2CH3 94. Identify the compound (C3H7Cl) that gives the following 1H NMR spectrum.

ANSWER: 2-chloropropane 95. Identify the compound (C3H7Cl) that gives the following 1H NMR spectrum.

ANSWER: 1-chloropropane 96. Identify the compound (C4H8O) that gives the following 1H NMR spectrum.

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Chapter 13: Nuclear Magnetic Resonance Spectroscopy

ANSWER: butanal 97. Identify the compound (C4H8O) that gives the following 1H NMR spectrum.

ANSWER: 2-butanone 98. Identify the compound (C8H10O2) that gives the following 1H NMR spectrum.

ANSWER: 3-phenylpropanoic acid, PhCH2CH2CO2H 99. Identify the compound (C8H11N) that gives the following 1H NMR spectrum.

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Chapter 13: Nuclear Magnetic Resonance Spectroscopy

ANSWER: 1-phenylethanamine, PhCH(NH2)CH3 100. Identify the compound (C8H10) that gives the following 1H NMR spectrum.

ANSWER: p-xylene (1,4-dimethylbenzene) 101. Identify the compound (C8H10) that gives the following 1H NMR spectrum.

ANSWER: m-xylene (1,3-dimethylbenzene) 102. Identify the compound (C8H10) that gives the following 1H NMR spectrum.

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Chapter 13: Nuclear Magnetic Resonance Spectroscopy

ANSWER: o-xylene (1,2-dimethylbenzene) 103. Identify the most appropriate intensity maintained for a pure cyclopentanol NMR spectrum. a. 1:1:4:6 b. 5:1 c. 4:3:2 d. 6:3:1 ANSWER: a 104. How many types of equivalent hydrogens are present in the following compound?

a. 0 b. 1 c. 2 d. 3 ANSWER: c 105. Identify the methyl hydrogen with the highest chemical shift. a. b. c. d. Copyright Cengage Learning. Powered by Cognero.

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Chapter 13: Nuclear Magnetic Resonance Spectroscopy ANSWER: a 106. What does “Y” denote in the coupling parameter xJy? a. Number of bonds involved in coupling b. Homonuclear or heteronuclear interaction c. Short-range coupling parameter d. Karplus empirical formula ANSWER: b 107. Identify the physical factor that influences the coupling constant. a. Hybridization b. Cryomagnetic ratio c. Chemical exchange d. Karplus empirical formula ANSWER: a 108. On which factor is chemical shielding not dependent? a. Hybridization of adjacent atoms b. Electronegativity of nearby atoms c. Operating frequency of the spectrometer d. Magnetic induction within an adjacent pi bond ANSWER: c 109. Identify the type of coupling that exists between the two protons in the following compound, given that the compound is asymmetrical.

a. Geminal coupling b. Vicinal coupling c. Long-range coupling d. Single-bond coupling ANSWER: a

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Chapter 14: Mass Spectrometry 1. What is the principle that allows us to use mass spectrometry to determine the molecular weight of a compound? a. higher molecular weight compounds are less volatile b. higher molecular weight compounds are more dense c. a beam of higher molecular weight cations is deflected less by a magnetic field d. ions with higher molecular weight absorb higher frequencies of light ANSWER: c 2. In mass spectrometry, which of the following phrases is shortened to the acronym "EI-MS"? a. electron identifier mass spectrometry b. electron ionization mass spectrometry c. electron identifier mass spectroscopy d. electron identifier mass spectrometer ANSWER: b 3. In mass spectrometry, which of the following phrases is shortened to the acronym "EI"? a. electron injection b. electron impact c. energy initiated d. energy insertion ANSWER: b 4. In mass spectrometry, which of the following phrases is shortened to the acronym "MALDI"? a. mass analysis by light-detected ions b. matrix assisted laser desorption ionization c. many atom loss-detecting ionization d. molecular and light detecting instrument ANSWER: b 5. What is the x-axis of a mass spectrum? a. mass b. mass/energy c. mass/charge d. charge ANSWER: c 6. What is the y-axis of a mass spectrum? a. mass b. energy c. abundance d. field strength ANSWER: c 7. Which of the following is the definition of the base peak of a mass spectrum? a. the peak corresponding to the most abundant ion Copyright Cengage Learning. Powered by Cognero.

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Chapter 14: Mass Spectrometry b. the peak corresponding to the ion with lowest m/e c. the peak corresponding to the molecular ion peak d. the peak corresponding to the ion arising to loss of a proton from the molecular ion ANSWER: a 8. Which of the following corresponds to the molecular ion in EI mass spectrometry? a. the most abundant ion b. the ion with the smallest m/e c. the ion formed by removal of an electron from the molecule d. any ion formed by fragmentation of the molecule ANSWER: c 9. What are products of the collision between high energy electrons and methane? a. CH4− ⋅ + 2 e− b. CH3− + H⋅ c. CH4+⋅ + 2 e− d. CH3⋅ + H+ + 2 e− ANSWER: c 10. Which of the following sets of molecular ions does an alkyl bromide possess? a. two molecular ions in a 2:1 ratio separated by two mass units b. two molecular ions in a 1:1 ratio separated by two mass units c. three molecular ions in a 1:2:1 ratio separated by two mass units d. two molecular ions in a 3:1 ratio separated by two mass units ANSWER: b 11. Which of the following sets of molecular ion peaks does methyl chloride possess? a. two molecular ion peaks in a 3:1 ratio at m/z values 50 and 51 b. two molecular ion peaks in a 1:1 ratio at m/z values 50 and 52 c. three molecular ion peaks in a 1:2:1 ratio at m/z values 50,52 and 54 d. two molecular ion peaks in a 3:1 ratio at m/z values 50 and 52 ANSWER: d 12. Which of the following sets of molecular ions does a dichloroalkane possess? a. three molecular ions in a 1:3:1 ratio, separated by one mass unit each b. two molecular ions in a 1:3 ratio separated by two mass units c. three molecular ions in a 9:6:1 ratio, separated by two mass units each d. two molecular ions in a ratio 1:2 separated by two mass units ANSWER: c 13. Which of the following is most consistent with a molecule having a molecular ion with m/e of 77? a. the molecule contains bromine b. the molecule contains nitrogen Copyright Cengage Learning. Powered by Cognero.

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Chapter 14: Mass Spectrometry c. the molecule is an alcohol d. the molecule is a hydrocarbon ANSWER: b 14. How many carbon atoms are present in a molecule which gives an M+1 peak that is 5.74% of the intensity of the molecular ion? a. 5 b. 6 c. 11 d. 12 ANSWER: a 15. How many carbon atoms are present in a molecule which gives an M+1 peak that is 12.59% of the intensity of the molecular ion? a. 10 b. 12 c. 11 d. 13 ANSWER: c 16. Which of the molecules gives rise to a molecular ion with an odd value of m/z? a. C4H8I2 b. C6H8N6 c. C7H7N3 d. C6H10Br2 ANSWER: c 17. Which of the molecules gives rise to a molecular ion with an odd value of m/z? a. C10H14O4 b. C7H10ClN c. C8H18N2 d. C6H12 ANSWER: b 18. What are the most common products of the fragmentation of a molecular ion? a. two radicals b. an anion and a cation c. a radical and a cation d. two cations ANSWER: c 19. Which of the following peaks is prominent in the mass spectrum of 1-butanol? Copyright Cengage Learning. Powered by Cognero.

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Chapter 14: Mass Spectrometry a. M − 17 b. M − 11 c. M − 10 d. M − 43 ANSWER: d 20. Which of the following bonds of the octane radical cation is least subject to fragmentation?

a. i b. ii c. iii d. iv ANSWER: a 21. Which of the following gives rise to a prominent M − 29 peak in the mass spectrum? a. 2-chloropentane b. 1-chloropentane c. 3-methylpentane d. 2-butanol ANSWER: c 22. Which of the following gives rise to a prominent M − 15 peak in the mass spectrum? a. heptane b. 2-bromopentane c. 1-heptanol d. 2-methylpropane ANSWER: d 23. Which of the following gives rise to a prominent peak in the mass spectrum at m/z of 43? a. 1-nonyne b. 4-octyne c. 3-nonyne d. 2-hexyne ANSWER: a 24. Which of the following does not give rise to a prominent M − 41 peak in the mass spectrum? a. 4-methyl-1-pentene b. 2,3-dimethyl-2-pentene c. 4-methyl-1-hexene d. 1-hexene ANSWER: b Copyright Cengage Learning. Powered by Cognero.

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Chapter 14: Mass Spectrometry 25. Which of the following is not prominent in the mass spectrum of 2-methyl-2-butanol? a. M − 15 b. M − 18 c. M − 21 d. M − 29 ANSWER: b 26. Which of the following alcohols does not give a prominent M − 15 ion? a. isopropyl alcohol b. tert-butyl alcohol c. 2-methyl-2-buthanol d. 1-heptanol ANSWER: d 27. Which of the following gives rise to a prominent M − 18 peak in the mass spectrum? a. cyclohexane b. hexane c. acetaldehyde d. 1-butanol ANSWER: d 28. Which of the following gives rise to a prominent M − 15 peak in the mass spectrum? a. cyclohexanone b. octane c. cyclopentanol d. 1,2-dimethylcyclohexane ANSWER: d 29. Which of the following gives rise to a prominent peak in the mass spectrum with m/z of 41, along with a strong molecular ion peak? a. 1-butene b. butyl chloride c. 1-pentanol d. pentanoic acid ANSWER: a 30. Which of the following gives rise to a prominent peak in the mass spectrum with m/z of 43? a. 3-octanol b. 2-octanol c. octanal d. octanoic acid ANSWER: c 31. Which of the following gives rise to a prominent peak in the mass spectrum with an m/z value of 45, resulting from a Copyright Cengage Learning. Powered by Cognero.

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Chapter 14: Mass Spectrometry radical cation formed by -cleavage of the main functional group? a. 1-butanol b. 2-butanol c. butanal d. butanoic acid ANSWER: d 32. Which of the following gives rise to a prominent peak in the mass spectrum with m/z of 60? a. 1-butanol b. 2-butanol c. butanal d. butanoic acid ANSWER: d 33. Which of the following gives rise to a prominent peak in the mass spectrum with m/z of M − 31? a. 2-methylhexanoic acid b. methyl 3-methylbutanoate c. ethyl hexanoate d. pentanoic acid ANSWER: b 34. Which of the following gives rise to a prominent peak in the mass spectrum with m/z of 91? a. 1-nonene b. 1-octanamine c. benzene d. isobutylbenzene ANSWER: d 35. Which of the following gives rise to a prominent peak in the mass spectrum with m/z of 30? a. 3-methyl-1-butanamine b. 2-methyl-2-pentanamine c. 1-pentanol d. pentanal ANSWER: a 36. Both mass spectrometry and infrared spectroscopy involve the interaction of molecules with electromagnetic energy. a. True b. False ANSWER: False 37. C6H15N could have a mass spectrum with M+ at m/z = 101 with a minor M+1 peak. a. True b. False ANSWER: True Copyright Cengage Learning. Powered by Cognero.

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Chapter 14: Mass Spectrometry 38. Loratidine is the active ingredient in the antihistamine Claritin®. Mass spectral analysis of loratidine shows M+ at m/z = 382 and M+ at m/z = 384 in an approximate ratio of 3:1 in intensity. This data indicates that loratidine contains fluorine. a. True b. False ANSWER: False 39. Alpha cleavage of the following compound would produce fragments at m/z = 43 and m/z = 119.

a. True b. False ANSWER: True 40. It is not possible distinguish 2,2-dimethylbutane from 2-methylpentane using mass spectrometry. a. True b. False ANSWER: False 41. Mass spectrometry and infrared spectroscopy are complementary techniques because mass spectrometry provides information about the molar mass and formula while infrared spectroscopy helps identify the functional groups in the formula. a. True b. False ANSWER: True 42. Consider the following mass spectrum

C5H12O might have been used to produce this spectrum. a. True b. False ANSWER: False

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Chapter 14: Mass Spectrometry 43. A monochloroalkane shows two parent ion peaks m/z at 92 and 94. The molecular formula of this compound

might be C3H7Cl. a. True b. False ANSWER: False 44. The mass spectrum of 1-pentanol shows an intense daughter ion peak at m/z = 31. This peak could be due to

the formation of CH3O+. a. True b. False ANSWER: True The following question(s) refer to the mass spectrum shown below.

Spectrum obtained from: SDBSWeb: http://www.aist.go.jp/RIODB/SDBS/ 45. The base peak in this spectrum occurs at a m/z of ______. ANSWER: 77 46. This compound contains C, H, and one other atom. The other atom from the mass spectrum is __________. ANSWER: Br bromine Bromine Refer to the mass spectrum of 2-methylbutane shown below to answer the following question(s). Copyright Cengage Learning. Powered by Cognero.

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Chapter 14: Mass Spectrometry

Spectrum obtained from: SDBSWeb: http://www.aist.go.jp/RIODB/SDBS/ 47. The peak at a m/z of _____ represents M+. ANSWER: 72 48. The peak at a m/z of _____ represents the base peak. ANSWER: 43 49. The peak at a m/z of _____ represents the following species.

ANSWER: 57 50. The peak at a m/z of _____ represents the following species.

ANSWER: 43 51. The peak at a m/z of _____ represents the following species. +CH2CH3 ANSWER: 29 52. The mass of the larger charged fragment produced by the dehydration of the following compound occurs at a m/z of _______. Copyright Cengage Learning. Powered by Cognero.

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Chapter 14: Mass Spectrometry

ANSWER: 126 53. Cyclohexene and hex-2-yne both have the molecular formula, C6H10. ___________________.

The mass spectrum below belongs to

ANSWER: cyclohexene Cyclohexene 54. Alpha cleavage of the following compound will produce a peak at a m/z of _______.

ANSWER: 31 55. Dehydration of the following compound will produce a peak at a m/z of _______.

ANSWER: 82 56. What is the most likely molecular formula of a compound that has a molecular ion in the EI mass spectrum with m/z of 97 and an M+1 peak that is 6.6% of the intensity of the molecular ion peak? ANSWER: C6H11N 57. What is the most likely molecular formula of a compound (that contains only C, H and O) which has a molecular ion in the EI mass spectrum with m/z of 104 and an M+1 peak that is 5.5% of the intensity of the molecular ion peak? Copyright Cengage Learning. Powered by Cognero.

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Chapter 14: Mass Spectrometry ANSWER: C5H12O2 58. What is the most likely molecular formula of a compound that has a molecular ion in the EI mass spectrum with m/z of 136, with a M+1 and M+2 peaks that are 4.4% and 49% of the intensity of the molecular ion peak, respectively. ANSWER: C4H9Br 59. What is the most likely molecular formula of a compound that has a molecular ion in the EI mass spectrum with m/z of 120, with a M+1 and M+2 peaks that are 6.6% and 24% of the intensity of the molecular ion peak, respectively. ANSWER: C6H13Cl 60. Provide the mass of the three most prominent fragment peaks that are observed in the EI mass spectrum of 2hexanone, CH3CH2CH2CH2COCH3 (molecular ion m/z = 100) and describe the processes that lead to each of these fragments. ANSWER: 85: loss of CH3• (15) by α-cleavage 72: loss of CH2=CH2 (28) by McLaferty rearrangement 43: loss of C4H9• (57) by α-cleavage 61. Provide the mass of the three most prominent fragment peaks that are observed in the EI mass spectrum of methyl pentanoate, CH3CH2CH2CH2CO2CH3 (molecular ion m/z = 116) and describe the processes that lead to each of these fragments. ANSWER: 88: loss of CH2=CH2 (28) by McLaferty rearrangement 85: loss of CH3O• (31) by α-cleavage 59: loss of C4H9• (57) by α-cleavage 62. Which C5H12O compound give the following EI mass spectrum?

ANSWER: 2-pentanol 63. Which C5H12O compound give the following EI mass spectrum?

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Chapter 14: Mass Spectrometry

ANSWER: 2-methyl-2-butanol 64. Which C6H12O carbonyl-containing compound shows a molecular ion peak at m/z 100 and significant

fragment peaks at m/z 85, 58, 57, 43 and 42 in the EI mass spectrum? ANSWER: 4-methyl-2-pentanone 65. Which C6H12O carbonyl-containing compound shows a molecular ion peak at m/z 100 and significant

fragment peaks at m/z 71, 58, 57, 43 and 29 in the EI mass spectrum? ANSWER: 2-methylpentanal 66. Mass spectrometry is an analytical technique used to determine the molecular masses, the molecular formulae, and the _____ of compounds. a. molecular radicals b. molecular structures c. functional groups d. solubilities ANSWER: b 67. Identify a basic function of a mass spectrometer. a. It separates molecules according to their functional groups. b. It measures only the abundance of isotopes present in molecules. c. It converts neutral molecules into positively or negatively charged ions. d. It separates ions according to their molecular masses. ANSWER: c Match the terms with their descriptions. a. EI-MS c. MALDI

b. FAB d. ESI-MS

68. Sample is bombarded with high-energy electrons ANSWER: a 69. Sample is bombarded with high-energy particles such as xenon atoms ANSWER: b Copyright Cengage Learning. Powered by Cognero.

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Chapter 14: Mass Spectrometry 70. Sample is bombarded with photons obtained from a laser source ANSWER: c 71. Sample is charged by passing it through a charged capillary tube ANSWER: d 72. Identify the compound(s) that will undergo McLafferty rearrangement during a mass spectral analysis.

a. Only I b. Only II c. Only I and II d. Only II and III ANSWER: c 73. Identify the ions “X” and “Y” in the given reaction.

a. X is

, and Y is

X is

, and Y is

X is

, and Y is

b. .

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Chapter 14: Mass Spectrometry d. X is

, and Y is

. ANSWER: d 74. The mass spectral analysis of toluene showed a base peak at m/z = 91. The base peak is because of _____. a.

ANSWER: c 75. A mass spectral analysis of 3-methyl-1-pentamine showed a base peak at m/z = 30. The base peak is because of _____. a. b. c. d. ANSWER: c

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Chapter 15: An Introduction to Organometallic Compounds 1. What term describes the process whereby an alkyl halide undergoes reaction with magnesium metal to give an alkylmagnesium bromide (Grignard reagent)? a. nucleophilic substitution b. electrophilic addition c. oxidative addition d. reductive elimination ANSWER: c 2. What is the change in oxidation state of the metal when magnesium reacts with an alkyl bromide to give an alkylmagnesium bromide (Grignard reagent)? a. 0 → +1 b. 0 → +2 c. 0 → −1 d. 0 → −2 ANSWER: b 3. Which of the following is the best choice of solvent for the formation of phenylmagnesium bromide by the reaction of bromobenzene with magnesium? a. isopropanol b. methanol c. diethyl ether d. acetic acid ANSWER: c 4. Which of the following is the best choice of solvent for the formation of phenyllithium by the reaction of bromobenzene with lithium? a. water b. ethanol c. THF d. acetic acid ANSWER: c 5. Which of the following bonds has the most ionic character? a. C−Zn b. C−Cu c. C−Al d. C−Hg ANSWER: c 6. Which of the following bonds has the most ionic character? a. C−Sn b. C−Cu c. C−Zn d. C−Li Copyright Cengage Learning. Powered by Cognero.

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Chapter 15: An Introduction to Organometallic Compounds ANSWER: d 7. Which of the following compounds is the strongest base? a. CH3CH2MgI b. CH3CH2CH2OH c. CH3CH2CH2OMgI d. CH3CH2CH3 ANSWER: a 8. Which of the following compounds is the strongest base? a. KOH b. PH3 c. CH3CH2CH2Li d. CH3CH2OH ANSWER: c 9. Which of the following molecules are deprotonated by magnesium bromide? a. propane, CH3CH2CH3 b. propene, CH2=CHCH3 c. triethylamine, (C2H5)3N d. methanethiol, CH3SH ANSWER: d 10. Which of the following mechanisms accounts for the acid-base reaction of ethylmagnesum bromide with acetylene to give acetylide anion?

a. 1 b. 2 c. 3 d. 4 ANSWER: a 11. What is the major organic product obtained from the following sequence of reactions?

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Chapter 15: An Introduction to Organometallic Compounds

a. 2-methylbutane b. 3-methyl-1-butanol c. 3-methyl-2-butene d. 3-methyl-2-butanol ANSWER: a 12. What is the major organic product obtained from the following sequence of reactions?

a. 2-pentanol b. pentane c. 1-pentene d. (E)-2-pentene ANSWER: b 13. What is the major organic product obtained from the following reaction?

a. 1 b. 2 c. 3 d. 4 ANSWER: b 14. What is the major organic product obtained from the following reaction?

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Chapter 15: An Introduction to Organometallic Compounds

a. 1 b. 2 c. 3 d. 4 ANSWER: d 15. Which of the following alcohols can be prepared from a Grignard reagent and ethylene oxide?

a. only 1 b. only 1 and 2 c. only 1, 2 and 3 d. 1, 2, 3 and 4 ANSWER: b 16. Which of the following alcohols can be prepared from a Grignard reagent and ethylene oxide?

a. only 1 and 2 b. only 1 and 4 c. only 1, 2 and 3 d. only 2 and 4 Copyright Cengage Learning. Powered by Cognero.

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Chapter 15: An Introduction to Organometallic Compounds ANSWER: d 17. What is the major organic product obtained from the following sequence of reactions?

a. 1 b. 2 c. 3 d. 4 ANSWER: b 18. What is the major organic product obtained from the following sequence of reactions?

a. 1 b. 2 c. 3 d. 4 ANSWER: c 19. Which combination(s) of alkyl bromide and epoxide can be used to prepare the following product by addition of the Grignard reagent derived from the alkyl bromide to the epoxide?

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Chapter 15: An Introduction to Organometallic Compounds

a. only 1 b. only 2 c. only 1 and 3 d. only 2 and 4 ANSWER: b 20. Which combination(s) of alkyl bromide and epoxide can be used to prepare the following product by addition of the Grignard reagent derived from the alkyl bromide to the epoxide?

a. only 1 b. only 2 c. only 1 and 3 d. only 2 and 4 ANSWER: a 21. What is the major organic product obtained from the following reaction?

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Chapter 15: An Introduction to Organometallic Compounds

a. 1 b. 2 c. 3 d. 4 ANSWER: a 22. What is the major organic product obtained from the following reaction?

a. (E) 2-iodo-2-butene b. 1-iodo-2-methylpropene c. methylcyclopropane d. (E) 2-butene ANSWER: d 23. What is the major organic product obtained from the following reaction?

a. 1 b. 2 c. 3 d. 4 ANSWER: a 24. What is the major organic product obtained from the following sequence of reactions?

a. 2-methylheptane b. 3-methylheptane c. 2-methyloctane d. 3-methyloctane Copyright Cengage Learning. Powered by Cognero.

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Chapter 15: An Introduction to Organometallic Compounds ANSWER: c 25. What is the major organic product obtained from the following sequence of reactions?

a. (E) 6,6-dimethyl-1-hexene b. (E) 5,5-dimethyl-1-heptene c. (E) 6,6-dimethyl-1-heptene d. (E) 6,6-dimethyl-2-heptene ANSWER: d 26. What is the major organic product obtained from the following sequence of reactions?

a. (Z)-6-methyl-2-heptene b. (E)-4-methyl-2-pentene c. 2-methylheptane d. 3-methylheptane ANSWER: c 27. What is the major organic product obtained from the following sequence of reactions?

a. 2-iodo-7-methyloctane b. (E)-7-methyl-1-octene c. (E)-7-methyl-2-octene d. (E)-7-methyl-3-octene ANSWER: d 28. Which of the following is not true regarding the carbon atom of the methylene carbene, H2C: ? a. it is sp2 hybridized b. it is an electron-rich compound c. it is highly reactive d. it has a lone pair of electrons in an sp2 molecular orbital ANSWER: b

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Chapter 15: An Introduction to Organometallic Compounds 29. What reactive intermediates are involved in the following reaction?

a. the trichloromethyl anion (Cl3C: −) and dichlorocarbene (Cl2C:) b. the trichloromethyl cation (Cl3C+) c. the cyclohexyl carbocation d. the cyclic chloronium ion derived from cyclohexene ANSWER: a 30. What is the major organic product obtained from the following reaction?

a. 1 b. 2 c. 3 d. 4 ANSWER: c 31. What is the major organic product obtained from the following reaction?

a. 1 b. 2 c. 3 d. 4 ANSWER: b 32. What is the major organic product obtained from the following reaction?

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Chapter 15: An Introduction to Organometallic Compounds a. 1 b. 2 c. 3 d. 4 ANSWER: c 33. What is the major organic product obtained from the following reaction?

a. 1 b. 2 c. 3 d. 4 ANSWER: a 34. What is the major organic product obtained from the following sequence of reactions?

a. 1 b. 2 c. 3 d. 4 ANSWER: b 35. What is the major organic product obtained from the following sequence of reactions?

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Chapter 15: An Introduction to Organometallic Compounds

a. 1 b. 2 c. 3 d. 4 ANSWER: c 36. The reaction of an alkene with dichlorocarbene is stereospecific. a. True b. False ANSWER: True 37. The following reaction would be classified as a Simmons-Smith reaction.

a. True b. False ANSWER: True 38. The product of the following reaction would be a cyclopropane.

a. True b. False ANSWER: True 39. The following conversion could be accomplished using a Grignard reaction.

a. True Copyright Cengage Learning. Powered by Cognero.

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Chapter 15: An Introduction to Organometallic Compounds b. False ANSWER: False 40. In a coupling reaction using a Gilman reagent, both of the Gilman reagent alkyl groups are transferred in the reaction a. True b. False ANSWER: False 41. Both Grignard reagents and Gilman reagents are synthetically useful because they form new carbon to carbon bonds. a. True b. False ANSWER: True 42. In the formation of the ether soluble complex in a Grignard reaction, magnesium acts as a Lewis base and the ether as a Lewis acid. a. True b. False ANSWER: False 43. The percent ionic character of a C—Mg bond is less than that of a C—Cu bond. a. True b. False ANSWER: False 44. In organometallic bonds, carbon attains a partial negative charge which makes it both basic and nucleophilic. a. True b. False ANSWER: True Consider the following reaction to answer the following question(s).

45. Substance A is termed a ___________reagent. ANSWER: Grignard grignard 46. Substance ____ is the nucleophile in the reaction. ANSWER: A 47. Substance ____ is the electrophile in the reaction. Copyright Cengage Learning. Powered by Cognero.

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Chapter 15: An Introduction to Organometallic Compounds ANSWER: B 48. Substance A is formed from the reaction of Mg with ______________. ANSWER: bromocyclohexane Consider the reaction below to answer the following question(s).

49. The reaction intermediate formed by the reaction of KOH with the alkene is called_____________. ANSWER: dichlorocarbene 50. In this reaction the alkene would be classified as the: a. electrophile b. nucleophile c. Lewis base d. both b and c ANSWER: a 51. Name the product of the following reaction.

ANSWER: cis-1,2-dimethylcyclopropane cis-1,2-dimethylcyclopropane Consider the following conversion.

Use this reacton to answer the following questions. 52. The first step in this conversion would be reaction with: a. Mg/ether b. PCC c. oxirane ANSWER: a 53. The second step in this conversion would be reaction with: a. Mg/ether b. PCC c. oxirane ANSWER: c Copyright Cengage Learning. Powered by Cognero.

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Chapter 15: An Introduction to Organometallic Compounds 54. The first step in this conversion would be reaction with: a. Mg/ether b. PCC c. oxirane ANSWER: b 55. The name of the product of the reaction of 2-chlorobutane with 1.) Li, 2.) CuI, 3.) 1-bromobutane would be _______________________. ANSWER: 3-methylheptane 56. Consider the following reaction.

The name of the product that should be placed in the box is __________________. ANSWER: ethylcyclohexane 57. What is the major organic product obtained from the following sequence of reactions?

ANSWER:

58. What is the major organic product obtained from the following reaction?

ANSWER:

59. What is the major organic product obtained from the following sequence of reactions?

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Chapter 15: An Introduction to Organometallic Compounds ANSWER:

60. What is the major organic product obtained from the following reaction?

ANSWER: 61. What is the major organic product obtained from the following sequence of reactions?

ANSWER:

62. What is the major organic product obtained from the following reaction?

ANSWER:

63. What is the major organic product obtained from the following reaction?

ANSWER:

64. What is the major organic product obtained from the following sequence of reactions?

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Chapter 15: An Introduction to Organometallic Compounds

ANSWER:

65. What is the major organic product obtained from the following reaction?

ANSWER:

66. What is the major organic product obtained from the following sequence of reactions?

ANSWER:

67. What is the oxidation state of Li in methyllithium? a. +2 b. +1 c. 0 d. –1 ANSWER: b 68. Diiodomethane and zinc dust activated by a small amount of copper in a diethyl ether solvent produce _____. ANSWER: iodomethylzinc iodide 69. What is the final product of the following reaction?

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Chapter 15: An Introduction to Organometallic Compounds

ANSWER: a 70. The addition of a dichlorocarbene to an alkene will show _____ stereoselectivity. ANSWER: syn 71. If the electronegativity of carbon is 2.5 and the electronegativity tin of is 1.8, then the percent ionic character of the carbon–tin bond is _____%. a. 28 b. 59 c. 64 d. 50 Copyright Cengage Learning. Powered by Cognero.

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Chapter 15: An Introduction to Organometallic Compounds ANSWER: a 72. Identify the final product of the following reaction.

ANSWER: a 73. Identify the final product of the following reaction.

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Chapter 15: An Introduction to Organometallic Compounds b.

ANSWER: d

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Chapter 16: Aldehydes and Ketones 1. What is the IUPAC name of the following compound?

a. 3-methyl-3-phenylpropanol b. 3-phenylbutanal c. 3-phenyl-1-butanone d. 3-phenylbutanoic acid ANSWER: b 2. What is the IUPAC name of the following compound?

a. 4-phenyl-3-hexanone b. 3-phenyl-4-hexanone c. 1,2-diethyl-2-phenylethanal d. 1-methyl-1-phenyl-2-butanone ANSWER: a 3. What is the IUPAC name of the following compound?

a. (E)-4-methyl-4-hepten-3-one b. (Z)-4-methyl-4-hepten-3-one c. (E)-4-methyl-3-hepten-5-one d. (Z)-4-methyl-3-hepten-5-one ANSWER: a 4. What is the IUPAC name of the following compound?

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Chapter 16: Aldehydes and Ketones

a. 4,4-diethyl-3-buten-2-one b. 4-ethyl-3-hexen-2-one c. (Z)-4-ethyl-3-hexen-2-one d. 3-ethyl-4-hexen-5-one ANSWER: b 5. What is the IUPAC name of the following compound?

a. (2S,4R)-dimethylpentanal b. (2S,4S)-dimethylpentanal c. (R)-2,4-dimethylpentanal d. (S)-2,4-dimethylpentanal ANSWER: d 6. What is the IUPAC name of the following compound?

a. (S)-3,4,4-trimethylpentanal b. (R)-3,4,4-trimethylpentanal c. (R)-3-tert-butyl-3-methylpropanal d. (R)-3-tert-butylbutanal ANSWER: b 7. What is the correct assignment of the names of the following ketones?

a. 1 = acetone; 2 = phenol; 3 = benzaldehyde b. 1 = acetone; 2 = acetophenone; 3 = benzophenone Copyright Cengage Learning. Powered by Cognero.

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Chapter 16: Aldehydes and Ketones c. 1 = formaldehyde; 2 = benzaldehyde; 3 = acetophenone d. 1 = acetaldehyde; 2 = acetophenone; 3 = benzaldehyde ANSWER: b 8. What is the correct assignment of the names of the following aldehydes and ketones?

a. 1 = acetone; 2 = acetaldehyde; 3 = formaldehyde b. 1 = acetaldehyde; 2 = acetophenone; 3 = benzophenone c. 1 = formaldehyde; 2 = acetaldehyde; 3 = acetone d. 1 = acetaldehyde; 2 = acetone; 3 = acetophenone ANSWER: c 9. What is the major organic product obtained from the following reaction?

a. 2,3-dimethyl-3-heptanol b. 2,4-dimethyl-4-heptanol c. 3,5-dimethyl-4-heptanol d. 3,5-dimethyl-3-heptanol ANSWER: b 10. What is the major organic product obtained from the following reaction?

a. 2,3-dimethyl-3-heptanol b. 2,4-dimethyl-4-heptanol c. 2,5-dimethyl-4-heptanol d. 2,5-dimethyl-3-heptanol ANSWER: c 11. What is the major organic product obtained from the following reaction?

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Chapter 16: Aldehydes and Ketones

a. 2-phenyl-2-butanol b. 3-phenyl-2-butanol c. 3-phenylbutanone d. propiophenone, PhCOCH2CH3 ANSWER: a 12. What is the major organic product obtained from the following reaction?

a. 1-phenyl-1-butanol b. 1-phenyl-2-butanol c. 2-phenyl-1-butanol d. butyrophenone, PhCOCH2CH2CH3 ANSWER: a 13. Which combination(s) of alkyl bromide and carbonyl compound can be used to prepare the following product by addition of the Grignard reagent derived from the alkyl bromide to the carbonyl compound?

a. only 1 b. only 3 c. only 1 and 4 d. only 2 and 3 Copyright Cengage Learning. Powered by Cognero.

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Chapter 16: Aldehydes and Ketones ANSWER: d 14. Which combination(s) of alkyl bromide and carbonyl compound can be used to prepare the following product by addition of the Grignard reagent derived from the alkyl bromide to the carbonyl compound?

a. only 1 b. only 3 c. only 1 and 3 d. only 2 and 4 ANSWER: b 15. Which combination(s) of alkyl bromide and carbonyl compound can be used to prepare the following product by addition of the Grignard reagent derived from the alkyl bromide to the carbonyl compound?

a. only 1 and 2 b. only 3 and 4 c. only 2 and 3 d. only 1, 2 and 3 ANSWER: d 16. Which combination(s) of alkyl bromide and carbonyl compound can be used to prepare the following product by Copyright Cengage Learning. Powered by Cognero.

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Chapter 16: Aldehydes and Ketones addition of the Grignard reagent derived from the alkyl bromide to the carbonyl compound?

a. only 1 and 2 b. only 3 and 4 c. only 2 and 3 d. only 1, 2 and 3 ANSWER: a 17. What is the major organic product obtained from the following reaction?

a. 1 b. 2 c. 3 d. 4 ANSWER: b 18. What is the major organic product obtained from the following sequence of reactions?

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Chapter 16: Aldehydes and Ketones

a. 1 b. 2 c. 3 d. 4 ANSWER: a 19. What is the major organic product obtained from the following reaction?

a. 1 b. 2 c. 3 d. 4 ANSWER: a 20. What is the major organic product obtained from the following reaction?

a. 1 b. 2 c. 3 Copyright Cengage Learning. Powered by Cognero.

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Chapter 16: Aldehydes and Ketones d. 4 ANSWER: a 21. What is the major organic product obtained from the following reaction?

a. 1-butene b. 2-butene c. 2-methylpropene d. 2-methyl-1-propanol ANSWER: c 22. What is the major organic product obtained from the following reaction?

a. 2-methyl-2-heptene b. 3-ethyl-2-pentene c. (Z) 2-methyl-3-heptene d. (E) 2-methyl-3-heptene ANSWER: b 23. What is the major organic product obtained from the following reaction?

a. (E)-3-methyl-2-pentene b. (Z)-3-methyl-2-pentene c. 2-methyl-2-pentene d. 4-methyl-1-pentene ANSWER: c 24. What is the major organic product obtained from the following reaction?

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Chapter 16: Aldehydes and Ketones

a. (E)-3-methyl-2-pentene b. (Z)-3-methyl-2-pentene c. 2-methyl-2-pentene d. 4-methyl-1-pentene ANSWER: c 25. Which combination(s) of alkyl bromide and carbonyl compound can be used to prepare the following product by reaction of the Wittig reagent derived from the alkyl bromide with the carbonyl compound?

a. only 1 and 2 b. only 2 and 4 c. only 2 and 3 d. only 1, 2 and 3 ANSWER: b 26. Which combination(s) of alkyl bromide and carbonyl compound can be used to prepare the following product by reaction of the Wittig reagent derived from the alkyl bromide with the carbonyl compound?

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Chapter 16: Aldehydes and Ketones

a. only 1 and 2 b. only 1 and 3 c. only 2 and 4 d. only 1, 2 and 3 ANSWER: a 27. Which of the following is not true about the Wittig reaction? a. triphenylphosphine reacts with 2° alkyl bromides by an SN2 reaction to give an alkyltriphenylphosphonium bromide b. treatment of a phosphine with a methyl, primary, or secondary alkyl halide gives a phosphonium salt by an SN2 pathway c. phosphonium ylides are nucleophilic d. Wittig reagents with anionstabilizing groups (such as carbonyls) adjacent to the negatively charged carbon are more Z selective ANSWER: d 28. Which of the following is the best description of the formation of alkene from oxaphosphetane involved in a Wittig reaction? a. formation of carbocation b. decomposition c. Ei elimination d. free radical rearrangement ANSWER: b 29. What is the correct assignment of the names of the following functional groups?

a. 1 = enol; 2 = hydrate; 3 = acetal; 4 = hemiacetal Copyright Cengage Learning. Powered by Cognero.

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Chapter 16: Aldehydes and Ketones b. 1 = acetal; 2 = hydrate; 3 = enol; 4 = hemiacetal c. 1 = hydrate; 2 = hemiacetal; 3 = acetal; 4 = enol d. 1 = enol; 2 = hydrate; 3 = hemiacetal; 4 = enol ANSWER: c 30. What is the correct assignment of the names of the following functional groups?

a. 1 = acetal; 2 = hydrate; 3 = acetal; 4 = hemiacetal b. 1 = acetal; 2 = enol; 3 = hydrate; 4 = hemiacetal c. 1 = hydrate; 2 = hemiacetal; 3 = acetal; 4 = enol d. 1 = enol; 2 = hydrate; 3 = hemiacetal; 4 = enol ANSWER: b 31. What is the major organic product obtained from the following reaction?

a. 1 b. 2 c. 3 d. 4 ANSWER: d 32. What is the major organic product obtained from the following reaction?

a. 1 b. 2 c. 3 d. 4 ANSWER: a Copyright Cengage Learning. Powered by Cognero.

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Chapter 16: Aldehydes and Ketones 33. Which ketone-diol undergoes cyclization to form the following acetal?

a. 1 b. 2 c. 3 d. 4 ANSWER: a 34. Which ketone-diol undergoes cyclization to form the following acetal?

a. 1 b. 2 c. 3 d. 4 ANSWER: d Copyright Cengage Learning. Powered by Cognero.

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Chapter 16: Aldehydes and Ketones 35. What is the major organic product obtained from the following reaction?

a. 1 b. 2 c. 3 d. 4 ANSWER: b 36. What is the major organic product obtained from the following reaction?

a. 1 b. 2 c. 3 d. 4 ANSWER: c 37. What is the correct assignment of the names of the following functional groups?

a. 1 = imine; 2 = amine; 3 = hydrazone; 4 = oxime b. 1 = hydrazone; 2 = amine; 3 = imine; 4 = oxime c. 1 = oxime; 2 = imine; 3 = amine; 4 = hydrazone d. 1 = imine; 2 = hydrazone; 3 = oxime; 4 = amine ANSWER: b 38. What is the correct assignment of the names of the following functional groups? Copyright Cengage Learning. Powered by Cognero.

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Chapter 16: Aldehydes and Ketones

a. 1 = imine; 2 = amine; 3 = hydrazone; 4 = oxime b. 1 = hydrazone; 2 = amine; 3 = imine; 4 = oxime c. 1 = oxime; 2 = imine; 3 = amine; 4 = hydrazone d. 1 = imine; 2 = hydrazone; 3 = oxime; 4 = amine ANSWER: c 39. What is the major organic product obtained from the following reaction?

a. 1 b. 2 c. 3 d. 4 ANSWER: a 40. What is the major organic product obtained from the following reaction?

a. 1 b. 2 c. 3 d. 4 ANSWER: d 41. What is the major organic product obtained from the following reaction? Copyright Cengage Learning. Powered by Cognero.

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Chapter 16: Aldehydes and Ketones

a. 1 b. 2 c. 3 d. 4 ANSWER: a 42. What is the major organic product obtained from the following reaction?

a. 1 b. 2 c. 3 d. 4 ANSWER: c 43. What is the major organic product obtained from the following reaction?

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Chapter 16: Aldehydes and Ketones

a. 1 b. 2 c. 3 d. 4 ANSWER: b 44. What is the major organic product obtained from the following reaction?

a. 1 b. 2 c. 3 d. 4 ANSWER: c 45. What is the major organic product obtained from the following reaction?

a. 1 b. 2 Copyright Cengage Learning. Powered by Cognero.

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Chapter 16: Aldehydes and Ketones c. 3 d. 4 ANSWER: a 46. What is the major organic product obtained from the following reaction?

a. 1 b. 2 c. 3 d. 4 ANSWER: b 47. What is the major organic product obtained from the following reaction?

a. 1 b. 2 c. 3 d. 4 ANSWER: c 48. Which combination(s) of amine and carbonyl compound can be used to prepare the following product by reductive Copyright Cengage Learning. Powered by Cognero.

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Chapter 16: Aldehydes and Ketones amination?

a. only 1 and 2 b. only 2 and 4 c. only 2 and 3 d. only 1, 2 and 3 ANSWER: a 49. Which combination(s) of amine and carbonyl compound can be used to prepare the following product by reductive amination?

a. only 1 b. only 3 c. only 1 and 3 d. only 1, 2 and 4 ANSWER: b 50. What is the major organic product obtained from the following reaction?

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Chapter 16: Aldehydes and Ketones

a. 1 b. 2 c. 3 d. 4 ANSWER: b 51. What is the major organic product obtained from the following reaction?

a. 1 b. 2 c. 3 d. 4 ANSWER: d 52. What is the major organic product obtained from the following reaction?

a. 2-pentanol b. pentane c. 1-pentene d. (E) 2-pentene ANSWER: a 53. What is the major organic product obtained from the following reaction?

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Chapter 16: Aldehydes and Ketones a. 2-methypentane b. 4-methyl-2-pentanol c. 4-methyl-1-pentene d. (E) 4-methyl-2-pentene ANSWER: b 54. What is the major organic product obtained from the following reaction?

a. 2-pentanone b. (E)-3-penten-2-ol c. 2-pentanol d. 4-hydroxy-2-pentanone ANSWER: b 55. What is the major organic product obtained from the following reaction?

a. 2-pentanone b. (E)-3-penten-2-ol c. 2-pentanol d. 4-hydroxy-2-pentanone ANSWER: a 56. What is the major organic product obtained from the following reaction?

a. 2-pentanone b. (E)-3-penten-2-ol c. 2-pentanol d. 4-hydroxy-2-pentanone ANSWER: c 57. What is the major organic product obtained from the following reaction?

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Chapter 16: Aldehydes and Ketones

a. 1 b. 2 c. 3 d. 4 ANSWER: c 58. What is the major organic product obtained from the following reaction?

a. 1 b. 2 c. 3 d. 4 ANSWER: d 59. What is the major organic product obtained from the following sequence of reactions?

a. 1 b. 2 Copyright Cengage Learning. Powered by Cognero.

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Chapter 16: Aldehydes and Ketones c. 3 d. 4 ANSWER: a 60. What is the major organic product obtained from the following sequence of reactions?

a. 1 b. 2 c. 3 d. 4 ANSWER: c 61. What is the major organic product obtained from the following sequence of reactions?

a. 1 b. 2 c. 3 d. 4 ANSWER: a 62. What is the major organic product obtained from the following sequence of reactions?

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Chapter 16: Aldehydes and Ketones

a. 1 b. 2 c. 3 d. 4 ANSWER: c 63. What is the major organic product obtained from the following sequence of reactions?

a. 1 b. 2 c. 3 d. 4 ANSWER: b 64. What is the major organic product obtained from the following sequence of reactions?

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Chapter 16: Aldehydes and Ketones

a. 1 b. 2 c. 3 d. 4 ANSWER: a 65. What is the relationship between the following two structures?

a. tautomers b. constitutional isomers, but not tautomers c. resonance structures d. stereoisomers ANSWER: a 66. What is the relationship between the following two structures?

a. tautomers b. constitutional isomers, but not tautomers c. resonance structures d. stereoisomers ANSWER: c 67. What is the relationship between the following two structures?

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Chapter 16: Aldehydes and Ketones

a. tautomers b. constitutional isomers, but not tautomers c. resonance structures d. stereoisomers ANSWER: a 68. Which of the following has the highest Keq for enolization?

a. 1 b. 2 c. 3 d. 4 ANSWER: c 69. Which of the following has the highest Keq for enolization?

a. 1 b. 2 c. 3 d. 4 ANSWER: c 70. What type of reaction takes place upon treatment of a ketone with organolithium reagent to form a tertiary alcohol? a. nucleophilic addition b. bimolecular elimination c. electrophilic addition d. nucleophilic substitution ANSWER: a Copyright Cengage Learning. Powered by Cognero.

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Chapter 16: Aldehydes and Ketones 71. Which of the following is the best description of the mechanism of the reaction between an aldehyde or a ketone and a secondary amine form an enamine after acidcatalyzed dehydration of the intermediate formed? a. concerted bimolecular substitution b. nucleophilic addition followed by elimination c. elimination followed by nucleophilic addition d. electrophilic addition followed by anionic rearrangement ANSWER: b 72. Which of the following statements is true? a. A carbon-oxygen double bond is non-polar in carbonyl compounds b. Addition of a nucleophile to a carbonyl group changes the hybridization of the carbonyl carbon from sp3 to sp2 hybridization c. In general, ketones are more electrophilic than aldehydes d. Nucleophilic addition to carbonyl groups can be catalyzed by acid or base ANSWER: d 73. Which of the following statements is not true? a. Reaction of pentanal with methanol in the presence of acid gives an acetal b. Reaction of propanal with methanol in the presence of base gives an acetal c. Reaction of acetone with methanol in the presence of acid or base gives a hemiacetal d. Reaction of hexanone with ethanol in the presence of acid gives an acetal ANSWER: b 74. Which of the following statements is not true? a. Hemiacetals are often not stable relative to starting materials, but they react further with alcohols to form acetals an d a molecule of water b. Acetals are considerably more stable than hemiacetals c. The formation of acetals from hemiacetals and its reverse is catalyzed by acids, not by bases d. Reaction of ketones with excess of alcohol in presence of acid gives a dialkyl hemiacetal ANSWER: d 75. Which of the following is an intermediate in the reaction of 2butanone with methyltriphenylphosphonium iodide to form 2-methyl-1-butene? a. free radical b. betaine c. enol d. tertiary carbocation ANSWER: b 76. Which of the following is a reactive intermediate in the base-catalyzed racemization of (R)-3-phenyl-2-butanone? a. carbanion Copyright Cengage Learning. Powered by Cognero.

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Chapter 16: Aldehydes and Ketones b. enol c. enolate d. radical ANSWER: c 77. What is the reactivity of Br2 in the acid-catalyzed bromination of acetophenone? a. acid b. base c. nucleophile d. electrophile ANSWER: d 78. An 1H NMR is run on a sample. This spectrum is shown below.

Based on this data the sample is probably an aldehyde. a. True b. False ANSWER: True 79. Of the types of reactions that characterize carbonyl groups, the following reaction would be classified as an α substitution.

a. True b. False ANSWER: True 80. The correct name for the following compound is 3-oxoheptanal.

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Chapter 16: Aldehydes and Ketones a. True b. False ANSWER: False 81. The correct name for the following compound is trans-1,3-cyclopentanedicarbaldehyde.

a. True b. False ANSWER: False 82. Consider the following reaction.

The mechanism for this reaction is shown below.

a. True b. False ANSWER: True 83. Consider the following reaction.

The product of this reaction is a vicinal diol. a. True b. False ANSWER: False 84. Many nucleophilic addition reactions of aldehydes and ketones are catalyzed by acid or base. Bases catalyze hydration by converting the water to hydroxide ion, a much better nucleophile a. True b. False ANSWER: True 85. The product of the following reaction would be an imine.

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Chapter 16: Aldehydes and Ketones

a. True b. False ANSWER: False 86. The following compound would be classified as a hemiacetal..

a. True b. False ANSWER: True 87. 3-hydroxybutanal can exist in equilibrium as a cyclic hemiacetal. a. True b. False ANSWER: False 88. The following compound can be produced by the reaction of cyclohexanecarbaldehyde and

a. True b. False ANSWER: False Consider the reaction below to answer the following question(s). Use letters where appropriate to answer the questions.

89. The nucleophile in this reaction is _____. ANSWER: A Copyright Cengage Learning. Powered by Cognero.

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Chapter 16: Aldehydes and Ketones 90. The catalyst in this reaction is _____. ANSWER: C 91. The product of this reaction is called a(n)___________. ANSWER: acetal 92. The first step in the reaction mechanism is the protonation of the ________group. ANSWER: carbonyl ketone Consider each of the spectrum and answer the following questions using the appropriate number. 93. The peak labeled _____ would allow the distinction of an aldehyde from a ketone based on this spectrum.

ANSWER: 2 94. The peak labeled _____ would allow the distinction of an aldehyde from a ketone based on this spectrum.

ANSWER: 1 Answer each of the following questions with the appropriate number. 95. The number of α-hydrogens in the following compound is _____.

ANSWER: 4 four Copyright Cengage Learning. Powered by Cognero.

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Chapter 16: Aldehydes and Ketones 96. The number of hydrogens in the following compound that will be exchanged for deuterium upon reaction

with D2O and an acid catalyst is _____.

ANSWER: 4 four 97. In the following compound, the most acidic hydrogen atom(s) are numbered as _____.

ANSWER: 2 two 98. Of the compounds shown below, the one numbered _____ has the highest boiling point.

ANSWER: 2 two 99. Of the compounds shown below, the one numbered _____ is an imine.

ANSWER: 2 two 100. Of the compounds shown below, the one numbered _____ is an enamine.

ANSWER: 3 three 101. Of the compounds shown below, the one numbered _____ is an enamine.

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Chapter 16: Aldehydes and Ketones

ANSWER: 3 three 102. What is the IUPAC name of the following compound?

ANSWER: (S)-2-chloropentanal 103. What is the IUPAC name of the following compound?

ANSWER: (S)-3-methyl-2-pentanone 104. What is the major organic product obtained from the following reaction?

ANSWER:

105. What is the major organic product obtained from the following reaction?

ANSWER:

106. What is the major organic product obtained from the following reaction? Copyright Cengage Learning. Powered by Cognero.

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Chapter 16: Aldehydes and Ketones

ANSWER:

107. What is the major organic product obtained from the following reaction?

ANSWER:

108. What is the major organic product obtained from the following reaction?

ANSWER:

109. What is the major organic product obtained from the following reaction?

ANSWER:

110. What is the major organic product obtained from the following reaction?

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Chapter 16: Aldehydes and Ketones ANSWER:

111. What is the major organic product obtained from the following reaction?

ANSWER:

112. What is the major organic product obtained from the following reaction?

ANSWER:

113. What is the major organic product obtained from the following reaction?

ANSWER:

114. What is the major organic product obtained from the following reaction?

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Chapter 16: Aldehydes and Ketones ANSWER:

115. What is the major organic product obtained from the following reaction?

ANSWER:

116. What is the major organic product obtained from the following reaction?

ANSWER:

117. What is the major organic product obtained from the following sequence of reactions?

ANSWER:

118. What is the major organic product obtained from the following sequence of reactions?

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Chapter 16: Aldehydes and Ketones ANSWER:

119. What is the major organic product obtained from the following sequence of reactions?

ANSWER:

120. What is the major organic product obtained from the following sequence of reactions?

ANSWER:

121. Identify “X” and “Y” in the given reaction.

a. X is LiAlH4/THF, and Y is H2/Rh. b. X is H2/Pt, and Y is LiAlH4. c. X is H2/Rh, and Y is LiAlH4/THF. d. X is H2, and Y is NaBH4. ANSWER: c 122. “X” is a substance involved in lysine biosynthesis. “X” is a dicarboxylic acid and can be synthesized by the oxidation of cycloheptanone. Identify “X”. Copyright Cengage Learning. Powered by Cognero.

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Chapter 16: Aldehydes and Ketones a. cycloheptanol b. heptanedioic acid c. heptan-1-oic acid d. heptamethylenediamine ANSWER: b 123. The reduction of aldehydes by LAH is carried out in aprotic solvents such as THF because _____. a. LAH reacts vigorously with aprotic solvents to release hydrogen gas b. LAH reacts vigorously with protic solvents to release hydrogen gas c. LAH reacts with aprotic solvents to form lithium hydroxide d. LAH reduces aldehydes to dienes only in aprotic solvents ANSWER: b 124. Identify the product obtained in the following reaction.

ANSWER: c 125. Identify the solvent(s) used in 1H-NMR spectroscopy. Copyright Cengage Learning. Powered by Cognero.

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Chapter 16: Aldehydes and Ketones

a. Only I and II b. Only II and III c. I, III, and IV d. I, II, and III ANSWER: d 126. What is the advantage of using deuterated solvents in 1H-NMR spectroscopy? ANSWER: 1H-NMR spectroscopy is used to study the structure of molecules containing hydrogen atoms. If solvents containing hydrogen atoms are used during the analysis, the 1H-NMR peak of the solvent would interfere with the spectrum of the compound. Hence, deuterated solvents are preferred as they lack hydrogen atoms. 127. When an acid is added to an enantiomerically pure R-3-phenyl-2-butanone dissolved in ethanol, its optical activity drops to zero. The zero optical activity occurs because of _____. a. racemization b. isomerism c. resonance d. mesomerism ANSWER: a

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Chapter 17: Carboxylic Acids 1. What is the IUPAC name of the following compound

a. 3,3-dimethylhexanoic acid b. 2,2-dimethylpentanoic acid c. 2,2-dimethylpentanal d. 4,4-dimethyl-6-hexanoyl acid ANSWER: a 2. What is the IUPAC name of the following compound?

a. 5,5-dimethyl-5-phenylpentanoic acid b. 5-methyl-5-phenylhexanoic acid c. 2,2-dimethylphenylpropanoic acid d. 5,5-dimethyl-5-phenylbutanal ANSWER: b 3. What is the IUPAC name of the following compound?

a. (E)-4-ethyl-3-pentenoic acid b. (Z)-4-ethyl-3-pentenoic acid c. (E)-4-methyl-3-hexenoic acid d. (Z)-4-methyl-3-hexenoic acid ANSWER: d 4. What is the IUPAC name of the following compound?

a. 4-methyl-3-phenyl-3-pentenoic acid b. 4,4-dimethyl-3-phenyl-3-butenoic acid c. 3-phenyl-2-methyl-2-penten-5-oic acid Copyright Cengage Learning. Powered by Cognero.

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Chapter 17: Carboxylic Acids d. (Z)-3-methyl-2-phenyl-2-butenoic acid ANSWER: a 5. What is the IUPAC name of the following compound?

a. (2R,3R)-dihydroxybutanedioic acid b. (2S,3S)-dihydroxybutanedioic acid c. (2R,3S)-dihydroxybutanedioic acid d. (2S,3R)-dihydroxybutanedioic acid ANSWER: b 6. What is the IUPAC name of the following compound?

a. cis-4-methylcyclohexanecarboxylic acid b. trans-4-methylcyclohexanecarboxylic acid c. cis-3-methylcyclohexanecarboxylic acid d. trans-3-methylcyclohexanecarboxylic acid ANSWER: a 7. What is the correct assignment of the names of the following substituted benzenes?

a. 1 = salicylic acid; 2 = benzoic acid; 3 = terephthalic acid; 4 = phthalic acid b. 1 = terephthalic acid; 2 = salicylic acid; 3 = benzoic acid; 4 = phthalic acid c. 1 = salicylic acid; 2 = terephthalic acid; 3 = phthalic acid; 4 = benzoic acid d. 1 = phthalic acid; 2 = benzoic acid; 3 = terephthalic acid; 4 = salicylic acid ANSWER: a 8. What is the correct assignment of the names of the following substituted benzenes? Copyright Cengage Learning. Powered by Cognero.

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Chapter 17: Carboxylic Acids

a. 1 = succinic acid; 2 = oxalic acid; 3 = malonic acid; 4 = adipic acid b. 1 = oxalic acid; 2 = malonic acid; 3 = succinic acid; 4 = adipic acid c. 1 = oxalic acid; 2 = succinic acid; 3 = adipic acid; 4 = malonic acid d. 1 = adipic acid; 2 = malonic acid; 3 = succinic acid; 4 = oxalic acid ANSWER: b 9. Which of the following is the most soluble in water? a. propane b. 2-butanol c. 2-pentanone d. ethanoic acid ANSWER: d 10. Which of the following is the most soluble in water? a. pentanoic acid b. 1-propanol c. caproic acid d. 2-hexanone ANSWER: a 11. Which of the following has the highest boiling point? a. heptane b. 3-hexanol c. valeric acid d. hexanal ANSWER: c 12. Which of the following has the highest boiling point? a. valeric acid b. 1-propanol c. octanoic acid d. hexanal ANSWER: c 13. What is the approximate pKa value of acetic acid a. −2 b. 5 c. 15 Copyright Cengage Learning. Powered by Cognero.

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Chapter 17: Carboxylic Acids d. 35 ANSWER: b 14. Which of the following statements is not true regarding benzoic acid? a. The neutral acid is the predominant species in aqueous solution at pH<2. b. The anionic carboxylate is the predominant species in aqueous solution at pH>7. c. Sodium benzoate is less soluble in water than benzoic acid. d. Benzoic acid is extracted out of diethyl ether by treatment with aqueous sodium bicarbonate. ANSWER: c 15. Which of the following is the correct order of increasing acid strength (less acidic < more acidic)? a. ICH2COOH < CH3COOH < CH3OH b. ICH2COOH < I2CHCOOH < I3CCOOH c. ClCH2COOH < CH3OH < CH3COOH d. Cl3CCOOH < Cl2CHCOOH < ClCH2COOH ANSWER: b 16. Which of the following is the correct order of decreasing acid strength (more acidic > less acidic)? a. ICH2COOH > ClCH2COOH > FCH2COOH b. Cl2CHCOOH > ClCH2COOH > CH3COOH c. CH3CH2OH > FCH2COOH > ClCH2COOH d. CH3COOH > FCH2COOH > CH3CH2OH ANSWER: b 17. Which of the following is the correct order of increasing acid strength (less acidic < more acidic)? a. CH3COOH < ICH2COOH < ClCH2COOH b. CH3COOH < FCH2COOH < ICH2COOH c. ClCH2COOH < CH3COOH < BrCH2COOH d. ClCH2COOH < BrCH2COOH < CH3COOH ANSWER: a 18. What is the major organic product obtained from the following reaction?

a. 1 b. 2 Copyright Cengage Learning. Powered by Cognero.

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Chapter 17: Carboxylic Acids c. 3 d. 4 ANSWER: b 19. What is the major organic product obtained from the following reaction?

a. 1 b. 2 c. 3 d. 4 ANSWER: c 20. What is the major organic product obtained from the following reaction?

a. 1 b. 2 c. 3 d. 4 ANSWER: b 21. What is the major organic product obtained from the following reaction?

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Chapter 17: Carboxylic Acids

a. 1 b. 2 c. 3 d. 4 ANSWER: c 22. What is the major organic product obtained from the following reaction?

a. 1 b. 2 c. 3 d. 4 ANSWER: a 23. What is the major organic product obtained from the following reaction?

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Chapter 17: Carboxylic Acids

a. 1 b. 2 c. 3 d. 4 ANSWER: a 24. What is the major organic product obtained from the following reaction?

a. 1 b. 2 c. 3 d. 4 ANSWER: b 25. What is the major organic product obtained from the following reaction?

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Chapter 17: Carboxylic Acids

a. 1 b. 2 c. 3 d. 4 ANSWER: b 26. What is the major organic product obtained from the following reaction?

a. 1 b. 2 c. 3 d. 4 ANSWER: c 27. What is the major organic product obtained from the following reaction?

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Chapter 17: Carboxylic Acids

a. 1 b. 2 c. 3 d. 4 ANSWER: a 28. What is the major organic product obtained from the following reaction?

a. 1 b. 2 c. 3 d. 4 ANSWER: c 29. What is the major organic product obtained from the following reaction?

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Chapter 17: Carboxylic Acids

a. 1 b. 2 c. 3 d. 4 ANSWER: a 30. What is the major organic product obtained from the following reaction?

a. 1 b. 2 c. 3 d. 4 ANSWER: d 31. What is the major organic product obtained from the following reaction?

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Chapter 17: Carboxylic Acids

a. 1 b. 2 c. 3 d. 4 ANSWER: d 32. What is the major organic product obtained from the following reaction?

a. 1 b. 2 c. 3 d. 4 ANSWER: c 33. Which of the following carboxylic acids undergoes the most rapid thermal decarboxylation reaction?

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Chapter 17: Carboxylic Acids

a. 1 b. 2 c. 3 d. 4 ANSWER: c 34. Which of the following reagents cannot bring about the following transformation?

a. CH3OH, H2SO4 b. CH3OH, TsCl c. both (a) and (b) d. CH3Li ANSWER: d 35. Which of the following reagents can perform the following transformation?

a. CH3I, H2SO4 b. CH3MgBr c. LiOCH3 d. CH2N2 ANSWER: d 36. What is the best choice of reagent(s) to perform the following transformation?

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Chapter 17: Carboxylic Acids

a. 1. LiAlH4; 2. H3O+ b. H2, Pt c. 1. NaBH4; 2. H2O d. NaH ANSWER: a 37. Which of the following reagent(s) cannot perform the following transformation?

a. H2, Pt b. NaH c. H2, Ni d. Both (a) and (c) ANSWER: b 38. What of the following reagent(s) cannot perform the following transformation?

a. H2, Pt b. 1. NaBH4; 2. H2O c. HI/Red P d. Both (a) and (b) ANSWER: c 39. What is the best choice of reagent to perform the following transformation?

a. NaCl b. HCl c. SOCl2 Copyright Cengage Learning. Powered by Cognero.

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Chapter 17: Carboxylic Acids d. Cl2 ANSWER: c 40. Which of the following reactive intermediate is formed during reaction of a carboxylic acid with thionyl chloride to give corresponding acid chloride? a. tetrahedral carbonyl addition intermediate b. ketone c. alcohol d. enol ANSWER: a 41. Which of the following best describes the key mechanistic steps in formation of a methyl ester by using diazomethane? a. proton transfer followed by nucleophilic displacement of dinitrogen b. nucleophilic displacement followed by proton addition c. addition followed by elimination d. substitution followed by addition ANSWER: a 42. The structure of cis-1,3-cyclopentanedicarboxylic acid is shown below.

a. True b. False ANSWER: True 43. Consider the data in the Table below to answer the following question:

Y H CN OCH3

Acidities of Substituted Benzoic and Acetic Acids pKas at 25°C Y−C6H4COOH meta Y−CH2COOH 4.75 4.19 2.47 3.64 3.57 4.09

para 4.19 3.55 4.46

The structure of the strongest acid in the table above is NC−CH2−COOH. a. True b. False ANSWER: True 44. Consider the data in the Table below to answer the following question: Copyright Cengage Learning. Powered by Cognero.

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Chapter 17: Carboxylic Acids

Y H CN OCH3

Acidities of Substituted Benzoic and Acetic Acids pKas at 25°C Y−C6H4COOH meta Y−CH2COOH 4.75 4.19 2.47 3.64 3.57 4.09

para 4.19 3.55 4.46

The structure of the acid with the strongest conjugate base in the table above is CH3COOH. a. True b. False ANSWER: True 45. Benzoic acid can be produced by the treatment of bromobenzene with 1. Mg, ether, and 2.) CO2 followed by acidification. a. True b. False ANSWER: True 46. Consider the following reaction.

The major organic product obtained is

a. True b. False ANSWER: False 47. Consider the following reaction.

The major organic product obtained is

a. True b. False ANSWER: False Copyright Cengage Learning. Powered by Cognero.

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Chapter 17: Carboxylic Acids 48. Consider the following 1H NMR to answer the following question.

Spectrum obtained from: SDBSWeb : http://riodb01.ibase.aist.go.jp/sdbs/ (National Institute of Advanced Industrial Science and Technology, 11-0708)

This compound is known to contain both a −C=O group and an −OH group. Based on this spectrum, this compound would be classified as aliphatic carboxylic acid. a. True b. False ANSWER: False 49. Based on the following IR spectrum, this compound would be classified as aromatic carboxylic acid.

Spectrum obtained from: SDBSWeb : http://riodb01.ibase.aist.go.jp/sdbs/ (National Institute of Advanced Industrial Science and Technology, 11-0708)

a. True b. False ANSWER: True Copyright Cengage Learning. Powered by Cognero.

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Chapter 17: Carboxylic Acids 50. Consider the following reaction.

The expected product is

a. True b. False ANSWER: True 51. Malonic acid is an example of a β-ketoacid. a. True b. False ANSWER: False 52. Provide the correct name for the following compound which can be used to produce aspirin.

ANSWER: o-hydroxybenzoic acid o-hydroxybenzoic acid 2-hydroxybenzoic acid 53. When CO2 is bubbled through an ether solution of benzylmagnesium bromide, and the resulting mixture is acidified, ____________ _____ is produced. ANSWER: phenylacetic acid phenylethanoic acid 54. The strongest acid of the following is indicated by the Roman numeral ______.

ANSWER: IV 55. The strongest acid of the following is indicated by the Roman numeral ______. Copyright Cengage Learning. Powered by Cognero.

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Chapter 17: Carboxylic Acids

ANSWER: III Based on the informaton presented below, answer the following questions. An ether solution contains the following components. 2,3,4,5-tetramethylbenzene

benzyl alcohol

2-hydroxybenzoic acid

This solution is extracted with a 1.0 M solution of NaOH, that is immiscible with ether. 56. The 2,3,4,5-tetramethylbenzene will be recovered from the _______ layer. ANSWER: ether 57. The benzyl alcohol will be recovered from the _______ layer. ANSWER: ether 58. The 2-hydroxybenzoic acid will be recovered from the _______ layer. ANSWER: base basic NaOH aqueous 59. In order to recover the 2-hydroxybenzoic acid, a strong ______ must be added to the appropriate layer. ANSWER: acid 60. Ethyl propanoate (CH3CH2COOCH2CH3) can be prepared by the reaction of ethanol with ____________

acid. ANSWER: propanoic propionic 61. Pentanoic acid can be converted to its methyl ester in very high yield by reaction with ___________________. ANSWER: diazomethane 62. What is the IUPAC name of the following compound?

ANSWER: (Z)-2-butenoic acid 63. What is the IUPAC name of the following compound?

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Chapter 17: Carboxylic Acids ANSWER: (E)-3-pentenoic acid 64. What is the major organic product obtained from the following reaction?

ANSWER:

65. What is the major organic product obtained from the following reaction?

ANSWER:

66. What is the major organic product obtained from the following reaction?

ANSWER:

67. What is the major organic product obtained from the following reaction? Copyright Cengage Learning. Powered by Cognero.

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Chapter 17: Carboxylic Acids

ANSWER:

68. What is the major organic product obtained from the following reaction?

ANSWER:

69. What is the major organic product obtained from the following reaction?

ANSWER:

70. What is the major organic product obtained from the following reaction?

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Chapter 17: Carboxylic Acids ANSWER:

71. What is the major organic product obtained from the following reaction?

ANSWER:

72. What is the major organic product obtained from the following sequence of reactions?

ANSWER:

73. What is the major organic product obtained from the following sequence of reactions?

ANSWER:

74. What is the common name of the given compound?

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Chapter 17: Carboxylic Acids

a. Azelaic acid b. Seabacic acid c. Suberic acid d. Adepic acid ANSWER: a 75. What is the IUPAC name of malonic acid? a. Propanedioic acid b. 1,1-Propanedioic acid c. Butanedioic acid d. Butane-1,4-dioic acid ANSWER: a Match the structures with the most appropriate boiling points. a. CH3COOH b. CH3(CH2)2COOH c. CH3(CH2)4COOH

d. CH3CH2COOH

76. 163oC ANSWER: b 77. 118oC ANSWER: a 78. 141.2oC ANSWER: d 79. 205oC ANSWER: c 80. Which is the carboxylic acid that is least acidic? a. Trichloroacetic acid b. Chloroacetic acid c. Acetic acid d. Bromoacetic acid ANSWER: c 81. Identify the final product of the following reaction.

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Chapter 17: Carboxylic Acids

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Chapter 17: Carboxylic Acids ANSWER: a 82. Select the compound that is most suitable to complete the given reaction.

a. PCl3 b. SOCl2 c. HCl d. PCl5 ANSWER: a 83. It is possible to reduce aldehydes and ketones selectively by using the less reactive _____ as the reducing agent. ANSWER: sodium borohydride (NaBH4)

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Chapter 18: Functional Derivatives of Carboxylic Acids 1. What is the correct assignment of the names of the following substituted benzenes?

a. 1 = benzonitrile; 2 = benzyl amine; 3 = benzyl alcohol b. 1 = benzyl amine; 2 = benzonitrile; 3 = benzamide c. 1 = benzamide; 2 = benzonitrile; 3 = benzoic acid d. 1 = benzonitrile; 2 = benzamide; 3 = benzoic acid ANSWER: d 2. What of the following is the correct assignment of the classes of the following compounds?

a. 1 = lactone; 2 = ester; 3 = amide b. 1 = ester; 2 = ester; 3 = imide c. 1 = ester; 2 = imide; 3 = amide d. 1 = lactone; 2 = anhydride; 3 = imide ANSWER: d 3. What is the correct assignment of the functional groups in the following compounds?

a. 1 = amide; 2 = ester; 3 = nitrile b. 1 = nitrile; 2 = ester; 3 = imide c. 1 = nitrile; 2 = ester; 3 = amide d. 1 = amide; 2 = carboxylic acid; 3 = imide ANSWER: c 4. What is the correct assignment of the functional groups in the following compounds?

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Chapter 18: Functional Derivatives of Carboxylic Acids a. 1 = amide; 2 = imide; 3 = nitrile b. 1 = lactam; 2 = amide; 3 = imide c. 1 = lactam; 2 = imide; 3 = amide d. 1 = imide; 2 = amide; 3 = lactam ANSWER: b 5. What is the IUPAC name of the following compound?

a. butyl isopropanoate b. isopropyl pentanoate c. pentanoyl isopropane d. isopropyloxybutanal ANSWER: b 6. What is the IUPAC name of the following compound?

a. dimethylamino-3-phenylpropanoic acid b. N,N-dimethyl 2-phenylethyl amide c. N,N-dimethyl 3-phenylpropanamide d. dimethyl 2-phenylpropanoylamine ANSWER: c 7. What is the IUPAC name of the following compound?

a. ethyl (R)-3-methylpentanoate b. ethyl (S)-3-methylpentanoate c. (R)-2-methylbutyl ethanoate d. (S)-2-methylbutyl ethanoate ANSWER: a 8. What is the IUPAC name of the following compound?

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Chapter 18: Functional Derivatives of Carboxylic Acids a. (E)-N-methyl 3-methyl-3-pentenamide b. (Z)-N-methyl 3-methyl-3-pentenamide c. (E)-1-methylamino-3-methyl-3-pentenal d. (Z)-1-methylamino-3-methyl-3-pentenal ANSWER: a 9. Which of the following compounds is a 2° amide?

a. 1 b. 2 c. 3 d. 4 ANSWER: c 10. Which of the following compounds is a 3° amide?

a. 1 b. 2 c. 3 d. 4 ANSWER: a 11. Which of the following is the correct order of decreasing acid strength of the following compounds (more acidic > less acidic)?

a. 1 > 2 > 3 b. 2 > 3 > 1 c. 1 > 3 > 2 d. 3 > 2 > 1 ANSWER: b Copyright Cengage Learning. Powered by Cognero.

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Chapter 18: Functional Derivatives of Carboxylic Acids 12. Which of the following is the correct order of decreasing acid strength of the following compounds (more acidic > less acidic)?

a. 1 > 2 > 3 b. 2 > 3 > 1 c. 1 > 3 > 2 d. 3 > 2 > 1 ANSWER: d 13. Which of the following best describes the key mechanistic steps in the reaction of an acid chloride and an alcohol to form an ester? a. elimination followed by addition b. addition followed by decarboxylation c. addition followed by elimination d. substitution followed by addition ANSWER: c 14. Which of the following best describes the key mechanistic steps in the reaction of an anhydride and an amine to form an amide? a. addition followed by elimination b. elimination followed by addition c. substitution followed by addition d. addition followed by decarboxylation ANSWER: a 15. Which of the following is the correct order of decreasing leaving group ability in nucleophilic acyl substitutions (better leaving group > worse leaving group)? a. Cl− > NH2− > CH3CH2O− b. NH2− > CH3CH2O− > Cl− c. Cl− > CH3CH2O− > NH2− d. CH3CH2O− > Cl− > NH2− ANSWER: c 16. Which of the following is the correct order of decreasing leaving group ability in nucleophilic acyl substitutions (better leaving group > worse leaving group)? a. Br− > CH3CH2COO− > CH3O− b. CH3CH2COO− > CH3O− > Br− Copyright Cengage Learning. Powered by Cognero.

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Chapter 18: Functional Derivatives of Carboxylic Acids c. Br− > CH3O− > CH3CH2COO− d. CH3O− > Br− > CH3CH2COO− ANSWER: a 17. Which of the following is the correct order of decreasing reactivity in hydrolysis reactions (more reactive > less reactive)? a. anhydrides > esters > acid iodides b. esters > acid iodides > anhydrides c. acid iodides > anhydrides > esters d. anhydrides > acid iodides > esters ANSWER: c 18. Which of the following is the correct order of decreasing reactivity in hydrolysis reactions (more reactive > less reactive)? a. anhydrides > amides > acid chlorides b. amides > acid chlorides > anhydrides c. anhydrides > acid chlorides > amides d. acid chlorides > anhydrides > amides ANSWER: d 19. Which of the following statements is not true in relation to the hydrolysis of esters? a.Hydrolysis of esters under acid conditions requires only a catalytic amount of a strong acid b Esters are hydrolyzed only in the presence of acid or base . c.Under acidic conditions for hydrolysis of esters protonation of the ester increases its electrophilicity d Under acidic conditions, the mechanism involves the direct addition of the strong nucleophile to the carbonyl carbo . n producing the tetrahedral addition intermediate ANSWER: d 20. Which of the following can be made by acid-promoted hydrolysis of an ester? 1. 2. 3. 4.

an imine an acid an alcohol an imide

a. only 2 and 3 b. only 1 c. only 1 and 4 d. only 3 ANSWER: a 21. What is the major organic product obtained from the following reaction? Copyright Cengage Learning. Powered by Cognero.

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Chapter 18: Functional Derivatives of Carboxylic Acids

a. 1 b. 2 c. 3 d. 4 ANSWER: b 22. What is the major organic product obtained from the following reaction?

a. 1 b. 2 c. 3 d. 4 ANSWER: d 23. What is the major organic product obtained from the following reaction?

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Chapter 18: Functional Derivatives of Carboxylic Acids

a. 1 b. 2 c. 3 d. 4 ANSWER: a 24. What is the major organic product obtained from the following reaction?

a. 1 b. 2 c. 3 d. 4 ANSWER: b 25. What is the major organic product obtained from the following reaction?

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Chapter 18: Functional Derivatives of Carboxylic Acids

a. 1 b. 2 c. 3 d. 4 ANSWER: b 26. What is the major organic product obtained from the following reaction?

a. 1 b. 2 c. 3 d. 4 ANSWER: c 27. What is the major organic product obtained from the following reaction?

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Chapter 18: Functional Derivatives of Carboxylic Acids

a. 1 b. 2 c. 3 d. 4 ANSWER: c 28. What is the major organic product obtained from the following reaction?

a. 1 b. 2 c. 3 d. 4 ANSWER: b 29. What is the major organic product obtained from the following reaction?

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Chapter 18: Functional Derivatives of Carboxylic Acids

a. 1 b. 2 c. 3 d. 4 ANSWER: d 30. What is the major organic product obtained from the following reaction?

a. 1 b. 2 c. 3 d. 4 ANSWER: b 31. What is the major organic product obtained from the following reaction?

a. 1 b. 2 c. 3 d. 4 Copyright Cengage Learning. Powered by Cognero.

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Chapter 18: Functional Derivatives of Carboxylic Acids ANSWER: c 32. What is the major organic product obtained from the following reaction?

a. 1 b. 2 c. 3 d. 4 ANSWER: b 33. What is the major organic product obtained from the following reaction?

a. 1 b. 2 c. 3 d. 4 ANSWER: b 34. What is the major organic product obtained from the following reaction?

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Chapter 18: Functional Derivatives of Carboxylic Acids

a. 1 b. 2 c. 3 d. 4 ANSWER: a 35. What is the major organic product obtained from the following reaction?

a. 1 b. 2 c. 3 d. 4 ANSWER: a 36. What is the major organic product obtained from the following reaction?

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Chapter 18: Functional Derivatives of Carboxylic Acids

a. 1 b. 2 c. 3 d. 4 ANSWER: b 37. What is the major organic product obtained from the following reaction?

a. 1 b. 2 c. 3 d. 4 ANSWER: b 38. What is the major organic product obtained from the following reaction?

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Chapter 18: Functional Derivatives of Carboxylic Acids a. 1 b. 2 c. 3 d. 4 ANSWER: b 39. What is the major organic product obtained from the following reaction?

a. 1 b. 2 c. 3 d. 4 ANSWER: c 40. What is the major organic product obtained from the following reaction?

a. 1 b. 2 c. 3 d. 4 ANSWER: b 41. What is the major organic product obtained from the following reaction?

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Chapter 18: Functional Derivatives of Carboxylic Acids

a. 1 b. 2 c. 3 d. 4 ANSWER: b 42. What is the major organic product obtained from the following reaction?

a. 1 b. 2 c. 3 d. 4 ANSWER: c 43. What is the major organic product obtained from the following reaction?

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Chapter 18: Functional Derivatives of Carboxylic Acids

a. 1 b. 2 c. 3 d. 4 ANSWER: a 44. What is the major organic product obtained from the following reaction?

a. 1 b. 2 c. 3 d. 4 ANSWER: b 45. What is the major organic product obtained from the following reaction?

a. 1 b. 2 Copyright Cengage Learning. Powered by Cognero.

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Chapter 18: Functional Derivatives of Carboxylic Acids c. 3 d. 4 ANSWER: a 46. What is the major organic product obtained from the following reaction?

a. 1 b. 2 c. 3 d. 4 ANSWER: c 47. What is the major organic product obtained from the following reaction?

a. 1 b. 2 c. 3 d. 4 ANSWER: d 48. What is the major organic product obtained from the following reaction?

a. 1 b. 2 c. 3 d. 4 ANSWER: b 49. What is the major organic product obtained from the following reaction?

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Chapter 18: Functional Derivatives of Carboxylic Acids

a. 1 b. 2 c. 3 d. 4 ANSWER: c 50. What is the major organic product obtained from the following reaction?

a. 1 b. 2 c. 3 d. 4 ANSWER: a 51. What is the major organic product obtained from the following reaction?

a. 1 b. 2 c. 3 d. 4 ANSWER: b 52. What is the major organic product obtained from the following reaction?

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Chapter 18: Functional Derivatives of Carboxylic Acids

a. 1 b. 2 c. 3 d. 4 ANSWER: c 53. What is the major organic product obtained from the following reaction?

a. 1 b. 2 c. 3 d. 4 ANSWER: b 54. What is the major organic product obtained from the following reaction?

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Chapter 18: Functional Derivatives of Carboxylic Acids

a. 1 b. 2 c. 3 d. 4 ANSWER: b 55. What is the major organic product obtained from the following reaction?

a. 1 b. 2 c. 3 d. 4 ANSWER: b 56. What is the major organic product obtained from the following reaction?

a. 1 Copyright Cengage Learning. Powered by Cognero.

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Chapter 18: Functional Derivatives of Carboxylic Acids b. 2 c. 3 d. 4 ANSWER: d 57. What is the best choice of reagent to achieve the following transformation?

a. CH3MgBr b. CH3Li c. CH3I d. (CH3)2CuLi ANSWER: d 58. What is the best choice of reagent(s) to achieve the following transformation?

a. H2O b. NaOH, H2O c. 1. LiAlH4; 2. H3O+ d. H2SO4 ANSWER: c 59. What is the best choice of reagent(s) to achieve the following transformation?

a. 1. LiAlH4; 2. H3O+ b. 1. 2 eq. CH3MgBr; 2. H3O+ c. 1. (CH3)2CuLi; 2. H3O+ d. 1. 2 eq. CH3I ANSWER: b 60. What is the major organic product of the following sequence of reactions? Copyright Cengage Learning. Powered by Cognero.

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Chapter 18: Functional Derivatives of Carboxylic Acids

a. 1 b. 2 c. 3 d. 4 ANSWER: b 61. What is the major organic product of the following sequence of reactions?

a. 1 b. 2 c. 3 d. 4 ANSWER: a 62. What is the major organic product of the following sequence of reactions?

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Chapter 18: Functional Derivatives of Carboxylic Acids

a. 1 b. 2 c. 3 d. 4 ANSWER: a 63. What is the major organic product of the following sequence of reactions?

a. 1 b. 2 c. 3 d. 4 ANSWER: b 64. What is the major organic product of the following sequence of reactions?

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Chapter 18: Functional Derivatives of Carboxylic Acids

a. 1 b. 2 c. 3 d. 4 ANSWER: a 65. What is the major organic product obtained from the following reaction?

a. 1 b. 2 c. 3 d. 4 ANSWER: a 66. What is the major organic product obtained from the following reaction?

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Chapter 18: Functional Derivatives of Carboxylic Acids

a. 1 b. 2 c. 3 d. 4 ANSWER: b 67. Which combination(s) of alkyl bromide and ester can be used to prepare the following product by reaction of the Grignard reagent derived from the alkyl bromide with the ester?

a. only 1 b. only 2 c. only 1 and 3 d. only 2 and 4 ANSWER: a 68. Which combination(s) of alkyl bromide and ester can be used to prepare the following product by reaction of the Grignard reagent derived from the alkyl bromide with the ester?

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Chapter 18: Functional Derivatives of Carboxylic Acids

a. only 1 b. only 3 c. only 1 and 3 d. only 2 and 4 ANSWER: b 69. Which combination(s) of organic bromide and carbonyl compound can be used to prepare the following product by reaction of the Grignard reagent derived from the alkyl bromide with the carbonyl compound?

a. only 1 b. only 1 and 2 c. only 1, 2 and 3 d. 1, 2, 3 and 4 ANSWER: c 70. Which combination(s) of organic bromide and carbonyl compound can be used to prepare the following product by reaction of the Grignard reagent derived from the alkyl bromide with the carbonyl compound?

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Chapter 18: Functional Derivatives of Carboxylic Acids

a. only 1 b. only 1 and 2 c. only 1 and 3 d. only 3 and 4 ANSWER: c 71. The following compound should be named as cyanopropane.

a. True b. False ANSWER: False 72. The product of the following reaction would be classified as a carboxylic acid.

a. True b. False ANSWER: True 73. Both amides and nitriles are acyl derivatives of carboxylic acids. a. True b. False ANSWER: False 74. The correct name of the following structure is phenyl benzoate.

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Chapter 18: Functional Derivatives of Carboxylic Acids a. True b. False ANSWER: True 75. Consider the following reaction.

The correct reactant to place in the box is PCl3. a. True b. False ANSWER: False 76. Consider the following reaction.

The reactant is a lactam. a. True b. False ANSWER: False 77. The correct name for the following compound is propyl cyclohexanoate.

a. True b. False ANSWER: False 78. Consider the isotopically tagged substance below.

Saponification of this substance will produce the following products.

a. True Copyright Cengage Learning. Powered by Cognero.

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Chapter 18: Functional Derivatives of Carboxylic Acids b. False ANSWER: False 79. Consider the following reaction.

The structure of the tetrahedral intermediate is

a. True b. False ANSWER: False 80. Of the following substances, the first and last substance shown are not derivatives of carboxylic acids.

a. True b. False ANSWER: True 81. It is possible to directly convert an acid anhydride to an acid chloride. a. True b. False ANSWER: False 82. Consider the following spectrum of a carboxylic acid derivative.

This spectrum indicates the presence of a ___________group. ANSWER: nitrile Consider the following general structures. Copyright Cengage Learning. Powered by Cognero.

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Chapter 18: Functional Derivatives of Carboxylic Acids

Use the Roman numeral of the substance to answer the following questions. 83. The substance that is the most reactive toward nucleophilic acyl substitution is _____. ANSWER: IV 84. The substance that is the least reactive toward nucleophilic acyl substitution is _____. ANSWER: II 85. The substance that is classified as an anhydride is _____. ANSWER: 1 86. Consider the following 1H NMR spectrum.

The line indicated with the number _____ would indicate the presence of a C=O group. ANSWER: 5 87. Consider the structure given below.

The systematic name for this compound is: ANSWER: Ethyl p-aminobenzoate ethyl p-aminobenzoate Ethyl 4-aminobenzoate ethyl 4-aminobenzoate 88. Consider the following reaction.

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Chapter 18: Functional Derivatives of Carboxylic Acids The name of the product of this reaction is_______________________. ANSWER: hexane-2,6-diol 89. Consider the following reaction

The name of the reactant that should be placed in the box is _____________. ANSWER: methanol methyl alcohol 90. The structure that best describes the double bond character of the amide bond in acetamide is shown by the

Roman numeral _______.

ANSWER: II Consider the following compounds.

Use the numbers shown to answer the following questions. If none of the structures is applicable enter the word none. 91. A lactone is represented by the structure numbered ____. ANSWER: 1 one 92. An anhydride is represented by the structure numbered ____. ANSWER: 2 two 93. An imide is represented by the structure numbered ____. ANSWER: 3 three 94. What is the IUPAC name of the following compound? Copyright Cengage Learning. Powered by Cognero.

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Chapter 18: Functional Derivatives of Carboxylic Acids

ANSWER: (Z)-ethyl 2-methyl-2-butenoate 95. What is the IUPAC name of the following compound?

ANSWER: (Z)-N,N-dimethyl-3-pentenamide 96. What is the major organic product obtained from the following reaction?

ANSWER:

97. What is the major organic product obtained from the following reaction?

ANSWER:

98. What is the major organic product obtained from the following reaction?

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Chapter 18: Functional Derivatives of Carboxylic Acids ANSWER:

99. What is the major organic product obtained from the following reaction?

ANSWER:

100. What two organic compounds are obtained from the following reaction?

ANSWER:

101. What two organic compounds are obtained from the following reaction?

ANSWER:

102. What two organic compounds are obtained from the following reaction?

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Chapter 18: Functional Derivatives of Carboxylic Acids

ANSWER:

103. What two organic compounds are obtained from the following reaction?

ANSWER:

104. What is the major organic product obtained from the following reaction?

ANSWER:

105. What is the major organic product obtained from the following reaction?

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Chapter 18: Functional Derivatives of Carboxylic Acids ANSWER:

106. What is the major organic product obtained from the following reaction?

ANSWER:

107. What is the major organic product obtained from the following reaction?

ANSWER:

108. What is the major organic product obtained from the following reaction?

ANSWER: 109. What is the major organic product obtained from the following reaction?

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Chapter 18: Functional Derivatives of Carboxylic Acids

ANSWER:

110. What is the major organic product obtained from the following reaction?

ANSWER:

111. What is the major organic product obtained from the following reaction?

ANSWER:

112. What is the major organic product obtained from the following sequence of reactions?

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Chapter 18: Functional Derivatives of Carboxylic Acids ANSWER:

113. What is the major organic product obtained from the following sequence of reactions?

ANSWER:

114. Esters react with alcohols in an acid-catalyzed reaction called _____.

a. combustion b. esterification c. transesterification d. rearrangement ANSWER: c 115. The reaction of a(n) _____ with an alcohol cannot be used to prepare an ester. a. acid halide b. carboxylic acid c. acid anhydride d. lactam ANSWER: d 116. _____ do not react with ammonia, primary amines, and secondary amines. a. Acid halides b. Esters c. Acid anhydrides d. Amides ANSWER: d 117. What is “X” in the following reaction? Copyright Cengage Learning. Powered by Cognero.

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Chapter 18: Functional Derivatives of Carboxylic Acids

ANSWER: b 118. Carboxylate anions are inert to nucleophilic acyl substitution because --_____. a. carboxylate anions are negatively charged and therefore repel nucleophiles b. carboxylate anions are resonance stabilized and therefore become neutral c. carboxylate ions are positively charged and therefore repel nucleophiles d. carboxylate anions are negatively charged and therefore attract nucleophiles ANSWER: a 119. What is “X” in the following reaction?

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Chapter 18: Functional Derivatives of Carboxylic Acids a.

ANSWER: a 120. What is “X” in the following reaction?

ANSWER: d Copyright Cengage Learning. Powered by Cognero.

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Chapter 18: Functional Derivatives of Carboxylic Acids

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Chapter 19: Enolate Anions and Enamines 1. How many different aldols (β-hydroxyaldehydes), including constitutional isomers and stereoisomers, are formed upon treatment of propanal with base? a. 3 b. 1 c. 2 d. 4 ANSWER: d 2. How many β-hydroxyketones, including constitutional isomers and stereoisomers, are formed upon treatment of butanone with base? a. 6 b. 4 c. 2 d. 0 ANSWER: a 3. How many different β-hydroxyaldehydes and β-hydroxyketones, including constitutional isomers and stereoisomers, are formed upon treatment of a mixture of acetone and 2,2-dimethylbutanal with base? a. 1 b. 10 c. 6 d. 2 ANSWER: c 4. How many different β-hydroxyaldehydes and β-hydroxyketones, including constitutional isomers and stereoisomers, are formed upon treatment of a mixture of acetone and 2-butanone with base? a. 6 b. 1 c. 12 d. 7 ANSWER: c 5. How many different β-hydroxyaldehydes and β-hydroxyketones, including constitutional isomers and stereoisomers, are formed upon treatment of a mixture of butanal and benzaldehyde with base? a. 1 b. 3 c. 4 d. 0 ANSWER: b 6. Which of the following are not intermediate in the acid catalysed aldol reaction of propanal to form 2-methyl-2pentenal? 1. enol 2. enolate 3. tetrahedral carbonyl intermediate Copyright Cengage Learning. Powered by Cognero.

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Chapter 19: Enolate Anions and Enamines 4.

aldol

a. only 1, 3 and 4 b. only 2 c. only 1 and 3 d. only 3 and 4 ANSWER: b 7. Which of the following are not intermediate in the acid catalysed aldol reaction of ethanal to form but-2-enal? 1. 2. 3. 4.

enol enolate tetrahedral carbonyl intermediate aldol

a. only 2, 3 and 4 b. only 1 and 2 c. only 2 d. only 3 and 4 ANSWER: c 8. What is the major organic product obtained from the following reaction?

a. 1 b. 2 c. 3 d. 4 ANSWER: a 9. What is the major organic product obtained from the following reaction?

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Chapter 19: Enolate Anions and Enamines

a. 1 b. 2 c. 3 d. 4 ANSWER: a 10. What is the major organic product obtained from the following reaction?

a. 1 b. 2 c. 3 d. 4 ANSWER: a 11. What is the major organic product obtained from the following reaction?

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Chapter 19: Enolate Anions and Enamines

a. 1 b. 2 c. 3 d. 4 ANSWER: a 12. Which of the following compounds can be prepared by an aldol condensation by treating a single carbonyl compound with base?

a. 1 b. 2 c. 3 d. 4 ANSWER: a 13. Which of the following compounds can be prepared by an aldol condensation by treating a single carbonyl compound with base?

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Chapter 19: Enolate Anions and Enamines

a. 1 b. 2 c. 3 d. 4 ANSWER: b 14. Which of the following compounds can be prepared by a mixed aldol condensation by treatment of a mixture of two carbonyl compounds and NaOH?

a. 1 b. 2 c. 3 d. 4 ANSWER: a 15. Which of the following compounds can be prepared by a mixed aldol condensation by treatment of a mixture of two carbonyl compounds and NaOH?

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Chapter 19: Enolate Anions and Enamines

a. 1 b. 2 c. 3 d. 4 ANSWER: a 16. What is the major organic product obtained from the following reaction?

a. 1 b. 2 c. 3 d. 4 ANSWER: c 17. What is the major organic product obtained from the following reaction?

a. 1 b. 2 c. 3 d. 4 Copyright Cengage Learning. Powered by Cognero.

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Chapter 19: Enolate Anions and Enamines ANSWER: d 18. What is the major organic product obtained from the following reaction?

a. 1 b. 2 c. 3 d. 4 ANSWER: c 19. What is the major organic product obtained from the following reaction?

a. 1 b. 2 c. 3 d. 4 ANSWER: c 20. What is the major organic product obtained from the following reaction?

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Chapter 19: Enolate Anions and Enamines

a. 1 b. 2 c. 3 d. 4 ANSWER: c 21. What is the major organic product obtained from the following reaction?

a. 1 b. 2 c. 3 d. 4 ANSWER: c 22. What is the major organic product obtained from the following reaction?

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Chapter 19: Enolate Anions and Enamines

a. 1 b. 2 c. 3 d. 4 ANSWER: c 23. What is the major organic product obtained from the following reaction?

a. 1 b. 2 Copyright Cengage Learning. Powered by Cognero.

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Chapter 19: Enolate Anions and Enamines c. 3 d. 4 ANSWER: b 24. What is the major organic product obtained from the following reaction?

a. 1 b. 2 c. 3 d. 4 ANSWER: a 25. What is the major organic product obtained from the following reaction?

a. 1 b. 2 c. 3 d. 4 ANSWER: a 26. What is the major organic product obtained from the following reaction? Copyright Cengage Learning. Powered by Cognero.

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Chapter 19: Enolate Anions and Enamines

a. 1 b. 2 c. 3 d. 4 ANSWER: a 27. What is the major organic product obtained from the following reaction?

a. 1 b. 2 c. 3 d. 4 ANSWER: b Copyright Cengage Learning. Powered by Cognero.

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Chapter 19: Enolate Anions and Enamines 28. What is the major organic product obtained from the following reaction?

a. 1 b. 2 c. 3 d. 4 ANSWER: c 29. What is the major organic product obtained from the following reaction?

a. 1 b. 2 c. 3 d. 4 ANSWER: d 30. What is the major organic product obtained from the following reaction?

a. 1 Copyright Cengage Learning. Powered by Cognero.

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Chapter 19: Enolate Anions and Enamines b. 2 c. 3 d. 4 ANSWER: b 31. What is the major organic product obtained from the following reaction?

a. 1 b. 2 c. 3 d. 4 ANSWER: a 32. What is the major organic product obtained from the following reaction?

a. 1 b. 2 c. 3 d. 4 ANSWER: b 33. What is the major organic product obtained from the following reaction?

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Chapter 19: Enolate Anions and Enamines

a. 1 b. 2 c. 3 d. 4 ANSWER: c 34. What is the major organic product obtained from the following reaction?

a. 1 b. 2 c. 3 d. 4 ANSWER: c 35. What is the major organic product obtained from the following reaction?

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Chapter 19: Enolate Anions and Enamines

a. 1 b. 2 c. 3 d. 4 ANSWER: b 36. What is the major organic product obtained from the following sequence of reactions?

a. 1 b. 2 c. 3 Copyright Cengage Learning. Powered by Cognero.

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Chapter 19: Enolate Anions and Enamines d. 4 ANSWER: c 37. What is the major organic product obtained from the following sequence of reactions?

a. 1 b. 2 c. 3 d. 4 ANSWER: d 38. What is the major organic product obtained from the following reaction?

a. 1 b. 2 c. 3 d. 4 ANSWER: b Copyright Cengage Learning. Powered by Cognero.

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Chapter 19: Enolate Anions and Enamines 39. What is the major organic product obtained from the following reaction?

a. 1 b. 2 c. 3 d. 4 ANSWER: b 40. Which one of the following ketones cannot be made via an acetoacetate ester synthesis?

a. 1 b. 2 c. 3 d. 4 ANSWER: b 41. Which of the following carboxylic acids can be made via a malonate ester synthesis?

a. 1 Copyright Cengage Learning. Powered by Cognero.

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Chapter 19: Enolate Anions and Enamines b. 2 c. 3 d. 4 ANSWER: d 42. What is the major organic product obtained from the following sequence of reactions?

a. 1 b. 2 c. 3 d. 4 ANSWER: a 43. What is the major organic product obtained from the following sequence of reactions?

a. 1 Copyright Cengage Learning. Powered by Cognero.

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Chapter 19: Enolate Anions and Enamines b. 2 c. 3 d. 4 ANSWER: b 44. What is the major organic product obtained from the following sequence of reactions?

a. 1 b. 2 c. 3 d. 4 ANSWER: a 45. What is the major organic product obtained from the following sequence of reactions?

a. 1 b. 2 c. 3 Copyright Cengage Learning. Powered by Cognero.

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Chapter 19: Enolate Anions and Enamines d. 4 ANSWER: a 46. What is the major organic product obtained from the following sequence of reactions?

a. 1 b. 2 c. 3 d. 4 ANSWER: c 47. What is the major organic product obtained from the following sequence of reactions?

a. 1 b. 2 c. 3 d. 4 ANSWER: b 48. What is the major organic product obtained from the following sequence of reactions?

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Chapter 19: Enolate Anions and Enamines

a. 1 b. 2 c. 3 d. 4 ANSWER: a 49. What is the major organic product obtained from the following sequence of reactions?

a. 1 b. 2 c. 3 d. 4 ANSWER: b 50. What is the major organic product obtained from the following sequence of reactions?

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Chapter 19: Enolate Anions and Enamines

a. 1 b. 2 c. 3 d. 4 ANSWER: c 51. What is the major organic product obtained from the following sequence of reactions?

a. 1 b. 2 c. 3 d. 4 ANSWER: c 52. What is the major organic product obtained from the following sequence of reactions?

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Chapter 19: Enolate Anions and Enamines

a. 1 b. 2 c. 3 d. 4 ANSWER: a 53. Which combination of organic bromide(s) and dicarbonyl compound can be used to prepare the following product (in a multistep synthesis)?

a. 1 b. 2 c. 3 d. 4 ANSWER: d 54. Which combination of organic bromide(s) and dicarbonyl compound can be used to prepare the following product (in a multistep synthesis)?

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Chapter 19: Enolate Anions and Enamines

a. 1 b. 2 c. 3 d. 4 ANSWER: a 55. Tautomerization is catalyzed by both acids and bases. a. True b. False ANSWER: True 56. The alkyl halide that should be used to produce octanoic acid via the malonic ester synthesis is 1-bromooctane. a. True b. False ANSWER: False 57. Using the acetoacetic ester synthesis, to produce 5-methyl-2-heptanone, the alkyl halide that should be used is 1bromo-2-methylbutane. a. True b. False ANSWER: True 58. The following molecule will not undergo an aldol condensation with another like molecule.

a. True b. False ANSWER: True 59. In carbonyl condensation reactions new carbon-to-carbon bonds are formed and enolate anions can act as a Copyright Cengage Learning. Powered by Cognero.

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Chapter 19: Enolate Anions and Enamines nucleophiles. a. True b. False ANSWER: True 60. A 1,6-diester will produce a five-membered ring via a Dieckmann cyclization. a. True b. False ANSWER: True 61. Claisen and aldol condensations can result in cyclization but the Robinson annulation cannot. a. True b. False ANSWER: False 62. An aldol condensation using 3-methylbutanal could produce the following compound.

a. True b. False ANSWER: True 63. A Claisen condensation could be considered to the an ester analog of an aldol condensation. a. True b. False ANSWER: True 64. The following compound can act as a nucleophile in an aldol reaction.

a. True b. False ANSWER: False Consider the following reaction.

Use this reaction to answer the following questions. Copyright Cengage Learning. Powered by Cognero.

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Chapter 19: Enolate Anions and Enamines 65. This reaction is an example of ______. a. an intramolecular Claisen condensation b. an intramolecular aldol condensation c. a Robinson annulation d. a Michael reaction ANSWER: b 66. The product of this reaction is ______. a. a β, γ-unsaturated aldehyde b. an α, β-unsaturated ketone c. an α, β-unsaturated aldehyde d. an enol ANSWER: c 67. In an aldol reaction the following substance could be produced by the reaction of acetone (propanone) and _______________. Enter the name of the substance.

ANSWER: methanal formaldehyde 68. In an aldol reaction the following substance could be produced by the reaction of benzaldehyde and _______________. Enter the name of the substance.

ANSWER: cyclopentanone 69. In a Claisen condensation the following substance could be produced by the reaction of ethylbenzoate and _______________. Enter the name of the substance.

ANSWER: ethyl acetate ethyl ethanoate 70. Consider the steps in the mechanism for a base catalyzed aldol condensation. The _______ step in the base

catalyzed aldol condensation is addition of an enolate to a carbonyl group. ANSWER: second 2nd 71. The structure of the aldol shown below can be produced by reacting _________ with NaOH. Enter the Copyright Cengage Learning. Powered by Cognero.

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Chapter 19: Enolate Anions and Enamines name of the compound.

ANSWER: acetone propanone 72. The class of compound formed in the reaction of the following two substance is a(n)__________.

ANSWER: enamine Consider the following types of reactions: 1. aldol condensation 2. Claisen condensation 3. Robinson annulation 4. Dieckmann condensation 5. Michael reaction Classify the following reactions by placing the appropriate number in the blank. 73. _______

ANSWER: 2 74. ______

ANSWER: 1 75. ______

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Chapter 19: Enolate Anions and Enamines

ANSWER: 4 76. ______

ANSWER: 2 77. ______

ANSWER: 5 78. What is the major organic product obtained from the following reaction?

ANSWER:

79. What is the major organic product obtained from the following reaction?

ANSWER:

80. What is the major organic product obtained from the following reaction?

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Chapter 19: Enolate Anions and Enamines

ANSWER:

81. What is the major organic product obtained from the following reaction?

ANSWER:

82. What is the major organic product obtained from the following reaction?

ANSWER:

83. What is the major organic product obtained from the following reaction?

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Chapter 19: Enolate Anions and Enamines ANSWER:

84. What is the major organic product obtained from the following reaction?

ANSWER:

85. What is the major organic product obtained from the following reaction?

ANSWER:

86. What is the major organic product obtained from the following reaction?

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Chapter 19: Enolate Anions and Enamines ANSWER:

87. What is the major organic product obtained from the following sequence of reactions?

ANSWER:

88. What is the major organic product obtained from the following reaction?

ANSWER:

89. What is the major organic product obtained from the following reaction?

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Chapter 19: Enolate Anions and Enamines ANSWER:

90. What is the major organic product obtained from the following reaction?

ANSWER:

91. What is the major organic product obtained from the following sequence of reactions?

ANSWER:

92. What is the major organic product obtained from the following sequence of reactions?

ANSWER: 93. What is the major organic product obtained from the following sequence of reactions?

ANSWER:

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Chapter 19: Enolate Anions and Enamines 94. State two differences between Claisen and Aldol condensations. ANSWER: The two differences between Claisen and Aldol condensations are as follows: 1. In the case of Claisen condensations, hydroxides cannot be used as a base as they could react with esters, while for Aldol condensations, hydroxides can be used. 2. In Aldol condensations, no group is lost, but in the case of Claisen condensations, an alkoxide group is lost. 95. Acetoacetyl-CoA reacts with acetyl-CoA to give product A in the presence of 3-hydroxy-3-methyl-glutaryl-CoA synthetase. Identify the special feature of this reaction. a. It is enantioselective, and only the S enantiomer is formed. b. It is enantioselective, and only the R enantiomer is formed. c. It produces a non-superimposable R enantiomer. d. It produces a racemic mixture used for various purposes.. ANSWER: a 96. Identify the final product of the following reaction.

ANSWER: a Copyright Cengage Learning. Powered by Cognero.

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Chapter 19: Enolate Anions and Enamines 97. The more the substitution of the _____ of an enolate anion, the greater its stability. ANSWER: double bond 98. The hydrolysis of an alkylated malonic ester in aqueous sodium hydroxide followed by acidification with aqueous hydrochloric acid gives a(n) _____ acid. ANSWER: β-dicarboxylic 99. In a Claisen condensation catalyzed by the enzyme thiolase, acetyl-CoA is converted to its _____ ion, which then adds to the carbonyl group of the second molecule of acetyl-CoA to give a tetrahedral addition intermediate. ANSWER: enolate Match the reactants with the most appropriate products. a.

100. ANSWER: c

101. ANSWER: a

102. ANSWER: d

103. ANSWER: b Copyright Cengage Learning. Powered by Cognero.

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Chapter 19: Enolate Anions and Enamines

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Chapter 20: Dienes, Conjugated Systems, and Pericyclic Reactions 1. Which of the following are conjugated dienes?

a. only 1 b. only 2 c. only 1 and 2 d. 1, 2 and 3 ANSWER: c 2. Which of the following are conjugated dienes?

a. only 1 b. only 2 c. only 1 and 2 d. 1, 2 and 3 ANSWER: b 3. What is the IUPAC name of the following compound?

a. 2,3-dimethyl-2,4-pentadiene b. (Z)-2,3-dimethyl-2,4-pentadiene c. 3,4-dimethyl-1,3-pentadiene d. (Z)-3,4-dimethyl-1,3-pentadiene ANSWER: c 4. What is the IUPAC name of the following compound?

a. (R)-3-vinyl-1-butene Copyright Cengage Learning. Powered by Cognero.

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Chapter 20: Dienes, Conjugated Systems, and Pericyclic Reactions b. 3-methyl-1,5-pentadiene c. 3-methyl-1,4-pentadiene d. (R)-3-methyl-1,4-pentadiene ANSWER: c 5. What is the systematic IUPAC name of the following compound?

a. (3S,4E)-3-ethyl-3,4-dimethyl-1,4-hexadiene b. (3R,4E)-3-ethyl-3,4-dimethyl-1,4-hexadiene c. (3S,4Z)-3-ethyl-3,4-dimethyl-1,4-hexadiene d. (3R,4Z)-3-ethyl-3,4-dimethyl-1,4-hexadiene ANSWER: a 6. Which of the following alkenes undergoes the least exothermic hydrogenation upon treatment with H2/Pd

a. 1 b. 2 c. 3 d. 4 ANSWER: c 7. What is the correct order of exothermicity for hydrogenation of the following hexadienes upon treatment with H2/Pd (more exothermic > less exothermic)?

a. 1 > 2 > 3 b. 3 > 1 > 2 c. 2 > 1 > 3 d. 3 > 2 > 1 ANSWER: b 8. Which of the following arrangements of p atomic orbitals gives the lowest energy π-bonding molecular orbital of 1,3Copyright Cengage Learning. Powered by Cognero.

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Chapter 20: Dienes, Conjugated Systems, and Pericyclic Reactions butadiene?

a. 1 b. 2 c. 3 d. 4 ANSWER: b 9. Which of the following arrangements of p atomic orbitals gives the highest energy π-antibonding molecular orbital of 1,3-butadiene?

a. 1 b. 2 c. 3 d. 4 ANSWER: c 10. Which of the following arrangements of p atomic orbitals of 1,3-butadiene has the greatest number of nodes?

a. 1 b. 2 c. 3 d. 4 ANSWER: c 11. What is the reactive intermediate in the reaction of 1,3-butadiene with HBr resulting in 1,2-addition? a. bromine cation b. secondary allylic carbocation c. allylic anion d. vinylic cation ANSWER: b 12. Which of the following terms describes the mechanism for the addition of Br2 to 1,3-butadiene? a. electrophilic addition Copyright Cengage Learning. Powered by Cognero.

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Chapter 20: Dienes, Conjugated Systems, and Pericyclic Reactions b. nucleophilic addition c. pericyclic addition d. conjugate addition ANSWER: a 13. What is (are) the major organic product(s) formed in the following reaction?

a. only 1 b. only 1 and 3 c. only 2 and 4 d. only 1 and 4 ANSWER: d 14. What is (are) the major organic product(s) formed in the following reaction?

a. only 1 b. only 1 and 2 c. only 1 and 3 d. only 2 and 4 ANSWER: b 15. Which of the following is(are) formed upon addition of 1 mol of Br2 to 1,3-cyclohexane?

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Chapter 20: Dienes, Conjugated Systems, and Pericyclic Reactions

a. only 2 b. only 1 and 3 c. only 2 and 4 d. 1, 2 and 3 ANSWER: c 16. Which of the following is not a major organic product obtained from the addition of 1 mole of bromine to (Z)-1,3pentadiene? a. (Z)-4,5-dibromo-2-pentene b. 3,4-dibromo-1-pentene c. (Z)-1,4-dibromo-2-pentene d. (E)-1,1-dibromo-2-pentene ANSWER: d 17. What is the thermodynamic product obtained from the addition of 1 mole of bromine to 1,3-heptadiene? a. 3,4-dibromo-1-heptene b. (E)-1,4-dibromo-2-heptene c. (Z)-1,4-dibromo-2-heptene d. (Z)-2,3-dibromo-2-heptene ANSWER: b 18. What is the kinetic product obtained from the addition of 1 mole of bromine to 1,3-heptadiene? a. 3,4-dibromo-1-heptene b. (E)-1,4-dibromo-2-heptene c. (Z)-1,4-dibromo-2-heptene d. (E)-2,3-dibromo-2-heptene ANSWER: a 19. What is (are) the major organic product(s) formed in the following reaction?

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Chapter 20: Dienes, Conjugated Systems, and Pericyclic Reactions

a. only 1 b. only 2 c. only 1 and 3 d. only 2 and 4 ANSWER: b 20. What is (are) the major organic product(s) formed in the following reaction?

a. only 1 b. only 3 c. only 1 and 3 d. only 2 and 4 ANSWER: b 21. What is (are) the major organic product(s) formed in the following reaction?

a. only 1 b. only 2 c. only 3 d. 1, 2 and 3 ANSWER: c Copyright Cengage Learning. Powered by Cognero.

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Chapter 20: Dienes, Conjugated Systems, and Pericyclic Reactions 22. Which of the following reaction coordinate diagrams explains the formation of different thermodynamic (T) and kinetic products from the same reactants (R)?

a. 1 b. 2 c. 3 d. 4 ANSWER: c 23. Which of the following energy diagrams represents the electronic state of the ground state of 1,3-butadiene?

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Chapter 20: Dienes, Conjugated Systems, and Pericyclic Reactions

a. 1 b. 2 c. 3 d. 4 ANSWER: a 24. Which of the following energy diagrams represents the electronic state of butadiene after absorption of radiation?

a. 1 b. 2 c. 3 d. 4 ANSWER: b 25. What range of wavelengths corresponds to the ultraviolet region of the electromagnetic spectrum? a. 200-400 nm b. 400-700 nm c. 2.5-25 μm Copyright Cengage Learning. Powered by Cognero.

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Chapter 20: Dienes, Conjugated Systems, and Pericyclic Reactions d. 2-10 mm ANSWER: a 26. Which of the following processes takes place upon absorption of ultraviolet-visible radiation? a. bond vibration b. electron excitation c. nuclear spin flip d. electron spin flip ANSWER: b 27. Which of the following relationships is not valid as applied to ultraviolet-visible spectroscopy? a. A = log (Io/I) b. A = εcl c. ΔE = hν d. A = λminE ANSWER: d 28. What quantity is abbreviated as λ in ultraviolet-visible spectroscopy? a. absorbance b. wavelength of maximum absorbance c. intensity of the transmitted light d. molar absorbtivity coefficient ANSWER: b 29. What are the units of absorbance, A, in ultraviolet-visible spectroscopy? a. J⋅mol−1 b. nm⋅mol−1 c. J⋅mol−1⋅M−1 d. none, A is a dimensionless quantity ANSWER: d 30. What are the units of ε in ultraviolet-visible spectroscopy? a. M–1·cm–1 b. M⋅cm c. J⋅mol−1⋅dm−1 d. none, it is a dimensionless quantity ANSWER: a 31. What are the units of λmax in ultraviolet-visible spectroscopy? a. J⋅mol−1 b. M−1 Copyright Cengage Learning. Powered by Cognero.

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Chapter 20: Dienes, Conjugated Systems, and Pericyclic Reactions c. nm d. none, λmax is a dimensionless quantity ANSWER: c 32. Which of the following has the highest value of λmax in the ultraviolet-visible spectrum?

a. 1 b. 2 c. 3 d. 4 ANSWER: a 33. Which of the following has the highest value of λmax in the ultraviolet-visible spectrum?

a. 1 b. 2 c. 3 d. 4 ANSWER: a 34. Which of the following laws relates absorbance to the concentration of a sample and the pathlength in ultravioletvisible spectroscopy? a. Buzz-Beer law b. Beer-Lambert law c. Duff-Beer law d. Christopher-Lambert law ANSWER: b 35. Which of the following electronic transitions is apparent in the ultraviolet-visible spectrum of 1,3-butadiene? a. n → π* b. π → π * c. σ → π * Copyright Cengage Learning. Powered by Cognero.

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Chapter 20: Dienes, Conjugated Systems, and Pericyclic Reactions d. σ → π ANSWER: b 36. Which of the following electronic transitions is (are) apparent in the ultraviolet-visible spectrum of acrolein, H2C=CHCHO? 1. 2. 3.

n → π* π → π* σ → π*

a. only 1 b. only 2 c. only 1 and 2 d. 1, 2 and 3 ANSWER: c 37. The conjugated portion of the following molecule is circled.

a. True b. False ANSWER: True 38. The conjugated portion of the following molecule is circled.

a. True b. False ANSWER: False 39. Electrophilic addition reaction of conjugated dienes that occur at high temperature and/or long reaction times (reversible conditions) are said to be under kinetic control. a. True b. False ANSWER: False 40. Consider the following structure.

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Chapter 20: Dienes, Conjugated Systems, and Pericyclic Reactions

This substance could be produced by the reaction of the following diene and dienophile.

a. True b. False ANSWER: True 41. For a diene to undergo a Diels-Alder reaction it must be able to adopt an s-trans conformation. a. True b. False ANSWER: False 42. For Diels-Alder cycloaddition reactions to take place most rapidly and in highest yield a dienophile must be substituted with electron-donating groups. a. True b. False ANSWER: False 43. The following compound could act as a diene in a Diels-Alder reaction.

a. True b. False ANSWER: True 44. When an organic molecule is irradiated with ultraviolet radiation, the energy absorbed by the molecule corresponds to the amount necessary to excite electrons from one molecular orbital to another. a. True b. False ANSWER: True 45. The following two compounds could be easily distinguished by NMR, IR, UV or MS spectra.

a. True b. False Copyright Cengage Learning. Powered by Cognero.

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Chapter 20: Dienes, Conjugated Systems, and Pericyclic Reactions ANSWER: False 46. The following spectrum could arise from π to π* transitions.

a. True b. False ANSWER: True 47. Sigmatropic shifts, cycloaddition reactions and anuulation reactions are all examples of pericyclic reactions. a. True b. False ANSWER: False 48. Consider the following reaction.

This is an example of a sigmatropic reaction with a [3,3]-shift. a. True b. False ANSWER: True 49. Consider the following reaction.

This is an example of a sigmatropic reaction with a [3,3]-shift. a. True b. False ANSWER: False Consider the reaction below to answer the following question(s):

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Chapter 20: Dienes, Conjugated Systems, and Pericyclic Reactions

Enter the appropriate letter in the blank for each the following statements. 50. The nucleophile in this reaction is ____. ANSWER: A 51. The electrophile in this reaction is ____. ANSWER: B 52. The kinetically controlled product in this reaction is _____. ANSWER: D 53. The product that results from 1,4-addition is _____. ANSWER: C 54. The product that results from following mechanistic step is _____.

ANSWER: D 55. Consider the following spectrum for a conjugated diene.

If a similar spectrum were taken for a conjugated tetraene, the λmax would be _________than 217 nm. ANSWER: greater longer 56. Based on the following table. Compound Copyright Cengage Learning. Powered by Cognero.

λmax (nm) Page 14

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Chapter 20: Dienes, Conjugated Systems, and Pericyclic Reactions W X Y Z

190 340 560 250

Compound ______ has the largest energy difference between the HOMO and LUMO. ANSWER: W Consider the reaction below to answer the following question(s).

Fill in the blank in the question with the appropriate letter. 57. The dienophile in the reaction is ____. ANSWER: B 58. The diene in the reaction is ____. ANSWER: A 59. This is an example of a(n) ____________ reaction. A. sigmatropic reaction B. electrophillic addition C. Diels-Alder reaction D. Cope rearrangement ANSWER: C 60. What is the IUPAC name of the following compound?

ANSWER: (E)-2,3-dimethyl-2,4-hexadiene 61. What is the IUPAC name of the following compound?

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Chapter 20: Dienes, Conjugated Systems, and Pericyclic Reactions ANSWER: (E)-2,3-dimethyl-1,3-pentadiene 62. What are the two major organic products obtained from the following reaction?

ANSWER:

63. What are the two major organic products obtained from the following reaction?

ANSWER:

64. Provide the structures of the constitutional isomers of the two major organic products obtained from the following reaction?

ANSWER:

65. What is the major organic product obtained from the following reaction?

ANSWER:

66. Draw two resonance structures of the reactive intermediate that accounts for the formation of 1,2- and 1,4-addition products upon reaction of 1,3-butadiene with one equivalent of bromine. ANSWER:

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Chapter 20: Dienes, Conjugated Systems, and Pericyclic Reactions 67. Draw two resonance structures of the reactive intermediate that accounts for the formation of 1,2- and 1,4-addition products upon reaction of 1,3-butadiene with one equivalent of HBr. ANSWER:

68. How would you be able to distinguish between 1,3-cyclohexadiene and 1,4-cyclohexadiene using ultraviolet spectroscopy? ANSWER: 1,3-Cyclohexadiene, in which the two pi-bonds are conjugated, absorbs at a higher wavelength than 1,4cyclohexadiene. 69. Which of 1,3-cyclohexadiene and 1,4-cyclohexadiene has the greatest heat of hydrogenation (i.e., the most exothermic reaction with H2 in the presence of a catalyst). Provide a brief explanation for your choice ? ANSWER: 1,4-Cyclohexadiene has a greater heat of hydrogenation. This is because 1,3-cyclohexadiene is stabilized by conjugation of the two pi bonds. 70. Identify the product of the given reaction.

a. I b. II c. IV d. III ANSWER: a 71. Identify the product of the given reaction.

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Chapter 20: Dienes, Conjugated Systems, and Pericyclic Reactions

a. I b. II c. IV d. III ANSWER: a 72. Why carbonyl groups of aldehydes and ketones on conjugation with carbon–carbon double bonds show strong absorption in the ultraviolet spectrum? ANSWER: The presence of conjugation in aldehydes and ketones decreases the energy gap between filled and unfilled π orbitals. Hence, the strong absorption observed in the ultraviolet spectrum is because of the π to π* transition. 73. Pericyclic reactions occur in a single step with the _____. a. formation of a radical b. formation of an ionic intermediate c. formation of a molecular ion d. formation of a transition state ANSWER: d 74. The molar absorptivity of ethylene in hexane is 11500 L mol−1 cm−1. What is the maximum absorbance observed at a concentration of 2.50 x 10−4 mol L−1? (Path length = 1.00 cm) a. 2.88 b. 1.15 c. 2.88 d. 0.288 ANSWER: a 75. A reaction in which two reactants add together in a single step to form a cyclic product is known as a _____. ANSWER: cycloaddition reaction Copyright Cengage Learning. Powered by Cognero.

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Chapter 20: Dienes, Conjugated Systems, and Pericyclic Reactions 76. The [2+2] cycloaddition reaction of ethylene to form cyclobutane does not occur because _____.

a. the reaction is forbidden as determined by the frontier molecular orbital analysis b. the reaction is allowed as determined by the frontier molecular orbital analysis c. the reaction is allowed, and ethylene collides in a suprafacial manner d. the reaction is allowed, and ethylene collides in an antarafacial manner ANSWER: a

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Chapter 21: Benzene and the Concept of Aromaticity 1. What is the IUPAC name of the following compound?

a. 2-nitro-6-carboxybromobenzene b. 2-bromo-1-nitro-4-benzoic acid c. 2-bromo-4-carboxynitrobenzene d. 3-bromo-4-nitrobenzoic acid ANSWER: d 2. What is the IUPAC name of the following compound?

a. 2,4-dibromotoluene b. 2,4-dibromophenol c. 2,4-dibromohydroxybenzene d. 4,6-dibromophenol ANSWER: b 3. What is the IUPAC name of the following compound?

a. 1-bromo-2-fluoro-4-toluene b. 4-bromo-2-fluorotoluene c. 2-bromo-4-fluorophenol d. 4-bromo-2-fluoroxylene ANSWER: b Copyright Cengage Learning. Powered by Cognero.

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Chapter 21: Benzene and the Concept of Aromaticity 4. What is the correct assignment of the names of the following substituted benzenes?

a. 1 = phenol; 2 = aniline; 3 = anisole b. 1 = benzaldehyde; 2 = anisole; 3 = toluene c. 1 = anisole; 2 = xylene; 3 = toluene d. 1 = anisole; 2 = aniline; 3 = toluene ANSWER: d 5. What is the correct assignment of the names of the following substituted benzenes?

a. 1 = styrene; 2 = benzaldehyde; 3 = cumene b. 1 = anisole; 2 = benzaldehyde; 3 = toluene c. 1 = styrene; 2 = xylene; 3 = toluene d. 1 = aniline; 2 = phenol; 3 = cumene ANSWER: a 6. Which is the correct assignment of the names of the following substituted benzenes?

a. 1 = phenol; 2 = m-cresol; 3 = toluene b. 1 = m-cresol; 2 = resorcinol; 3 = m-xylene c. 1 = anisole; 2 = catechol; 3 = m-xylene d. 1 = m-cresol; 2 = anisole; 3 = cumene ANSWER: b Copyright Cengage Learning. Powered by Cognero.

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Chapter 21: Benzene and the Concept of Aromaticity 7. Which of the following represents the energy levels of the molecular orbitals of benzene?

a. 1 b. 2 c. 3 d. 4 ANSWER: c 8. Which of the following is not one of Hückel's criteria for aromaticity? a. The compound must be cyclic b. The compound must have (4n+2) pi electrons in the aromatic system, where n is a positive integer c. No atom on the ring can be sp3 hybridized d. The compound must have (4n) pi electrons in the aromatic system, where n is a positive integer ANSWER: d 9. What is the correct assignment of the names of the following heterocycles?

a. 1 = pyrrole; 2 = thiophene; 3 = pyridine b. 1 = thiophene; 2 = furan; 3 = pyrrole c. 1 = pyridine; 2 = thiophene; 3 = furan d. 1 = pyridine; 2 = thiophene; 3 = pyrrole ANSWER: c 10. What is the correct assignment of the names of the following heterocycles?

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Chapter 21: Benzene and the Concept of Aromaticity

a. 1 = pyrrole; 2 = thiophene; 3 = pyridine b. 1 = thiophene; 2 = furan; 3 = pyrrole c. 1 = furan; 2 = pyrrole; 3 = thiophene d. 1 = furan; 2 = thiophene; 3 = pyrrole ANSWER: c 11. What is the correct assignment of the names of the following fused arenes?

a. 1 = naphthalene; 2 = anthracene; 3 = pyrene b. 1 = naphthalene; 2 = phenanthrene; 3 = coronene c. 1 = naphthalene; 2 = anthracene; 3 = benzo[a]pyrene d. 1 = anthracene; 2 = naphthalene; 3 = coronene ANSWER: a 12. What is the approximate length of the carbon-carbon bonds in benzene? a. 110 pm b. 121 pm c. 139 pm d. 156 pm ANSWER: c 13. Which of the following statements is not true about the structure of benzene? a. The carbon-carbon bond lengths in benzene are all intermediate between a single and a double bond b. The carbon-carbon bonds lengths in benzene are all equivalent to that of a carbon-carbon double bond c. The structure is an average of two resonance contributors d. The hybridization of each carbon atom on the benzene ring is sp2 ANSWER: b 14. The number of unshared electron pair(s) lying in an unhybridized orbital of the oxygen atom of furan is ____. a. 4 b. 3 Copyright Cengage Learning. Powered by Cognero.

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Chapter 21: Benzene and the Concept of Aromaticity c. 1 d. 2 ANSWER: c 15. What is the hybridization of the nitrogen atom of pyridine? a. s b. sp c. sp2 d. sp3 ANSWER: c 16. The lone pair on the nitrogen atom of pyridine _______. a. can't participate in the interactions with other species b. is a part of the aromatic pi system c. contributes towards the Huckel's number of electrons d. is free to interact with other species ANSWER: d 17. The lone pair on the nitrogen atom of pyrrole _________. a. does not form the part of the pi system b. contributes towards the Huckel's number of pi electrons c. is available to interact with other species d. does not contribute towards the Huckel's number of pi electrons ANSWER: b 18. Which orbitals contain the lone pairs on the nitrogen atoms labeled i and ii in the imidazole ring?

a. i = sp2;; ii = sp3 b. i = p;; ii = sp3 c. i = p;; ii = sp3 d. i = p;; ii = sp2 ANSWER: d 19. Which of the following statements is not true about the structure of benzene? a. Each carbon atom on the benzene ring is bonded to a hydrogen atom by an sp2-1s overlap b. The lowest-lying filled molecular orbital has two torus-shaped lobes c. The unhybridized 2p orbital on each carbon atom contains one electron d. The bonding molecular orbitals of benzene lie higher in energy than the isolated 2p orbitals Copyright Cengage Learning. Powered by Cognero.

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Chapter 21: Benzene and the Concept of Aromaticity ANSWER: d 20. Which of the following compounds is aromatic? a. butane b. 1,3,5-cycloheptatriene c. phenol d. 1,3-cyclohexadiene ANSWER: c 21. Which of the following heterocycles is not aromatic?

a. 1 b. 2 c. 3 d. 4 ANSWER: c 22. Which of the following ions is aromatic?

a. 1 b. 2 c. 3 d. 4 ANSWER: b 23. Which of the following compounds is antiaromatic? a. pentane b. cyclobutadiene c. tropylium cation d. cyclopentadiene ANSWER: b 24. Which of the following molecules is the most acidic? Copyright Cengage Learning. Powered by Cognero.

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Chapter 21: Benzene and the Concept of Aromaticity

a. 1 b. 2 c. 3 d. 4 ANSWER: b 25. Which of the following compounds undergoes heterolytic carbon-halogen bond cleavage to form a stable organic cation?

a. 1 b. 2 c. 3 d. 4 ANSWER: d 26. Which of the following has the compounds shown in the correct order of decreasing acidity (i.e., more acidic > less acidic)?

a. 1 > 2 > 3 b. 2 > 1 > 3 c. 3 > 2 > 1 d. 1 > 3 > 2 ANSWER: a 27. Which of the following has the compounds shown in the correct order of decreasing acidity (i.e., more acidic > less Copyright Cengage Learning. Powered by Cognero.

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Chapter 21: Benzene and the Concept of Aromaticity acidic)?

a. 1 > 2 > 3 b. 2 > 3 > 1 c. 3 > 2 > 1 d. 1 > 3 > 2 ANSWER: a 28. Which of the following has the compounds shown in the correct order of decreasing acidity (i.e., more acidic > less acidic)?

a. 1 > 2 > 3 b. 2 > 1 > 3 c. 3 > 2 > 1 d. 1 > 3 > 2 ANSWER: a 29. Which of the following has the compounds shown in the correct order of decreasing acidity (i.e., more acidic > less acidic)?

a. 1 > 2 > 3 b. 2 > 3 > 1 c. 3 > 2 > 1 d. 1 > 3 > 2 Copyright Cengage Learning. Powered by Cognero.

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Chapter 21: Benzene and the Concept of Aromaticity ANSWER: b 30. Which of the following has the compounds shown in the correct order of decreasing acidity (i.e., more acidic > less acidic)?

a. 1 > 2 > 3 b. 2 > 3 > 1 c. 3 > 2 > 1 d. 2 > 1 > 3 ANSWER: d 31. What is the major organic product obtained from the following reaction?

a. 1 b. 2 c. 3 d. 4 ANSWER: a 32. What is the major organic product obtained from the following reaction?

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Chapter 21: Benzene and the Concept of Aromaticity

a. 1 b. 2 c. 3 d. 4 ANSWER: a 33. What is the major organic product obtained from the following reaction?

a. 1 b. 2 c. 3 d. 4 ANSWER: c 34. What is the major organic product obtained from the following reaction?

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Chapter 21: Benzene and the Concept of Aromaticity

a. 1 b. 2 c. 3 d. 4 ANSWER: b 35. What is the major organic product obtained from the following reaction?

a. 1 b. 2 c. 3 d. 4 ANSWER: a 36. What is the major organic product obtained from the following reaction?

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Chapter 21: Benzene and the Concept of Aromaticity

a. 1 b. 2 c. 3 d. 4 ANSWER: a 37. What is the best choice of reagent to achieve the following reaction?

a. H2SO4 b. NaOH, H2O c. AgI d. LiAlH4 ANSWER: c 38. What is the best choice of reagent?

a. H2SO4 b. NaOH, H2O c. K2Cr2O7, H2SO4 Copyright Cengage Learning. Powered by Cognero.

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Chapter 21: Benzene and the Concept of Aromaticity d. H2/Fe ANSWER: d 39. What is the best choice of reagent to achieve the following reaction?

a. Br2, CCl4 b. NBS, base catalyst c. Br2, light d. NaBr ANSWER: c 40. Which of the following represents the energy levels of the molecular orbitals of cyclopentadienyl anion?

a. 1 b. 2 c. 3 d. 4 ANSWER: a 41. Which of the following represents the energy levels of the molecular orbitals of cyclobutadiene?

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Chapter 21: Benzene and the Concept of Aromaticity

a. 1 b. 2 c. 3 d. 4 ANSWER: a 42. Which of the following is not true about cyclooctatetraene? a. Cyclooctatetraene is large enough to pucker into a nonplanar conformation and become nonaromatic b. In the planar conformation, there are six electrons in the bonding pi orbitals c. Cyclooctatetraene adopts a nonplanar geometry with alternating double and single bonds d. It is a [6]annulene ANSWER: d 43. What are the relative positions of the substituents in the following structure?

a. anti b. meta c. ortho d. para ANSWER: c 44. What are the relative positions of the substituents in the following structure?

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Chapter 21: Benzene and the Concept of Aromaticity

a. anti b. meta c. ortho d. para ANSWER: b 45. What are the relative positions of the substituents in the following structure?

a. anti b. meta c. ortho d. para ANSWER: d 46. Which of the following is not true about [18]annulene?

a. To achieve planarity, several of the carbon-carbon double bonds in [18]annulene have the trans configuration b. Resonance energy of [18]annulene is 418 kJ/mol c. The 6 hydrogens lying inside the ring of [18]annulene, come into resonance at δ -3.0 d. [18]annulene has 9 pi electrons ANSWER: d 47. Which of the following is not true about [10]annulene? Copyright Cengage Learning. Powered by Cognero.

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Chapter 21: Benzene and the Concept of Aromaticity

a. The ten membered ring can easily accommodate the two hydrogen that point inward towards the center of the ring b. [10]annulene is nonaromatic c. [10]annulene undergoes addition reactions similar to simple alkenes d. [10]annulene has 10 pi electrons ANSWER: a 48. Which of the following is not true about the bridged [10]annulene shown below?

a. bridged [10]annulene is antiaromatic b. bridged [10]annulene satisfies the Huckel's criteria of aromaticity c. bridged [10]annulene undergoes substitution reactions d. bridged [10]annulene has 5 pi bonds ANSWER: a 49. What is the intermediate in the reaction of ethylbenzene with NBS in the presence of benzoyl peroxide to give 1bromo-1-phenylethane? a. Benzylic anion b. Benzylic cation c. Benzylic radical d. Benzylic carbene ANSWER: c 50. Which of the following does not undergo oxidation in the presence of H2CrO4?

a. 1 b. 2 c. 3 d. 4 ANSWER: d Copyright Cengage Learning. Powered by Cognero.

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Chapter 21: Benzene and the Concept of Aromaticity 51. How many p orbital electrons are present in imidazole? a. 4 b. 6 c. 8 d. 2 ANSWER: b 52. How many p orbital electrons are present in cyclopropenyl cation? a. 4 b. 2 c. 3 d. 1 ANSWER: b 53. The following compound is named (Z)-2,3-diphenyl-2-hexene.

a. True b. False ANSWER: False 54. Furan has the structure shown below.

The π orbitals in furan are shown below.

a. True b. False ANSWER: True 55. Consider the following structures,

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Chapter 21: Benzene and the Concept of Aromaticity A

Structure A is more acidic than B. a. True b. False ANSWER: False 56. Phenols are stronger acids than alcohols because of the resonance stabilization of alkoxide ions. a. True b. False ANSWER: False 57. The product of the following reaction would be a dicarboxylic acid.

a. True b. False ANSWER: False 58. The product of the following reaction would be 1-bromo-1-phenylethane.

a. True b. False ANSWER: True 59. The following compound should be name as 1-((1S, 3R)-3-methylcyclohexyl)benzene.

a. True b. False ANSWER: True 60. Consider the following structure. Copyright Cengage Learning. Powered by Cognero.

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Chapter 21: Benzene and the Concept of Aromaticity

The 1H NMR spectrum of this compound −60°C shows a peak at 7.6 ppm, this would indicate aromaticity. a. True b. False ANSWER: True 61. The following compound could be produced by reaction of phenol with bromobenzene.

a. True b. False ANSWER: False 62. Consider the following general structure.

Positions 1,4 and 2,6 and 3,5 are termed para, ortho, and meta, respectively. a. True b. False ANSWER: True Answer the following questions concerning sulfathiazole below by filling ieach blank with the appropriate response.

63. The hybridization of the nitrogen atom in sulfathiazole is ______. A. sp B. sp2 C. sp3 ANSWER: B Copyright Cengage Learning. Powered by Cognero.

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Chapter 21: Benzene and the Concept of Aromaticity 64. Assuming that the sulfur atom is sp2-hybridized, there are _____ π-electrons in the sulfathiazole ring. ANSWER: six 6 65. According to Hückel criteria, sulfathiazole is predicted to be ___________. ANSWER: aromatic Consider the cycloheptatrienyl anion. Complete the following questions by filling in the blank with the appropriate word. 66. According the Hückel criteria this anion would be classified as ______________. ANSWER: antiaromatic 67. This anion has______ π electrons. ANSWER: 8 eight 68. Consider the following two compounds.

An ether solution containing these two substances was mixed with an aqueous 1 M NaOH solution. will be found in the basic layer. ANSWER: B

Substance _____

69. Consider the following compound.

When treated with acidic K2Cr2O7 the product would be classified as a ___________. ANSWER: quinone Consider the following structure.

70. If named as an annulene, the name would be [ __ ] annulene. ANSWER: 16 Copyright Cengage Learning. Powered by Cognero.

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Chapter 21: Benzene and the Concept of Aromaticity 71. This structure contains ____ π electrons. ANSWER: 16 72. Using the Hückel criteria, the compound would be ______________. ANSWER: antiaromatic Consider the following structure.

The 1H NMR spectrum of [14]annulene at −60°C shows two peaks, one at 0 ppm and one at 7.6 ppm. 73. The NMR data would seem to indicate that this compound is ____________. ANSWER: aromatic 74. The ratio of peak areas, respectively for the 7.6 ppm and 0 ppm, peaks would be_______. ANSWER: 5:2 5 to 2 5/2 75. What is the IUPAC name of the following compound?

ANSWER: 3-bromo-4-nitrophenol 76. What is the IUPAC name of the following compound?

ANSWER: 4-chloro-3-nitrobenzoic acid Copyright Cengage Learning. Powered by Cognero.

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Chapter 21: Benzene and the Concept of Aromaticity 77. What is the IUPAC name of the following compound?

ANSWER: 3,4-dichloroaniline 78. What is the IUPAC name of the following compound?

ANSWER: 4-bromo-2-propylbenzonitrile 79. What is the major organic product obtained from the following reaction?

ANSWER:

80. What is the major organic product obtained from the following reaction?

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Chapter 21: Benzene and the Concept of Aromaticity ANSWER:

81. What is the major organic product obtained from the following reaction?

ANSWER:

82. What are the two major organic products obtained from the following reaction?

ANSWER:

83. List all of the requirements of a molecule for it to be considered aromatic. ANSWER: An aromatic molecule has an uninterrupted cycle of overlapping p orbitals (i.e., the cyclic structure should be planar) that contains 2n+2 (i.e., 2, 6, 8, ...) electrons 84. Provide a brief explanation of why furan (below) is aromatic. Your answer should identify the hybridization of the oxygen atom and account for which electrons are in the pi system.

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Chapter 21: Benzene and the Concept of Aromaticity ANSWER: The oxygen is sp2 hybridized. One lone pair is in a p orbital and is part of the pi system, along with one electron in the p orbital on each of the four carbon atoms. The other lone pair of the oxygen is in an sp2 orbital, which is in the plane of the ring and not involved in the pi system. 85. Provide a brief explanation of why the cyclopentadienyl anion (below) is aromatic. Your answer should identify the hybridization of each carbon atom and account for which electrons are in the pi system.

ANSWER: The all five carbons are sp2 hybridized. The lone pair is in a p orbital and is part of the pi system, along with one electron in the p orbital on each of the other four carbon atoms for a total of six pi electrons. 86. What is the chemical name of the following compound?

a. 2,3-dichloro-5,6-dicyano-1,4-benzoquinone b. 2,3-dichloro-5,6-dicyano-1,4-benzodione c. 5,6-dicyano-2,3-dichloro-1,4-benzodione d. 2,3-dicyano-5,6-dichloro-1,4-benzoquinone ANSWER: a 87. Aspirin, also known as acetylsalicylic acid, is used to treat fever and inflammation. It is prepared from an unknown compound “A” by the process of esterification, using acetic anhydride. Identify compound “A”. a.

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Chapter 21: Benzene and the Concept of Aromaticity c.

ANSWER: a 88. Identify the major product of the following reaction.

ANSWER: a 89. The ______ substituent is affected during the oxidation of 1-chloro-2-butyl-4-nitrobenzene using chromic acid. a. butyl b. chloro c. nitro d. none of the substituents is affected Copyright Cengage Learning. Powered by Cognero.

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Chapter 21: Benzene and the Concept of Aromaticity ANSWER: a 90. Which of the following compound is nonaromatic? a.

ANSWER: b 91. Why are nitrophenols more acidic than phenols? ANSWER: Nitro phenols are more acidic than phenols because of the electron-withdrawing inductive effect of the –NO2 group. Also, the negative charge of the phenoxide ion on the ortho and para positions of nitrophenol is delocalized onto the oxygen atom of the –NO2 group, thus making it more stable and acidic. 92. Identify the most acidic compound. a.

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Chapter 21: Benzene and the Concept of Aromaticity c.

ANSWER: d

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Chapter 22: Reactions of Benzene and Its Derivatives 1. What is the major organic product obtained from the following reaction?

a. 1 b. 2 c. 3 d. 4 ANSWER: b 2. What is the major organic product obtained from the following reaction?

a. 1 b. 2 c. 3 d. 4 ANSWER: b 3. What is the major organic product obtained from the following reaction?

a. 1 b. 2 c. 3 d. 4 ANSWER: d Copyright Cengage Learning. Powered by Cognero.

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Chapter 22: Reactions of Benzene and Its Derivatives 4. What is the major organic product obtained from the following reaction?

a. 1 b. 2 c. 3 d. 4 ANSWER: b 5. What is the major organic product obtained from the following reaction?

a. 1 b. 2 c. 3 d. 4 ANSWER: b 6. What is the electrophile in the reaction of benzene with concentrated sulfuric acid containing dissolved sulfur trioxide? a. Benzene b. HSO2+ c. SO2 d. HSO3+ ANSWER: d 7. What is the electrophile in the reaction of benzene with isopropyl chloride and ferric chloride? a. (CH3)2CH+ Copyright Cengage Learning. Powered by Cognero.

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Chapter 22: Reactions of Benzene and Its Derivatives b. (CH3)2CH2 c. CH3+ d. benzene ANSWER: a 8. What is the electrophile in the reaction of benzene with tert-butyl chloride and AlCl3? a. CH3+ b. Cl+ c. (CH3)C+ d. benzene ANSWER: c 9. What is the role of AlCl3 in Friedel Crafts acylations using acid chlorides? a. Lewis acid b. electrophile c. base d. nucleophile ANSWER: a 10. What is the role of FeCl3 in electrophilic aromatic chlorination of benzene using Cl2? a. nucleophile b. electrophile c. catalyst d. base ANSWER: c 11. Which of the following undergoes the most rapid nitration upon treatment with HNO3/H2SO4? a. toluene b. benzene c. bromobenzene d. nitrobenzene ANSWER: a 12. Which of the following undergoes the most rapid chlorination upon treatment with Cl2/FeCl3? a. ethylbenzene b. bromobenzene c. benzene d. nitrobenzene ANSWER: a 13. Which of the following undergoes the most rapid sulfonation upon treatment with fuming sulfuric acid? Copyright Cengage Learning. Powered by Cognero.

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Chapter 22: Reactions of Benzene and Its Derivatives a. benzene b. benzoic acid c. benzonitrile d. nitrobenzene ANSWER: a 14. Which of the following undergoes the most rapid acylation upon treatment with acetyl chloride and AlCl3? a. benzene b. toluene c. chlorobenzene d. 1,4-dichlorobenzene ANSWER: b 15. Which of the following sets of substituents are all ortho/para directing in electrophilic aromatic substitution reactions? a. Br, CF3, C2H5 b. Cl, OH, COOCH3 c. Br, OCH3, C2H5 d. NO2, CF3, COOCH3 ANSWER: c 16. Which of the following sets of substituents are all ortho/para directing in electrophilic aromatic substitution reactions? a. Cl, CH3, CF3 b. CH3, NHCH3, Cl c. F, OCH3, COCH3 d. CF3, COCH3, COOCH3 ANSWER: b 17. Which of the following sets of substituents are all meta directing in electrophilic aromatic substitution reactions? a. SO3H, CN, CONH2 b. CH3, Br, COCH3 c. OCOCH3, C6H5, F d. NHCH3, Cl, CF3 ANSWER: a 18. Which of the following sets of substituents are all meta directing in electrophilic aromatic substitution reactions? a. C2H5, OCH3, NH2 b. I, NH2, CCl3 c. COOCH3, CF3, CONH2 d. NHCH3, COOCH3, CN Copyright Cengage Learning. Powered by Cognero.

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Chapter 22: Reactions of Benzene and Its Derivatives ANSWER: c 19. Which of the following sets of substituents are all activating groups in electrophilic aromatic substitution reactions? a. C2H5, NHCH3, COOCH3 b. NHCOCH3, NO2, NH3+ c. F, NH2, C6H5 d. C6H5, OCH3, NHCOCH3 ANSWER: d 20. Which of the following sets of substituents are all activating groups in electrophilic aromatic substitution reactions? a. CH3, CN, NH2 b. C6H5, NHCH3, OCOC6H5 c. OCH3, COOCH3, SO3H d. F, SO3H, NO2 ANSWER: b 21. Which of the following sets of substituents are all deactivating groups in electrophilic aromatic substitution reactions? a. Br, NO2, CCl3 b. Br, NH2, COCH3 c. OCH3, NHCH3, CH3 d. OH, NHCH3, COCH3 ANSWER: a 22. Which of the following sets of substituents are all deactivating groups in electrophilic aromatic substitution reactions? a. Br, OCH3, C2H5 b. CH3, I, COOCH3 c. C6H5, NHCH3, OCH3 d. COOCH3, NO2, Cl ANSWER: d 23. Which of the following substituents is ortho/para directing and deactivating in electrophilic aromatic substitution reactions? a. NH2 b. F c. NHCOCH3 d. CF3 ANSWER: b 24. Which of the following substituents is ortho/para directing and deactivating in electrophilic aromatic substitution reactions? Copyright Cengage Learning. Powered by Cognero.

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Chapter 22: Reactions of Benzene and Its Derivatives a. COCH3 b. NH3 c. Br d. CH2CH3 ANSWER: c 25. Which of the following reactions or reaction sequences will not give ethylbenzene as the major product? a. treatment of benzene with ethyl alcohol and H2SO4 b. treatment of benzene with chloroethane and AlCl3 c. treatment of benzene with ethanoyl chloride and AlCl3 d. treatment of benzene with ethene and HF ANSWER: c 26. Which of the following reactions or sequences will provide 1-hexylbenzene as the major product? a. treatment of benzene with isohexyl alcohol and HF b. treatment of benzene with hexanoyl chloride and AlCl3; followed by reaction with Zn(Hg) and HCl c. treatment of benzene with 1-chlorohexane and AlCl3 d. treatment of benzene with 1-hexene and HF ANSWER: b 27. Which of the following are valid resonance structures of the electophile involved in Friedel-Crafts acylation of benzene upon treatment with CH3COCl and AlCl3?

a. 1 b. 2 c. 3 d. 4 ANSWER: a 28. Which of the following is the structure of the complex of Br2 with FeBr3 involved in the electrophilic bromination of benzene?

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Chapter 22: Reactions of Benzene and Its Derivatives

a. 1 b. 2 c. 3 d. 4 ANSWER: d 29. Which of the following sets of reagents does not result in alkylation of benzene? a. isopropyl chloride + AlCl3 b. isopropyl alcohol + H3PO4 c. propene + HF d. propane + H2SO4 ANSWER: d 30. Why does nitrobenzene fail to undergo Friedel-Crafts alkylation with tert-butyl chloride and AlCl3? a. nitrobenzene reacts with AlCl3 b. nitrobenzene is a poor nucleophile c. the nitro group is a strong electron donating group d. the tert-butyl cation is a poor electrophile ANSWER: b 31. Why does anisole undergo bromination with Br2 in the absence of FeBr3 whereas bromination of benzene requires the presence of FeBr3? a. anisole is a better nucleophile than benzene b. the methoxy group of anisole is an inductive electron withdrawing substituent c. Br2 is a good nucleophile d. the reaction is accelerated by light ANSWER: a 32. What is the major organic product obtained from the following reaction?

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Chapter 22: Reactions of Benzene and Its Derivatives

a. 1 b. 2 c. 3 d. 4 ANSWER: b 33. What is the major organic product obtained from the following reaction?

a. 1 b. 2 c. 3 d. 4 ANSWER: c 34. What is the major organic product obtained from the following reaction?

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Chapter 22: Reactions of Benzene and Its Derivatives a. 1 b. 2 c. 3 d. 4 ANSWER: a 35. What is the major organic product obtained from the following reaction?

a. 1 b. 2 c. 3 d. 4 ANSWER: b 36. What is the major organic product obtained from the following reaction?

a. 1 b. 2 c. 3 d. 4 ANSWER: b 37. What is the major organic product obtained from the following reaction?

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Chapter 22: Reactions of Benzene and Its Derivatives

a. 1 b. 2 c. 3 d. 4 ANSWER: d 38. What is the major organic product obtained from the following reaction?

a. 1 b. 2 c. 3 d. 4 ANSWER: d 39. What is the major organic product obtained from the following reaction?

a. 1 b. 2 c. 3 d. 4 ANSWER: d Copyright Cengage Learning. Powered by Cognero.

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Chapter 22: Reactions of Benzene and Its Derivatives 40. What is the major organic product obtained from the following reaction?

a. 1 b. 2 c. 3 d. 4 ANSWER: b 41. What is the major organic product obtained from the following reaction?

a. 1 b. 2 c. 3 d. 4 ANSWER: d 42. What is the major organic product obtained from the following sequence of reactions? Copyright Cengage Learning. Powered by Cognero.

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Chapter 22: Reactions of Benzene and Its Derivatives

a. 1 b. 2 c. 3 d. 4 ANSWER: a 43. What is the major organic product obtained from the following sequence of reactions?

a. 1 b. 2 c. 3 d. 4 ANSWER: c 44. What is the major organic product obtained from the following sequence of reactions?

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Chapter 22: Reactions of Benzene and Its Derivatives

a. 1 b. 2 c. 3 d. 4 ANSWER: a 45. What is the major organic product obtained from the following sequence of reactions?

a. 1 b. 2 c. 3 d. 4 ANSWER: c 46. What is the major organic product obtained from the following sequence of reactions?

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Chapter 22: Reactions of Benzene and Its Derivatives

a. 1 b. 2 c. 3 d. 4 ANSWER: d 47. What is the major organic product obtained from the following sequence of reactions?

a. 1 b. 2 c. 3 d. 4 ANSWER: a 48. Which of the following cannot be prepared from benzene in two synthetic steps?

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Chapter 22: Reactions of Benzene and Its Derivatives

a. 1 b. 2 c. 3 d. 4 ANSWER: d 49. Which of the following cannot be prepared from benzene in two synthetic steps?

a. 1 b. 2 c. 3 d. 4 ANSWER: a 50. Which of the following is the reactive intermediate in the nucleophilic substitution of 4-bromo-1-nitrobenzene with sodium hydroxide?

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Chapter 22: Reactions of Benzene and Its Derivatives a. 1 b. 2 c. 3 d. 4 ANSWER: a 51. Which of the following is the reactive intermediate in the nucleophilic substitution of 4-bromo-1-toluene with sodium amide?

a. 1 b. 2 c. 3 d. 4 ANSWER: d 52. Which of the following is the reactive intermediate formed in the electrophilic bromination of toluene with Br2, FeBr3?

a. 1 b. 2 c. 3 d. 4 ANSWER: c 53. Which of the following is the reactive intermediate formed in the electrophilic nitration of nitrobenzene with HNO3 and H2SO4? Copyright Cengage Learning. Powered by Cognero.

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Chapter 22: Reactions of Benzene and Its Derivatives

a. 1 b. 2 c. 3 d. 4 ANSWER: b 54. Which of the following is the reactive intermediate formed in the electrophilic Friedel-Crafts acylation of toluene with CH3COCl and AlCl3?

a. 1 b. 2 c. 3 d. 4 ANSWER: d 55. Which of the following compounds undergoes the most rapid nucleophilic substitution with hydroxide ion?

a. 1 Copyright Cengage Learning. Powered by Cognero.

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Chapter 22: Reactions of Benzene and Its Derivatives b. 2 c. 3 d. 4 ANSWER: d 56. Which of the following compounds undergoes the most rapid nucleophilic substitution with hydroxide ion?

a. 1 b. 2 c. 3 d. 4 ANSWER: c 57. Which of the following chlorobenzenes produces a single isomer upon treatment with NaNH2?

a. 1 b. 2 c. 3 d. 4 ANSWER: d 58. Which of the following chlorobenzenes does not undergo nucleophilic aromatic substitution upon treatment with NaNH2?

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Chapter 22: Reactions of Benzene and Its Derivatives

a. 1 b. 2 c. 3 d. 4 ANSWER: a 59. Which mechanism accounts for the reaction of 4-bromo-1-nitrobenzene with sodium hydroxide to form 4-nitrophenol? a. Bimolecular nucleophilic substitution (SN2) b. Nucleophilic aromatic substitution by elimination-addition c. Nucleophilic aromatic substitution by addition-elimination d. Electrophilic aromatic substitution ANSWER: c 60. Which mechanism accounts for the reaction of chlorobenzene with acetyl chloride and AlCl3 to form 4chloroacetophenone? a. Bimolecular nucleophilic substitution (SN2) b. Nucleophilic aromatic substitution by elimination-addition c. Nucleophilic aromatic substitution by addition-elimination d. Electrophilic aromatic substitution ANSWER: d 61. Which mechanism accounts for the reaction of benzyl chloride with sodium cyanide to form cyanomethylbenzene (phenylacetonitrile, PhCH2CN)? a. Bimolecular nucleophilic substitution (SN2) b. Nucleophilic aromatic substitution by elimination-addition c. Nucleophilic aromatic substitution by addition-elimination d. Electrophilic aromatic substitution ANSWER: a 62. Which mechanism accounts for the reaction of 4-chlorotoluene with sodium amide to form a mixture of 3- and 4aminotoluene? a. Bimolecular nucleophilic substitution (SN2) b. Nucleophilic aromatic substitution by elimination-addition c. Nucleophilic aromatic substitution by addition-elimination Copyright Cengage Learning. Powered by Cognero.

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Chapter 22: Reactions of Benzene and Its Derivatives d. Electrophilic aromatic substitution ANSWER: b 63. What type of intermediate is formed in the reaction between fluorobenzene and isopropyl chloride and AlCl3 to give 4-fluoroisopropylbenzene? a. benzyl radical b. Meisenheimer complex c. cyclohexadienyl cation d. benzyne ANSWER: c 64. What type of intermediate is formed in the reaction between bromobenzene and sodium amide to give aniline? a. Meisenheimer complex b. benzyne c. cyclohexadienyl cation d. benzyl radical ANSWER: b 65. What type of intermediate is formed in upon irradiation of a mixture of toluene and iodine to give benzyl iodide ? a. benzyne b. cyclohexadienyl cation c. Meisenheimer complex d. benzyl radical ANSWER: d 66. What type of intermediate is formed upon treatment of 1-chloro-2,4-dinitrobenzene with sodium hydroxide to give 2,4-dinitrophenol? a. Meisenheimer complex b. benzyne c. cyclohexadienyl cation d. benzyl radical ANSWER: a 67. Which of the following is not true about Meissenheimer complexes? a. They are resonance-stabilized anions b. They are formed upon addition of a nucleophile to aryl halides c. They are not aromatic d. They are intermediates in nucleophilic aromatic substitution reaction which takes place by an eliminationaddition mechanism ANSWER: d 68. Which of the following is not true about benzynes? a. They are planar and aromatic b. Elimination reaction between the haloarene and strong base gives rise to benzyne intermediate Copyright Cengage Learning. Powered by Cognero.

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Chapter 22: Reactions of Benzene and Its Derivatives c. They are intermediates in nucleophilic aromatic substitution reaction which takes place by an eliminationaddition mechanism d. Nucleophilic addition of amide ion to a carbon of the benzyne triple bond gives a carbocation intermediate ANSWER: d 69. All of the following can act as an electrophile in an electrophilic aromatic substitution reaction.

SO3 (CH3)3C+

NO2+

a. True b. False ANSWER: True 70. The predominant intermediate in the electrophilic nitration of toluene is shown below.

a. True b. False ANSWER: False 71. The predominant intermediate in the electrophilic nitration of benzenesulfonic acid is shown below.

a. True b. False ANSWER: True 72. Among the following groups, 2, 3, and 5 are meta-directing.

1. –Cl 2. –NO2 3. –SO3H 4. –CH3 5. –COCH3 a. True b. False ANSWER: True Copyright Cengage Learning. Powered by Cognero.

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Chapter 22: Reactions of Benzene and Its Derivatives 73. The electrophile that could be used to make acetophenone (methyl phenyl ketone) from benzene is shown

below. a. True b. False ANSWER: True 74. The predominant product from sequential nitration and bromination of benzenesulfonic acid is shown below.

a. True b. False ANSWER: True 75. The best sequence in which to carry out the following reaction is 1) Br2, AlBr3, 2) H2SO4, SO3.

a. True b. False ANSWER: False 76. The compound shown below is (nitromethyl)benzene. One would expect this compound to more reactive than toluene toward electrophilic substitution.

a. True b. False ANSWER: False 77. Tetracyclone (shown below) is often used to trap benzynes as Diels-Alder adducts.

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Chapter 22: Reactions of Benzene and Its Derivatives

The structure of the Diels-Alder adduct that results when benzyne is trapped by tetracyclone would be

a. True b. False ANSWER: True 78. The product of the following reaction would be 2-nitrotoluene.

a. True b. False ANSWER: False 79. The number of mononitro products that can be produced when the following reactant is treated with nitric

and sulfuric acids is _______.

ANSWER: one 1 80. In electrophilic aromatic substitution reactions, the following molecule are considered to be ______ reactive

than benzene

ANSWER: more Copyright Cengage Learning. Powered by Cognero.

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Chapter 22: Reactions of Benzene and Its Derivatives Consider the following compounds.

Use the number of the compound to answer the following question. Place the number in the blank provided. 81. The compound that is the most reactive to nitration is ______. ANSWER: 3 three 82. The compound that is the least reactive to nitration is ______. ANSWER: 4 four 83. The name of the expected product from the following reaction is ___________________.

ANSWER: 4-ethyl-1,3-dimethylbenzene Consider the reaction below to answer the following question(s).

Fill in the blank with the appropriate letter or response. 84. The nucleophile in the reaction is _____. ANSWER: A 85. The Lewis acid catalyst in the reaction is _____. ANSWER: C 86. This reaction proceeds _____ (faster or slower) than when benzene is used. ANSWER: slower 87. The name of product D is ________________________. ANSWER: m-bromonitrobenzene m-bromonitrobenzene 1-bromo-3-nitrobenzene MATCH a structure or term from the following list with each description below. Place the letter of the structure or term in Copyright Cengage Learning. Powered by Cognero.

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Chapter 22: Reactions of Benzene and Its Derivatives the blank to the left of the description. a. benzyne b. +NO2 c. R3C+ d. electron-donating e. +NO f. Meisenheimer complex g. h. electron-withdrawing 88. ______ The reactive electrophile in Friedel-Crafts acylation reactions. ANSWER: g 89. ______ The electrophile in aromatic nitration. ANSWER: b 90. ______ Groups which activate aromatic rings towards electrophilic substitution. ANSWER: d 91. ______ Groups which activate aromatic rings towards nucleophilic substitution. ANSWER: h 92. ______ Intermediate in the elimination-addition mechanism of nucleophilic aromatic substitution. ANSWER: a 93. What is the major organic product obtained from the following reaction?

ANSWER:

94. What is the major organic product obtained from the following reaction?

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Chapter 22: Reactions of Benzene and Its Derivatives

ANSWER:

95. What is the major organic product obtained from the following reaction?

ANSWER:

96. What is the major organic product obtained from the following reaction?

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Chapter 22: Reactions of Benzene and Its Derivatives ANSWER:

97. What is the major organic product obtained from the following reaction?

ANSWER:

98. What is the major organic product obtained from the following reaction?

ANSWER:

99. What is the major organic product obtained from the following sequence of reactions (if a reaction is likely to give you a mixture of ortho and para disubstituted compounds you should assume that they can be separated; continue the synthesis with either one)? Copyright Cengage Learning. Powered by Cognero.

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Chapter 22: Reactions of Benzene and Its Derivatives

ANSWER:

100. What is the major organic product obtained from the following reaction (if a reaction is likely to give you a mixture of ortho and para disubstituted compounds you should assume that they can be separated; continue the synthesis with either one)?

ANSWER:

101. What is the major organic product obtained from the following sequence of reactions (if a reaction is likely to give you a mixture of ortho and para disubstituted compounds you should assume that they can be separated; continue the synthesis with either one)?

ANSWER:

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Chapter 22: Reactions of Benzene and Its Derivatives 102. What is the major organic product obtained from the following reaction (assume that mixtures of ortho and para disubstituted compounds can be separated; continue the synthesis with either one)?

ANSWER:

or ortho isomer 103. What is the major organic product obtained from the following reaction (assume that mixtures of ortho and para disubstituted compounds can be separated; continue the synthesis with either one)?

ANSWER:

104. Provide the structure (a single resonance contributor) of the key intermediate in the electrophilic aromatic nitration of chlorobenzene.

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Chapter 22: Reactions of Benzene and Its Derivatives ANSWER:

105. Provide the structure (a single resonance contributor) of the key intermediate in the electrophilic aromatic chlorination of nitrobenzene.

ANSWER:

106. Provide the structure (a single resonance contributor) of the key intermediate in the following reaction.

ANSWER:

107. Provide the structure (a single resonance contributor) of the key intermediate in the following reaction.

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Chapter 22: Reactions of Benzene and Its Derivatives

ANSWER:

108. Identify the product of the given reaction.

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Chapter 22: Reactions of Benzene and Its Derivatives c.

ANSWER: d 109. Identify “X” in the given reaction.

a. 3-methyl-2-propanol b. 2-methyl-2-butanol c. 2-methyl-2-propanol d. 3-methyl-2-butanol ANSWER: c 110. An example of a metal-reducing agent is _____. a. tin b. krypton c. chlorine d. silicon ANSWER: a 111. What is “X” in the following reaction?

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Chapter 22: Reactions of Benzene and Its Derivatives

a. H2CrO4 b. H2 c. LiAlH4 d. H2/Pt ANSWER: d 112. Identify a limitation of the Friedel-Crafts alkylation of benzene. a. Acylium ion does not undergo rearrangement. b. A benzene ring with electron-withdrawing groups can undergo alkylation under normal reaction conditions. c. The alkylated products are less reactive than benzene. d. Alkyl carbocation formed during a reaction can rearrange to a more stable carbocation. ANSWER: d 113. Identify “X” and “Y” in the following reaction.

a. X is butanoyl chloride, and Y is

b. X is pentanoyl chloride, and Y is

c. X is butanoyl chloride, and Y is

d. X is pentanoyl chloride, and Y is

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Chapter 22: Reactions of Benzene and Its Derivatives ANSWER: a 114. Nitroanisole can be synthesized by treating ______ with nitric acid in the presence of sulfuric acid. a. cresol b. methoxybenzene c. DHT d. phenol ANSWER: b

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Chapter 23: Amines 1. Which of the following compounds are primary (1°) amines?

a. 1 and 2 b. 1 and 3 c. 1, 2 and 3 d. 1, 2, 3 and 4 ANSWER: c 2. Which of the following compounds are secondary (2°) amines? 1. CH3CH2NHCH2CH3 2. CH3NH2 3. CH3CH2NHCH3 4. CH3CH2NH2 a. 1 and 2 b. 1 and 3 c. 2 and 3 d. only 1 ANSWER: b 3. Which of the following compounds are tertiary (3°) amines? 1. 2. 3. 4.

(CH3)3CN(CH3)2 CH3NHCH3 CH3CH2NH2 CH3NHCH2CH3

a. only 1 b. 1 and 2 c. 1 and 3 d. 2 and 3 ANSWER: a 4. What is the correct assignment of the names of the functional groups in the following nitrogen-containing compounds?

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Chapter 23: Amines a. 1 = amide; 2 = 2 amine; 3 = oxime b. 1 = imine; 2 = oxime; 3 = hydrazone c. 1 = 2° amine; 2 = oxime; 3 = hydrazine d. 1 = imine; 2 = hydrazone; 3 = 2° amine ANSWER: b 5. What is the correct assignment of the names of the functional groups in the following nitrogen-containing compounds?

a. 1 = imine; 2 = hydrazone; 3 = amide b. 1 = 2° amine; 2 = amide; 3 = hydrazone c. 1 =oxime; 2 = hydrazone; 3 = nitrile d. 1 = amide; 2 = nitrile; 3 = hydrazone ANSWER: d 6. What is the correct assignment of the names of the functional groups in the following nitrogen-containing compounds?

a. 1 = 2° amine; 2 = enamine; 3 = hydrazine b. 1 = 2° amine; 2 = amide; 3 = nitrile c. 1 =oxime; 2 = hydrazone; 3 = nitrile d. 1 = imine; 2 = hydrazone; 3 = amide ANSWER: a 7. What is the IUPAC name of the following compound?

a. (R)-4-amino-2-methylhexane b. (S)-4-amino-2-methylhexane c. N-ethyl N-(3-methylpropyl) amine d. (R)-3-amino-5-methylhexane ANSWER: a 8. What is the IUPAC name of the following compound?

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Chapter 23: Amines a. (E)-1-amino-4-hexene b. (E)-6-amino-2-hexene c. 3-allyl 1-aminopropane d. (Z)-1-amino-2-hexene ANSWER: b 9. What is the IUPAC name of the following compound?

a. (3R,4S)-3-amino-4-methylcyclohexene b. (3R,4R)-3-amino-4-methylcyclohexene c. (4R,5S)-5-amino-4-methylcyclohexene d. (4R,5R)-5-amino-4-methylcyclohexene ANSWER: a 10. What is the IUPAC name of the following compound?

a. 1-aminobicyclo[2.2.2]octane b. 2-aminobicyclo[2.2.2]octane c. 4-aminobicyclo[2.2.2]octane d. 2-aminobicyclo[6.4.4]octane ANSWER: b 11. What is the approximate pKa value of (CH3)3NH+, the conjugate acid of trimethylamine? a. –2 b. 17 c. 10 d. 25 ANSWER: c 12. Which of the following is the strongest base? a. methylamine Copyright Cengage Learning. Powered by Cognero.

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Chapter 23: Amines b. ethylamine c. ammonia d. pyridine ANSWER: b 13. Which of the following is the weakest base? a. 4-hydroxyaniline b. 4-cyanoaniline c. 3-ethyl-4-methylaniline d. 4-fluoroaniline ANSWER: b 14. Which of the following is the weakest base? a. propylamine b. dioctylamine c. 4-methoxy-m-phenylenediamine d. dimethylethylamine ANSWER: c 15. Which of the following is the strongest base? a. aniline b. pyridine c. triethylamine d. 4-nitroaniline ANSWER: c 16. Which of the following will remove diethylamine from a solution of diethylamine in diethyl ether? a. aqueous KI b. aqueous HF c. aqueous LiOH d. aqueous CH3COONH4 ANSWER: b 17. What is the hybridization of the nitrogen atom of pyridine? a. s b. sp c. sp2 d. sp3 ANSWER: c 18. What is the hybridization of the nitrogen atoms labeled i and ii in the aromatic imidazole ring?

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Chapter 23: Amines

a. i = sp2;; ii = sp2 b. i = sp2; ii = sp3 c. i = sp3; ii = sp3 d. i = sp3; ii = sp2 ANSWER: a 19. What is the major organic product obtained from the following reaction?

a. 1 b. 2 c. 3 d. 4 ANSWER: c 20. What is the major organic product obtained from the following reaction?

a. 1 b. 2 c. 3 d. 4 ANSWER: b 21. What is the major organic product obtained from the following reaction?

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Chapter 23: Amines

a. 1 b. 2 c. 3 d. 4 ANSWER: c 22. What is the major organic product obtained from the following reaction?

a. 1 b. 2 c. 3 d. 4 ANSWER: c 23. What is the major organic product obtained from the following reaction?

a. 1 b. 2 c. 3 d. 4 ANSWER: c 24. What is the major organic product obtained from the following reaction?

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Chapter 23: Amines

a. 1 b. 2 c. 3 d. 4 ANSWER: c 25. What is the major organic product obtained from the following reaction?

a. 1 b. 2 c. 3 d. 4 ANSWER: d 26. What is the major organic product obtained from the following reaction?

a. 1 b. 2 c. 3 d. 4 ANSWER: a Copyright Cengage Learning. Powered by Cognero.

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Chapter 23: Amines 27. What is the major organic product obtained from the following reaction?

a. 1 b. 2 c. 3 d. 4 ANSWER: a 28. What is the major organic product obtained from the following reaction?

a. 1 b. 2 c. 3 d. 4 ANSWER: b 29. What is the major organic product obtained from the following reaction?

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Chapter 23: Amines a. 1 b. 2 c. 3 d. 4 ANSWER: c 30. What is the major organic product obtained from the following reaction?

a. 1 b. 2 c. 3 d. 4 ANSWER: d 31. What is the major organic product obtained from the following reaction?

a. 1 b. 2 c. 3 d. 4 ANSWER: c 32. What is the major organic product obtained from the following reaction?

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Chapter 23: Amines

a. 1 b. 2 c. 3 d. 4 ANSWER: a 33. What is the intermediate in the Tiffeneau-Demjanov reaction, which produces a cyclic ketone? a. a diazonium ion b. a tertiary amine c. a cyclic aminoalcohol d. a N-nitrosamine ANSWER: a 34. What is the intermediate in the Sandmeyer reaction? a. a 3° carbocation b. an aryldiazonium salt c. an amine oxide d. phthalimide ANSWER: b 35. What is the major organic product obtained from the following sequence of reactions?

a. 1 Copyright Cengage Learning. Powered by Cognero.

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Chapter 23: Amines b. 2 c. 3 d. 4 ANSWER: a 36. What is the major organic product obtained from the following sequence of reactions?

a. 1 b. 2 c. 3 d. 4 ANSWER: b 37. What is the major organic product obtained from the following sequence of reactions?

a. 1 b. 2 c. 3 d. 4 Copyright Cengage Learning. Powered by Cognero.

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Chapter 23: Amines ANSWER: a 38. What is the major organic product obtained from the following sequence of reactions?

a. 1 b. 2 c. 3 d. 4 ANSWER: b 39. What is the major organic product obtained from the following sequence of reactions?

a. 1 b. 2 c. 3 d. 4 ANSWER: d 40. What is the major organic product obtained from the following sequence of reactions? Copyright Cengage Learning. Powered by Cognero.

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Chapter 23: Amines

a. 1 b. 2 c. 3 d. 4 ANSWER: c 41. What is the major organic product obtained from the following sequence of reactions?

a. 1 b. 2 c. 3 d. 4 ANSWER: a 42. What is the major organic product obtained from the following sequence of reactions?

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Chapter 23: Amines

a. 1 b. 2 c. 3 d. 4 ANSWER: a 43. What is the major organic product obtained from the following sequence of reactions?

a. 1 b. 2 c. 3 d. 4 ANSWER: d 44. Which combination of carbonyl compound and amine can be used to prepare the following product by reductive amination?

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Chapter 23: Amines

a. only 1 b. only 3 c. only 1 and 3 d. only 2 and 4 ANSWER: b 45. Which combination of carbonyl compound and amine can be used to prepare the following product by reductive amination?

a. only 1 b. only 3 c. only 1 and 3 d. only 2 and 4 ANSWER: c 46. Which of the following amines can be prepared from an organic bromide reaction with potassium cyanide followed by reduction? a. 1-pentanamine Copyright Cengage Learning. Powered by Cognero.

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Chapter 23: Amines b. aniline c. dimethylamine d. N, N-diethylbutan-2-amine ANSWER: a 47. Which of the following amines can be prepared from an organic bromide by reaction with sodium azide followed by reduction? a. pyridine b. 4-phenylbutylamine c. N-propyl-2-hexanamine d. N, N-dimethylbutan-2-amine ANSWER: b 48. Which of the following amines can be prepared by reduction of a tertiary amide? a. ethanamine b. 1-butanamine c. N, N-diethylbenzylamine d. 1-octanamine ANSWER: c 49. Which of the following amines can be prepared by ring opening of an epoxide with sodium amide followed by reduction?

a. only 1 b. only 1 and 2 c. only 1 and 4 d. only 2 ANSWER: c 50. Which of the following amines cannot be prepared from 1-chloro-2-phenyl-2propanol by reaction with potassium cyanide followed by reduction?

a. only 4 b. 1, 2 and 4 Copyright Cengage Learning. Powered by Cognero.

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Chapter 23: Amines c. only 2 and 4 d. only 3 ANSWER: b 51. The following structure is classified as a 3° amine.

a. True b. False ANSWER: False 52. To separate a mixture of p-toluidine and p-nitrotoluene dissolved in ether,extract the ether solution with

aqueous HCl and treat the water layer with aqueous NaOH. a. True b. False ANSWER: True o

53. Aliphatic 3 amines with three different groups on nitrogen can be resolved. a. True b. False ANSWER: False 54. The following amine can be converted to an aryl diazonium salt.

a. True b. False ANSWER: True 55. Consider the following reaction.

The products of this reaction are shown below.

a. True b. False Copyright Cengage Learning. Powered by Cognero.

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Chapter 23: Amines ANSWER: False 56. The reaction of a 2o amine with nitrous acid gives a nitrosamine. a. True b. False ANSWER: True 57. The following represents an acid-base reaction between the given amine and HCl.

a. True b. False ANSWER: True 58. The pKa of methyl amine is represented by the following reaction.

a. True b. False ANSWER: True 59. The compound circled below represents a heterocyclic amine.

a. True b. False ANSWER: True Consider the following compounds.

Answer the following questions by filling in the blank with the appropriate number from the diagram or an appropriate term. 60. The ammonia ion of substance ____ will have the largest pKa. ANSWER: 2 two Copyright Cengage Learning. Powered by Cognero.

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Chapter 23: Amines 61. The ammonia ion of substance ____ will have the smallest pKa. ANSWER: 4 four 62. Substance _____ is a primary alkyl amine. ANSWER: 2 two 63. The name of the product formed by reacting CuCl and HCl with benzenediazonium chloride is

________________________. ANSWER: chlorobenzene 64. The name of the product formed by reacting KCN and CuCN with benzenediazonium chloride is

________________________. ANSWER: benzonitrile 65. The IUPAC name of the product of the following reaction is ____________________.

ANSWER: 4-methylpentanamine From the list provided below, choose the best reagent(s) for each step in the following synthesis. There is only one answer for each reaction. Enter the appropriate letter in the blank provided. a. b. c.

1. 2.

NaBH4 , ethanol KCN, acetone LiAlH4 , THF H2O

d e. f.

1. 2. 1. 2.

NaNO2 , H3O+ CuCN, KCN SnCl2 , H3O+ NaOH, H2O HNO3 , H2SO4

66. _____Step 1 ANSWER: e 67. _____Step 2 ANSWER: d 68. _____Step 3 ANSWER: c Copyright Cengage Learning. Powered by Cognero.

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Chapter 23: Amines Consider the following substances.

Complete the following statements using the appropriate number. 69. Substance _____ is pyrrole. ANSWER: 2 two 70. Substance _____ is aniline. ANSWER: 1 one 71. Substance _____ is pyridine. ANSWER: 3 three 72. What is the IUPAC name of the following compound?

ANSWER: (S)-2-butanamine 73. What is the IUPAC name of the following compound?

ANSWER: 2-methyl-1-propanamine 74. Provide a line-bond structure of N,N-dimethylcyclopentanamine. ANSWER:

75. Provide a line-bond structure of N-methylaniline. ANSWER:

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Chapter 23: Amines 76. Provide a brief explanation, based on features of the molecules, for the following difference in pKa values? CH3NH2 > NH3 10.64 9.26 ANSWER: The methyl group of methanamine is a weak electron donating group thereby increasing the electron density of the nitrogen (relative to ammonia) and increasing the basicity. Another way of thinking abut this is that the electron donation of the methyl group stabilizes the conjugate acid of methanamine. 77. Provide a brief explanation, based on features of the molecules, for the following difference in pKa values? CH3NH2 > PhNH2 10.64 4.63 ANSWER: The phenyl group of aniline can serve as a resonance electron withdrawing substitutent, thereby reducing the electron density of the nitrogen (relative to methyl amine) and lowering its basicity. 78. Provide a brief explanation, based on features of the molecules, for the following trend in pKa values?

4.15 4.63 1.0 ANSWER: The para nitro group of 4-nitroaniline is a resonance electron withdrawing substitutent, thereby reducing the electron density of the nitrogen and lowering its basicity relative to aniline. The 4-methyl group of toluidine is a weak inductive electron donating group, thereby increasing the electron density of the nitrogen and increasing its basicity relative to aniline. 79. What is the major organic product obtained from the following reaction?

ANSWER:

80. What is the major organic product obtained from the following sequence of reactions?

ANSWER:

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Chapter 23: Amines 81. What is the major organic product obtained from the following sequence of reactions?

ANSWER:

82. What is the major organic product obtained from the following sequence of reactions?

ANSWER:

83. What is the major organic product obtained from the following sequence of reactions?

ANSWER:

84. What is the major organic product obtained from the following sequence of reactions?

ANSWER:

85. What is the major organic product obtained from the following sequence of reactions?

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Chapter 23: Amines ANSWER:

86. What is the major organic product obtained form the following sequence of reactions?

ANSWER:

87. What is the major organic product obtained form the following sequence of reactions?

ANSWER:

88. What is the major organic product obtained from the following sequence of reactions (assume that mixtures of ortho and para disubstituted compounds can be separated; continue the synthesis with either one)?

ANSWER:

89. What is the major organic product obtained from the following sequence of reactions (assume that mixtures of ortho and para disubstituted compounds can be separated; continue the synthesis with either one)?

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Chapter 23: Amines

ANSWER:

90. What is the major organic product obtained form the following sequence of reactions (assume that mixtures of ortho and para disubstituted compounds can be separated; continue the synthesis with either one)?

ANSWER:

91. What is the major organic product obtained form the following sequence of reactions?

ANSWER: 92. What is the major organic product obtained form the following sequence of reactions?

ANSWER:

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Chapter 23: Amines 93. Identify the type of reaction shown below.

a. Balz–Schiemann reaction b. Sandmeyer reaction c. Azo-coupling reaction d. Pschorr reaction ANSWER: a 94. The given compound is commonly used as an indicator in acid–base titrations. Identify the compound.

a. Methyl orange b. Phenolphthalein c. Bromocresol green d. Bromothymol blue ANSWER: a 95. Which of the following compounds is most soluble in water? a.

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Chapter 23: Amines c.

ANSWER: a 96. Identify the most basic compound. a.

ANSWER: a 97. Identify the final product of the following reaction.

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Chapter 23: Amines

ANSWER: a Copyright Cengage Learning. Powered by Cognero.

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Chapter 23: Amines 98. _____ is the rapid oscillation of a nitrogen atom from one side of the plane of the three atoms bonded to it to the other side of that plane. ANSWER: Pyramidal inversion 99. In the presence of hydrogen peroxide and suitable heat, N,N-dimethyl-cyclooctylamine results in the formation of _____. ANSWER: cyclooctene

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Chapter 24: Catalytic Carbon-Carbon Bond Formation 1. What is the major organic product obtained from the following reaction?

a. 1 b. 2 c. 3 d. 4 ANSWER: a 2. What is the major organic product obtained from the following reaction?

a. 1 b. 2 c. 3 d. 4 ANSWER: c 3. What is the major organic product obtained from the following reaction?

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Chapter 24: Catalytic Carbon-Carbon Bond Formation

a. 1 b. 2 c. 3 d. 4 ANSWER: d 4. What is the major organic product obtained from the following reaction?

a. 1 b. 2 c. 3 d. 4 ANSWER: c 5. What is the major organic product obtained from the following reaction?

a. 1 b. 2 c. 3 d. 4 ANSWER: b Copyright Cengage Learning. Powered by Cognero.

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Chapter 24: Catalytic Carbon-Carbon Bond Formation 6. What is the major organic product obtained from the following reaction?

a. 1 b. 2 c. 3 d. 4 ANSWER: d 7. What is the major organic product obtained from the following reaction?

a. 1 b. 2 c. 3 d. 4 ANSWER: d 8. What is the major organic product obtained from the following reaction?

a. 1 b. 2 c. 3 d. 4 ANSWER: c 9. What is the major organic product obtained from the following reaction? Copyright Cengage Learning. Powered by Cognero.

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Chapter 24: Catalytic Carbon-Carbon Bond Formation

a. 1 b. 2 c. 3 d. 4 ANSWER: a 10. What is the major organic product obtained from the following reaction?

a. 1 b. 2 c. 3 d. 4 ANSWER: d 11. What is the major organic product obtained from the following sequence of reactions?

a. 1 b. 2 Copyright Cengage Learning. Powered by Cognero.

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Chapter 24: Catalytic Carbon-Carbon Bond Formation c. 3 d. 4 ANSWER: a 12. What is the major organic product obtained from the following reaction?

a. 1 b. 2 c. 3 d. 4 ANSWER: a 13. What is the major organic product obtained from the following reaction?

a. 1 b. 2 c. 3 d. 4 ANSWER: b 14. Which term describes the following mechanistic step in the catalytic cycle of the Heck reaction?

a. oxidative addition b. syn addition Copyright Cengage Learning. Powered by Cognero.

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Chapter 24: Catalytic Carbon-Carbon Bond Formation c. syn elimination d. reductive elimination ANSWER: a 15. Which term describes the following mechanistic step in the catalytic cycle of the Heck reaction?

a. oxidative addition b. syn addition c. syn elimination d. reductive elimination ANSWER: b 16. Which term describes the following mechanistic step in the catalytic cycle of the Heck reaction?

a. oxidative addition b. syn addition c. syn elimination d. reductive elimination ANSWER: c 17. Which term describes the following mechanistic step in the catalytic cycle of the Heck reaction?

a. oxidative addition b. syn addition c. syn elimination d. reductive elimination ANSWER: d 18. What is the major organic product obtained from the following reaction?

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Chapter 24: Catalytic Carbon-Carbon Bond Formation

a. 1 b. 2 c. 3 d. 4 ANSWER: b 19. What is the major organic product obtained from the following reaction?

a. 1 b. 2 c. 3 d. 4 ANSWER: b 20. In the general reaction for the Suzuki coupling, which of the following does not serve as the leaving group "X"?

a. Br b. OTf c. CH3CH2CH2CH2CH2 Copyright Cengage Learning. Powered by Cognero.

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Chapter 24: Catalytic Carbon-Carbon Bond Formation d. Both (a) and (b) ANSWER: c 21. What is the major organic product obtained from the following reaction?

a. 1 b. 2 c. 3 d. 4 ANSWER: a 22. What is the major organic product obtained from the following reaction?

a. 1 b. 2 c. 3 d. 4 ANSWER: d Copyright Cengage Learning. Powered by Cognero.

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Chapter 24: Catalytic Carbon-Carbon Bond Formation 23. Which diene can be used to prepare the following product by alkene metathesis?

a. 1 b. 2 c. 3 d. 4 ANSWER: b 24. Which of the following compounds is the most reactive dienophile?

a. 1 b. 2 c. 3 d. 4 ANSWER: c 25. Which of the following is the least reactive dienophile?

a. 1 b. 2 c. 3 d. 4 ANSWER: b 26. Which of the following is the least reactive diene in Diels Alder reactions? Copyright Cengage Learning. Powered by Cognero.

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Chapter 24: Catalytic Carbon-Carbon Bond Formation

a. 1 b. 2 c. 3 d. 4 ANSWER: a 27. Which of the following is the least reactive diene in Diels Alder reactions?

a. 1 b. 2 c. 3 d. 4 ANSWER: b 28. What is the major organic product obtained from the following reaction?

a. 1 b. 2 c. 3 d. 4 ANSWER: b Copyright Cengage Learning. Powered by Cognero.

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Chapter 24: Catalytic Carbon-Carbon Bond Formation 29. What is the major organic product obtained from the following reaction?

a. 1 b. 2 c. 3 d. 4 ANSWER: b 30. What is the major organic product obtained from the following reaction?

a. 1 b. 2 c. 3 d. 4 ANSWER: c Copyright Cengage Learning. Powered by Cognero.

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Chapter 24: Catalytic Carbon-Carbon Bond Formation 31. What is the major organic product obtained from the following reaction?

a. 1 b. 2 c. 3 d. 4 ANSWER: a 32. What is the major organic product obtained from the following reaction?

a. 1 b. 2 c. 3 d. 4 ANSWER: c 33. What is the major organic product obtained from the following reaction?

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Chapter 24: Catalytic Carbon-Carbon Bond Formation

a. 1 b. 2 c. 3 d. 4 ANSWER: a 34. What is the major organic product obtained from the following reaction?

a. 1 b. 2 c. 3 d. 4 ANSWER: b 35. What is the major organic product of the following sequence of reactions?

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Chapter 24: Catalytic Carbon-Carbon Bond Formation

a. 1 b. 2 c. 3 d. 4 ANSWER: a 36. What is the major organic product of the following sequence of reactions?

a. 1 b. 2 c. 3 d. 4 ANSWER: b 37. What is the major organic product of the following sequence of reactions? Copyright Cengage Learning. Powered by Cognero.

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Chapter 24: Catalytic Carbon-Carbon Bond Formation

a. 1 b. 2 c. 3 d. 4 ANSWER: c 38. What is the major organic product of the following sequence of reactions?

a. 1 b. 2 c. 3 d. 4 ANSWER: a 39. What is the major organic product of the following sequence of reactions?

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Chapter 24: Catalytic Carbon-Carbon Bond Formation

a. 1 b. 2 c. 3 d. 4 ANSWER: a 40. Which of the following is not a pericyclic reaction? a. Cope rearrangement b. Claisen rearrangement c. Heck reaction d. Diels-Alder reaction ANSWER: c 41. Which of the following terms describes the mechanism of a last step of the Sonogashira Coupling? a. electrophilic addition b. nucleophilic addition c. reductive elimination d. conjugate addition ANSWER: c 42. Organopalladium compounds are particularly useful in forming biaryl compounds. a. True b. False ANSWER: True 43. Consider diorganocopper reagents and organopalladium compounds. Only the latter is useful in forming new carbonto-carbon bonds a. True b. False ANSWER: False 44. During oxidative addition and reductive elimination, the ionic charge of the metal changes. Copyright Cengage Learning. Powered by Cognero.

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Chapter 24: Catalytic Carbon-Carbon Bond Formation a. True b. False ANSWER: False 45. Consider the following reactants.

This is an example of a Heck reaction. a. True b. False ANSWER: False 46. Consider the following reactants.

The product of this reaction is shown below.

a. True b. False ANSWER: True 47. The following product is a simplified penicillin analog.

When the reaction is carried out in the presence of a palladium catalyst the structure of the missing reactant is shown below.

a. True b. False Copyright Cengage Learning. Powered by Cognero.

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Chapter 24: Catalytic Carbon-Carbon Bond Formation ANSWER: True 48. The intermediate in a Heck reaction can be described as a tetrahedral Pd(II) species. a. True b. False ANSWER: False 49. In the Heck reaction, alkenes with large substituent groups are the most reactive. a. True b. False ANSWER: False 50. In the Heck reaction, polar aprotic solvents are generally used. a. True b. False ANSWER: True 51. In the Heck reaction, all reactants are required in stoichiometric amounts except the Pd(0) species. a. True b. False ANSWER: True 52. Cross-coupled reactions involve a transmetallation step. a. True b. False ANSWER: True 53. During oxidative addition, the coordination (number) of the metal ________ by two. ANSWER: increases Use the reaction types given below in answering the following questions relating to reaction conditions. A. Heck reaction B. Stille coupling C. Suzuki coupling D. Sonogashira coupling E. Alkene metathesis Place the appropriate letter in the blank provided. 54. ______involves the use of alkynyl complexes. ANSWER: D 55. ______involves the use of stannates. ANSWER: B 56. ______involves the use of organoboron compounds. ANSWER: C Copyright Cengage Learning. Powered by Cognero.

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Chapter 24: Catalytic Carbon-Carbon Bond Formation 57. ______involves the substitution of a vinylic hydrogen. ANSWER: A 58. ______involves an interchange of alkenyl groups. ANSWER: E 59. In an alkene metathesis reaction where both alkenyl groups are in the same molecule, the product formed is a _______________. ANSWER: cycloalkene 60. The following polymer segment can be produced using an olefinic metathesis reaction. To produce the polymer, the reaction is repeated many times.

The name of the reactant is__________. ANSWER: 4-ethylcyclopentene 61. What is the major organic product obtained from the following reaction?

ANSWER:

62. What is the major organic product obtained from the following reaction?

ANSWER:

63. What is the major organic product obtained from the following reaction? Copyright Cengage Learning. Powered by Cognero.

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Chapter 24: Catalytic Carbon-Carbon Bond Formation

ANSWER:

64. What is the major organic product obtained from the following reaction?

ANSWER:

65. What is the major organic product obtained from the following reaction?

ANSWER:

66. What is the major organic product obtained from the following reaction?

ANSWER:

67. What is the major organic product obtained from the following reaction?

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Chapter 24: Catalytic Carbon-Carbon Bond Formation

ANSWER:

68. What is the major organic product obtained from the following reaction?

ANSWER:

69. What is the major organic product obtained from the following reaction?

ANSWER:

70. What is the major organic product obtained from the following reaction?

ANSWER:

71. What is the major organic product obtained from the following reaction?

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Chapter 24: Catalytic Carbon-Carbon Bond Formation

ANSWER:

72. What is the major organic product obtained from the following reaction?

ANSWER:

73. What is the major organic product obtained from the following reaction?

ANSWER:

74. What is the major organic product obtained from the following sequence of reactions?

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Chapter 24: Catalytic Carbon-Carbon Bond Formation ANSWER:

75. What is the major organic product obtained from the following sequence of reactions?

ANSWER:

76. What are the two major organic products obtained from the following reaction?

ANSWER:

77. Provide descriptions for each of the mechanistic steps in the following Heck reaction.

ANSWER: Oxidative insertion followed by syn addition, and then syn elimination. 78. Identify “X” and “Y” in the given sequence of reactions.

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Chapter 24: Catalytic Carbon-Carbon Bond Formation

a. X is

, and Y is

X is

, and Y is

X is

, and Y is

X is

, and Y is

ANSWER: c 79. Identify “X” in the given reaction.

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Chapter 24: Catalytic Carbon-Carbon Bond Formation d.

ANSWER: b 80. Identify “X” in the given reaction.

ANSWER: d 81. A pairwise interchange of ligands between two different metals or metalloids is known as _____. ANSWER: transmetallation 82. Identify the correct statement. a. Catalysts do not change the thermodynamics of a reaction. b. Catalysts change the thermodynamics of a reaction. c. Catalysts do not change the kinetics of a reaction. d. Catalysts are degenerated in the course of a reaction. ANSWER: a 83. What is the product of the given reaction?

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Chapter 24: Catalytic Carbon-Carbon Bond Formation

a. II b. III c. IV d. I ANSWER: d 84. _____ of configuration at the carbon with the leaving group is observed in catalytic allylic alkylation. a. Racemization b. Retention c. Inversion d. Assertion ANSWER: b

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Chapter 25: Carbohydrates 1. What is the relationship between D-threose and L-threose?

a. constitutional isomers b. enantiomers c. diastereomers d. tautomers ANSWER: b 2. What is the relationship between D-erythrose and D-threose?

a. constitutional isomers b. enantiomers c. diastereomers d. tautomers ANSWER: c 3. What is the relationship between D-ribose and D-xylose?

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Chapter 25: Carbohydrates

a. constitutional isomers b. enantiomers c. diastereomers d. tautomers ANSWER: c 4. What is the relationship between D-arabinose and L-arabinose?

a. constitutional isomers b. enantiomers c. diastereomers d. tautomers ANSWER: b 5. Which of the following structures represent the same carbohydrate?

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Chapter 25: Carbohydrates a. only 1 and 2 b. only 1 and 3 c. only 2 and 3 d. 1, 2 and 3 ANSWER: d 6. Which of the following structures represent the same carbohydrate?

a. only 1 and 2 b. only 1 and 3 c. only 2 and 3 d. 1, 2 and 3 ANSWER: c 7. Which carbon in the following carbohydrate is the anomeric carbon?

a. i b. ii c. iii d. iv ANSWER: a 8. Which carbon in the following carbohydrate is the anomeric carbon?

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Chapter 25: Carbohydrates

a. i b. ii c. iii d. iv ANSWER: a 9. Which of the following is a D-galactose?

a. only 1 b. none c. only 2 d. only 3 ANSWER: b 10. Which of the following is a D-glucose?

a. only 1 b. none c. only 3 d. only 2 ANSWER: d 11. What are the R/S stereochemical designations of C2 and C3 of D-erythrose?

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Chapter 25: Carbohydrates

a. 2R,3R b. 2R,3S c. 2S,3R d. 2S,3S ANSWER: a 12. What are the R/S stereochemical designations of C2 and C3 of L-threose?

a. 2R,3R b. 2R,3S c. 2S,3R d. 2S,3S ANSWER: b 13. What is (are) the major organic product(s) obtained from the following reaction?

a. only 1 b. only 2 c. only 2 and 3 d. 1, 2 and 3 ANSWER: c 14. What is the major organic product obtained from the following reaction?

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Chapter 25: Carbohydrates

a. only 1 b. only 2 c. only 3 d. only 1 and 2 ANSWER: a 15. What is the major organic product obtained from the following reaction?

a. 1 b. 2 c. 3 d. 4 ANSWER: b 16. Which of the following represents a erythrose?

a. only 2 b. only 1 c. only 3 d. both 1 and 2 ANSWER: b Copyright Cengage Learning. Powered by Cognero.

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Chapter 25: Carbohydrates 17. Which of the following represents pyranose?

a. only 1 b. only 2 c. only 3 d. only 1 and 2 ANSWER: a 18. Which of the following represents a ketose?

a. only 1 and 2 b. only 1 and 3 c. only 2 and 3 d. 1, 2 and 3 ANSWER: d 19. Which of the following represents an aldopentose?

a. only 1 and 2 b. only 3 c. only 2 and 3 d. 1, 2 and 3 ANSWER: b Copyright Cengage Learning. Powered by Cognero.

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Chapter 25: Carbohydrates 20. Which of the following is a monosaccharide? a. lactose b. dextrin c. glucose d. amylose ANSWER: c 21. Which of the following is an alditol? a. glucopyranose b. glucopyranoside c. glucuronic acid d. erythritol ANSWER: d 22. Which of the following is also known as vitamin C? a. Gluconic acid b. L-Sorbose c. L-Ascorbic acid d. D-Glucopyranoside ANSWER: c 23. Which of the following is not a polysaccharide? a. cellulose b. amylose c. amylopectin d. glucose ANSWER: d 24. A 1,4-α-linkage between two glucose units produces a disaccharide called maltose. a. True b. False ANSWER: True 25. Starch, cellulose, and surcrose are all classified as polysaccharides. a. True b. False ANSWER: True 26. The difference between the pyranose and furanose forms of a given aldohexose is the ring size. a. True b. False ANSWER: True Copyright Cengage Learning. Powered by Cognero.

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Chapter 25: Carbohydrates 27. Consider the structure shown below.

The Haworth projection formula for the pyranose form of β-D-galactose is given below.

a. True b. False ANSWER: False 28. Reduction of an optically active aldopentose with NaBH4 gives an optically inactive alditol. The

aldopentose could be:

a. True b. False ANSWER: True 29. Oxidation of optically active D-erythrose with nitric acid produces optically inactive meso-tartaric acid (below).

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Chapter 25: Carbohydrates The structure of D-erythrose is shown below.

a. True b. False ANSWER: False 30. A glycoside is formed upon reaction of glucopyranose with NaBH4. a. True b. False ANSWER: False 31. The following compound will react with Tollens' solution.

a. True b. False ANSWER: False 32. The following structure shows the correct assignment of the R or S configuration to each chirality center in sorbose.

a. True b. False ANSWER: True 33. The following are two different methods of representing the same structure.

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Chapter 25: Carbohydrates

a. True b. False ANSWER: True 34. Consider the following Fisher projections.

They all convert to the same tetrahedral representation as shown below..

a. True b. False ANSWER: True Consider the following structures.

Answer the following questions by placing the appropriate number or indicated letter in the blank. 35. Structure ____ represents a ketohexose. ANSWER: 2 two 36. Structure ____ represents a aldopentose. ANSWER: 1 one 37. The structures that represent reducing sugars are: a. only the ketoses. b. only the aldoses. c. all of these structures. Copyright Cengage Learning. Powered by Cognero.

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Chapter 25: Carbohydrates ANSWER: c 38. The number of hydroxyl groups in the pyranose form of glucose is _____. ANSWER: 6 six 39. The number of the anomeric carbon in the following structure is _____.

ANSWER: 2 two C2 40. The formula for maltose is:

The number of the acetal carbon is _____. ANSWER: 1’ 1' 41. The following monosaccharide has ________ equatorial hydroxyl groups.

ANSWER: 3 three From the sugars below, choose the one that best fits each description below. Place the letter of the sugar in the blank to the left of the description. There is only one correct answer for each question.

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Chapter 25: Carbohydrates

42. _____ is a D-sugar. ANSWER: d 43. _____ is a deoxy sugar. ANSWER: b 44. _____ is a sugar with three chirality centers. ANSWER: a 45. _____ is a sugar which yields a single alditol upon reduction. ANSWER: b 46. The name of the following Fischer projection including stereochemistry is _____________________.

ANSWER: (2R,3S)-dibromobutane (2R,3S)-dibromobutane (2R,3S)-dibromobutane (2R,3S)-dibromobutane 47. The fundamental difference between the monosaccharide, disaccharide, and polysaccharide classifications of carbohydrates is the number of _________________present. ANSWER: monosaccharides monosaccharide units Refer to the equilibrium below to answer the following question(s).

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Chapter 25: Carbohydrates

48. The enantiomer of ribose is drawn is _______. (D or L) ANSWER: D 49. The anomer of ribose is drawn is _______. (alpha or beta) ANSWER: beta β 50. The correct name for the cyclic structure is__________________________. ANSWER: β-D-ribofuranose beta-D-ribofuranose 51. Complete the structure on the right so that it represents the pyranose form of the carbohydrate shown on the left as a Fischer projection. Place the substituents carefully so that their position in axial or equatorial positions accurately reflects the stereochemistry of the carbohydrate.

ANSWER:

52. Complete the structure on the right so that it represents the pyranose form of the carbohydrate shown on the left as a Fischer projection. Place the substituents carefully so that their position in axial or equatorial positions accurately reflects the stereochemistry of the carbohydrate.

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Chapter 25: Carbohydrates ANSWER:

53. What are the two major organic products obtained from the following reaction? What is the relationship between them? (What type of isomers are they?)

ANSWER:

The two methyl glycosides are diastereomers of one another 54. What is the major organic product obtained from the reaction of glucose with glucose oxidase?

ANSWER:

55. What is the major organic product obtained from the following reduction of glucose?

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Chapter 25: Carbohydrates ANSWER:

56. What are the two major organic products obtained from treatment of an α-hydroxyketone with periodic acid in water?

ANSWER:

57. What are the major organic products obtained from treatment of a 1,2,3-triol with periodic acid in water?

ANSWER:

58. What are the major organic products obtained from treatment of a methyl glycoside with periodic acid in water?

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Chapter 25: Carbohydrates ANSWER:

59. The textile rayon is produced by treatment of cellulose with carbon disulfide in aqueous sodium hydroxide. What type of functional group is introduced on the cellulose under these conditions?

ANSWER:

a sodium xanthate salt 60. The textile cellulose acetate is produced by treatment of cellulose with acetic anhydride. What type of functional group is introduced on the cellulose under these conditions?

ANSWER:

an acetate ester Match the following compounds used to produce rayon and acetate rayon with the most appropriate roles. a. Sodium salt of xanthate ester b. Acetylated cellulose c. Carbon disulfide d. Dilute sulfuric acid 61. Treats materials containing cellulose ANSWER: c 62. Causes fibers to dissolve in an alkali ANSWER: a 63. Hydrolyzes the xanthate ester group ANSWER: d 64. Forms acetate rayon on precipitation ANSWER: b 65. Identify the given compound. Copyright Cengage Learning. Powered by Cognero.

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Chapter 25: Carbohydrates

a. β lactose b. β maltose c. α sucrose d. α maltose ANSWER: a 66. _____ is the change in specific rotation that accompanies the interconversion of α and β anomers in an aqueous solution. ANSWER: Mutarotation 67. Identify the following compound.

a. Hyaluronic acid b. Heparin c. Cellulose d. Amylopectin ANSWER: a 68. Identify the products of the following reaction.

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Chapter 25: Carbohydrates

a. D-mannitol and D-glucitol b. D-xylitol and D-mannitol c. D-glucitol and D-xylitol d. D-xylitol and D-glucitol ANSWER: a 69. There are only 2 trioses: the aldotriose 2,3-dihydroxypropanal and the ketotriose _____. ANSWER: 1,3-dihydroxypropanone 70. Identify the major product of the following reaction.

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Chapter 25: Carbohydrates b.

ANSWER: b

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Chapter 26: Organic Polymer Chemistry 1. What is the name of the following polymer?

a. poly(ethylene terephthalamide) b. poly(ethylene terephthalate) c. poly(ethylene succinate) d. poly(ethylene phenylate) ANSWER: b 2. What is the name of the following polymer?

a. poly(hexamethylene adipate) b. poly(hexamethylene adipamide) c. poly(hexamethylene succinate) d. poly(tetramethylene adipamide) ANSWER: b 3. What is the common name of the following polymer?

a. Kevlar b. PET c. Nylon-6 d. Nylon-6,6 ANSWER: b 4. What is the common name of the following polymer?

a. Kevlar b. PET c. Nylon-6 d. Nylon-6,6 ANSWER: a Copyright Cengage Learning. Powered by Cognero.

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Chapter 26: Organic Polymer Chemistry 5. What type of polymer is shown?

a. polycarbonate b. polyester c. polyurethane d. polyether ANSWER: a 6. What type of polymer is shown?

a. polycarbonate b. polyester c. polyurethane d. polyether ANSWER: b 7. What type of polymer is shown?

a. polyamide b. polyurea c. polyurethane d. polyamine ANSWER: c 8. What type of polymer is shown?

a. polyamide Copyright Cengage Learning. Powered by Cognero.

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Chapter 26: Organic Polymer Chemistry b. polyurea c. polyurethane d. polyamine ANSWER: a 9. What type of intermediate is formed in the polymerization of styrene with AIBN? a. radical anion b. carbocation c. radical d. radical cation ANSWER: c 10. What type of intermediate is formed in the polymerization of isobutylene with BF3/water? a. radical cation b. carbocation c. radical d. carbanion ANSWER: b 11. What type of intermediate is formed in the polymerization of butadiene with butyllithium? a. carbanion b. radical cation c. radical d. organometallic complex ANSWER: a 12. Which of the following combinations of terms best describes the polymerization of a diacid and a diamine to form nylons? a. step-growth or addition polymerization b. step-growth or condensation polymerization c. chain-growth or addition polymerization d. chain-growth or condensation polymerization ANSWER: b 13. Which of the following combinations of terms best describes the polymerization of a dicarboxylic acid and a diamine to form a polyamide? a. step-growth or condensation polymerization b. step-growth or addition polymerization c. chain-growth or addition polymerization d. radical chain-growth polymerization ANSWER: a 14. Which of the following combinations of terms best describes the polymerization of caprolactum to form nylon-6? a. radical chain-growth condensation Copyright Cengage Learning. Powered by Cognero.

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Chapter 26: Organic Polymer Chemistry b. cationic chain-growth condensation c. step-growth or condensation polymerization d. anionic chain-growth condensation ANSWER: c 15. Which term describes the arrangement of substituents on the segment of polypropylene shown below?

a. atactic b. isotactic c. syndiotactic d. stereoirregular ANSWER: b 16. Which term describes the arrangement of substituents on the segment of polypropylene shown below?

a. atactic b. isotactic c. syndiotactic d. stereoregular ANSWER: a 17. Which term describes the arrangement of substituents on the segment of polypropylene shown below?

a. atactic b. isotactic c. syndiotactic d. stereoirregular ANSWER: c 18. Which of the following relationships is not true? a. Tg < Tm b. Mw

c. polydispersity index

d. ANSWER: c Copyright Cengage Learning. Powered by Cognero.

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Chapter 26: Organic Polymer Chemistry 19. Which of the following is not true? a. There is a corresponding increase in strength and stiffness of a polymer with increase in its crystallinity. b.Thermosetting polymers are composed of long chains that are cross-linked by covalent bonds. c. A polymer that can be molded when it is first prepared but once cooled, hardens irreversibly and cannot be remelte d is called a thermosetting polymer. d.Polymers in the solid state are composed of only ordered crystalline domains. ANSWER: d 20. Which type of polymerization can be used to polymerize methyl-2-cyanoacrylate, CH2=C(CN)CO2CH3? a. anionic chain-growth b. cationic chain-growth c. radical chain-growth d. ring-opening metathesis ANSWER: a 21. Which type of polymerization can be used to polymerize isobutylene, (CH3)2C=CH2? a. anionic chain-growth b. cationic chain-growth c. step-growth or condensation polymerization d. radical chain-growth ANSWER: b 22. Which type of polymerization is initiated by a mixture of naphthalene and sodium metal? a. anionic b. cationic c. radical d. Ziegler-Natta ANSWER: a 23. Which type of polymerization is used to make dacron? a. ring-opening metathesis b. anionic chain-growth polymerization c. step-growth addition d. step-growth or condensation polymerization ANSWER: d 24. The following arrangement indicates a crosslinked polymer.

a. True Copyright Cengage Learning. Powered by Cognero.

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Chapter 26: Organic Polymer Chemistry b. False ANSWER: True 25. 2,4-Toluene diisocyanate is a very important chemical in the synthesis of polyurethanes used in foam

pillows and freezer insulation and has the following structure.

a. True b. False ANSWER: True 26. The following is an example of a polyurethane.

a. True b. False ANSWER: False 27. A polymer has the repeating unit drawn below:

The two monomers used to make the polymer are shown below.

a. True b. False ANSWER: False 28. Consider the following two structures.

The following represents the repeating unit of the polymer formed by these two substances. Copyright Cengage Learning. Powered by Cognero.

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Chapter 26: Organic Polymer Chemistry

a. True b. False ANSWER: True 29. Ziegler-Natta catalysts, used to prepare linear polymer molecules, consist of: organoaluminum compounds

and transition metal salts. a. True b. False ANSWER: True 30. A good initiator for a free radical addition polymerization is acetyl chloride. a. True b. False ANSWER: False 31. Thermosetting polymers continue to crosslink on heating followed by cooling to irreversibly produce an

extremely hard material that cannot be remelted. a. True b. False ANSWER: True 32. Consider the polymeric structure below for amylose (a type of starch).

The structure for the monomer is given below. a. True b. False ANSWER: True 33. High degrees of crystallinity are associated with polymers with weak intermolecular forces. Copyright Cengage Learning. Powered by Cognero.

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Chapter 26: Organic Polymer Chemistry a. True b. False ANSWER: False 34. The name of the polymer formed by the molecule shown below is _________________.

ANSWER: polypropylene 35. Consider the structure shown below.

This is an example of a. a polyurethane b. a polyester c. a polyamide d. a polycarbonate ANSWER: b Consider the structure given below which might be found in a protein.

Answer the following questions by filling in the blank with the appropriate word or term. 36. The number of types of monomers in this structure is _______. ANSWER: 3 three 37. This polymer would be classified as a poly______. ANSWER: amide 38. Nitroethylene is expected to be _______ reactive than ethylene toward cationic polymerization.

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Chapter 26: Organic Polymer Chemistry ANSWER: less 39. Nitroethylene is expected to be _______ reactive than ethylene toward anionic polymerization.

ANSWER: more Classify each polymer below as step-growth or chain-growth. Place the appropriate term in the blank provided. 40. _________________

ANSWER: chain-growth 41. _________________

ANSWER: chain-growth 42. _________________

ANSWER: step-growth MATCH a term or structure from the list below to each of the following definitions or names. Place the letter of the term or structure in the blank to the left of the definition or name which it describes. A. crystallite C. chain-growth polymer

B. elastomer D. Al(CH2CH3)3 + TiCl4

G. thermoplastic I. Tm K. copolymers M. “catalyst” O.

H. homopolymer J. epoxy resins L. step-growth polymer N. Tg

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Chapter 26: Organic Polymer Chemistry

43. ____ Produced by reactions in which each bond in the polymer is formed independently of the others. ANSWER: L 44. ___ Isotactic propylene ANSWER: E 45. ____ Polymers obtained when two or more different monomers are allowed to polymerize together. ANSWER: K 46. ____ A polyurethane ANSWER: O 47. ____ Amorphous polymers that have the ability to stretch out and spring back to their original shape. ANSWER: B 48. ____ Bakelite is this type of polymer. ANSWER: J 49. ____ a Ziegler-Natta catalyst ANSWER: D 50. ____ Characteristic of crystallites ANSWER: I 51. ____ Absent in amorphous domains ANSWER: A 52. Provide the structure of poly(ethylene succinate). ANSWER:

53. Provide the structure of poly(butylene adipamide).

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Chapter 26: Organic Polymer Chemistry ANSWER:

54. Provide the structure of polystyrene. ANSWER:

55. Provide the structure of poly(methyl methacrylate). ANSWER:

56. Provide the structure of azoisobutyronitrile, AIBN, and show the mechanism whereby it undergoes thermal decomposition to give two radicals and a molecule of N2. ANSWER:

57. Provide the mechanism whereby two radical chain ends undergo dispropotionation to give two dead chain ends.

ANSWER:

58. Provide the mechanism for backbiting of a radical chain end of polyethylene, which results in a butyl side chain on the Copyright Cengage Learning. Powered by Cognero.

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Chapter 26: Organic Polymer Chemistry polymer backbone. ANSWER:

59. Provide the structure of polyacetylene that is formed by ring-opening metathesis polymerization of 1,3,5,7cyclooctatetraene.

ANSWER:

60. Provide the structure of the poly(lactic acid) that is formed by base catalyzed ring opening polymerization of the dilactone shown below.

ANSWER:

61. Provide the structure of poly(propylene oxide) that is formed by base catalyzed ring opening polymerization of the propylene oxide shown below.

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Chapter 26: Organic Polymer Chemistry ANSWER:

62. The ratio of the weight average molecular weight to the number average molecular weight of a polymer was found to be 3:2. Which of the following statements is true about the polymer? a. It has chains of equal length. b. It has chains of varying length. c. It has polydispersity index equal to 1. d. It has polydispersity index less than 1. ANSWER: b 63. Which of the following cycloalkenes is least reactive toward ROMP? a.

ANSWER: d 64. The weight average molecular weight of a polymer was found to be 100,000, and the number average molecular weight of the compound was 5,000. What is the PDI of the polymer? a. 0.005 b. 0.05 c. 20 d. 2 ANSWER: c 65. Identify the compound that is not a conductive polymer. a. Polyphenylene vinylene b. Bakelite c. Polypyrrole d. Polyacetylene ANSWER: b

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Chapter 26: Organic Polymer Chemistry 66. Which of the following compounds is not a free radical initiator? a. tert-butyl hydroperoxide b. Azoisobutyronitrile c. Peracetic acid d. Ziegler-Natta catalyst ANSWER: d 67. Rubber materials must have low _____ to behave as elastomers. ANSWER: glass transition temperatures (Tg) 68. Identify the final product of the following reaction.

a. Terephthalic acid b. Kevlar c. Lexan d. Nylon 6 ANSWER: d

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Chapter 27: Lipids 1. What is the structure of arachidic acid? a. CH3(CH2)18COOH b. CH3(CH2)11CH=CH(CH2)11COOH c. CH3(CH2)24COOH d. CH3CH2(CH=CHCH2)6(CH2)2COOH ANSWER: a 2. What is the structure of linolenic acid? a. CH3(CH2)10COOH b. CH3CH2(CH=CHCH2)3(CH2)6COOH c. CH3(CH2)8COOH d. CH3CH2(CH=CHCH2)5(CH2)10COOH ANSWER: b 3. Which of the following fatty acids has the highest melting point? a. palmitoleic acid b. oleic acid c. linoleic acid d. palmitic acid ANSWER: d 4. Which of the following fatty acids has the highest melting point? a. stearic acid b. oleic acid c. linoleic acid d. linolenic acid ANSWER: a 5. How many triglycerides (including stereoisomers) are there which contain three molecules of palmitoleic acid? a. 2 b. 6 c. 1 d. 8 ANSWER: d 6. How many triglycerides (including stereoisomers) are there which contain three molecules of palmitic acid? a. 1 b. 2 c. 3 d. 4 ANSWER: a Copyright Cengage Learning. Powered by Cognero.

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Chapter 27: Lipids 7. Which of the following is not true? a. sodium chloride is used to precipitate the soap as thick curds b. roughness that build up on textiles after repeated washings is due to calcium, magnesium, and iron salts of fatty aci ds c. soap micelles have negative charges on their surface d. soaps are magnesium salt of fatty acids ANSWER: d 8. Which of the following is a synthetic detergent? a. sodium 2-dodecylbenzenesulfonate b. N-(2-hydroxypropyl)dodecanamide c. sodium perchlorate dihydrate d. sodium laurate ANSWER: a 9. Which of the following processes is used to convert carboncarbon single bond in the hydrocarbon chain of a fatty acid to carbon-carbon double bond? a. hydration b. oxidation c. hydrolysis d. reduction ANSWER: b 10. What is the structure of choline, a component of phosphatidylcholine phospholipids?

a. 1 b. 2 c. 3 d. 4 ANSWER: c 11. What is the structure of inositol, a component of phospholipids?

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Chapter 27: Lipids a. 2 b. 3 c. 1 d. 4 ANSWER: d 12. What is the biological precursor of Vitamin D? a. lauric acid b. 7-dehydrocholesterol c. palmitic acid d. choline ANSWER: b 13. Which of the following is not an eicosanoid? a. prostaglandin H2 b. leukotriene C4 c. thromboxane B2 d. serine ANSWER: d 14. What is the R/S configuration of C-9 and C-11 of prostaglandin F2α?

a. 9R,11R b. 9R,11S c. 9S,11R d. 9S,11S ANSWER: c 15. What is the R/S configuration of C-8 and C-12 of prostaglandin F2α?

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Chapter 27: Lipids

a. 8R,12R b. 8R,12S c. 8S,12R d. 8S,12S ANSWER: a 16. What is the E/Z configuration of the carbon-carbon double bonds at C-5 and C-13 of prostaglandin F2α?

a. 5E,13E b. 5E,13Z c. 5Z,13E d. 5Z,13Z ANSWER: c 17. Which of the following is not an intermediate in the biosynthesis of cholesterol? a. acetyl coenzyme A b. isopentenyl pyrophosphate c. squalene d. linoleic acid ANSWER: d 18. What functional group of the protein opsin reacts with retinal to form rhodopsin, a light-sensitive pigment? a. carboxylic acid b. amide c. 1° amine d. alcohol ANSWER: c 19. Which of the following is not found in a fluid mosaic lipid bilayer? a. phospholipid Copyright Cengage Learning. Powered by Cognero.

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Chapter 27: Lipids b. cholesterol c. protein d. dodecylsulfonates ANSWER: d 20. What is the approximate value of pKa of a bile acid? a. −4 b. 1 c. 5 d. 25 ANSWER: c 21. The general formula for a fat or oil is shown below.

a. True b. False ANSWER: False 22. Salts of long chain fatty acids are called detergents. a. True b. False ANSWER: False 23. Compounds that are obtained from the saponification of triglycerides are glycerol and fatty acid salts. a. True b. False ANSWER: True 24. Ca+2, Mg+2, and/or Fe+3 are responsible for producing soap scum in water. a. True b. False ANSWER: True 25. The main difference between fats and oils is that oils contain a lower percentage of unsaturated alkyl chains. a. True b. False Copyright Cengage Learning. Powered by Cognero.

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Chapter 27: Lipids ANSWER: False 26. An example of a cationic detergent is shown below.

a. True b. False ANSWER: False 27. All steroids have the common skeleton shown below.

a. True b. False ANSWER: False 28. The structure of andosterone is given below.

The following is produced when andosterone is treated with NaBH4 in ethanol.

a. True b. False ANSWER: True 29. The major lipid component of cell membranes is phospholipids. a. True b. False Copyright Cengage Learning. Powered by Cognero.

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Chapter 27: Lipids ANSWER: True 30. CH3(CH2)12CO2H would be expected to be found in higher concentration in butter versus olive oil. a. True b. False ANSWER: True 31. The structure of acetyl-CoA is shown below and is a building block from which steroids are produced.

a. True b. False ANSWER: True 32. Cell membranes, which form an effective barrier to the passage of ions and other components into and out of the cell, are composed of a lipid bilayer. a. True b. False ANSWER: True 33. The chiral centers in α-santonin are indicated by asterisks in the following.

a. True b. False ANSWER: True 34. The number of carbon atoms in the unsaturated fatty acid from which prostaglandins are derived is _____. ANSWER: twenty 20 35. Consider the following.

Structure ____ would be classified as an ordinary soap. ANSWER: II II. Copyright Cengage Learning. Powered by Cognero.

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Chapter 27: Lipids 36. Consider the following.

Structure ____ would be classified as an synthetic detergent. ANSWER: IV IV. 37. Lipids are substances that are

in water and

in nonpolar organic solvents. Enter the answers

separated by a comma. ANSWER: insoluble, soluble 38. Consider the following substance.

The melting point of the above substance will be _________ than that of the substance listed below.

ANSWER: less lower Consider the following structures.

Use these to answer the following questions by placing the appropriate Roman numerical in the blank. 39. Saponification followed by protonation of structure _____ produces three moles of the same saturated fatty

acid. ANSWER: III Copyright Cengage Learning. Powered by Cognero.

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Chapter 27: Lipids 40. Saponification followed by protonation of structure _____ produces two moles of the salt of stearic acid and

one mole of the salt of oleic acid. ANSWER: II 41. When soaps disperse in water, the long hydrocarbon tails cluster together in a hydrophobic ball, while the ionic heads on the surface of the cluster stick out into the water. These spherical clusters are called ___________. ANSWER: micelles 42. The family of C20 lipids that contain a five-membered ring with two long side chains are called ____________________. ANSWER: prostaglandins 43. Male sex hormones like testosterone are called _____________. ANSWER: androgens 44. Female sex hormones like estrone are called _____________. ANSWER: estrogens 45. Briefly describe the chemical reaction that is used to “harden” a vegetable oil to give a fat. ANSWER: The carbon-carbon double bonds of the oil undergo hydrogenation in the presence of a transition metal catalyst. 46. Why do hydrogenated fats have higher boiling points than the triglycerides from which they are derived? ANSWER: The saturated side chains of hydrogenated fats pack together more efficiently than the unsaturated side chains of triglycerides, which contain cis double bonds, thereby raising the melting point. 47. Provide the general structure of a triglyceride. ANSWER:

R, R’ and R” are typcially C10-C19 chains, with or without cis C-C double bonds. 48. Circle the hydrophilic part of sodium palmitate, a soap that is the sodium salt of a fatty acid, and put a rectangle around the hydrophobic part.

ANSWER:

49. Circle the hydrophilic part of sodium 4-dodecylbenzenesulfonate, a synthetic detergent, and put a rectangle around the hydrophobic part. Copyright Cengage Learning. Powered by Cognero.

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Chapter 27: Lipids

ANSWER:

50. Arachidonic acid is a C20 acid that is involved in the biosynthesis of prostaglandins, an important class of biomolecules. Provide the IUPAC name of arachidinic acid.

ANSWER: (5Z,8Z,11Z,14Z)-5,8,11,14-icosatetraenoic acid 51. Explain the formation of “soap scum”, formed in areas which have “hard” water. What chemical reaction takes place, and what physical process results? ANSWER: The sodium ion of a water-soluble (micelle-forming) sodium soap is exchanged for a calcium ion. The calcium salt is not soluble in water and precipitates. 52. The following tetracylic structure is common to steroids, an importnat class of biomolecules that have a number of sterocenters. Modify the structure on the right by placing the hydrogen atoms and methyl groups to accurately depict the structure on the left (including steeochemistry).

ANSWER: `

53. Describe how the structure of a phospholipid differs from that of a trigyceride fat, and what influence this difference has on the interaction of these molecules with water. Copyright Cengage Learning. Powered by Cognero.

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Chapter 27: Lipids ANSWER: A triglyceride fat has three long-chain esters; in a phospholipid one of these is replaced with a phosphate ester. The phosphase ester is polar. Whereas triglyceride fats are hydrophobic and insoluble in water, phospholipids are amphiphilic and self assemble in water to form bilayer structures. 54. What are the roles of LDL and HDL? Which one is “good” cholesterol, which one is bad”? ANSWER: Low density lipoprotein (LDL) is a protein that carries cholesterol from the site where it is synthesized to the rest of the body. High density lipoprotein (HDL) carries unused cholesterol to the liver where it is subject to degradation. Since build up of cholesterol in the arteries is a bad thing, LDL is “bad” cholesterol, and HDL is “good”. 55. The hydrolysis of a triglyceride in an aqueous base followed by acidification gives _____ and _____ fatty acids. a. glycerol; four b. glycerol; three c. glycine; three d. glycerin; four ANSWER: b 56. The richest source of 'X' is wheat germ oil. 'X' is also found in fish oil and leafy green vegetables. It is fatsoluble, and αtocopherol is the active compound present in it. It was first identified in 1922 as a dietary factor essential for reproduction in rats. Identify 'X'. a. Vitamin D b. Vitamin E c. Thiamine d. Riboflavin ANSWER: b 57. Identify the given structure.

a. Retinol b. Vitamin E c. Thiamine d. Riboflavin ANSWER: a 58. 'X' are longchain carboxylic acids derived from the hydrolysis of animal fats, vegetable oils, and the phospholipids of biological mem branes. They are named by the number of carbons in the chain and the number of carboncarbon double bonds present. Identify 'X'. a. Prostaglandins b. Lipids Copyright Cengage Learning. Powered by Cognero.

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Chapter 27: Lipids c. Lipoprotein d. Fatty acids ANSWER: d 59. _____ is a detergent molecule secreted by the gallbladder into the intestine to assist in the absorption of dietary lipids. a. Prostaglandins b. Bile acid c. Anabolic steroid d. Phospholipids ANSWER: b Match the terms with the most appropriate descriptions. a. Progesterone b. Testosterone c. Cholic acid d. Vitamin D e. Lipid bilayer 60. Suppresses ovulation ANSWER: a 61. Development of facial hair in men ANSWER: b 62. A constituent of bile acid ANSWER: c 63. Regulation of calcium and phosphorus metabolism ANSWER: d 64. Self-assembly of phospholipids ANSWER: e 65. The increase in the rigidity of a phospholipid bilayer is because of the _____. a. close packing of saturated hydrocarbon chains b. disordered packing of saturated hydrocarbon chains c. ordered packing of unsaturated hydrocarbon chains d. close packing of unsaturated hydrocarbon chains ANSWER: a

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Chapter 28: Amino Acids and Proteins 1. Which of the following amino acids is not chiral? a. leucine b. glycine c. alanine d. proline ANSWER: b 2. Which of the following amino acids has a basic side chain? a. lysine b. serine c. leucine d. valine ANSWER: a 3. Which of the following amino acids has an acidic side chain? a. leucine b. asparagine c. tyrosine d. histidine ANSWER: c 4. Which of the following amino acids has a polar side chain? a. valine b. leucine c. glycine d. asparagine ANSWER: d 5. Which of the following amino acids has a non-polar side chain? a. asparagine b. arginine c. glutamine d. tryptophan ANSWER: d 6. Which of the following amino acids is has a primary amine group in the side chain? a. lysine b. alanine c. methionine d. tyrosine ANSWER: a 7. Which of the following natural amino acids is an R-isomer? a. cysteine Copyright Cengage Learning. Powered by Cognero.

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Chapter 28: Amino Acids and Proteins b. serine c. valine d. phenylalanine ANSWER: a 8. Which of the following amino acids is not an L-isomer? a. serine b. valine c. glycine d. proline ANSWER: c 9. Which of the following amino acids contains two stereocenters? a. isoleucine b. proline c. phenylalanine d. glutamine ANSWER: a 10. Which of the following amino acids has an aromatic side chain? a. histidine b. glutamine c. aspargine d. glycine ANSWER: a 11. Which of the following amino acids has an amide group? a. histidine b. glutamine c. lysine d. phenylalanine ANSWER: b 12. What are the R/S designations of the two stereocenters of isoleucine?

a. 2R,3R b. 2R,3S c. 2S,3R d. 2S,3S Copyright Cengage Learning. Powered by Cognero.

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Chapter 28: Amino Acids and Proteins ANSWER: d 13. What are the R/S designations of the two stereocenters of L-threonine?

a. 2R,3R b. 2R,3S c. 2S,3R d. 2S,3S ANSWER: c 14. What is the approximate value of the pKa of the α-CO2H of amino acids? a. 2 b. 5 c. 9 d. 12 ANSWER: a 15. What is the approximate value of the pKa of the α-NH3+ of amino acids? a. 2 b. 5 c. 9 d. 12 ANSWER: c 16. Which of the following is a definition of zwitterion? a. An internal salt of an amino acid b. A molecule containing two amino acid units joined by a peptide bond c. A positively charged amino acid ion d. A negatively charged amino acid ion ANSWER: a 17. What is the isoelectric point of alanine (pKa of α-CO2H, 2.35; pKa of α-NH3+, 9.87)? a. 6.11 b. 5.11 c. 7.11 d. 3.11 ANSWER: a 18. What is the isoelectric point of aspartic acid (pKa of α-CO2H, 2.1; pKa of α-NH3+ 9.82; pKa of side chain, 3.86)? Copyright Cengage Learning. Powered by Cognero.

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Chapter 28: Amino Acids and Proteins a. 2.98 b. 5.96 c. 1.98 d. 3.89 ANSWER: a 19. Which of the following amino acids migrates to the positive electrode on paper electrophoresis at a pH of 7.0? a. glutamine b. arginine c. histidine d. lysine ANSWER: a 20. Which of the following amino acids migrates to the negative electrode on paper electrophoresis at a pH of 7.0? a. histidine b. aspartic acid c. glutamic acid d. methionine ANSWER: a 21. Which of the bonds in the following structure is cleaved by cyanogen bromide?

a. i b. ii c. iii d. iv ANSWER: c 22. Which of the following tripeptides is not hydrolyzed by trypsin? a. Arg-Ala-Phe b. Lys-Pro-Tyr c. Ala-Asp-Gly d. Val-Arg-Lys ANSWER: c 23. Which of the following tripeptides is not hydrolyzed by chymotrypsin? a. Pro-Phe-Tyr b. Trp-Ala-Val Copyright Cengage Learning. Powered by Cognero.

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Chapter 28: Amino Acids and Proteins c. Val-Ala-Tyr d. Asp-Phe-Tyr ANSWER: c 24. Which of the following dipeptides is L-Ser-L-Phe?

a. 1 b. 2 c. 3 d. 4 ANSWER: a 25. Which of the following dipeptides is D-Ala-L-Cys?

a. 2 b. 1 c. 3 d. 4 ANSWER: b Copyright Cengage Learning. Powered by Cognero.

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Chapter 28: Amino Acids and Proteins 26. How does phenyl isothiocyanate, Ph−N=C=S, react with a peptide in the Edman degradation? a. the sp carbon acts as an electrophile in a reaction with an amino group of the peptide b. addition of the C-terminal amino group to the C-N bond of phenyl isothiocyanate gives a derivative of Cphenylthiourea c. The sp2 carbon of the isothiocyanate acts as a nucleophile and adds to the N-terminal amino group d. The N atom acts as an electrophile in a reaction with carboxylate of the peptide ANSWER: a 27. Which of the following reagents can be used to cleave a benzyloxycarbonyl protecting group from a peptide? a. H2/Fe b. H2O c. Na2CO3, H2O d. LiAlH4 ANSWER: a 28. Which of the following reagents can be used to cleave a benzyloxycarbonyl protecting group from a peptide? a. HI, CH3CO2H b. conc. NaOH c. heat d. NaCl, H2O ANSWER: a 29. To what structural feature does the term "primary structure" refer? a. the sequence of amino acids in proteins b. the overall folding pattern of proteins c. the aggregation of polypeptides d. the conformation of local regions of polypeptides ANSWER: a 30. To what structural feature does the term "secondary structure" refer? a. the sequence of amino acids in proteins b. the overall folding pattern of proteins c. the aggregation of polypeptides d. the conformation of local regions of polypeptides ANSWER: d 31. To what structural feature does the term "tertiary structure" refer? a. the sequence of amino acids in proteins b. the overall folding pattern of proteins c. the aggregation of polypeptides d. the conformation of local regions of polypeptides Copyright Cengage Learning. Powered by Cognero.

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Chapter 28: Amino Acids and Proteins ANSWER: b 32. To what structural feature does the term "quaternary structure" refer? a. the sequence of amino acids in proteins b. the overall folding pattern of proteins c. the aggregation of polypeptides d. the conformation of local regions of polypeptides ANSWER: c 33. Which of the following is not a polypeptide? a. lactate dehydrogenase b. aldolase c. glutamine synthetase d. RNA ANSWER: d 34. What is the major organic product of the following reaction?

a. 1 b. 2 c. 3 d. 4 ANSWER: c 35. The molecule shown below is an α-amino acid.

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Chapter 28: Amino Acids and Proteins a. True b. False ANSWER: False 36. Valylalanine and alanylvaline are constitutional isomers. a. True b. False ANSWER: True 37. Ninhydrin is used to determine the N-terminal amino acid of a peptide. a. True b. False ANSWER: False 38. Consider the following octapeptide.

Ala-Val-Trp-Lys-Phe-Gly-Arg-Met The fragments that would be obtained by a trypsin hydrolysis are Ala-Val-Trp-Lys and Phe-Gly-Arg and Met. a. True b. False ANSWER: True 39. The following structure is that of Sanger’s reagent.

a. True b. False ANSWER: False 40. Bradykinin is a nonapeptide, Arg-Pro-Pro-Gly-Phe-Ser-Pro-Phe-Arg. In addition to one mole of Arg, the

following peptides are present after hydrolysis of bradykinin with chymotrypsin, Arg-Pro-Pro-Gly-Phe-Ser and Pro-Phe a. True b. False ANSWER: False 41. For leucine the pI is the average of pKa1 and pKa2. a. True b. False ANSWER: True Copyright Cengage Learning. Powered by Cognero.

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Chapter 28: Amino Acids and Proteins 42. Consider the following image.

This represents the tertiary structure of a protein. a. True b. False ANSWER: False 43. Consider the following image.

This represents the quaternary structure of a protein. a. True b. False ANSWER: False 44. In Cys-Ile-Ser-Asp-Gly-His-Gly-Gly, the three-letter abbreviation for the N-terminal amino acid is

________. ANSWER: Cys Copyright Cengage Learning. Powered by Cognero.

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Chapter 28: Amino Acids and Proteins 45. In Phe-Ile-Ser-Asp-Gly-His-Gly-Tyr, the three-letter abbreviation for the C-terminal amino acid is

________. ANSWER: Tyr 46. In terms of the number of amino acid residues Cys-Ile-Ser-Asp-Gly-His-Gly-Gly would be classified as a(n)

________________. ANSWER: octapeptide 47. The number of different combinations that are possible for a tripeptide containing one of each of the

following amino acids: Phe, Val, Asp is ______. ANSWER: 6 six 48. Hydrogen bonds, α-helices, and pleated sheets are properties of ANSWER: secondary

structure of proteins.

49. Consider the following form of phenylalanine.

This form would exist at a pH _______than the pI. ANSWER: greater higher more 50. Structure _____ (shown below) will migrate toward the positive electrode in an electrophoresis experiment.

ANSWER: II 51. Structure _____ (shown below) will remain at the origin in an electrophoresis experiment.

ANSWER: I 52. The structure of the phenylhydantoin derived from the _____ cycle of the Edman degradation of Phe-Ala-

Ser is

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Chapter 28: Amino Acids and Proteins

ANSWER: first 1st 53. The Edman degradation is used to identify the ___-terminal amino acid of a peptide. ANSWER: N N 54. A tetrapeptide contains the amino acids Phe, Ala, Gly, and Leu. Partial hydrolysis produces the dipeptides

Phe-Ala, Ala-Gly, and Leu-Phe. The structure of the tetrapeptide is _________________________. Use the three-letter designations for the amino acids separated by dashes (-). ANSWER: Leu-Phe-Ala-Gly MATCH a structure from the list below to each of the following terms. Place the letter of the structure in the blank to the left of the term which it describes.

C. Val−Phe−Leu−Met−Tyr−Pro−Gly−Trp−Cys−Glu D. F.

E. Asp−Tyr−Ile−His−Pro−Phe−Arg−Val

G. BOC group

Val−Lys−Phe−Gly−Arg−Met−Arg−Phe

M. Z group Page 11

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Chapter 28: Amino Acids and Proteins 55. _____ is an octapeptide with a C-terminal valine. ANSWER: F 56. _____ is an amino acid in its zwitterionic form. ANSWER: B 57. _____ is a polypeptide which gives four fragments on treatment with chymotrypsin. ANSWER: C 58. _____ is the product of an Edman degradation. ANSWER: J 59. _____ is a carboxyl-protected amino acid. ANSWER: D 60. _____ is a peptide coupling reagent. ANSWER: H 61. What fragments are produced when porcine dynorphin, a peptide that contains 17 amino acid residues (shown below), is cleaved with trypsin? Tyr−Gly−Gly−Phe−Leu−Arg−Arg−Ile−Arg−Pro−Lys−Leu−Lys−Trp−Asp−Asn−Gln ANSWER: Tyr−Gly−Gly−Phe−Leu−Arg Arg Ile−Arg Pro−Lys Leu−Lys Trp−Asp−Asn−Gln 62. What fragments are produced when porcine dynorphin, a peptide that contains 17 amino acid residues (shown below), is cleaved with chymotropsin? Tyr−Gly−Gly−Phe−Leu−Arg−Arg−Ile−Arg−Pro−Lys−Leu−Lys−Trp−Asp−Asn−Gln ANSWER: Tyr Gly−Gly−Phe Leu−Arg−Arg−Ile−Arg−Pro−Lys−Leu−Lys−Trp Asp−Asn−Gln 63. Edman degradation of the peptide saralasin shows that it has a sarcosine residue at the N-terminus. Sarcosine is Partial hydrolysis of saralasin with dilute hydrochloric acid gives the following fragments: His−Pro−Ala Val−Tyr−Val Arg−Val−Tyr Sar−Arg−Val Copyright Cengage Learning. Powered by Cognero.

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Chapter 28: Amino Acids and Proteins Tyr−Val−His What is the structure of saralasin? ANSWER: Sar−Arg−Val−Tyr−Val−His−Pro−Ala 64. What are the products of the reaction of alanine and ninhydrin (shown below)?

ANSWER:

65. Provide the structure of Ser-Ala. ANSWER:

66. Provide the structure of Ser-Phe-Asp. ANSWER:

67. Provide the major organic product of the following reaction that is used in the chemical synthesis of peptides. Copyright Cengage Learning. Powered by Cognero.

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Chapter 28: Amino Acids and Proteins

ANSWER:

68. Provide the structure of dicylcohexylcarbodiimide, a common reagent that is used to couple two amino acid residues by formation of a peptide bond, and the structure N,N’-dicyclohexylurea, the byproduct of this reaction. ANSWER:

69. Disulfide bonds form between the thiol side chains of cysteine. What is the best term to describe the reaction of two thiols to give a disulfide bond? ANSWER: Oxidation. 70. In the Edman degradation analysis of the N-terminus of a peptide the terminal residue reacts with phenyl isocyanate, an example is shown below. Provide the structure of both of the products of this reaction.

ANSWER:

71. In the case of paper electrophoresis, a paper strip saturated with an aqueous buffer of predetermined pH serves as a bridge between the two _____. ANSWER: electrode vessels 72. Which of the following is not a strategy for the synthesis of polypeptides? Copyright Cengage Learning. Powered by Cognero.

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Chapter 28: Amino Acids and Proteins a Protect the α. amino group of the amino acid aa1 to reduce its nucleophilicity so that the group does not participate in nucleophili c addition to the carboxyl group of either aa1 or aa2. b Treating a polypeptide with a group of proteolytic enzymes, like trypsin and chymotrypsin, to catalyze the hydrolys . is of specific peptide bonds. c Activate the α-carboxyl group of the amino acid aa1 so that the group is susceptible to nucleophilic attack by the α. amino group of aa2. d Joining the C. terminal amino acid as a benzyl ester to the solid polymer support and extending the polypeptide chain with one am ino acid at a time. ANSWER: b 73. The combination of the two sidechains of the given compounds leads to the formation of a special bond. Identify the type of bond formed.

a. Disulfide bond b. Disulfite bond c. Hydrogen bond d. Vibrational bond ANSWER: a 74. Identify the compound shown below.

a. L-Thyroxine b. L-Triiodothyronine c. L-Omithine d. L-Citrulline ANSWER: a 75. Identify the function of the following group in protein synthesis.

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Chapter 28: Amino Acids and Proteins

a. Protection b. Hydrolysis c. Hydrogenation d. Alkylation ANSWER: a 76. Identify the technique that has almost replaced the automated Edman degradation. a. Gas chromatography b. Infrared spectroscopy c. Mass spectroscopy d. N-terminal Amino acid analysis ANSWER: c 77. Which of the following is not an endopeptidase? a. Pepsin b. Chymotrypsin c. Elastase d. Carboxypeptidase A ANSWER: d

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Chapter 29: Nucleic Acids 1. Which of the following is a purine base? a. uracil b. cytosine c. thymine d. adenine ANSWER: d 2. Which of the following is a pyrimidine base? a. guanine b. guanidine c. cytosine d. trimethylamine ANSWER: c 3. Which of the following is 2-deoxy-D-ribose?

a. 1 b. 2 c. 3 d. 4 ANSWER: b 4. Which of the following is D-ribose?

a. 1 b. 2 c. 3 d. 4 ANSWER: a 5. Which of the following is a pyrimidine base? Copyright Cengage Learning. Powered by Cognero.

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Chapter 29: Nucleic Acids

a. only 3 b. only 2 c. only 1 d. only 4 ANSWER: d 6. Which of the following is adenine?

a. 3 b. 2 c. 1 d. 4 ANSWER: d 7. Which of the following is a complimentary pair of hydrogen-bonded bases found in DNA? a. U-T b. A-G c. G-C d. A-C ANSWER: c 8. Which of the following is a complimentary pair of hydrogen-bonded bases found in RNA? a. A-T Copyright Cengage Learning. Powered by Cognero.

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Chapter 29: Nucleic Acids b. G-T c. A-G d. A-U ANSWER: d 9. Which of the following is a definition of transfer RNA (tRNA)? a. RNA found in the ribosome, the site in cells where synthesis of proteins takes place b. RNA which carries a specific amino acid to the site of protein synthesis c. RNA which has coded genetic information d. RNA which allows transfer of a protein out of a cell ANSWER: b 10. Which of the following is a definition of messenger RNA (mRNA)? a. RNA found in the ribosome, the site in cells where synthesis of proteins takes place b. RNA which carries a specific amino acid to the site of protein synthesis c. RNA which has coded genetic information d. RNA which signals cell death ANSWER: c 11. Which of the following is a definition of a codon? a. a complimentary pair of hydrogen bonded bases in RNA b. a sequence of three bases on RNA that directs incorporation of a specific amino acid into a protein c. a complex between DNA and RNA d. RNA found in the ribosome, the site in cells where synthesis of proteins takes place ANSWER: b 12. Where is the amino acid linked to the ribose unit of transfer RNA in the process of transferring the amino acid to ribosomes? a. the base b. C2'-OH c. 3'-OH d. 5'-OH ANSWER: c 13. What sequence is fully complementary to the following sequence? 5'-TCGTCAATCC-3' a. 5'-TAGATCATTA-3' b. 5'-GGATTGACGA-3' c. 3'-ATTCGAAGGC-5' d. 3'-ACATTGCTCC-5' ANSWER: b 14. What sequence is fully complementary to the following sequence? 5'-GTTCAAGT-3' Copyright Cengage Learning. Powered by Cognero.

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Chapter 29: Nucleic Acids a. 3'-GTTCGACT-5' b. 3'-TCAGCATG-5' c. 5'-ACTTGAAC-3' d. 5'-CACGGTGA-3' ANSWER: c 15. A _______ is an oligonucleotide capable of forming a short section of double-stranded DNA by basepairing with its complement on a single-stranded DNA. a. tRNA b. primer c. codon d. mRNA ANSWER: b 16. How many bases are present in each strand of a complete turn of B-DNA? a. 3 b. 7 c. 10 d. 15 ANSWER: c 17. What is the approximate distance between stacked bases in a double helix of DNA? a. 340 pm b. 800 pm c. 2000 pm d. 3400 pm ANSWER: a 18. What is the approximate diameter of double helix of DNA? a. 340 pm b. 800 pm c. 2000 pm d. 3400 pm ANSWER: a 19. What is the approximate length of a complete turn of a double helix of DNA? a. 340 pm b. 800 pm c. 2000 pm d. 3400 pm ANSWER: d 20. What tetrapeptide is coded by the following sequence of mRNA? 5'-AUG-AUA-ACC-CUG-3' Copyright Cengage Learning. Powered by Cognero.

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Chapter 29: Nucleic Acids a. Met-Ile-Thr-Leu b. Ile-Leu-Val-Met c. Met-Met-Ala-Thr d. Ile-Ala-Thr-Leu ANSWER: a 21. The following structures is a pyrimidine.

a. True b. False ANSWER: False 22. A correct abbreviation for the following nucleotide is ADP.

a. True b. False ANSWER: False 23. The structure below represents a nucleoside.

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Chapter 29: Nucleic Acids

a. True b. False ANSWER: True 24. Relative to the secondary structure of DNA, the purine and pyrimidine bases lie inside the helix, in planes

perpendicular to the helical axis; the deoxyribose and phosphate groups form the outside of the helix. a. True b. False ANSWER: True 25. Relative to the secondary structure of DNA, there is no restriction on the sequence of bases along a

polynucleotide chain. The exact sequence carries the genetic information. a. True b. False ANSWER: True 26. Relative to the secondary structure of DNA, the helices are left handed and the two strands run in same

directions relative to their 3'and 5' ends. a. True b. False ANSWER: False 27. The structural arrangement of DNA is

a. True b. False ANSWER: True 28. The structure of the sugar in RNA is shown below.

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Chapter 29: Nucleic Acids

a. True b. False ANSWER: False 29. The G-C base pair is the weaker than the A-T base pair as it has two hydrogen bonds whereas the A-T base pair has three. a. True b. False ANSWER: False 30. If ranked for largest to smallest, the correct order of DNA, mRNA, and tRNA would be DNA > mRNA > tRNA. a. True b. False ANSWER: True 31. The name of the base in the following nucleotide is __________________.

ANSWER: thymine 32. The name of the following nucleotide is_____________________________.

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Chapter 29: Nucleic Acids

ANSWER: 2'-deoxyadenosine monophosphate

2’-deoxyadenosine monophosphate 2'-deoxyadenosine 2'-monophosphate 2’-deoxyadenosine 2’-monophosphate 33. A three base sequence called a “codon” codes for one _______________. ANSWER: amino acid MATCH each of the following terms to a structure from the list below. There is only one correct answer for each question and structures may be used more than once. Place the letter of the structure in the blank to the left of the corresponding term. A. C.

Sanger dideoxy method Watson-Crick

G. I.

GAUCGUAAA translation

transcription AUGGCUGAG

B. D.

H. J.

Maxam-Gilbert method replication

AGATCGCTC

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Chapter 29: Nucleic Acids 34. _____ is a pyrimidine nucleoside. ANSWER: E 35. _____ is a RNA base sequence with guanine at the 3' end. ANSWER: I 36. _____ is a DNA base sequence with cytosine at the 3' end. ANSWER: M 37. _____ is uridine. ANSWER: E 38. _____ is the DNA sequencing method for the human genome. ANSWER: A 39. _____ is the RNA base sequence complementary to the DNA base sequence shown below which codes for Leu−Ala−Phe. CTAGCATTT ANSWER: B 40. _____ is process by which mRNA directs protein synthesis. ANSWER: D 41. _____ is a pyrimidine nucleoside. ANSWER: E 42. A double-stranded DNA molecule that contains 22%, on a mole basis, T must also contain ___% G. ANSWER: 78 43. Provide the structure of 2-deoxyribose. ANSWER:

44. Number each position in the ribose below according to the normal convention.

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Chapter 29: Nucleic Acids ANSWER:

45. Provide the structure of guanine, a heterocyclic base found in DNA. ANSWER:

46. Provide the structure of adenosine, a nucleoside. ANSWER:

47. Provide the structure of cytidine 5’-monophosphate, a nucleotide consisting of a cytosine base, a ribose and a phosphate group. ANSWER:

48. Provide the structure of adenosine triphosphate, ATP.

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Chapter 29: Nucleic Acids ANSWER:

49. What sequence is fully complementary to the following sequence? 5'-AGTCAATTC-3' ANSWER: 5'-GAATTGAC-3' 50. What sequence is fully complementary to the following sequence? 5'-TAGCGATC-3' ANSWER: 5'-GATCGCTA-3" 51. Provide the structure of a T-A base pair, showing hydrogen bonds as dotted lines. ANSWER:

52. Provide the structure of a G-C base pair, showing hydrogen bonds as dotted lines. ANSWER:

53. Identify the given structure.

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Chapter 29: Nucleic Acids

a. Adenine b. Guanine c. Cytosine d. Uracil ANSWER: a 54. Identify the given structure.

a. Guanine-uracil b. Guanine-cytosine c. Thymine-uracil d. Thymine-adenine ANSWER: d 55. _____ is a double-stranded DNA in which the two ends of each DNA strand are joined by phosphodiester bonds. ANSWER: Circular DNA 56. The complex between negatively charged DNA and positively charged histones is called _____. ANSWER: chromatin 57. List the major differences between the structure of RNA and DNA. ANSWER: The major differences between the structure of RNA and DNA are as follows: 1. The pentose unit in RNA is β-D-ribose, whereas the pentose unit in DNA is β-D-deoxy-D-ribose. 2. The pyrimidine bases in RNA are uracil and cytosine, whereas the pyrimidine bases in DNA are thymine and cytosine. 3. RNA is single-stranded, whereas DNA is double-stranded. 58. EcoRI is a restriction endonuclease that recognizes the hexanucleotide sequence, GAATTC. Identify the fragments cleaved by EcoRI in the given DNA strand.

a. Copyright Cengage Learning. Powered by Cognero.

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Chapter 29: Nucleic Acids b. c. d. ANSWER: a 59. Identify the given structure.

a. 2’,2’-dideoxynucleoside triphosphate b. 3’,2’-dideoxynucleoside triphosphate c. 3’,3’-dideoxynucleoside triphosphate d. 2’,3’-dideoxynucleoside triphosphate ANSWER: d

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