CHAPTER 1 1)
What is the ground-state electronic configuration of a carbon atom? A) 1s 2, 2s 2, 2p 5 B) 1s 2, 2s 2, 2p 2 C) 1s2, 2s2, 2p6 D) 1s2, 2s2, 2p4
2)
What is the ground-state electronic configuration of a fluorine atom? A) 1s2, 2s2, 2p2 B) 1s2, 2s2, 2p3 C) 1s2, 2s2, 2p4 D) 1s2, 2s2, 2p5
3)
What is the ground-state electronic configuration of a magnesium cation (Mg2+)? A) 1s2, 2s2, 2p6 B) 1s2, 2s2, 2p6, 3s1 C) 1s2, 2s2, 2p6, 3s2 D) 1s2, 2s2, 2p6, 3s2, 3p2
4)
What is the ground-state electronic configuration of a chlorine anion (Cl−)? A) 1s2, 2s2, 2p6 B) 1s2, 2s2, 2p6, 3s2, 3p6 C) 1s2, 2s2, 2p6, 3s2, 3p5 D) 1s2, 2s2, 2p6, 3s2, 3p4
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5)
Which of the following statements about valence electrons is true? A) They are the most tightly held electrons. B) They do not participate in chemical reactions. C) They are the outermost electrons. D) They reveal the period number of a second-row element.
6)
Which of the following atoms will have a full 3s orbital in the ground state? A) Hydrogen B) Lithium C) Potassium D) Rubidium
7)
Which of the following statements about bonding is true? A) Covalent bonds result from the transfer of electrons from one element to another. B) Ionic bonds result from the transfer of electrons from a metal to a non-metal. C) Ionic bonds result from the sharing of electrons between two non-metals. D) Covalent bonds result from the sharing of electrons between two metals.
8)
Which of the following would you expect to have ionic bonds? A) CO B) FBr C) NF3 D) NaCl
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9)
Which of the following molecules has nonpolar covalent bonds?
A) HCl B) N2 C) CHCl 3 D) NO
10)
Which of the following molecules contain both covalent and ionic bonds?
A) I, II B) I, IV C) II, III D) II, IV
11)
Which of the following would most likely form an ionic bond?
A) I B) II C) III D) IV
12) Which of the following statements correctly describes the typical number of bonds for carbon, nitrogen, and oxygen in most neutral organic molecules?
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A) Carbon forms 4 covalent bonds, nitrogen forms 2 covalent bonds, and oxygen forms 3 covalent bonds. B) Carbon forms 4 covalent bonds, nitrogen forms 3 covalent bonds, and oxygen forms 2 covalent bonds. C) Carbon forms 4 covalent bonds, nitrogen forms 5 covalent bonds, and oxygen forms 2 covalent bonds. D) Carbon forms 4 covalent bonds, nitrogen forms 5 covalent bonds, and oxygen forms 4 covalent bonds.
13)
Which is not an acceptable Lewis structure for the anion CH2NCO−?
A) I B) II C) III D) IV
14)
Which of the following Lewis structures is correct?
A) I B) II C) III D) IV
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15)
Which of the following Lewis structures is correct?
A) I, II B) I, III C) II, III D) III, IV
16)
Which is the correct Lewis structure for acetic acid (CH3CO2H)?
A) I B) II C) III D) IV
17)
In which of the following ions does carbon have a formal charge?
A) I B) II C) III D) None of these
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18)
In which of the following ions does carbon have a formal charge?
A) I B) II C) III D) None of these
19) What is the formal charge of carbon in carbon monoxide (CO) when drawn with a triple bond?
A) 0 B) −2 C) −1 D) +1
20) What is the formal charge of the carbon in carbon dioxide (CO2) when drawn with two double bonds? A) +1 B) 0 C) −1 D) −2
21)
Which of the following statements about constitutional isomers is true?
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A) Constitutional isomers are different molecules having the different molecular formula. B) Constitutional isomers are different molecules having the same molecular formula. C) Constitutional isomers are same molecules having the different molecular formula. D) Constitutional isomers are same molecules having the same molecular formula.
22) How many constitutional isomers are there for a molecule having the molecular formula C2H6O? A) 1 B) 2 C) 3 D) 4
23) How many constitutional isomers are there for a molecule having the molecular formula C3H8O? A) 1 B) 2 C) 3 D) 4
24) How many constitutional isomers are there for a molecule having the molecular formula C3H6? A) 1 B) 2 C) 3 D) 4
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25) How many constitutional isomers are there for a molecule having the molecular formula C2H4Cl2? A) 1 B) 2 C) 3 D) 4
26) How many different isomers are there for a compound having the molecular formula C3H6O? A) 4 B) 5 C) 6 D) 7
27)
Which of the following molecules are constitutional isomers?
A) I, II, IV B) II, III, IV C) I, III, IV D) I, II, III
28) Which of the following compounds has an atom with an unfilled valence shell of electrons?
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A) H2O B) BCl3 C) CH 4 D) CO2
29)
Which of the following compounds has an atom with more than eight valence electrons?
A) H2CO3 B) H2SO4 C) H 2O D) HBr
30)
How many electrons are around phosphorus in phosphoric acid (H3PO4)? A) 6 B) 8 C) 10 D) 12
31)
Which of the following statements about resonance structures is true?
A) Resonance structures have the same placement of electrons but different arrangement of atoms. B) Resonance structures have the same placement of atoms but different arrangement of electrons. C) Resonance structures have the same placement of atoms and the same arrangement of electrons. D) Resonance structures have different placement of atoms and different arrangement of electrons.
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32)
Which of the following statements about resonance structures is not true? A) There is no movement of electrons from one form to another. B) Resonance structures are not isomers. C) Resonance structures differ only in the arrangement of electrons. D) Resonance structures are in equilibrium with each other.
33)
Which of the following pair does not represent resonance structures?
A) I B) II C) III D) IV
34)
What 2 things will change between two resonance structures?
A) The position of multiple bonds and non-bonded electrons. B) The position of multiple bonds and single bonds. C) The placement of atoms and single bonds. D) The placement of atoms and non-bonded electrons.
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35)
Which of the following is a resonance structure of the compound below?
A) I B) II C) III D) IV
36) Which of the following resonance structures is the least important contributor to the resonance hybrid of the formate anion, HCOO−?
A) I B) II C) III D) IV
37) Rank the following in order of decreasing importance as contributing structures to the resonance hybrid of formaldehyde, H2CO.
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A) I > II > III B) I > III > II C) II > I > III D) III > II > I
38)
Follow the curved arrows to draw the second resonance structure for the ion below.
A) I B) II C) III D) IV
39)
Which is more important in each pair of contributing resonance structures?
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A) II, IV, V B) II, III, V C) II, III, VI D) I, IV, V
40)
What is the approximate value of the H-C-H bond angle in methane, CH4? A) 90° B) 109.5° C) 120° D) 180°
41)
What is the approximate C-C-C bond angle in propene, CH3CH = CH2? A) 90° B) 109.5° C) 120° D) 180°
42)
What is the approximate H-C-O bond angle in formaldehyde, H2CO? A) 90° B) 109.5° C) 120° D) 180°
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43)
Determine the geometry around the indicated atom in each species.
A) I = Linear; II = tetrahedral; III = trigonal planar; IV = tetrahedral B) I = Linear; II = tetrahedral; III = trigonal planar; IV = linear C) I = Trigonal planar; II = linear; III = tetrahedral; IV = trigonal planar D) I = Tetrahedral; II = trigonal planar; III = linear; IV = tetrahedral
44)
What is the approximate bond angle for the C-C-N bond in acetonitrile, CH3CN? A) 90° B) 109.5° C) 120° D) 180°
45)
What is the molecular geometry around the boron atom in BH3? A) Tetrahedral B) Trigonal Planar C) Trigonal Pyramidal D) Linear
46)
What is the molecular geometry around the carbon atom in CH4?
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A) Tetrahedral B) Trigonal Planar C) Trigonal Pyramidal D) Linear
47) Which of the following is the appropriate conversion of the condensed structure, CH3COCH3, to a Lewis structure?
A) I B) II C) III D) IV
48) Which of the following is the appropriate conversion of (CH3)2CHCH2CHClCH3to a skeletal structure?
A) I B) II C) III D) IV
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49)
Which of the following is the appropriate conversion of (CH3)4C to a skeletal structure?
A) I B) II C) III D) IV
50)
What is the condensed formula of the compound below?
A) I B) II C) III D) IV
51) Which of the following is the appropriate conversion of (CH3)2CHOCH2CH2CH2OH to a skeletal structure?
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A) I B) II C) III D) IV
52)
Convert the following skeletal structure to a condensed structure.
A) I B) II C) III D) IV
53) Avobenzone is an active ingredient in some common sunscreens. Which of the following is the correct molecular formula for avobenzone?
A) C22O22O3 B) C20H22O3 C) C21H23O3 D) C20H24O3
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54)
In which structure is the hybridization incorrect?
A) I B) II C) III D) IV
55)
What is the hybridization for each of the indicated atoms in the following compound?
A) I = sp2; II = sp2; III = sp2. B) I = sp2; II = sp3; III = sp3. C) I = sp; II = sp2; III = sp3. D) I = sp2; II = sp2; III = sp3.
56)
What is the hybridization of the carbon atom in the methyl cation, (CH3+)? A) sp3 B) sp2 C) sp D) p
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57)
What is the hybridization of the nitrogen atom in the ammonium cation, NH4+? A) sp3 B) sp2 C) sp D) p
58) Which atomic orbitals overlap to form the C-H s bonding molecular orbitals of ethane, CH3CH3? A) Csp2+ H1s B) Csp3+ H1s C) C2p + H1s D) Csp + H1s
59) Which atomic orbitals overlap to form the C-H s bonding molecular orbitals of ethylene, H2C=CH2? A) C2p + H1s B) Csp + H1s C) Csp3+ H1s D) Csp2+ H1s
60) Which atomic orbitals overlap to form the carbon-carbon s and p bonding molecular orbitals of ethylene, H2C=CH2? A) Csp3+ Csp3, and C2p + C2p B) Csp3+ Csp3, and Csp2+ Csp2 C) Csp2+ Csp2, and C2p + C2p D) Csp2+ Csp2, and Csp2+ Csp2
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61) Which atomic orbitals overlap to form the C-H s bonding molecular orbitals of acetylene, C2H2? A) Csp + H1s B) C2p +H1s C) Csp3+ H1s D) Csp2+ H1s
62) Which atomic orbitals overlap to form the carbon-carbon s bonding molecular orbital of acetylene, C2H2? A) Csp2+ Csp2 B) Csp + Csp C) Csp3+ Csp3 D) C2p + C2p
63) When forming molecular orbitals from atomic orbitals, what is the order of increasing CH bond strength for the following set?
A) II < I < III B) III < I < II C) III < II < I D) I < II < III
64) What is the order of decreasing bond length for a C-C bond composed of the following molecular orbitals?
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A) I > III > II B) I > II > III C) III > II > I D) II > III > I
65)
Which of the following statements about electronegativity and the periodic table is true? A) Electronegativity decreases across a row of the periodic table. B) Electronegativity increases down a column of the periodic table. C) Electronegativity increases across a row of the periodic table. D) Electronegativity does not change down a column of the periodic table.
66) Rank the following atoms in order of increasing electronegativity, putting the least electronegative first.
A) I < II < III < IV B) I < IV < II < III C) III < II < IV < I D) I < II < IV < III
67) Rank the following atoms in order of decreasing electronegativity, putting the most electronegative first.
A) I > IV > II > III B) II > III > IV > I C) III > IV > II > I D) III > II > IV > I
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68) Which molecule has the greatest difference in electronegativity (DE) between the two different elements?
A) CO2 B) H2S C) NH3 D) H2O
69)
Which compound contains the most polar bond?
A) I B) II C) III D) IV
70)
Which of the following compounds are non-polar?
A) I, IV B) I, II C) II, III D) II, IV
71)
Which of the following molecules has non-polar covalent bonds?
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A) CO2 B) N2 C) CCl4 D) HF
72)
Which of the following molecules has polar covalent bonds?
A) MgO B) NH3 C) Cl2 D) NaBr
73)
Which of the following covalent bonds has the largest dipole moment?
A) C-H B) C-C C) C-O D) H-F
74)
Which of the following molecules has the smallest dipole moment?
A) CO2 B) HCl C) H2O D) NH3
75)
Which of the following molecules does not have a net dipole moment of zero?
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A) CCl4 B) BF3 C) CO2 D) NH3
76)
Which of the following molecules has a net dipole moment of zero?
A) I B) II C) III D) IV
77) Consider compounds which contain both a heteroatom and a double bond. For which compound is no additional Lewis structure possible?
A) I B) II C) III D) IV
78)
Which of the following molecules has a net dipole moment of zero?
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A) CH4 B) CO 2 C) BH3 D) All of these are correct.
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Answer Key Test name: Chap 01_6e 1) B 2) D 3) A 4) B 5) C 6) D 7) B 8) D 9) B 10) D 11) D 12) B 13) C 14) D 15) C 16) D 17) D 18) B 19) C 20) B 21) B 22) B 23) C 24) B 25) B 26) D Version 1
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27) D 28) B 29) B 30) C 31) B 32) D 33) C 34) A 35) D 36) B 37) A 38) C 39) B 40) B 41) C 42) C 43) A 44) D 45) B 46) A 47) B 48) B 49) D 50) A 51) D 52) A 53) B 54) B 55) D 56) B Version 1
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57) A 58) B 59) D 60) C 61) A 62) B 63) D 64) B 65) C 66) B 67) D 68) D 69) B 70) A 71) B 72) B 73) D 74) A 75) D 76) B 77) C 78) D
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CHAPTER 2 1)
Which of the following statements is a correct definition for a Brønsted-Lowry acid?
A) Proton acceptor B) Electron pair donor C) Electron pair acceptor D) Proton donor
2)
Which of the following statements about a Brønsted-Lowry base is true?
A) The net charge may be zero, positive, or negative. B) All Brønsted-Lowry bases contain a lone pair of electrons or a π bond. C) All Brønsted-Lowry bases contain a proton. D) The net charge may be zero or positive.
3)
Which of the following compounds is both a Brønsted-Lowry acid and base?
A) I, II B) I, III C) II, IV D) I, IV
4)
Which of the following species cannot act as both a Brønsted-Lowry acid and base?
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A) HCO 3 − B) HSO 4 − C) HO − D) H 2PO 4 −
5)
Which of the following species is not a Brønsted-Lowry base?
A) BF 3 B) NH 3 C) H 2O D) PO 4 3−
6)
Which of the following statements about Brønsted-Lowry acids and bases is true?
A) Loss of a proton from a base forms its conjugate acid. B) Loss of a proton from an acid forms its conjugate base. C) Gain of a proton by an acid forms its conjugate base. D) Brønsted-Lowry acid-base reactions always result in the transfer of a proton from a base to an acid.
7)
Which of the following species is the conjugate base of methanol, CH 3OH? A) CH 3OH 2 + B) CH 3O − C) CH 3 − D) CH 4
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8)
Which of the following species is the conjugate base of the hydronium ion, H 3O
+
A) H 3O B) H 2O − C) H 2O D) HO −
9)
Which of the following species is the conjugate acid of ammonia, NH 3?
A) H 4N B) H 3N + C) H 2N − D) H 4N +
10)
Which is the conjugate acid in the following reaction?
A) I B) II C) III D) IV
11)
Which is the conjugate base in the following reaction?
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?
A) I B) II C) III D) IV
12)
Which is the conjugate acid in the following reaction?
A) I B) II C) III D) IV
13)
Which is the conjugate base in the following reaction?
A) I B) II C) III D) IV
14)
Which of the following statements about acid strength is true?
A) The stronger the acid, the further the equilibrium lies to the left. B) The stronger the acid, the smaller the K a. C) The stronger the acid, the larger the pK a. D) The stronger the acid, the smaller the pK a.
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15)
Which of the following compounds is the strongest acid?
A) I B) II C) III D) IV
16)
Which of the following compounds is the strongest acid?
A) CH 3OH B) BrCH 2OH C) CH 3NH 2 D) CH 3Cl
17)
Which of the following compounds is the weakest acid?
A) HF B) HCl C) HBr D) HI
18)
Which of the following compounds is the weakest acid?
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A) H 2S B) PH 3 C) HCl D) SiH 4
19)
Which of the following species is the strongest base? A) HO − B) H 2N − C) CH 3COO − D) Cl −
20) Which of the following ranks the compounds in order of increasing basicity, putting the least basic first?
A) CH 3NH 2 < CH 3OH < CH 4 B) CH 3OH < CH 3NH 2 < CH 4 C) CH 4 < CH 3NH 2 < CH 3OH D) CH 4 < CH 3OH < CH 3NH 2
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21) Consider the following molecule with protons labeled, I-III. Rank these protons in order of decreasing acidity, putting the most acidic first.
A) I > II > III B) I > III > II C) III > II > I D) III > I > II
22) first.
Rank the following compounds in order of increasing acidity, putting the least acidic
A) III < I < IV < II B) III < IV < I < II C) II < I < IV < III D) III < I < II < IV
23) first.
Rank the following compounds in order of increasing acidity, putting the least acidic
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A) I < IV < III < II B) I < III < IV < II C) II < III < IV < I D) II < IV < III < I
24) first.
Rank the following compounds in order of decreasing acidity, putting the most acidic
A) IV > II > III > I B) III > II > IV > I C) I > II > IV > III D) III > IV > II > I
25) first.
Rank the following compounds in order of decreasing acidity, putting the most acidic
A) IV > II > III > I B) IV > III > II > I C) III > IV > II > I D) III > IV > I > II
26) first.
Rank the following conjugate bases in order of increasing basicity, putting the least basic
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A) II < I < III B) II < III < I C) I < II < III D) I < III < II
27) first.
Rank the following conjugate bases in order of decreasing basicity, putting the most basic
A) II > I > III B) I > II > III C) III > I > II D) III > II > I
28)
Which of the following is the strongest base?
A) CH 3COCH 3 B) CH 3COOH C) NH 3 D) H 2O
What is the direction of equilibrium when acetylene (C2H2) reacts with H2N−in an acid29) base reaction?
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A) Left B) Right C) Neither D) Cannot be determined
What is the direction of equilibrium when acetylene (C2H2) reacts with ethoxide 30) (CH3CH2O−) in an acid-base reaction?
A) Left B) Right C) Neither D) Cannot be determined
31)
Which of the following statements explains why H 2O is a stronger acid than CH
4?
A) H 2O can form hydrogen bonds while CH 4 cannot. B) H 2O forms a less stable conjugate base, HO −. C) CH 4 forms a more stable conjugate base, CH 3 −. D) H 2O forms a more stable conjugate base, HO −.
32)
Which of the following statements explain why HBr is a stronger acid than HF? A) Br − is more stable than F − because Br − is larger than F −. B) Br − is less stable than F − because Br − is larger than F −. C) Br − is more stable than F − because Br − is less electronegative than F −. D) Br − is less stable than F − because Br − is less electronegative than F −.
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33)
Which of the following compounds has the lowest pK a?
A) H 2O B) H 2S C) NH 3 D) CH 4
34) Which of the following concepts can be used to explain the difference in acidity between acetic acid (CH 3COOH) and ethanol (CH 3CH 2OH)?
A) Hybridization B) Electronegativity C) Resonance D) Size
35) Which of the following concepts can be used to explain the difference in acidity between acetylene (C 2H 2) and ethylene (C 2H 4)?
A) Size B) Resonance C) Inductive effect D) Hybridization
36) Which of the following concepts can be used to explain the difference in acidity between ethanol (CH 3CH 2OH) and 2-fluoroethanol (FCH 2CH 2OH)?
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A) Size B) Inductive effect C) Resonance D) Hybridization
37) first.
Rank the following compounds in order of decreasing acidity, putting the most acidic
A) I > II > III B) III > II > I C) II > III > I D) III > I > II
38)
Which of the following statements about Lewis acids is true?
A) Lewis acids are proton donors. B) Lewis acids are proton acceptors. C) Lewis acids are electron pair donors. D) Lewis acids are electron pair acceptors.
39)
Which of the following statements about Lewis bases is true?
A) Lewis bases are electron pair acceptors. B) Lewis bases are electron pair donors. C) Lewis bases are proton donors. D) Lewis bases are proton acceptors.
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40)
Which of the following is a Lewis acid but not a Brønsted-Lowry acid?
A) CH 3OH B) H 2O C) CH 3COOH D) BF 3
41)
Which of the following species can be both Lewis acid and Lewis base?
A) I, III, IV B) I, II, IV C) II, III, IV D) I, II, III
42) What is the correct classification of the following compound? CH3-O-CH3 A) Brønsted-Lowry acid and Lewis acid B) Brønsted-Lowry base and Lewis base C) Brønsted-Lowry base D) Lewis base
43)
Identify the Lewis acid in the following reaction.
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A) I B) II C) III D) IV
44)
Identify the Lewis base in the following reaction.
A) I B) II C) III D) IV
45)
Which of the following compounds is not a Lewis acid?
A) AlCl 3 B) HCl C) H 2O D) CBr 4
46)
What is the role of methylchloride (CH3Cl) in the following reaction?
A) Lewis acid B) Lewis base C) Brønsted-Lowry acid D) Brønsted-Lowry base
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47)
What is the electrophilic site in the following compounds?
A) I = Carbon; II = carbon; III = boron. B) I = Chlorine; II = carbon; III = boron. C) I = Carbon; II = oxygen; III = boron. D) I = Carbon; II = carbon; III = fluorine.
48)
What is the nucleophilic site in the following compounds?
A) I = Hydrogen; II = π electrons in bond; III = nitrogen. B) I = Oxygen; II = carbon; III = nitrogen. C) I = Hydrogen; II = carbon; III = carbon. D) I = Oxygen; II = π electrons in bond; III = nitrogen.
What is the conjugate base of HSO4−? 49) SO4 2 − H2SO4 SO3 H2O I II III IV A) I B) II C) III D) IV
50)
What are the products of the following proton transfer reaction?
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A) I B) II C) III D) IV
51)
What is the correct rank of the following compounds in order of increasing acidity?
A) I > II > III > IV B) IV > III > II > I C) IV > I > II > III D) III > I > IV > II
52) Consider the following structures I-IV. Which two species represent a conjugate acidbase pair?
A) I and II B) I and III C) I and IV D) II and III
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53) Consider the following structures I-IV. Which two species represent resonance structures?
A) I and II B) I and III C) I and IV D) II and IV
54) Consider the following structures I-IV. Which two species represent constitutional isomers?
A) I and II B) I and III C) I and IV D) II and IV
55)
Identify the acid/conjugate acid (in that order) in the following reaction:
A) I, III B) I, IV C) II, III D) II, IV
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56)
Identify the base/conjugate base (in that order) in the following reaction:
A) I, III B) I, IV C) II, III D) II, IV
57) Which of the following ranks the compounds in order of increasing acidity, putting the least acidic first?
A) CH 4< H 2O < NH 3 B) H 2O < NH 3< CH 4 C) NH 3< CH 4<H 2O D) CH 4< NH 3< H 2O
58)
Which of the following will proceed as written?
A) CH 3ONa + HCl → CH 3OH + NaCl B) CH 3OH + NaCl → NaOEt + HCl C) CH 3OH + H 2O → CH 3O − + H 3O+ D) CH 3OH + NH 3 → CH 3O − + NH 4 ±
59)
Which of the following would have the lowest pKa?
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A) ClCH 2CH 2CH 2CH 2COOH B) CH 3CHClCH 2CH 2COOH C) CH 3CH 2CHClCH 2COOH D) CH 3CH 2CH 2CHClCOOH
60)
Which of the following species is the weakest base? A) HO− B) H2N− C) CH3COO− D) Cl−
61)
Which of the following is an acid commonly used it organic reactions?
A) HCl B) NaOH C) KOH D) NaNH 2
62)
Which of the following is an acid commonly used it organic reactions?
A) HCl B) H 2SO 4 C) KOH D) HNO 3
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Answer Key Test name: Chap 02_6e 1) D 2) B 3) B 4) C 5) A 6) B 7) B 8) C 9) D 10) C 11) D 12) D 13) C 14) D 15) D 16) B 17) A 18) D 19) B 20) D 21) C 22) B 23) A 24) D 25) B 26) A Version 1
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27) C 28) C 29) B 30) A 31) D 32) A 33) B 34) C 35) D 36) B 37) D 38) D 39) B 40) D 41) A 42) B 43) B 44) A 45) D 46) B 47) A 48) D 49) A 50) B 51) C 52) A 53) C 54) B 55) C 56) B Version 1
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57) D 58) A 59) D 60) D 61) A 62) C
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CHAPTER 3 1)
Which of the following lists contains common heteroatoms found in organic molecules?
A) N, O, S, P, Cl B) Na, O, S, P, Cl C) Na, Mg, S, N, Cl D) Na, Mg, O, N, Cl
2)
Why do heteroatoms confer reactivity on a particular molecule?
A) Because they have lone pairs and create electron-rich sites on carbon. B) Because they have lone pairs and create electron-deficient sites on carbon. C) Because they are electronegative and act as electrophiles. D) Because they are electropositive and act as nucleophiles.
3)
Why do π bonds confer reactivity on a particular molecule?
A) Because π bonds are difficult to break in chemical reactions. B) Because π bonds make a molecule an acid. C) Because π bonds are easily broken in chemical reactions. D) Because π bonds make a molecule an electrophile.
4)
Which of the following molecules contain the same functional groups?
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A) I, II, III B) I, II, IV C) II, III, IV D) I, III, IV
5)
Which of the following molecules contain the same functional groups?
A) I, II, IV B) I, II, III C) II, III, IV D) I, III, IV
6)
Which of the following molecules are aliphatic hydrocarbons?
A) I, II, III B) I and III C) II, III, IV D) II and IV
7)
Which of the following molecules are aromatic hydrocarbons?
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A) I B) II C) III D) I and III
8) Which of the following correctly matches the molecules to the names of the functional group? I. II. III. IV.
CH3OH CH3CO2CH3 CH3COCH3 H2CO
Carboxylic acid Ester Ketone Alcohol
A) I and II B) III and IV C) II and III D) II and IV
9) Which of the following correctly matches the molecules to the names of the functional group? I. II. III. IV.
CH3OCH3 CH3CONH2 CH3SH CH3CHO
Ether Amine Thiol Alcohol
A) I and II B) II and III C) III and IV D) I and III
10) Which of the following correctly matches the molecules to the names of the functional group?
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I. II. III. IV.
CH3NH2 CH3SCH3 CH3CONH2 CH3CO2CH3
Amide Sulfide Amine Ester
A) I and II B) II and IV C) III and IV D) II and III
11) Consider the molecule donepezil (used to treat Alzheimer's disease). Which of the following lists the correct functional groups present in donepezil?
A) Amide, aromatic, ether, ketone B) Amide, aromatic, ester, ketone C) Amine, aromatic, ester, ketone D) Amine, aromatic, ether, ketone
12) Consider the molecule atenolol (a β blocker used to treat hypertension). Which of the following lists the correct functional groups present in atenolol?
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A) Primary alcohol, amide, primary amine, aromatic, ether B) Secondary alcohol, amide, secondary amine, aromatic, ether C) Secondary alcohol, amide, primary amine, aromatic, ether D) Secondary alcohol, amide, secondary amine, aromatic, ester
13)
Which of the following structures contains a secondary amine?
A) I B) II C) III D) IV
14)
Which of the following structures contains a primary amine?
A) I B) II C) III D) IV
15)
Which of the following structures contains an amide?
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A) I B) II C) III D) IV
16)
Which of the following structures contains an alkene?
A) I B) II C) III D) IV
17)
Which of the following is a tertiary amine?
A) I B) II C) III D) IV
18)
Which of the following is a secondary alcohol?
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A) I B) II C) III D) IV
19) Which of the following statements best describes the relationship between the surface area of a molecule and the strength of the intermolecular forces?
A) The larger the surface area, the weaker the intermolecular forces. B) The larger the surface area, the stronger the intermolecular forces. C) The smaller the surface area, the stronger the intermolecular forces. D) There is no relationship between surface area and intermolecular forces.
20) Rank the following compounds in order of increasing strength of intermolecular forces, putting the molecule with the weakest intermolecular force first.
A) I < II < III B) II < I < III C) I < III < II D) II < III < I
21)
Which of the following compounds has the lowest boiling point?
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A) I B) II C) III D) IV
22)
Which of the following compounds has the highest boiling point?
A) I B) II C) III D) IV
23)
Which of the following compounds has the highest boiling point?
A) I B) II C) III D) IV
24)
Which of the following compounds has the highest boiling point?
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A) I B) II C) III D) IV
25)
Which of the following compounds has the highest boiling point?
A) I B) II C) III D) IV
26) Rank the following compounds in order of decreasing boiling point, putting the compound with the highest boiling point first.
A) I > II > III > IV B) III > IV > II > I C) III > II > IV > I D) I > IV > II > III
27) Which of the following compounds can form intermolecular hydrogen bonds with a molecule similar to itself?
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A) I B) II C) III D) IV
28)
What is the strongest intermolecular force present in 1-propanol?
A) Ion-ion B) Hydrogen bonding C) Dipole-dipole D) Induced dipole-induced dipole
29)
What intermolecular force is generally considered the strongest?
A) Hydrogen bonding B) London dispersion forces C) Covalent bonds D) Dipole-dipole
30)
What intermolecular force is generally considered the weakest?
A) Hydrogen bonding B) London dispersion forces C) Dipole-dipole D) Ion-ion
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31) Rank the following compounds in order of increasing melting point, putting the compound with the least melting point first.
A) II < I < III B) I < III < II C) I < II < III D) III < II < I
32) Rank the following compounds in order of decreasing melting point, putting the compound with the highest melting point first.
A) I > II > III B) II > III > I C) III > II > I D) III > I > II
33) Which of the following intermolecular forces would not form between similar molecules of the structure below?
A) London dispersion forces B) Ion-ion C) Hydrogen bonding D) Dipole-dipole
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34)
Which of the following alkanes is expected to have the highest melting point?
A) I B) II C) III D) IV
35)
Which of the following compounds is expected to be the least soluble in H2O?
A) I B) II C) III D) IV
36)
Which of the following compounds is expected to be the most soluble in H2O?
A) I B) II C) III D) IV
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37) Which of the following compounds would be expected to be more soluble in hexane (C6H14)?
A) I B) II C) III D) IV
38) true?
Which of the following statements about the solubility of organic compounds in H 2O is
A) The non-polar part of a molecule that is not attracted to water is said to be hydrophilic. B) The non-polar part of a molecule that is not attracted to water is said to be hydrophobic. C) The polar part of a molecule that can that can bond hydrogen to water is said to be hydrophobic. D) For an organic compound with one functional group that contains an O or N atom, the compound is water soluble only if it has 35 carbons.
39)
Which of the following compounds is expected to be H2O soluble?
A) I B) II C) III D) IV
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40)
What molecular features are required for soap to properly dissolve grease and oil?
A) The molecule must be large. B) The molecule must contain a polar head. C) The molecule must contain a non-polar tail. D) The molecule must contain both a polar head and a non-polar tail.
41)
Which of the following statements about vitamin A, drawn below, is true?
A) Vitamin A is soluble in H 2O. B) Vitamin A is insoluble in organic solvents. C) Vitamin A contains an aromatic ring. D) Vitamin A is insoluble in H 2O.
42)
Which of the following statements about vitamin C, drawn below, is true?
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A) Vitamin C is insoluble in H 2O. B) Vitamin C is soluble in H 2O. C) Vitamin C is an aliphatic hydrocarbon. D) Vitamin C contains a ketone functional group.
43)
Which of the following could most likely serve as an ionophore?
A) I B) II C) III D) IV
44)
The indicated carbon atom is:
A) Electrophilic because it is electron-deficient. B) Nucleophilic because it is electron-deficient. C) Electrophilic because it is electron-rich. D) Nucleophilic because it is electron-rich.
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45)
The indicated bond is:
A) Nucleophilic because it is electron-deficient. B) Electrophilic because it is electron-deficient. C) Nucleophilic because it is electron-rich. D) Electrophilic because it is electron-rich.
46)
The indicated bond is:
A) Nucleophilic because it is electron-deficient. B) Electrophilic because it is electron-rich. C) Nucleophilic because it is electron-rich. D) Electrophilic because it is electron-deficient.
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47) Which of the following lists the correct functional groups found in aspartame, the artificial sweetener?
A) Amine, aromatic, carboxylic acid, ether, ketone B) Amine, amide, aromatic, carboxylic acid, ester C) Amide, alcohol, aromatic, carboxylic acid, ether D) Amine, aromatic, carboxylic acid, ester, nitrile
48) Rank the following compounds in order of decreasing boiling point, putting the compound with the highest boiling point first.
A) I > III > IV > II B) IV > II > I > III C) IV > I > II > III D) I > IV > II > III
49)
Rank the following compounds in order of increasing strength of intermolecular forces.
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A) I > III > IV > II B) IV > II > I > III C) IV > I > III > II D) I > IV > II > III
50)
Which of the following molecules can bond hydrogen to another molecule of itself?
A) I B) II C) III D) IV
51)
Which C=O functional group is present in the following molecule?
A) Carboxylic Acid B) Ester C) Ketone D) Aldehyde
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52)
Which C=O functional group is present in the following molecule?
A) Carboxylic acid B) Ester C) Ketone D) Aldehyde
53)
Which C=O functional group is present in the following molecule?
A) Carboxylic acid B) Ester C) Ketone D) Aldehyde
54)
List the intermolecular forces present in the following molecule:
A) Van der Waals B) Dipole-dipole interactions C) Hydrogen bonding D) More than one of these answer choices is correct.
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55)
List the intermolecular forces present in the following molecule:
A) Van der Waals B) Dipole-dipole interactions C) Hydrogen bonding D) More than one of these answer choices is correct.
56)
List the intermolecular forces present in the following molecule:
A) Van der Waals B) Dipole-dipole interactions C) Hydrogen bonding D) More than one of these answer choices is correct.
57)
Which of the following is one of the families of biomolecules?
A) Amino acids B) Lipids C) Simple sugars D) All of these are correct.
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58)
How many naturally occurring amino acids are there?
A) 16 B) 18 C) 20 D) 21
59)
Which of the following is also known as a simple sugar?
A) Monosaccharide B) Disaccharide C) Polysaccharide D) Nucleic Acid
60)
How many fatty acids are there in a triacylglycerol?
A) 1 B) 2 C) 3 D) 4
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Answer Key Test name: Chap 03_6e 1) A 2) B 3) C 4) D 5) A 6) B 7) D 8) C 9) D 10) B 11) D 12) B 13) C 14) A 15) D 16) B 17) B 18) D 19) B 20) C 21) D 22) D 23) B 24) D 25) A 26) C Version 1
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27) D 28) B 29) A 30) B 31) C 32) D 33) B 34) D 35) A 36) B 37) A 38) B 39) B 40) D 41) D 42) B 43) D 44) A 45) C 46) D 47) B 48) D 49) C 50) C 51) A 52) C 53) B 54) D 55) D 56) A Version 1
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57) A 58) C 59) A 60) C
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CHAPTER 4 1)
Which of the following statements about alkanes is not true?
A) Alkanes are aliphatic hydrocarbons. B) Alkanes contain only C-C and C-H σ bonds. C) Alkanes are acyclic or cyclic. D) Acyclic alkanes have two fewer H atoms than cyclic alkanes with the same number of carbons.
2)
Which of the following statements about alkanes is true?
A) Alkanes are aliphatic hydrocarbons having only C-C and C-H π bonds. B) Cyclic alkanes have two fewer H atoms than acyclic alkanes with the same number of carbons. C) Acyclic alkanes contain carbons joined in one or more rings. D) Acyclic alkanes have the general molecular formula C nH 2n.
3)
What is the molecular formula of an alkane that has twenty-three carbon atoms?
A) C 23H 46 B) C 23H 48 C) C 23H 50 D) C 23H 44
4)
What is the molecular formula of a cycloalkane that has six carbon atoms?
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A) C 6H 14 B) C 6H 10 C) C 6H 12 D) C 6H 16
5)
What is the approximate C−C−C bond angle in propane?
A) 90° B) 109.5° C) 120° D) 180°
6)
What is the hybridization of a carbon atom in an alkane? A) sp3 B) sp2 C) sp D) p
7)
How many constitutional isomers are there with the molecular formula C
5H
12?
6H
14?
A) 2 B) 3 C) 4 D) 5
8)
How many constitutional isomers are there with the molecular formula C
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A) 2 B) 3 C) 4 D) 5
9)
Which of the following is not another representation for 2-methylbutane?
A) I B) II C) III D) IV
10) Which of the following compounds has primary, secondary, tertiary, and quaternary carbon atoms?
A) Pentane B) 2-Methylpentane C) 2,2-Dimethylpentane D) 2,2,3-Trimethylpentane
11)
Which of the following compounds has only primary and secondary carbon atoms?
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A) Pentane B) 2-Methylpentane C) 2,2-Dimethylpentane D) 2,3,3-Trimethylpentane
12) Which of the following compounds has only primary, secondary, and tertiary carbon atoms?
A) Pentane B) 2-Methylpentane C) 2,2-Dimethylpentane D) 2,2,3-Trimethylpentane
13) Which of the following compounds has only primary, secondary, and quaternary carbon atoms?
A) Pentane B) 2-Methylpentane C) 2,2-Dimethylpentane D) 2,2,3-Trimethylpentane
14)
Which of the following compounds has primary, secondary, and tertiary hydrogen atoms?
A) Pentane B) Hexane C) 2-Methylpentane D) 2,2-Dimethylpentane
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15)
Which of the following compounds has only primary and secondary hydrogen atoms?
A) 2-Methylpentane B) 2,2,3-Trimethylpentane C) 3-Methylpentane D) 2,2-Dimethylpentane
16) How many cycloalkane constitutional isomers (excluding stereoisomers) are there with molecular formula C 5H 10?
A) 2 B) 3 C) 4 D) 5
17)
What is the parent chain for the following compound?
A) Hexane B) Heptane C) Octane D) Nonane
18)
What is the parent chain for the following compound?
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A) Heptane B) Octane C) Nonane D) Decane
19) What is the name of the alkyl group that contains two carbons in a straight chain and onecarbon branch?
A) Ethyl B) Propyl C) Isopropyl D) None of these
20)
What is the IUPAC name for the following compound?
A) 4-Ethyl-5-methyloctane B) 4-Methyl-5-ethyloctane C) 4-Methyl-3-propylheptane D) 4-Methyl-5-propyloctane
21)
What is the IUPAC name for the following compound?
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A) 3,5-Diethyl-6-methylheptane B) 3,5-Diethyl-2-methylheptane C) 3-Ethyl-5-isopropylheptane D) 5-Ethyl-3-isopropylheptane
22)
What is the IUPAC name for the following compound?
A) 2,3-Dimethyl-4- sec-butylheptane B) 4- sec-Butyl-2,3-dimethylheptane C) 3,5,6-Trimethyl-4-propylheptane D) 2,3,5-Trimethyl-4-propylheptane
23)
What is the IUPAC name for the following compound?
A) 5-Ethyl-3,6-dimethylheptane B) 3-Ethyl-2,5-dimethylheptane C) 3-Ethyl-2,5-dimethyloctane D) 5-Ethyl-3,6-dimethyloctane
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24)
What is the IUPAC name for the following compound?
A) 2,3,5-Trimethylhexane B) 2,4,5-Triethylhexane C) 2,4-Diethyl-5-methylheptane D) 4-Ethyl-3,6-dimethyloctane
25)
What is the IUPAC name for the following compound?
A) 3-Ethyl-2,7-dimethyl-5- sec-butyldecane B) 5- sec-Butyl-3-ethyl-2,7-dimethyldecane C) 2,7-Dimethyl-3-ethyl-5- sec-butyldecane D) 3-Ethyl-2,7-dimethyl-5-isobutyldecane
26)
What is the IUPAC name for the following compound?
A) 3-Ethyl-1-methylcyclohexane B) 1-Ethyl-3-methylcyclohexane C) 1-Ethyl-3-methylhexane D) 3-Ethyl-1-methylhexane
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27)
What is the IUPAC name for the following compound?
A) 1- sec-Butyl-4-isopropyl-2-methylcyclohexane B) 1-Isopropyl-3-methyl-4- sec-butylcyclohexane C) 4-Isopropyl-2-methyl-1- sec-butylcyclohexane D) 1- sec-Butyl-3-isopropyl-2-methylcyclohexane
28)
What is the IUPAC name for the following compound?
A) 1,4-Dimethylcyclohexane B) 1,3-Dimethylcyclohexane C) 1,3-Dimethylcyclopentane D) 1,4-Dimethylcyclopentane
29)
What is the IUPAC name for the following compound?
A) 1-Butylcyclohexane B) Cyclohexanebutane C) 1-Cyclohexylbutane D) Butylcyclohexane
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30)
What is the IUPAC name for the following compound?
A) Hexylcyclopentane B) 1-Hexylcyclopentane C) 1-Cyclopentylhexane D) 1-Cyclopentylheptane
31)
What is the IUPAC name for the following compound?
A) 1-Butyl-3-methylcyclohexane B) 1- sec-Butyl-3-methylcyclohexane C) 1-Methyl-3- sec-butylcyclohexane D) 1- sec-Butyl-3-methylhexane
32)
What is the common name of the following alkyl group?
A) Isobutyl B) sec-Butyl C) Isopropyl D) tert-Butyl
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33)
What is the common name of the following alkyl group?
A) Isopropyl B) Isobutyl C) sec-Butyl D) tert-Butyl
34) Rank the following alkanes in order of decreasing boiling point, putting the alkane with the highest boiling point first.
A) I > II > III B) I > III > II C) II > III > I D) III > II > I
35) Rank the following alkanes in order of increasing melting point, putting the alkane with the lowest melting point first.
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A) I < III < II B) I < II < III C) II < III < I D) III < II < I
36)
Which of the following statements about the conformations of acyclic alkanes is true?
A) Conformations are the same arrangements of atoms that cannot be interconverted by rotation about single bonds. B) In the eclipsed conformation, the C-H bonds on one carbon bisect the H-C-H bond angle on the adjacent carbon. C) In the staggered conformation, the C-H bonds on one carbon are directly aligned with the C-H bonds on the adjacent carbon. D) Rotating the atoms on one carbon by 60° converts an eclipsed conformation into a staggered conformation, and vice versa.
37) true?
Which of the following statements about the conformations of acyclic alkanes is not
A) The staggered and eclipsed conformations are equally stable. B) The staggered conformations are more stable than the eclipsed conformations. C) An energy minimum and maximum occur every 60° as the conformation changes from staggered to eclipsed. D) Conformations that are neither staggered nor eclipsed are intermediate in energy.
38)
Which of the following statements about the conformations of acyclic alkanes is true?
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A) A staggered conformation with two larger groups 180° from each other is called gauche. B) Staggered conformations are at energy maxima and eclipsed conformations are energy minima. C) A staggered conformation with two larger groups 60° from each other is called anti. D) Gauche conformations are generally higher in energy than anti conformations.
39)
Which of the following is not a conformer of butane?
A) I B) II C) III D) IV
40)
Which of the following are gauche conformers of butane?
A) I and II B) I and III C) II and IV D) II and III
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41)
Which of the following are anti conformers of butane?
A) I and II B) II and III C) I and IV D) II and IV
42)
Which of the following conformers of butane has the highest energy?
A) I B) II C) III D) IV
43) first.
Rank the conformers of butane in order of decreasing stability, putting the most stable
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A) IV > I > II > III B) IV > I > III > II C) II > III > I > IV D) I > IV > II > III
44)
Which of the following is the highest energy conformer of 2,3-dimethylbutane?
A) I B) II C) III D) IV
45)
Which of the following is the lowest energy conformer of 2,3-dimethybutane?
A) I B) II C) III D) IV
46)
Which of the following cycloalkanes has the most angle strain?
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A) Cyclopropane B) Cyclobutane C) Cyclopentane D) Cyclohexane
47)
Which of the following cycloalkanes has the least angle strain?
A) Cyclopropane B) Cyclohexane C) Cyclopentane D) Cycloheptane
48)
Which of the following chair conformations represents trans-1,3-dimethylcyclohexane?
A) I B) II C) III D) IV
49)
Which of the following chair conformations represents trans-1,4-dimethylcyclohexane?
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A) I B) II C) III D) IV
50) Which of the following is the most stable conformation of cis-1-ethyl-3isopropylcyclohexane?
A) I B) II C) III D) IV
51) Which of the following is the most stable conformation of trans-1-isopropyl-3methylcyclohexane?
A) I B) II C) III D) IV
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52)
Select the most stable conformer of cis-1,3-cyclohexanediol.
A) I B) II C) III D) IV
53)
What is the alternate chair conformation of the following compound?
A) I B) II C) III D) IV
54)
Which of the following is the most stable conformation of the following compound?
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A) I B) II C) III D) IV
55) Rank the conformers of 1,2,4-trimethylcyclohexane in order of decreasing stability, putting the most stable first.
A) I > II > III > IV B) III > II > IV > I C) III > IV > II > I D) I > II > IV > III
56)
What are the products of the combustion of alkanes?
A) Carbon and hydrogen B) Carbon and water C) Carbon dioxide and hydrogen D) Carbon dioxide and water
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57)
What is the IUPAC name of the following compound?
A) Pentane B) 2-Methylpentane C) 2-Methyl-3-ethylpentane D) 3-Ethyl-2-methylpentane
58)
Rank the following alkanes in order of increasing boiling point.
A) I > II > III > IV B) IV > III > II > I C) II > III > IV > I D) IV > III > I > II
59)
Which of the following conformation is highest in energy?
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A) I B) II C) III D) IV
60)
What is the relation between the following pair of compounds?
A) Constitutional isomers B) Stereoisomers C) Identical molecules D) Not isomers of each other
61)
Which formula represents a cycloalkane with 6 carbons?
A) C 6H 12 B) C 6H 14 C) C 6H 16 D) C 6H 18
62)
Which formula represents a cycloalkane with 5 carbons?
A) C 5H 8 B) C 5H 10 C) C 5H 12 D) C 5H 14
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63)
Which formula represents a cycloalkane with 6 carbons?
A) Cyclopropane B) Cyclobutane C) Cyclopentane D) Cyclohexane
64)
Which formula represents a cycloalkane with 5 carbons?
A) Cyclopropane B) Cyclobutane C) Cyclopentane D) Cyclohexane
65)
Which of the following represents the oxidation of an organic compound?
A) Adding nitrogen to the molecule B) Adding chlorine to the molecule C) Adding oxygen to the molecule D) All of these are correct.
66)
What is the IUPAC name for the following alkane?
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A) 2,5,6,7-tetramethyloctane B) 2,3,4,7-tetramethyloctane C) 2,5,6,7-tetramethylheptane D) 2,3,4,7-tetramethylheptane
67)
What is the IUPAC name for the following alkane?
A) 3-isopropyl-6-methyloctane B) 3-isopropyl-3.7-methyloctane C) 3-ethyl-2,6-dimethyloctane D) 6-ethyl-3,7-dimethyloctane
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Answer Key Test name: Chap 04_6e 1) D 2) B 3) B 4) C 5) B 6) A 7) B 8) D 9) D 10) D 11) A 12) B 13) C 14) C 15) D 16) D 17) B 18) C 19) C 20) A 21) B 22) D 23) B 24) D 25) B 26) B Version 1
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27) A 28) C 29) D 30) C 31) B 32) B 33) A 34) B 35) A 36) D 37) A 38) D 39) D 40) B 41) D 42) B 43) B 44) C 45) B 46) A 47) B 48) D 49) A 50) C 51) D 52) B 53) B 54) A 55) C 56) D Version 1
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57) D 58) B 59) D 60) B 61) A 62) B 63) B 64) C 65) D 66) B 67) C
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CHAPTER 5 1)
What is the main carbohydrate in the seeds and roots of plants?
A) Starch B) Glucose C) Cellulose D) Glycogen
2)
Which of the following statements about starch and cellulose is true?
A) Starch and cellulose are not stereoisomers. B) In cellulose, the O atom joins two rings using one equatorial and one axial bond. C) In starch, the O atom joins two rings using two equatorial bonds. D) In cellulose, the O atom joins two rings using two equatorial bonds.
3)
Which of the following statements about constitutional isomers is not true?
A) They have different IUPAC names. B) They always have the same functional groups. C) They have different physical properties. D) They have different chemical properties.
4)
Which of the following statements about stereoisomers is not true?
A) Stereoisomers have identical IUPAC names except for a prefix like cis or trans. B) Stereoisomers differ in configuration. C) Stereoisomers always have the same functional groups. D) Stereoisomers differ only in their structural formula.
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5)
What is the relationship between the following two compounds?
A) Stereoisomers B) Constitutional isomers C) Identical D) Not isomers, different compounds
6)
What is the relationship between the following two compounds?
A) Constitutional isomers B) Identical C) Stereoisomers D) Not isomers, different compounds
7)
What is the relationship between the following two compounds?
A) Constitutional isomers B) Identical C) Stereoisomers D) Not isomers, different compounds
8)
What is the relationship between the following two compounds?
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A) Constitutional isomers B) Stereoisomers C) Identical D) Not isomers, different compounds
9)
Which of the following is the definition of chirality?
A) The existence of a molecule with a mirror image. B) The existence of a molecule with a carbon atom that has four different substituents. C) The existence of a molecule that is superimposable on its mirror image. D) The existence of a molecule that is not superimposable on its mirror image.
10)
Which of the following statements is not true?
A) A molecule that is superimposable on its mirror image is said to achiral. B) A molecule that is not superimposable on its mirror image is said to be chiral. C) A molecule that is superimposable on its mirror image is said to be chiral. D) A carbon atom bonded to four different groups is a stereogenic center.
11)
Which of the following statements is true?
A) Enantiomers are mirror images that are not superimposable. B) A molecule that is superimposable on its mirror image is chiral. C) A chiral molecule usually contains a plane of symmetry. D) An achiral molecule does not contain a plane of symmetry.
12)
Which of the following statements is true?
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A) Achiral molecules usually contain a plane of symmetry. B) With one tetrahedral stereogenic center, a molecule may or may not be chiral. C) With two or more stereogenic centers, a molecule is always chiral. D) Chiral molecules usually contain a plane of symmetry.
13)
Which of the following is the correct definition for a pair of enantiomers?
A) A pair of stereoisomers that have a plane of symmetry. B) A pair of stereoisomers that are not mirror images of each other. C) A pair of stereoisomers that are not superimposable mirror images of each other. D) A pair of stereoisomers that are superimposable mirror images of each other.
14)
Which of the following molecules has a plane of symmetry?
A) I B) II C) III D) IV
15)
Which of the following statements is true?
A) The presence of a plane of symmetry makes a molecule chiral. B) An achiral molecule must have one or more stereogenic centers. C) All molecules that have stereogenic centers are chiral. D) Stereoisomers that are not superimposable on their mirror image are enantiomers.
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16) Which of the following molecules are chiral? I. cis-1,3-Dibromocyclohexane II.1-Bromo-1-methylcyclohexane III. trans-1-Bromo-3-methylcyclohexane IV. cis-1-Bromo-3-methylcyclohexane A) I, II B) II, III C) I, IV D) III, IV
17) Which of the following molecules are chiral? I. 2-Chlorobutane II. 3-Bromopentane III. 1-Bromo-2-methylpropene IV. 2-Bromo-3-methylbutane A) I, II B) I, IV C) II, III D) III, IV
18)
Which of the following molecules are achiral?
A) II, III B) I, II C) I, IV D) III, IV
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19)
Which of the following molecules are chiral?
A) II, III B) I, II C) I, IV D) III, IV
20) How many stereogenic centers are present in ephedrine, a bronchodilator and decongestant?
A) 0 B) 1 C) 2 D) 3
21)
How many stereogenic centers are present in the following compound?
A) 0 B) 1 C) 2 D) 3
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22)
How many stereogenic centers are present in fructose, a simple sugar?
A) 1 B) 2 C) 3 D) 4
23)
How many stereogenic centers are present in the following compound?
A) 1 B) 2 C) 3 D) 4
24)
How many stereogenic centers are present in menthol?
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A) 1 B) 2 C) 3 D) 4
25)
How many stereogenic centers are present in the following compound?
A) 1 B) 2 C) 3 D) 4
26)
How many stereogenic centers are present in the following molecule?
A) 1 B) 2 C) 4 D) 5
How many stereoisomers are possible for a molecule with formula CH 3CHB 27) rCH(OH)CH 3?
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A) 1 B) 2 C) 3 D) 4
28) How many stereoisomers can be drawn for a molecule with formula CH 3CH(OH)CH(OH)CH 3?
A) 1 B) 2 C) 3 D) 4
29)
What is the total number of possible stereoisomers for the following molecule?
A) 2 B) 4 C) 6 D) 8
30) How many isomers can be drawn (constitutional and stereoisomers) for dimethycyclopropane?
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A) 2 B) 3 C) 4 D) 6
31)
How many chiral stereoisomers can be drawn for dimethycyclopropane?
A) 1 B) 2 C) 3 D) 4
32) How many stereogenic centers are present in gabapentin, used clinically to treat seizures and certain types of chronic pain?
A) 0 B) 1 C) 2 D) 3
33)
How many stereogenic centers are present in the following compound?
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A) 0 B) 1 C) 2 D) 3
34) Rank the following groups in order of decreasing priority according to the Cahn-IngoldPrelog system.
A) III > I > II > IV B) I > II > IV > III C) III > II > IV > I D) III > IV > II > I
35) Rank the following groups in order of decreasing priority according to the Cahn-IngoldPrelog system.
A) I > II > III > IV B) II > I > IV > III C) II > I > III > IV D) I > II > IV > III
36) Rank the following groups in order of decreasing priority according to the Cahn-IngoldPrelog system.
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A) I > III > IV > II B) III > IV > I > II C) IV > III > I > II D) IV > I > III > II
37) Rank the following groups in order of decreasing priority according to the Cahn-IngoldPrelog system.
A) I > II > IV > III B) IV > II > I > III C) IV > I > II > III D) III > II > I> IV
38) Rank the following groups in order of decreasing priority according to the Cahn-IngoldPrelog system.
A) IV > III > I > II B) IV > I > III > II C) III > IV > I > II D) II > I > III > IV
39)
Which of the following compounds has a plane of symmetry?
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A) I and II B) II and III C) II, III, and IV D) III and IV
40)
Which of the following structures has a different configuration from the other three?
A) I B) II C) III D) IV
41)
Which of the following structures has a different configuration from the other three?
A) I B) II C) III D) IV
42)
Which of the following structures has the S configuration?
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A) Only I B) Only II C) Only I and II D) I, II, and III
43)
Which of the following structures has the R configuration?
A) Only I B) Only II C) Only I and II D) I, II, and III
44)
Which of the following structures has the R configuration?
A) Only I B) Only II C) Only I and II D) I, II, and III
45)
Which of the following is the definition for a pair of diastereomers?
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A) A pair of stereoisomers with stereogenic centers but is not chiral. B) A pair of stereoisomers that are superimposable mirror images of each other. C) A pair of stereoisomers that are not superimposable mirror images of each other. D) A pair of stereoisomers that are not mirror images of each other.
46)
What is the relationship between the following compounds?
A) Constitutional isomers B) Diastereomers C) Enantiomers D) Identical
47)
What is the relationship between the following compounds?
A) Constitutional isomers B) Diastereomers C) Enantiomers D) Identical
48)
What is the relationship between the following compounds?
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A) Constitutional isomers B) Diastereomers C) Enantiomers D) Identical
49)
What is the relationship between the following compounds?
A) Constitutional isomers B) Diastereomers C) Enantiomers D) Identical
50)
What is the relationship between the following compounds?
A) Constitutional isomers B) Diastereomers C) Enantiomers D) Identical
51)
What is the relationship between the following compounds?
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A) Constitutional isomers B) Diastereomers C) Enantiomers D) Identical
52)
What is the relationship between the following compounds?
A) Constitutional isomers B) Diastereomers C) Enantiomers D) Identical
53)
What is the relationship between the following compounds?
A) Constitutional isomers B) Diastereomers C) Enantiomers D) Identical
54)
Which of the following statements about meso compounds is not true?
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A) A meso compound generally has a plane of symmetry. B) A meso compound and its mirror image are identical. C) A meso compound is achiral. D) A meso compound is chiral.
55)
Which of the following compounds is a meso compound?
A) (2R, 3S)-dichlorobutane B) (2R, 3R)-dichlorobutane C) (2R, 3S)-3-chloro-2-butanol D) (2R, 3R)-3-chloro-2-butanol
56)
Which of the following compounds are meso?
A) Only I B) Only II C) I and II D) Neither
57)
Which of the following compounds can have a meso stereoisomer?
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A) I B) II C) III D) IV
58)
How many stereoisomers of 1,3-dibromocyclopentane exist?
A) 1 B) 2 C) 3 D) 4
59)
Which of the following compounds does not have a plane of symmetry?
A) Only I and II B) Only II C) Only III and IV D) Only I, II, and IV
60)
Which of the following cyclic molecules is a meso compound?
A) I B) II C) III D) IV
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61)
How many isomers (constitutional and stereoisomers) exist for dimethylcyclobutane?
A) 3 B) 4 C) 5 D) 6
62) A natural product was isolated in the laboratory, and its observed rotation was +10° when measured in a 1 dm sample tube containing 1.0 g of compound in 10 mL of H 2O. What is the specific rotation of this compound?
A) −10° B) +100° C) +10° D) −100°
63) A solution containing 0.08 g/mL of a pure R enantiomer in a 1 dm polarimeter rotates plane polarized light by +4°. What is the specific rotation of the S enantiomer?
A) +50° B) −40° C) +40° D) −50°
64) How much of the R enantiomer is present in 10 g of a mixture that has an enantiomeric excess of 30% of the S isomer?
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A) 3.0 g B) 3.5 g C) 6.5 g D) 7.0 g
65) A solution containing 0.4 g/mL of a pure S enantiomer is a 1 dm polarimeter rotates plane polarized light by +5.6°. What is the rotation of a solution containing 0.8 g/mL of the S enantiomer in the same polarimeter?
A) +5.6° B) +11.2° C) +2.8° D) +1.4°
66) What is the percent ee of a mixture that has 70% of one enantiomer and 30% of the other?
A) 70 B) 85 C) 40 D) 30
67)
If a mixture has an ee of 90%, what is the percentage of each enantiomer?
A) 65% : 35% B) 55% : 45% C) 80% : 20% D) 95% : 5%
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68) A reaction mixture is three parts of one enantiomer and one part of the other. What is the percent ee of this mixture?
A) 75 B) 40 C) 65 D) 50
69)
Which of the following compounds are chiral?
A) I and II B) II and III C) III and IV D) I and IV
70)
Which of the following compounds is identical to compound A?
A) I and II B) II and III C) I and III D) II
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71)
Give the IUPAC name for the following compound:
A) R-3-methylhexane B) S-3-methylhexane C) R-4-methylhexane D) S-4-methylhexane
72)
Give the IUPAC name for the following compound:
A) R-3-methylhexane B) S-3-methylhexane C) R-4-methylhexane D) S-4-methylhexane
73)
Give the IUPAC name for the following compound:
A) R-2,3-dimethylhexane B) S-2,3-dimethylhexane C) R-4,5-dimethylhexane D) S-4,5-dimethylhexane
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74)
Give the IUPAC name for the following compound:
A) (1R,3R)-1-ethyl-3-methylcyclohexane B) (1R,3S)-1-ethyl-3-methylcyclohexane C) (1S,3R)-1-ethyl-3-methylcyclohexane D) (1S,3S)-1-ethyl-3-methylcyclohexane
75)
Give the IUPAC name for the following compound:
A) (1R,3R)-1-ethyl-3-methylcyclohexane B) (1R,3S)-1-ethyl-3-methylcyclohexane C) (1S,3R)-1-ethyl-3-methylcyclohexane D) (1S,3S)-1-ethyl-3-methylcyclohexane
76)
Give the IUPAC name for the following compound:
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A) (1R,2R)-1,2-dimethylcyclopentane B) (1R,2S)-1,2-dimethylcyclopentane C) (1S,2R)-1,2-dimethylcyclopentane D) (1S,2S)-1,2-dimethylcyclopentane
77)
Which of the following would have the same physical properties?
A) A pair of diastereomers B) A pair of enantiomers C) A pair of constitutional isomers D) Two of these choices are correct.
78)
Give the IUPAC name for the following compound:
A) (3R,4R)-4-chloro-3-hexanol B) (3R,4S)-4-chloro-3-hexanol C) (3S,4R)-4-chloro-3-hexanol D) (3S,4S)-4-chloro-3-hexanol
79)
Give the IUPAC name for the following compound:
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A) (3R,4R)-4-chloro-3-hexanol B) (3R,4S)-4-chloro-3-hexanol C) (3S,4R)-4-chloro-3-hexanol D) (3S,4S)-4-chloro-3-hexanol
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Answer Key Test name: Chap 05_6e 1) A 2) D 3) B 4) D 5) B 6) A 7) B 8) B 9) D 10) C 11) A 12) A 13) C 14) B 15) D 16) D 17) B 18) C 19) A 20) C 21) D 22) C 23) B 24) C 25) B 26) B Version 1
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27) D 28) C 29) D 30) C 31) B 32) A 33) B 34) D 35) B 36) C 37) C 38) A 39) D 40) A 41) D 42) C 43) B 44) C 45) D 46) B 47) C 48) B 49) D 50) B 51) C 52) A 53) B 54) D 55) A 56) B Version 1
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57) D 58) C 59) B 60) B 61) D 62) B 63) D 64) B 65) B 66) C 67) D 68) D 69) B 70) D 71) B 72) A 73) A 74) A 75) D 76) A 77) B 78) C 79) B
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CHAPTER 6 1)
Which of the following statements about substitution reactions is true?
A) Substitution reactions involve π bonds. B) Substitution reactions involve σ bonds. C) One σ bond breaks and another forms at a different carbon atom. D) One π bond breaks and another forms at the same carbon atom.
2)
What kind of reaction does the conversion of A to B represent?
A) Addition reaction B) Substitution reaction C) Elimination reaction D) Acid-base reaction
3)
Which of the following statements about elimination reactions is true?
A) Two σ bonds are broken. B) Two σ bonds are formed. C) Two π bonds are broken. D) Two π bonds are formed.
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4)
What kind of reaction does the conversion of A to B represent?
A) Addition reaction B) Elimination reaction C) Substitution reaction D) Oxidation-reduction reaction
5)
Which of the following statements about addition reactions is true?
A) Two π bonds are formed. B) Two π bonds are broken. C) Two σ bonds are formed. D) One π bond is formed.
6)
What kind of reaction does the conversion of A to B represent?
A) Acid-base reaction B) Elimination reaction C) Substitution reaction D) Addition reaction
7)
Which of the following statements about bond breaking is true?
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A) Homolysis and heterolysis require energy. B) In homolysis, the electrons in the bond are divided unequally. C) In heterolysis, the electrons in the bond are divided equally. D) Homolysis generates charged intermediates.
8)
Which of the following statements about bond breaking is not true?
A) Homolysis generates uncharged reactive intermediates with unpaired electrons. B) Homolysis require energy but heterolysis does not require energy. C) Heterolysis generates charged intermediates. D) Heterolysis involves unequal sharing of bonding electrons by atoms.
9)
Which of the following statements is true?
A) Ionic intermediates are formed in radical reactions. B) Radicals are intermediates in polar reactions. C) Carbocations are electrophiles. D) Radicals are nucleophiles.
10)
Which of the following statements is not true?
A) In polar reactions, a nucleophile reacts with an electrophile. B) Carbocations are electrophiles. C) Carbanions are nucleophiles. D) A half-headed curved arrow shows the movement of an electron pair.
11)
Which of the following statements is not true?
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A) Bond breaking is endothermic. B) The bond dissociation energy for bond breaking is always negative. C) Bond making is exothermic. D) The bond dissociation energy for bond formation is always negative.
12)
Which of the following statements is true?
A) Bond dissociation energies increase down a column of the periodic table. B) When DH° is positive, more energy is released in forming bonds than is needed to break bonds. C) When DH° is negative, more energy is needed to break bonds than is released in forming bonds. D) Bond dissociation energies decrease down a column of the periodic table.
13)
Using the bond dissociation energies given, calculate DH° for the following reaction.
Bond A-B
DH° KJ/mol
(CH3)3C-Cl
331
H-OH
498
(CH3)3C-OH
401
H-Cl
431
A) +3 KJ/mol B) −3 KJ/mol C) −67 KJ/mol D) +70 KJ/mol
14)
Using the bond dissociation energies given, calculate DH° for the following reaction.
Bond A-B
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DH° KJ/mol
4
CH3CH2-Br
285
H-OH
498
CH3CH2-OH
393
H-Br
368
A) +108 KJ/mol B) −130 KJ/mol C) −22 KJ/mol D) +22 KJ/mol
15)
Which of the following statements about the equilibrium constant, Keq, is true?
A) When Keq> 1, the equilibrium favors the reactants. B) When Keq< 1, the equilibrium favors the products. C) The size of Keqtells about the position of equilibrium. D) For a reaction to be useful, the equilibrium must favor the reactants.
16)
Which of the following statements about equilibrium is true?
A) Equilibrium favors the products when the energy of the products is higher than the energy of the reactants. B) Equilibrium favors the reactants when the energy of the product is lower than the energy of the reactants. C) Equilibrium favors the products when they are less stable than the starting material of a reaction. D) Equilibrium favors the products when they are more stable than the starting material of a reaction.
17) Which of the following expressions summarizes the correct relationship between the free energy change, DG°, and the equilibrium constant, Keq?
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A) Keq> 1 when DG° > 0 B) Keq> 1 when DG° < 0 C) Keq < 1 when DG° < 0 D) Keq< 1 when DG° = 0
18)
Which of the Keqcorresponds to the lowest value of DG°?
A) Keq= 10 −3 B) Keq= 10 −2 C) Keq= 10 −1 D) DG° cannot be determined.
19)
Which of the Keqcorresponds to the highest value of DG°?
A) Keq= 10 −1 B) Keq= 10 −2 C) Keq= 10 −3 D) Keq= 10 −5
20)
Which of the Keqcorresponds to the most negative value of DG°?
A) Keq= 1 B) Keq= 10 1 C) Keq= 10 2 D) Keq= 10 3
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21)
Which of the following statements is true?
A) The product is favored in reaction in which DH° is a positive value. B) Entropy decreases when an acyclic compound forms a ring. C) In homolytic bond cleavage, entropy decreases and favors formation of products. D) The starting material is favored in a reaction in which DH° is a negative value.
22)
Which of the following statements is true?
A) The size of the activation energy tells us about the reaction mechanism. B) The size of the activation energy tells us about the reaction rate. C) A slow reaction has low activation energy. D) A fast reaction has high activation energy.
23)
Which of the following statements is not true?
A) Two reactions can have identical values for DH° but very different E avalues. B) The larger the activation energy, the slower the reaction. C) DH° determines the height of the energy barrier. D) The lower the activation energy, the faster the reaction.
24) What is the name given to the reaction species that lies at an energy minimum between steps on a reaction energy diagram?
A) Transition state B) Activation energy C) Reactive intermediate D) Equilibrium product
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25)
Which of the following statements about a two-step reaction mechanism is true?
A) The transition states are located at energy minima. B) Each step is characterized by its own value of DH° and E a. C) The rate-determining step has the lower energy transition state. D) The reactive intermediate is located at an energy maximum.
26)
Which reaction is fast and has Keq= 1?
A) A B) B C) C
27) Which reaction has a positive DG°, assuming that entropy changes are negligible compared to enthalpy changes?
A) A B) B C) C
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28)
Which reaction is slowest?
A) A B) B C) C
29)
In which reaction is Keq> 1?
A) A B) B C) C
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30)
How many transition states are present in the reaction in the energy diagram?
A) 0 B) 1 C) 2 D) 3
31) Which of the following letters represents DH° for the forward reaction in the following energy diagram?
A) A B) B C) C D) D
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32) How many transition states and intermediates would the reaction profile have for the reaction shown below?
A) Three transition states and three intermediates B) Two transition states and two intermediates C) Three transition states and two intermediates D) Two transition states and three intermediates
33)
Which step would most likely have the largest energy of activation?
A) Step one B) Step two C) Step three D) It cannot be determined from the information provided
34) A decrease in which of the following results in an increase in the rate of a chemical reaction?
A) Energy of activation B) Concentration C) Temperature D) Kinetic energy
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35)
Which of the following reaction quantities will have an effect on reaction rate?
A) DG° B) DH° C) K eq D) E a
36)
Which of the following statements is true?
A) Fast reactions have small rate constants. B) Slow reactions have large rate constants. C) A rate equation contains concentration terms for all reactants involved in a one-step mechanism. D) A rate equation contains concentration terms for all the reactants involved in a multistep reaction.
37) The equilibrium constant for the conversion of A to D is predicted to be which of the following?
A) Keq= 1 B) Keq< 1 C) Keq> 1 D) Cannot be determined from the information provided
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38) The DG° (free energy change) for the conversion of A to B is predicted to be which of the following?
A) DG° = 0 B) DG° < 0 C) DG° > 0 D) Cannot be determined from the information provided
39)
What kind of reaction does the conversion of A to D represent?
A) Addition reaction B) Substitution reaction C) Elimination reaction D) Oxidation-reduction reaction
40) If the conversion of A to B is slow and B to C is fast, what is the rate equation for this reaction?
A) Rate = k[(CH 3) 2CHCl][H 2O] B) Rate = k[(CH 3) 2CHCl] C) Rate = k[(CH 3) 2CH] +[H 2O] D) Rate = k[(CH 3) 2CH] +
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41)
Which compound would you predict to be highest in energy?
A) A B) B C) C D) D
42)
Calculate Eafor the conversion of C ® B.
Ea (A ® B) = +10 kcal Ea (B ® C) = +4 kcal DH (A ® B) = +8 kcal DH (B ® C) = −5 kcal A) +3 kcal B) +7 kcal C) +9 kcal D) None of these
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43) The following is an energy diagram for the conversion of A ® B ® C. The energies of activation and DH's for each step are also given. Calculate DH overall as shown on the energy diagram for A ® B ® C.
Ea (A ® B) = +10 kcal Ea (B ® C) = +4 kcal DH (A ® B) = +8 kcal DH (B ® C) = −5 kcal A) +3 kcal B) +7 kcal C) +9 kcal D) None of these
44)
Which of the following statements about a catalyst is true?
A) A catalyst accelerates a reaction by changing the amount of reactant and product at equilibrium. B) A catalyst accelerates a reaction by lowering the energy of activation. C) A catalyst accelerates a reaction by raising the energy of activation. D) A catalyst accelerates a reaction by lowering the equilibrium constant.
45)
Which of the following statements about enzymes is true?
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A) Enzymes increase the activation energy for a reaction. B) Enzymes decrease the equilibrium constant. C) Enzymes shift the equilibrium to favor the product. D) Enzymes lower the transition state for the rate-determining step.
46)
For which of the following reactions is ΔS° a positive value?
A) I B) II C) III D) IV
47) The conversion of acetyl chloride to methyl acetate occurs via the following two-step mechanism:
What is the rate equation for this reaction if the first step is rate determining? A) Rate = k [acetyl chloride] [ −OCH 3] B) Rate = k [acetyl chloride] C) Rate = k [ −OCH 3] D) Rate = k [acetyl chloride] [ −OCH 3] 2
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48) The conversion of acetyl chloride to methyl acetate occurs via the following two-step mechanism:
If the concentration of −OCH3were increased 5 times, what would happen to the rate of the reaction? A) Rate would become one fifth B) Rate would increase 25 times C) Rate would increase 5 times D) Rate would remain unchanged
49) The conversion of acetyl chloride to methyl acetate occurs via the following two-step mechanism:
If the concentrations of both −OCH3and acetyl chloride were increased 2 times, what would happen to the rate of the reaction? A) Rate would become one-fourth B) Rate would increase 4 times C) Rate would increase 16 times D) Rate would increase 2 times
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50) The conversion of acetyl chloride to methyl acetate occurs via the following two-step mechanism:
The conversion of acetyl chloride to methyl acetate would be classified as which of the following? A) Addition B) Elimination C) Substitution D) None of these
51)
The symbol h ν stands for
in a chemical reaction.
A) light B) heat C) reactant D) product
52)
The symbol Δ stands for
in a chemical reaction.
A) light B) heat C) reactant D) product
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53) What type of bond cleavage takes place in/what type of intermediate is produced in the following reaction?
A) Homolysis/Radical B) Homolysis/Carbocation C) Heterolysis/Carbocation D) Heterolysis/Carbanion
54) What type of bond cleavage takes place in/what type of intermediate is produced in the following reaction?
A) Homolysis/Radical B) Homolysis/Carbocation C) Heterolysis/Carbocation D) Heterolysis/Carbanion
55)
What type of reaction does the following conversion represent?
A) Addition reaction B) Elimination reaction C) Substitution reaction D) Oxidation-reduction reaction
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56)
How many steps are there in a concerted mechanism?
A) 1 B) 2 C) 3 D) 4
57) A reaction that results in the formation of a carbocation is most likely to occur from the following:
A) Homolytic bond cleavage B) Heterolytic bond cleavage C) All of the above D) None of these are correct.
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Answer Key Test name: Chap 06_6e 1) B 2) B 3) A 4) B 5) C 6) D 7) A 8) B 9) C 10) D 11) B 12) D 13) B 14) D 15) C 16) D 17) B 18) C 19) D 20) D 21) B 22) B 23) C 24) C 25) B 26) B Version 1
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27) A 28) A 29) C 30) C 31) D 32) C 33) A 34) A 35) D 36) C 37) C 38) C 39) C 40) B 41) B 42) C 43) A 44) B 45) D 46) A 47) A 48) C 49) B 50) C 51) A 52) B 53) C 54) A 55) B 56) A Version 1
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57) B
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CHAPTER 7 1)
Which of the following alkyl halides is a primary alkyl halide?
A) I B) II C) III D) IV
2)
Which of the following alkyl halides is a secondary alkyl halide?
A) I B) II C) III D) IV
3)
Which of the following alkyl halides is a tertiary alkyl halide?
A) I B) II C) III D) IV
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4)
Which of the following alkyl halides is a vinyl alkyl halide?
A) I B) II C) III D) IV
5)
Which of the following structures have the correct common name?
A) I and II B) II and IV C) II and III D) III and IV
6)
Which of the following structures have the correct common name?
A) I and II B) II and III C) I and III D) III and IV
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7)
Which of the following structures have the correct common name?
A) I and II B) II and III C) II and IV D) III and IV
8)
What is the IUPAC name of the following compound?
A) 2-Methyl-4-chloropentane B) 2-Chloro-4-methylpentane C) 2-Chloro-1-isopropylpropane D) 2-Chloro-2-methylpentane
9)
What is the IUPAC name of the following compound?
A) 2-Bromo-5-methyloctane B) 2-Bromo-3-methylheptane C) 2-Bromo-5-methylheptane D) 6-Bromo-3-methylheptane
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10)
What is the IUPAC name of the following compound?
A) 2-Bromo-5,5-dimethylheptane B) 3,3-Dimethyl-6-bromoheptane C) 6-Bromo-3,3-dimethylheptane D) 2-Bromo-5,5-dimethyloctane
11)
What is the IUPAC name of the following compound?
A) 2-Chloro-4-isopropyl-2,6-dimethyloctane B) 2-Chloro-4-isopropyl-2,7-dimethylnonane C) 2,6-Dimethyl-2-chloro-4-isopropyloctane D) 7-Chloro-5-isopropyl-3,7-dimethyloctane
12)
What is the IUPAC name of the following compound?
A) (R)-3-Chloro-6-ethyloctane B) (S)-3-Chloro-6-ethyloctane C) (S)-6-Chloro-3-ethyloctane D) (R)-6-Chloro-3-ethyloctane
13)
What is the IUPAC name of the following compound?
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A) trans-4-Methylcyclohexyl chloride B) trans-p-Chloromethylcyclohexane C) trans-4-Methyl-1-chlorocyclohexane D) trans-1-Chloro-4-methylcyclohexane
14)
What is the IUPAC name of the following compound?
A) (R)-3-Bromo-1-methylcyclohexene B) (S)-3-Bromo-1-methylcyclohexene C) (S)-1-Bromo-3-methyl-2-cyclohexene D) (R)-1-Bromo-3-methyl-2-cyclohexene
15)
What is the IUPAC name of the following compound?
A) (E)-2-Bromo-3,4-dimethyl-2-pentene B) (Z)-1-Bromo-1,2,3-trimethyl-1-butene C) (Z)-2-Bromo-3,4-dimethyl-2-pentene D) (E)-1-Bromo-1,2,3-trimethyl-1-butene
16)
Rank the following halides in order of decreasing polarity, putting the most polar first.
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A) II > IV > I > III B) IV > II > I > III C) I > II > III > IV D) IV > III > II > I
17)
Rank the following molecules in order of increasing polarity, putting the least polar first.
A) IV < III < II < I B) I < IV < III < II C) I < II < III < IV D) II < I < III < IV
18)
Which of the following statements about the reactions of alkyl halides is true?
A) The characteristic reactions of alkyl halides are addition and elimination. B) The characteristic reactions of alkyl halides are addition and substitution. C) The characteristic reactions of alkyl halides are elimination and substitution. D) The characteristic reactions of alkyl halides are oxidation and reduction.
19)
Which of the following statements is true?
A) All good leaving groups are strong bases with weak conjugate acids. B) Left-to-right across a row of the periodic table, leaving group ability decreases. C) Down a column of the periodic table, leaving group ability decreases. D) The conjugate bases of strong acids are good leaving groups.
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20)
Rank the following in order of decreasing leaving group ability, putting the best first.
A) III > II > IV > I B) III > II > I > IV C) IV > I > II > III D) II > III > I > IV
21)
Which of the following statements is not true?
A) All good leaving groups are weak bases with strong conjugate acids. B) Left-to-right across a row of the periodic table, leaving group ability increases. C) Down a column of the periodic table, leaving group ability increases. D) Equilibrium favors the products of the nucleophilic substitution when the leaving group is a stronger base than the nucleophile.
22) Rank the following in order of increasing leaving group ability, putting the worst leaving group first.
A) IV < II < III < I B) III < IV < I < II C) II < IV < I < III D) I < III < II < IV
23)
Which of the following statements is not true?
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A) Sodium ethoxide is a better nucleophile than sodium tert-butoxide. B) Sodium tert-butoxide and sodium ethoxide have similar strengths as bases. C) Sterically hindered bases are also called nonnucleophilic bases. D) Steric hindrance decreases basicity but not nucleophilicity.
24)
Which of the following statements is not true?
A) In polar protic solvents, nucleophilicity decreases down a column of the periodic table as the size of the anion increases. B) Nucleophilicity is affected by the solvent used in a substitution reaction. C) Polar protic solvents are capable of intermolecular hydrogen bonding. D) Polar protic solvents solvate both cations and anions.
25)
Which of the following solvents is not a polar protic solvent?
A) I B) II C) III D) IV
26) Rank the following ions in order of increasing nucleophilicity in polar protic solvents, starting with the least nucleophilic ion.
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A) I < II < III < IV B) IV < III < II < I C) I < II < IV < III D) IV < III < I < II
27)
Which of the following anions is the most nucleophilic in polar aprotic solvents? A) F − B) Cl − C) Br − D) I −
28) first.
Rank the following in order of decreasing nucleophilicity, putting the most nucleophilic
A) II > III > I > IV B) III > II > IV > I C) II > III > IV > I D) III > II > I > IV
29)
Which of the following is the most nucleophilic?
A) CH 4 B) H 2O C) NH 3 D) HF
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30) Rank the following in order of increasing nucleophilicity, putting the least nucleophilic first, when run in a protic solvent.
A) II < IV < I < III B) IV < III < II < I C) III < IV < I < II D) II < I < IV < III
31) The reaction of bromoethane with sodium acetate affords the substitution product methyl acetate. What is the effect of doubling the concentration of sodium acetate 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.
32) The reaction of 1-bromobutane with sodium hydroxide affords the substitution product 1butanol. What would happen to the rate of the reaction if the concentration of both 1bromobutane and sodium hydroxide were doubled?
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.
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The reaction of tert-butyl bromide, (CH 3) 3CBr, with ethanol affords the substitution 33) product tert-butyl ethyl ether, (CH 3) 3COCH 2CH 3, in acidic conditions. What would happen to the rate of the reaction if the concentration of ethanol was doubled?
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.
34)
Which of the following statements about S N2 reactions is true?
A) The rate of reaction is dependent on just the substrate. B) The fastest reaction will occur with a tertiary alkyl halide. C) The mechanism is a two-step process. D) Displacement occurs with inversion of configuration.
Which of the following statements about the S N2 mechanism for nucleophilic 35) substitution reactions is true?
A) Involves one step and occurs with retention of configuration. B) Involves two steps and occurs with inversion of configuration. C) Involves one step and occurs with inversion of configuration. D) Involves one step and occurs with racemization.
36) Which compound is most likely to follow second-order kinetics in a substitution reaction?
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A) CH 3Br B) (CH 3) 3CCH 2Br C) CH 3CH 2Br D) (CH 3) 2CHBr
Which of the following alkyl halides undergoes the fastest S N2 reaction with sodium 37) hydroxide?
A) 1-Iodobutane B) 1-Chlorobutane C) 1-Fluorobutane D) 1-Bromobutane
38) first.
Rank the alkyl halides in order of decreasing SN2 reactivity, putting the most reactive
A) I > II > III B) II > I > III C) III > I > II D) I > III > II
39) Given the following substitution reaction, what would be the effect of changing the solvent from CH3OH to (CH3)2S=O? CH3(CH2)5Br + NaOH ® CH3(CH2)5OH + Br−
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A) The rate would decrease because S N1 reactions are favored by polar protic solvents. B) The rate would increase because S N2 reactions are favored by polar aprotic solvents. C) The rate would increase because S N1 reactions are favored by polar protic solvents. D) The rate would decrease because S N2 reactions are favored by polar aprotic solvents.
40)
Which of the following is a polar aprotic solvent?
A) I B) II C) III D) IV
41)
Which of the following statements about an S N1 reaction mechanism is true?
A) The reaction is fastest with primary alkyl halide. B) The reaction exhibits a one-step mechanism. C) The reaction rate increases as the leaving group ability increases. D) The reaction rate increases as the strength of the nucleophile increases.
42)
Which of the following statements about an S N1 reaction mechanism is true?
A) The reaction involves two steps and occurs fastest with primary alkyl halides. B) The reaction involves one step and occurs fastest with primary alkyl halides. C) The reaction involves one step and occurs fastest with tertiary alkyl halides. D) The reaction involves two steps and occurs fastest with tertiary alkyl halides.
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Which of the following alkyl halides will react fastest with CH3OH in an SN1 43) mechanism?
A) I B) II C) III D) IV
44)
What is the rate-determining step of an S N1 reaction mechanism?
A) Reaction of the nucleophile with the carbocation to form the product. B) Breaking the bond between the carbon and the leaving group to generate a carbocation. C) Attack of the nucleophile on the substrate to generate a pentavalent carbon. D) None of these.
45)
Which of the following rate laws describes the kinetics of an S N1 reaction?
A) Rate = k[alkyl halide] B) Rate = k[alkyl halide][nucleophile] C) Rate = k[nucleophile] D) Rate = k[solvent]
46)
Which of the following carbocations is the most stable?
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A) I B) II C) III D) IV
47) first.
Rank the following carbocations in order of decreasing stability, putting the most stable
A) I > II > III B) II > I > III C) III > I > II D) III > II > I
48)
Which of the following is not a characteristic of an S
N1 reaction?
A) The rate is proportional to the concentration of substrate. B) The reaction is favored in polar protic solvents. C) The rate is independent of the concentration of the nucleophile. D) The electrophilic carbon undergoes inversion of stereochemistry.
49)
Which of the following statements about carbocation stability is true?
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A) Carbocations are stabilized by electron-withdrawing inductive effects only. B) Carbocations are stabilized by electron-withdrawing inductive effects and hyperconjugation. C) Carbocations are stabilized by electron-donating inductive effects only. D) Carbocations are stabilized by electro-donating inductive effects and hyperconjugation.
50)
Which of the following statements about the Hammond postulate is not true?
A) The Hammond postulate provides a quantitative estimate of the energy of a transition state. B) In endothermic reactions, the transition state is closer in energy to the products. C) In exothermic reactions, the transition state is closer in energy to the reactants. D) The Hammond postulate provides a qualitative estimate of the energy of a transition state.
51)
Which of the following statements about the Hammond postulate is true?
A) In an exothermic reaction, lowering the energy of the transition state increases the activation energy, E a. B) In an endothermic reaction, the more stable product forms faster. C) In an endothermic reaction, the less stable product forms faster. D) In an endothermic reaction, the activation energy, E a, is similar for both products.
52) The reaction of what nucleophile and substrate is represented by the following transition state?
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A) Methanol with 2-bromopropane B) Methoxide with 2-bromopropane C) Methoxide with 1-bromopropane D) Methanol with 1-bromopropane
53) For the following reaction, use the identity of the alkyl halide and nucleophile to determine which substitution mechanism occurs. Then determine which solvent affords the faster reaction.
A) S N1, CH 3OH B) S N1, DMSO C) S N2, CH 3OH D) S N2, DMSO
54) For the following reaction, use the identity of the alkyl halide and nucleophile to determine which substitution mechanism occurs. Then determine which solvent affords the faster reaction.
A) S N1, H 2O B) S N1, DMF C) S N2, H 2O D) S N2, DMF
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55) For the following reaction, use the identity of the alkyl halide and nucleophile to determine which substitution mechanism occurs. Then determine which solvent affords the faster reaction.
A) S N1, CH 3OH B) S N1, HMPA C) S N2, CH 3OH D) S N2, HMPA
56)
What is the product of the nucleophilic substitution reaction shown below?
A) Only I B) Only II C) I and II D) None
57)
What is the product of the nucleophilic substitution reaction shown below?
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A) Only I B) Only II C) I and II D) None
58)
What is the product of the nucleophilic substitution reaction shown below?
A) Only I B) Only II C) I and II D) None
59)
What is the product of the nucleophilic substitution reaction shown below?
A) Only I B) Only II C) I and II D) None
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60)
What is the product of the nucleophilic substitution reaction shown below?
A) Only I B) Only II C) I and II D) None
61)
What is the product of the nucleophilic substitution reaction shown below?
A) Only I B) Only II C) I and II D) None
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62)
What is the starting material in the reaction shown below?
A) I B) II C) III D) IV
63)
What is the starting material in the reaction shown below?
A) I B) II C) III D) IV
64) Which of the following statements explain why aryl halides and vinyl halides do not undergo nucleophilic substitution by either the S N1 or S N2 mechanism?
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A) They don't undergo S N1 reactions because a higher percent s-character makes the bond longer and stronger. B) They don't undergo S N2 reactions because a higher percent s-character makes the bond shorter and stronger. C) They don't undergo S N2 reactions because heterolysis of the C-X bond forms a highly unstable carbocation. D) They don't undergo S N1 reactions because the carbocation is highly electronegative.
Which of the following alkyl halides would react the fastest with −OH in SN2 reaction? 65) CH3CH2Br, CH3CH2Cl, CH3CH2F, CH3CH2I A) CH 3CH 2Br B) CH 3CH 2Cl C) CH 3CH 2F D) CH 3CH 2I
66) 3.
Pick the solvent that gives the fastest S N2 reaction between CH
2CH
2Br and
−
OCH
A) CH 2CH 2OH B) CH 3OH C) DMSO D) H 2O
Which of the following alkyl halides would react the fastest with H2O in SN1 reaction? 67) CH3CH2CH2CH2Br, (CH3)2CHCH2Br, CH3CH2CH(CH3)Br, (CH3)3CBr
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A) CH 3CH 2CH 2CH 2Br B) (CH 3) 2CHCH 2Br C) CH 3CH 2CH(CH 3)Br D) (CH 3) 3CBr
68)
Rank the following compounds in order of increasing SN2 reactivity?
A) I > II > III > IV B) IV > I > II > III C) IV > III > II > I D) III > II > I > IV
69)
Rank the following compounds in order of increasing SN1 reactivity?
A) I > II > III > IV B) IV > I > II > III C) IV > III > II > I D) III > II > I > IV
70)
What is the IUPAC name of the following compound?
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A) (3R,4R)-3-chloro-4-methylhexane B) (3R,4S)-3-chloro-4-methylhexane C) (3S,4R)-3-chloro-4-methylhexane D) (3S,4S)-3-chloro-4-methylhexane
71)
What is the IUPAC name of the following compound?
A) (1R,3R)-1-bromo-3-isopropylcyclopentane B) (1R,3S)-1-bromo-3-isopropylcyclopentane C) (1S,3R)-1-bromo-3-isopropylcyclopentane D) (1S,3S)-1-bromo-3-isopropylcyclopentane
72)
Identify the nucleophile and type of substitution reaction in the following:
A) CN −, S n1 B) CN −, S n2 C) Br −, S n1 D) Br −, S n2
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73)
Which alkyl halide will form the most stable carbocation?
A) I B) II C) III D) IV
74)
Which is the best reagent to carry out the following organic synthesis?
A) MeOH B) NaOMe, DMSO C) H 2O D) NaOH, DMSO
75)
Which is the best reagent to carry out the following organic synthesis?
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A) MeOH B) HCl C) H 2O D) H 2S
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Answer Key Test name: Chap 07_6e 1) A 2) C 3) B 4) D 5) C 6) B 7) D 8) B 9) C 10) A 11) A 12) B 13) D 14) B 15) C 16) D 17) B 18) C 19) D 20) B 21) D 22) A 23) D 24) A 25) B 26) A Version 1
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27) A 28) B 29) C 30) C 31) C 32) D 33) A 34) D 35) C 36) A 37) A 38) B 39) B 40) B 41) C 42) D 43) D 44) B 45) A 46) B 47) A 48) D 49) D 50) A 51) B 52) B 53) A 54) D 55) D 56) B Version 1
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57) A 58) C 59) D 60) C 61) B 62) D 63) D 64) B 65) D 66) C 67) D 68) B 69) D 70) C 71) A 72) B 73) A 74) B 75) A
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CHAPTER 8 1)
Which of the following statements about an E1 mechanism is not true?
A) It is a two-step process and has the same first step as an S N1 mechanism. B) It involves the formation of a carbocation from eliminating a good leaving group. C) A common competing reaction is rearrangement of a less stable carbocation to a more stable carbocation. D) The loss of a proton by the carbocation is a slow step.
2)
How many unique β carbons are found in the alkyl halide below?
A) 1 B) 2 C) 3 D) 4
3)
How many unique β carbons are found in the alkyl halide below?
A) 1 B) 2 C) 3 D) 4
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Classify each alkene in vitamin D3 labeled I, II, III by the number of carbon substituents 4) bonded to the double bond.
A) I = Disubstituted; II = trisubstituted; III = trisubstituted B) I = Monosubstituted; II = disubstituted; III = trisubstituted C) I = Disubstituted; II = disubstituted; III = trisubstituted D) I = Disubstituted; II = trisubstituted; III = disubstituted
5)
Which of the following represents the rate law for an E2 reaction?
A) Rate = k[alkyl halide] B) Rate = k[alkyl halide][base] C) Rate = k[alkyl halide] 2 D) Rate = k[base] 2
6)
Which of the following statements about the mechanism of an E2 reaction is true?
A) All bonds are broken and formed in multiple steps. B) The reaction is not concerted. C) Entropy favors the reactants of an E2 reaction. D) Entropy favors the products of an E2 reaction.
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7) How many different E2 products can form from the dehydrohalogenation of 2bromobutane?
A) 1 B) 2 C) 3 D) 4
8) What is the major elimination product in the reaction of 1-bromobutane with potassium tert-butoxide in tert-butanol?
A) cis-2-Butene B) 1-Butene C) trans-2-Butene D) Butanol
9)
What is the major product of the following reaction?
A) I B) II C) III D) IV
10)
Which of the following statements about the mechanism of an E2 reaction is not true?
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A) It is fastest with tertiary halides. B) It exhibits first-order kinetics. C) A better leaving group should make a faster reaction. D) All bonds are broken and formed in a single step.
11)
What is the major elimination product obtained from the following reaction?
A) I B) II C) III D) IV
12)
What is the major elimination product obtained from the following reaction?
A) I B) II C) III D) IV
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13)
What is the major elimination product obtained from the following reaction?
A) I B) II C) III D) IV
14)
What is the major elimination product obtained from the following reaction?
A) I B) II C) III D) IV
15)
Which of the following is the most reactive substrate in an E2 reaction?
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A) I B) II C) III D) IV
16)
Which of the following is the least reactive substrate in an E2 reaction?
A) I B) II C) III D) IV
17)
Which of the following statements about an E1 mechanism is not true?
A) The reaction is fastest with tertiary alkyl halides. B) A better leaving group makes the reaction rate increase. C) The reaction follows first-order kinetics. D) Stronger bases favor the E1 reaction.
18)
Which of the following statements about an E1 mechanism is true?
A) The identity of the leaving group affects the rate of reaction. B) The reaction follows second-order kinetics. C) The reaction is slowest with tertiary substrates. D) Polar aprotic solvents favor the E1 mechanism. Version 1
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19)
Which of the following is the most reactive substrate in an E1 reaction?
A) I B) II C) III D) IV
20)
Which of the following is the major elimination product of the following reaction?
A) I B) II C) III D) IV
21) Which of the following alkyl halides would afford the indicated product upon reaction with sodium methoxide?
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A) I B) II C) III D) IV
22)
Which of the following is the major E2 product formed from the following alkyl halide?
A) I B) II C) III D) IV
23) Which of the labeled protons in the compound below is most readily abstracted under E2 conditions?
A) Ha B) Hb C) Hc D) Hd
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24) Which of the following alkyl halides will afford the product below as the major product in an E2 reaction?
A) I B) II C) III D) IV
25)
What is the product of the following reaction?
A) I B) II C) III D) IV
26)
What is the product of the following reaction?
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A) I B) II C) III D) IV
27)
What is the product of the following reaction?
A) I B) II C) III D) IV
28)
What is the product of the following reaction?
A) Only I B) Only II C) Only III D) II and III
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29)
Which of the following is most likely to react as a base rather than a nucleophile?
A) I B) II C) III D) IV
30)
Which of the following is most likely to react as a nucleophile rather than a base?
A) I B) II C) III D) IV
31)
Which of the following is the dihalide that can be used to prepare the alkyne below?
A) Only I B) Only II C) Only III D) II and III
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32)
Which of the following is the dihalide that can be used to prepare the alkyne below?
A) I and II B) II and III C) I and III D) I, II, and III
33) Select the elimination product(s) formed by treating the indicated alkyl halide with a base.
A) Only I B) Only II C) Only III D) I, II, and III
34)
What is (are) the product(s) of the following reaction?
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A) I and II B) II and III C) I and III D) I, II, and III
35)
What is (are) the product(s) of the following reaction?
A) Only I B) Only II C) Only III D) II and III
36)
What is (are) the elimination product(s) of the following reaction?
A) Only I B) Only II C) Only III D) II and III
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37)
What is (are) the elimination product(s) of the following reaction?
A) Only I B) Only II C) Only III D) II and III
38)
What is (are) the product(s) of the following reaction?
A) Only I B) Only II C) Only III D) I and II
39)
What is (are) the product(s) of the following reaction?
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A) Only I B) Only II C) Only III D) I and II
40)
What is (are) the starting material(s) in the reaction below?
A) Only I B) Only II C) Only III D) II and III
41) Which alkyl halide(s) would give the following alkene as the only product in an elimination reaction?
A) Only I B) Only II C) Only III D) I and II
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42)
What is the most likely mechanism for the reaction below?
A) S N1 B) S N2 C) E1 D) E2
43)
What is the most likely mechanism for the reaction below?
A) S N1 B) S N2 C) E1 D) E2
44) Consider the following E2 reaction. What rate equation would be observed for this reaction?
A) Rate = k[CH 3CH 2CH 2Br] B) Rate = k[CH 3CH 2CH 2Br][KOC(CH 3) 3] C) Rate = k[CH3CH2CH2Br][KOC(CH3)3]2 D) Rate = k[CH 3CH 2CH 2Br] 2[KOC(CH 3) 3]
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45)
Which of the following alkenes is the most stable?
A) I B) II C) III D) IV
46) Which of the following alkyl chloride affords alkene A exclusively under E2 reaction condition?
A) I B) II C) III D) IV
47)
Which of the following alkyl halide would react the fastest with –OH in E2 reaction?
A) I B) II C) III D) IV
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48)
Which of the following alkyl halide reacts the fastest in an E2 reaction?
A) I B) II C) III D) IV
49)
Which of the following is the most stable alkene?
A) I B) II C) III D) IV
50)
Which is the most likely mechanism for the following reaction?
A) S N1 B) S N2 C) E1 D) E2
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51)
What is the major product and likely mechanism for the following reaction?
A) I, E1 B) I, E2 C) II, E1 D) II, E2
52)
What is the most likely mechanism for the following reaction?
A) S N1 B) S N2 C) E1 D) E2
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53)
What is the major elimination product obtained from the following reaction?
A) I B) II C) III D) IV
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Answer Key Test name: Chap 08_6e 1) D 2) B 3) B 4) A 5) B 6) D 7) C 8) B 9) D 10) B 11) A 12) A 13) B 14) A 15) D 16) A 17) D 18) A 19) B 20) D 21) D 22) B 23) D 24) D 25) D 26) B Version 1
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27) D 28) D 29) D 30) B 31) D 32) D 33) D 34) D 35) D 36) D 37) D 38) A 39) B 40) A 41) B 42) B 43) D 44) B 45) A 46) A 47) A 48) B 49) D 50) D 51) D 52) A 53) C
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CHAPTER 9 1)
Which of the following compounds is (are) primary alcohols?
A) Only I B) Only II C) Only I and II D) Only II and III
2)
Which of the following compounds is (are) secondary alcohols?
A) Only I B) Only II C) Only II and III D) Only III and IV
3)
Which of the following compounds are ethers?
A) Only I and II B) Only III and IV C) Only I, II, and III D) I, II, III, and IV
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4)
Which of the following compounds are epoxides?
A) Only I and III B) Only III and IV C) Only I, III, and IV D) I, II, III, and IV
5)
Which of the following compounds is (are) symmetrical ethers?
A) Only I B) Only IV C) Only III and IV D) Only I, III, and IV
6)
Which of the following explains why epoxides are much more reactive than ethers?
A) The C-O-C bond angle of an epoxide is 109°, making epoxides to have angle strain. B) The oxygen atom of an epoxide is sp2 hybridized. C) The C-O-C bond angle of an epoxide is 120°, making epoxides to have angle strain. D) The C-O-C bond angle of an epoxide is 60°, making epoxides to have angle strain.
7) What is the IUPAC of the following compound? (CH3CH2)3COH
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A) 2-Ethyl-2-pentanol B) 2-Ethyl-3-pentanol C) 3-Ethyl-3-pentanol D) 2,2-Diethyl-1-butanol
8)
What is the IUPAC of the following compound?
A) 3,3,6-Trimethylcyclohexanol B) 2,5,5-Trimethylcyclohexanol C) 1,4,4-Trimethyl-2-cyclohexanol D) 1,1,4-Trimethyl-2-cyclohexanol
9)
What is the IUPAC of the following compound?
A) 5-Hydroxy-3-methyl-1-pentene B) 3-Methyl-5-penten-1-ol C) 3-Methyl-1-penten-5-ol D) 3-Methyl-4-penten-1-ol
10)
What is the IUPAC of the following compound?
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A) ( S)-2,2-Dimethyl-3-pentanol B) ( R)-2,2-Dimethyl-3-pentanol C) ( R)-4,4-Dimethyl-3-pentanol D) ( S)-1- tert-Butyl-1-propanol
11)
What is the IUPAC of the following compound?
A) Ethoxyoctane B) 5-Ethoxyoctane C) 4-Ethoxyoctane D) Ethyl octyl ether
12)
What is the common name of the following compound?
A) Isobutyl isopropyl ether B) Diisobutyl ether C) Di- sec-butyl ether D) Diisopropyl ether
13)
What is the common name of the following compound?
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A) Methyl sec-butyl ether B) Isobutyl methyl ether C) sec-Butyl methyl ether D) Butyl methyl ether
14)
What is the common name of the following compound?
A) Methyl vinyl ether B) Allyl methyl ether C) Propenyl methyl ether D) Methylene propylene ether
15)
What is the IUPAC of the following compound?
A) 1,2-Epoxy-4-methylcyclohexane B) 3,4-Epoxy-1-methylcyclohexane C) 1,2-Epoxy-3-methylcyclohexane D) 1,2-Epoxy-5-methylcyclohexane
16)
What is the IUPAC of the following compound?
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A) 1,2-Epoxy-2-methylcyclopentane B) 1,2-Epoxy-1-methylcyclopentane C) 1,2-Epoxy-1-methylpentane D) 1,2-Epoxy-2-methylpentane
17)
What is the IUPAC of the following compound?
A) 1,1-Dimethyloxirane B) 2-Methylpropylane C) 2-Methylpropylene oxide D) 2,2-Dimethyloxirane
18)
Which of the following compounds has the highest boiling point?
A) I B) II C) III D) IV
19)
Which of the following compounds has the highest boiling point?
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A) I B) II C) III D) IV
20) Rank the following compounds in order of increasing boiling point, putting the compound with the lowest boiling point first.
A) III < II < I < IV B) II < III < I < IV C) IV < I < II < III D) I < II < III < IV
21)
Which of the following statements about a crown ether-cation complex is not true?
A) It is a host-guest complex. B) The crown ether is the guest and the cation is the host. C) The crown ether is the host and the cation is the guest. D) The host-guest complex is soluble in nonpolar solvents.
22) Which of the following reactions will provide the best yield of ether by the Williamson ether synthesis?
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A) Sodium methoxide and tert-butyl bromide. B) Sodium tert-butoxide and iodomethane. C) Methanol and tert-butyl alcohol in the presence of KOH. D) Iodomethane and tert-butyl bromide in the presence of KOH.
23) Which of the following reactions will provide the best yield of ether by the Williamson ether synthesis?
A) Bromobenzene and sodium methoxide B) Phenol and sodium methoxide C) Bromobenzene and bromomethane D) Sodium phenoxide and bromomethane
24)
Which of the following ethers cannot be prepared by the Williamson ether synthesis?
A) Isopropyl methyl ether B) tert-Butyl methyl ether C) tert-Butyl phenyl ether D) Methyl phenyl ether
25)
What is the best choice of reagent to accomplish the following transformation?
A) HCl B) SOCl 2, pyridine C) Cl 2 D) H 3O +, H 2O
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26)
What is the product of the following reaction?
A) I B) II C) III D) IV
27)
What is the major organic product(s) obtained in the following reaction?
A) I B) II C) III D) I and II
28)
What is the best choice of reagent to accomplish the following transformation?
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A) HCl B) H 2SO 4 C) NaOH D) TsCl, pyridine
29) Which of the following alcohols reacts the fastest with HCl to give the corresponding alkyl halide?
A) I B) II C) III D) IV
30)
What is the major organic product obtained from the following sequence of reactions?
A) 2-Methyl-1-butene B) 3-Methyl-3-butene C) 1-Chloro-2-methylbutane D) 1-Bromo-2-methylbutane
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31)
Determine the product(s) of the following reaction.
A) Only I B) Only II C) Only III D) Only II and III
32)
Determine the product(s) of the following reaction.
A) Only I B) Only II C) Only III D) Only I and II
Rank the alcohols in order of increasing reactivity when dehydrated with H2SO4, putting 33) the least reactive first.
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A) I < III < II B) I < II < III C) II < III < I D) III < II < I
34)
Which of the following statements about carbocation rearrangement is not true?
A) A less stable carbocation can rearrange to a more stable carbocation by shift of a hydrogen atom. B) A less stable carbocation can rearrange to a more stable carbocation by shift of an alkyl group. C) 1,2-Shifts convert a less stable carbocation to a more stable carbocation. D) The migrating group in a 1,2-shift moves with one bonding electron.
35) Which of the following alcohols is most likely to yield a carbocation that is susceptible to rearrangements?
A) I B) II C) III D) IV
36)
What is the best choice of reagent to accomplish the following transformation?
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A) TsCl, pyridine B) POCl 3, pyridine C) HCl, ZnCl 2 D) NaOH
37)
What is the major organic product obtained from the following reaction?
A) I B) II C) III D) IV
38)
What is the major organic product obtained from the following reaction?
A) (±)-2-Chlorobutane B) ( R)-2-Chlorobutane C) ( S)-2-Chlorobutane D) trans-2-Butene
39)
What is the major organic product obtained from the following sequence of reactions?
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A) ( R)-2-Methylpentanenitrile B) ( S)-2-Methylpentanenitrile C) (±)-2-Methylpentanenitrile D) trans-2-Butene
40)
What is the major organic product obtained from the following sequence of reactions?
A) ( S)-2-Methoxypentane B) ( R)-2-Methoxypentane C) (±)-2-Methoxypentane D) trans-2-Butene
41) What are the major products obtained upon treatment of ethyl methyl ether with excess HBr?
A) Bromomethane and ethanol B) Bromoethane and methanol C) Bromoethane and bromomethane D) Ethanol and methanol
42) What are the major products obtained upon treatment of tert-butyl methyl ether with excess HI?
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A) tert-Butyl alcohol and iodomethane B) tert-Butyl iodide and iodomethane C) tert-Butyl alcohol and methanol D) tert-Butyl iodide and methanol
43)
Which of the following statements about the reaction of ethers with strong acids is true?
A) HCl, HBr, and HI can all be used. B) The mechanism of ether cleavage is S N1 only. C) The mechanism of ether cleavage is S N2 only. D) The mechanism of ether cleavage is S N1 and S N2.
44) What are the major products obtained upon treatment of methyl phenyl ether with excess HBr?
A) Phenol and bromomethane B) Phenol and methanol C) Bromobenzene and bromomethane D) Bromobenzene and methanol
45)
Determine the product in the following reaction (ignoring possible stereoisomers).
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A) I B) II C) III D) IV
46)
Determine the product in the following reaction (ignoring possible stereoisomers).
A) I B) II C) III D) IV
47)
What is the product of the following reaction?
A) I B) II C) III D) IV
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48)
What is the major alkene formed when compound A is dehydrated with H2SO4?
A) I B) II C) III D) IV
49) What is the major alkene formed when compound A is dehydrated with POCl3 and pyridine?
A) I B) II C) III D) IV
50)
What is the major organic product of the following reaction?
A) I B) II C) III D) IV
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51)
What is the major organic product of the following reaction?
A) I B) II C) III D) IV
52)
What is the IUPAC name of the following compound?
A) 5-Ethylthio-4-isopropylpentane B) 1-Ethylthio-3-methyl-2-propylbutane C) 1-Ethylthio-2-isopropylpentane D) Isooctylthioethane
53)
What is the IUPAC name of the following compound?
A) 3-Ethyl-5-methylcyclohexanethiol B) 3-Ethyl-5-methylcyclohexane-1-thiol C) 5-Ethyl-2-methylcyclohexanethiol D) 5-Ethyl-2-methylcyclohexylthiol
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54)
What is the IUPAC name of the following compound?
A) (2R, 4R)-4-chloro-2-pentanol B) (2R, 4S)-4-chloro-2-pentanol C) (2S, 4R)-4-chloro-2-pentanol D) (2S, 4S)-4-chloro-2-pentanol
55)
What is the IUPAC name of the following compound?
A) R-2,2-dimethylcyclohexanol B) S-2,2-dimethylcyclohexanol C) R-1,1-dimethyl-2-cyclohexanol D) S-1,1-dimethyl-2-cyclohexanol
56)
What is the IUPAC name of the following compound?
A) R-2-methoxy-5,5-dimethylhexane B) S-2-methoxy-5,5-dimethylhexane C) R-5-methoxy-2,2-dimethylhexane D) S-5-methoxy-2,2-dimethylhexane
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57)
What is the major product of the following reaction?
A) I B) II C) III D) IV
58)
What is the major product of the following reaction?
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A) I B) II C) III D) IV
59)
Which of the following drugs has been shown to treat the cause of asthma?
A) Zileuton B) S-Adenosylmethionine C) P-Toluenesulfonyl chloride D) 18-Crown-6
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Answer Key Test name: Chap 09_6e 1) B 2) D 3) D 4) B 5) B 6) D 7) C 8) B 9) D 10) B 11) C 12) B 13) C 14) B 15) A 16) B 17) D 18) D 19) B 20) A 21) B 22) B 23) D 24) C 25) B 26) B Version 1
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27) D 28) B 29) C 30) D 31) D 32) D 33) A 34) D 35) D 36) B 37) D 38) B 39) A 40) B 41) C 42) B 43) D 44) A 45) A 46) B 47) A 48) B 49) A 50) B 51) D 52) C 53) C 54) D 55) A 56) A Version 1
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57) A 58) D 59) A
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CHAPTER 10 1)
Which of the following alkenes are terminal alkenes?
A) I and II B) II and III C) I and IV D) I and III
2)
Which of the following alkenes are internal alkenes?
A) I and II B) II and III C) I and III D) II and IV
3) true?
Which of the statements about the properties of the carbon-carbon double bond is not
A) There is restricted rotation around the carbon-carbon double bond. B) Whenever the two groups on each end of a carbon-carbon double bond are the same, two diastereomers are possible. C) Trans alkenes are generally more stable than cis alkenes. D) The stability of the carbon-carbon double bond increases as the number of substituent groups increases.
4)
Calculate the degree of unsaturation for a molecule with molecular formula C 6H
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1
A) 1 B) 2 C) 3 D) 0
5)
Calculate the degree of unsaturation for a molecule with molecular formula C 8H
9N.
A) 2 B) 3 C) 4 D) 5
6)
What is the IUPAC name for the following compound?
A) 6-Ethyl-1-heptene B) 2-Ethyl-1-heptene C) 2-Ethyl-1-octene D) 6-Ethyl-6-heptene
7)
What is the IUPAC name for the following compound?
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A) 1-Methylcyclopentene B) 2-Methyl-1-cyclopentene C) 1-Methylene-1-methylcyclopentane D) 1-Methylcyclohexene
8)
What is the IUPAC name for the following compound?
A) 1,2-Dimethylcyclohexene B) 2,3-Dimethylcyclohexene C) 1,6-Dimethylcyclohexene D) 1,2-Dimethyl-3-cyclohexene
9)
What is the IUPAC name for the following compound?
A) 5-Methyl-5-hexen-2-ol B) 6-Methyl-6-hepten-2-ol C) 6-Hydroxy-2-methylheptene D) 6-Hydroxy-2-methyl-1-heptene
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10)
What is the IUPAC name for the following compound?
A) 4-Ethyl-3-methyl-1-octen-5-ol B) 3-Ethyl-4-methyl-2-octen-5-ol C) 5-Ethyl-6-methyl-7-octen-4-ol D) 4-Ethyl-6-methyl-1-octen-5-ol
11)
Label each C-C double bond in Kavain, a naturally occurring relaxant, as E or Z.
A) I = Z and II = Z B) I = Z and II = E C) I = E and II = E D) I = E and II = Z
12)
What is the common name of the following compound?
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A) 2-Vinylcyclohexene B) 2-Allylcyclohexene C) 1-Allylcyclohexene D) 1-Vinylcyclohexene
13)
Rank the following isomers in order of increasing boiling point, putting the least first.
A) I < II < III B) I < III < II C) II < III < I D) II < I < III
14)
Which of the following compounds has the highest boiling point?
A) I B) II C) III D) IV
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15)
Which of the following is a terpene?
A) I B) II C) III D) IV
16)
What is the major product of the following reaction?
A) I B) II C) III D) IV
17)
Which of the following statements about alkenes is not true? A) They are less reactive than alkanes. B) They can exist as cis/trans isomers. C) The bond angle around the C-C double bond is approximately 120°. D) The carbon of the C-C double bond is sp 2hybridized.
18)
Which of the following statements about alkenes is true?
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A) Alkenes react with nucleophiles and bases. B) Alkenes contain double bonds from two sp-hybridized carbon atoms. C) In the reactions of alkenes, the D) Alkenes react with electrophiles.
19) first.
bond is not always broken.
Rank the following compounds in order of decreasing stability, putting the most stable
A) I > II > III B) II > I > III C) III > II > I D) III > I > II
20) Which of the following reaction conditions would result in anti-Markovnikov addition to an alkene? A) H 2O/H 3O + B) HBr C) HCl D) [1] BH 3; [2] H 2O 2/HO −
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21) Which of the following alkenes will undergo a carbocation rearrangement when reacting with H2O in the presence of a small amount of H2SO4?
A) Only I and II B) Only I and III C) Only II and III D) I, II, and III
22) In which of the following alkene addition reactions will carbocation rearrangements occur?
A) Addition of Br 2and H 2O B) Addition of Br 2 C) Addition of Cl 2and H 2O D) Addition of H 2O in the presence of H 2SO 4
23)
Markovnikov addition of HBr to CH 3CH=CH
2involves which of the following?
A) Initial attack by bromide anion (Br −). B) Initial attack by bromine radical (Br •). C) Formation of a primary carbocation. D) Formation of a secondary carbocation.
24)
Rearrangements can occur in which of the following reactions?
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A) Addition of Cl 2to an alkene. B) Addition of HOBr to an alkene. C) Addition of H 2O/H 3O +to an alkene. D) None of these.
25)
Which of the following alkenes reacts fastest with HCl?
A) I B) II C) III D) IV
26)
Predict the major product of the following reaction.
A) I B) II C) III D) IV
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27)
Predict the product(s) of the following reaction.
A) Only I and II B) Only I and III C) Only II and III D) Only III and IV
28)
Predict the product of the following reaction.
A) I B) II C) III D) IV
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29)
Predict the major product of the following reaction.
A) I B) II C) III D) IV
30)
Predict the major product of the following reaction.
A) I B) II C) III D) IV
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31)
Predict the major product(s) of the following reaction.
A) Only I and II B) Only II and III C) Only III and IV D) Only I and IV
32)
Predict the major product(s) of the following reaction.
A) Only I and II B) Only II and IV C) Only II and III D) Only I and IV
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33)
What is the major product obtained from the following reaction?
A) I B) II C) III D) IV
34) What is the major product obtained from the following reaction (assume enantiomer is also formed)?
A) I B) II C) III D) IV
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35)
What is (are) the major product(s) obtained from the following reaction?
A) Only I B) Only II C) Only III D) Only I and II
36)
What is (are) the major product(s) obtained from the following reaction?
A) Only I B) Only II C) Only III D) Only I and II
37)
What is the best choice of reagent to accomplish the following transformation?
A) HBr B) Br 2, H 2O C) Br 2 D) H 2O 2/Br 2
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38)
What is the best choice of reagent to accomplish the following transformation?
A) H 2O, Br 2 B) [1] BH 3; [2] H 2O 2/HO − C) H 2O, H 2SO 4 D) [1] BH 3; [2] H 2O
39) What type of reactive intermediate is formed in the reaction of an alkene with HI to give an iodoalkane?
A) Carbanion B) Carbocation C) Cyclic bromonium ion D) Radical
What type of reactive intermediate is formed in the reaction of an alkene with Br 2and H 40) 2O to give a bromohydrin?
A) Carbanion B) Radical C) Carbocation D) Cyclic bromonium ion
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41)
Rank the carbocation in order of increasing stability, putting the least stable first.
A) III < I < II B) III < II < I C) I < II < III D) I < III < II
42) Which of the following statements about the stereochemistry of electrophilic addition of HX to alkenes is true?
A) Achiral starting materials yield an unequal mixture of two enantiomers. B) Hydrohalogenation occurs with syn stereochemistry only. C) Hydrohalogenation occurs with anti stereochemistry only. D) Hydrohalogenation occurs with syn and anti addition of HX.
43)
Which of the following reactions of alkenes takes place with anti stereochemistry only?
A) Addition of HBr B) Addition of H 2O in the presence of H 2SO 4 C) Addition of BH 3followed by H 2O 2/HO − D) Addition of Br 2
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44)
Predict the product of the following reaction, ignoring stereochemistry.
A) I B) II C) III D) IV
45)
What is the starting material in the following reaction?
A) I B) II C) III D) IV
46)
What is (are) the missing reagent(s) in the following reaction?
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A) Br 2/CCl 4 B) NBS, DMSO/H 2O C) [1] Br 2; [2] H 2O D) [1] BH 3; [2] H 2O 2/HO −
47)
Which of the following statements about hydroboration/oxidation of alkenes is true?
A) In hydroboration, the boron atom bonds to the more substituted carbon. B) Hydroboration occurs with anti addition. C) Oxidation occurs with retention of configuration. D) 9-BBN does not undergo hydroboration in the same manner as BH 3.
48)
Which of the following alkenes is an E alkene?
A) I B) II C) III D) IV
49)
Which alkene reacts fastest with HBr?
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A) I B) II C) III D) IV
50)
Calculate the degree of unsaturation for the following molecule:
A) 2 B) 3 C) 4 D) 5
51)
Calculate the degree of unsaturation for the following molecule:
A) 2 B) 3 C) 4 D) 5
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52)
What is the IUPAC name of the following compound?
A) (E,R)-4-bromo-4-hexen-2-ol B) (Z,R)-4-bromo-4-hexen-2-ol C) (E,S)-4-bromo-4-hexen-2-ol D) (Z,S)-4-bromo-4-hexen-2-ol
53)
What is the IUPAC name of the following compound?
A) R-4,4-dibromo-2-cyclohexen-1-ol B) S-4,4-dibromo-2-cyclohexen-1-ol C) R-4,4-dibromo-5-cyclohexen-1-ol D) S-4,4-dibromo-5-cyclohexen-1-ol
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54)
What is the major product of the following reaction?
A) I B) II C) III D) IV
55)
The addition of excess HBr to the following molecule will result in:
A) An alkene B) A geminal dihalide C) A vicinal dihalide D) An alcohol
56) The addition of water in the presence of sulfuric acid to the following compound will result in:
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A) An aldehyde B) A ketone C) An alcohol D) An alkyl halide
57)
The hydroboration-oxidation to the following compound will result in:
A) An aldehyde B) A ketone C) An alcohol D) An alkyl halide
58)
What is the major product of the following reaction?
A) I B) II C) III D) IV
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59) Which of the following molecular formulas is consistent with the formula for a molecule containing one alkyne and no other degrees of unsaturation?
A) I B) II C) III D) IV
60)
Which of the following represents a terminal alkyne?
A) Only I and II B) Only II and III C) Only I and III D) Only II and IV
61)
Which of the following represents an internal alkyne?
A) Only I and II B) Only I and III C) Only II and IV D) Only II and III
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62)
Which of the following alkynes is a symmetrical alkyne?
A) I B) II C) III D) IV
63)
How many degrees of unsaturation are introduced by a triple bond? A) 0 B) 1 C) 2 D) 3
64)
How many s bonds and p bonds are present in a triple bond?
A) One s bond and one p bond. B) One s bond and two p bonds. C) Two s bonds and one p bond. D) Two s bonds and two p bonds.
65)
Which of the following statements about alkynes is not true?
A) Alkynes undergo many addition reactions. B) Alkynes are more polarizable than alkenes. C) Both p bonds of a C-C triple bond are weaker than a C-C s bond. D) The electrons in the p bonds of alkynes are more tightly held than those of alkenes.
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66)
Give the IUPAC name for the following compound.
A) 6,6-Dimethyl-3-octyne B) 3,3-Dimethyl-3-octyne C) 3,3-Dimethy-5-octyne D) 6-Ethyl-6-methyl-3-heptyne
67)
Give the IUPAC name for the following compound.
A) 4,4-Diethyl-1-octyne B) 4,4-Dipropyl-1-heptyne C) 4,4-Dipropyl-6-heptyne D) 4,4-Diethyl-6-octyne
68)
Give the IUPAC name for the following compound.
A) 4-Chloro-4-methyl-2-heptyne B) 3-Chloro-3-methyl-4-heptyne C) 3-Chloro-3-methyl-4-hexyne D) 4-Chloro-4-methyl-2-hexyne
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69)
Give the IUPAC name for the following compound.
A) 3- sec-Butyl-1,4-octadiyne B) 3-Isopropyl-1,5-octadiyne C) 3-Isopropyl-1,5-nonadiyne D) 3- sec-Butyl-1,4-nonadiyne
70)
Give the IUPAC name for the following compound.
A) trans-2-Acetylenecyclohexanol B) trans-2-Ethynylcyclohexanol C) trans-2-Acetylene-1-cyclohexanol D) trans-2-Ethylenecyclohexanol
71)
Give the IUPAC name for the following compound.
A) 2,5-Dimethyl-3-heptyne B) 3,6-Dimethy-4-heptyne C) 2,5-Dimethyl-3-octyne D) 3,6-Dimethyl-4-octyne
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72)
Give the IUPAC name for the following compound.
A) 4-Methyl-4-penten-1-yne B) 2-Methyl-2-hexen-5-yne C) 5-Methyl-4-hexen-1-yne D) 2-Methyl-2-penten-4-yne
73)
Which of the following about the physical properties of alkynes is not true?
A) Alkynes have low melting and boiling points. B) Melting and boiling points increase as the number of carbons increases. C) Alkynes are soluble in organic solvents. D) Alkynes are soluble in water.
74) Which of the following explains why 1-pentyne has a slightly higher boiling point than 1pentene?
A) 1-Pentyne has more carbons than 1-pentene. B) 1-Pentyne has more carbons per hydrogen than 1-pentene. C) 1-Pentyne is linear while 1-pentene is trigonal planar. D) The C-C triple bond in 1-pentyne is more polar than the C-C double bond in 1pentene.
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75)
What is the product of the following reaction?
A) I B) II C) III D) IV
76)
What is the product of the following sequence of reactions?
A) I B) II C) III D) IV
77)
What is the product of the following reaction?
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A) I B) II C) III D) IV
78)
Which method would work the best in accomplishing the following transformation?
A) [1] HBr; [2] 2eq. NaNH 2 B) [1] Br 2; [2] 2eq. NaNH 2 C) [1] Br 2, H 2O; [2] NaNH 2 D) [1]BH 3, THF; [2] H 2O 2, NaOH; [3] NaNH 2
79)
Which of the following statements about the reactions of alkynes is not true?
A) Alkynes contain easily broken p bonds. B) Alkynes undergo addition reactions. C) When alkynes undergo two sequential addition reactions, four new s bonds are formed. D) When alkynes undergo two sequential addition reactions, two new s bonds and a p bond are formed.
80)
Which of the indicated hydrogen in the following compounds is the least acidic?
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A) I B) II C) III D) IV
81)
Which of the indicated hydrogen in the following compounds is the most acidic?
A) I B) II C) III D) IV
82) first.
Rank the following compounds in order of decreasing basicity, putting the most basic
A) I > II > III B) III > II > I C) III > I > II D) II > III > I
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83)
Which of the following anions is the most basic?
A) I B) II C) III D) IV
84) Which of the following bases can deprotonate acetylene? You are given the pKavalues of the conjugate acids in parentheses.
A) Only I and II B) Only I and III C) Only II and III D) Only II and IV
85) Which of the following bases cannot deprotonate acetylene? You are given the pKavalues of the conjugate acids in parentheses.
A) Only I and II B) Only I and III C) Only II and III D) Only II and IV
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86)
What is the major product of the following reaction?
A) Only I B) Only II C) Only III D) I, II, and III
87)
What is the reagent required to accomplish the following transformation?
A) SOCl 2 B) 2eq. HCl C) Cl 2 D) Br 2/CCl 4
88)
In the addition of HBr to 1-butyne, the electrophile in the first step of the mechanism is
A) the C sp-H1 s bond of 1-butyne. B) the C-C triple bond of 1-butyne. C) the H atom in HBr. D) the Br ion.
89)
In the addition of HBr to 1-butyne, the nucleophile in the first step of the mechanism is
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A) the C sp-H1 s bond of 1-butyne. B) the C-C triple bond of 1-butyne. C) the H atom in HBr. D) the Br ion.
90)
What is (are) the product(s) of the following reaction?
A) Only I B) Only II C) Only III D) I, II, and III
91)
Which of the following statements about tautomers is true?
A) Tautomers differ in the position of a single bond and a hydrogen atom. B) Tautomers differ in the position of a double bond and a carbon atom. C) Tautomers differ in the position of a double bond and a hydrogen atom. D) Tautomers differ in the position of a single bond and a carbon atom.
92)
What is the relationship between the keto and enol forms of acetone, CH
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3?
A) Same compounds B) Diastereomers C) Enantiomers D) Constitutional isomers
93)
Which of the following compounds is a tautomer of 2-hexanone?
A) Only I and II B) Only I and III C) Only II and III D) I, II, and III
94)
Which of the following compounds can be an enol tautomer of 1,3-cyclohexandione?
A) Only I and II B) Only I and III C) Only II and III D) I, II, and III
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95)
Which of the following represents a keto-enol tautomeric pair?
A) I B) II C) III D) IV
96)
What is the major organic product of the following reaction?
A) I B) II C) III D) IV
97)
What is the major organic product of the following reaction?
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A) I B) II C) III D) IV
98)
What is the major organic product of the following reaction?
A) I B) II C) III D) IV
99)
What is the major organic product of the following reaction?
A) I B) II C) III D) IV
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100)
What is the major organic product of the following reaction?
A) I B) II C) III D) IV
101)
What is (are) the major organic product(s) of the following reaction?
A) Only I and II B) Only II and III C) Only I and III D) I, II, and III
102)
Determine the product of the following reaction.
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A) I B) II C) III D) IV
103)
What is the starting material in the following reaction?
A) I B) II C) III D) IV
104)
What is the major product of the following reaction?
A) I B) II C) III D) IV
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105)
Give the IUPAC name for the following compound. A) R-4-bromo-1-pentyne B) S-4-bromo-1-pentyne C) R-3-bromo-5-pentyne D) S-3-bromo-5-pentyne
106)
Give the IUPAC name for the following compound. A) R-1-butyn-3-ol B) S-1-butyn-3-ol C) R-3-butyn-1-ol D) S-3-butyn-1-ol
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107)
What is the major product of the following reaction?
A) I B) II C) III D) IV
108)
What is the major product of the following reaction?
A) I B) II C) III D) IV
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109)
Which of the following would be a reasonable synthesis of 1-butanol?
A) I B) II C) III D) IV
110)
Which of the following would be a reasonable synthesis of 2-butanol?
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A) I B) II C) III D) IV
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Answer Key Test name: Chap 10_6e 1) D 2) D 3) B 4) A 5) D 6) B 7) A 8) C 9) B 10) C 11) C 12) D 13) B 14) B 15) D 16) C 17) A 18) D 19) B 20) D 21) C 22) D 23) D 24) C 25) D 26) A Version 1
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27) A 28) C 29) D 30) B 31) A 32) B 33) A 34) B 35) D 36) C 37) B 38) B 39) B 40) D 41) B 42) D 43) D 44) B 45) B 46) D 47) C 48) C 49) C 50) B 51) D 52) B 53) A 54) D 55) B 56) B Version 1
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57) A 58) B 59) C 60) D 61) B 62) C 63) C 64) B 65) D 66) A 67) B 68) D 69) B 70) B 71) A 72) C 73) D 74) D 75) B 76) B 77) A 78) B 79) D 80) D 81) C 82) B 83) D 84) B 85) D 86) A Version 1
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87) B 88) C 89) B 90) A 91) C 92) D 93) A 94) B 95) D 96) C 97) A 98) D 99) D 100) D 101) A 102) A 103) A 104) C 105) B 106) D 107) C 108) A 109) B 110) A
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CHAPTER 11 1)
Which of the following statements about oxidation and reduction is not true?
A) The conversion of an alkyne to an alkene is reduction. B) The conversion of an alkene to an alkane is reduction. C) Oxidation results in a decrease in the number of C-H bonds. D) Reduction results in an increase in the number of C-Z bonds.
2)
What is the correct classification of the following reaction?
A) Reduction reaction B) Oxidation reaction C) Elimination reaction D) Substitution reaction
3)
What is the correct classification of the following reaction?
A) Reduction reaction B) Oxidation reaction C) Elimination reaction D) Substitution reaction
4)
What is the correct classification of the following reaction?
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A) Reduction reaction B) Oxidation reaction C) Elimination reaction D) Substitution reaction
5)
What is the correct classification of the following reaction?
A) Reduction reaction B) Oxidation reaction C) Elimination reaction D) Substitution reaction
6)
What is the correct classification of the following reaction?
A) Reduction reaction B) Oxidation reaction C) Elimination reaction D) Substitution reaction
7)
What is the correct classification of the following reaction?
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A) Reduction reaction B) Oxidation reaction C) Elimination reaction D) Substitution reaction
8)
What is the correct classification of the following reaction?
A) Reduction reaction B) Oxidation reaction C) Elimination reaction D) Substitution reaction
9)
What is the correct classification of the following reaction?
A) Reduction reaction B) Oxidation reaction C) Elimination reaction D) Substitution reaction
10)
What is the correct classification of the following reaction?
A) Reduction reaction B) Oxidation reaction C) Elimination reaction D) Substitution reaction
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11) Rank the following compounds in order of increasing oxidation level (from lowest to highest).
A) I < III < II < IV B) II < III < I < IV C) IV < I < III < II D) II < IV < III < I
12) What happens to the carbon atom in the transformation of chloromethane to methyllithium? CH3Cl + 2Li ® CH3Li + LiCl A) Oxidized B) Reduced C) Oxidized and reduced D) Neither oxidized nor reduced
13) Rank the following compounds in order of decreasing oxidation level, putting the compound with the highest oxidation level first.
A) II > IV > I > III B) I > III > IV > II C) III > I > II > IV D) III > I > IV > II
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14)
Which of the following classes of organic compounds cannot undergo reduction easily?
A) Alkanes B) Alkenes C) Alkynes D) Carboxylic acids
15)
Determine the product(s) of the following reaction.
A) I and III B) II and III C) I, II, and III D) I or II
16)
Rank the following alkenes in order of decreasing heat of hydrogenation.
A) I > II > III B) III > I > II C) II > I > III D) III > II > I
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17) Which of the following explains why heats of hydrogenation cannot be used to determine the relative stability of compounds A and B below?
A) Compound A is trisubstituted while compound B is monosubstituted. B) Compound A has E configuration while compound B has no E/ Z configuration. C) Both compounds A and B have no E/ Z configurations. D) Hydrogenation of A and B give different alkanes.
18)
Rank the following alkenes in order of increasing rate of hydrogenation.
A) I < III < IV < II B) IV < III < II < I C) I < II < III < IV D) IV < II < III < I
A compound X of molecular formula C 8H 12 with no triple bonds reacts with one 19) equivalent of H 2 to give a new compound having molecular formula C 8H 14. What can be inferred about the structure of compound X?
A) Compound X has 3 rings. B) Compound X has 3 p bonds. C) Compound X has 1 ring and 2 p bonds. D) Compound X has 2 rings and 1 p bond.
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20)
Determine the product of the following reaction.
A) I B) II C) III D) IV
21)
What reagent is required to accomplish the following transformation?
A) Na, NH 3 B) H 2, Pd-C C) H 2, Ni D) H 2, Lindlar catalyst
22)
What reagent is required to accomplish the following transformation?
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A) Na, NH 3 B) H 2, Pd-C C) H 2, Ni D) H 2, Lindlar catalyst
23)
What is the starting material in the following reaction?
A) I B) II C) III D) IV
24)
Determine the product of the following reaction.
A) I B) II C) III D) IV
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25) true?
Which of the following statements about the reduction of epoxides with LiA1H 4 is
A) The nucleophile is a hydride (H −). B) In unsymmetrical epoxides, nucleophilic attack of H − occurs at the more substituted carbon atom. C) The reaction follows S N1 mechanism. D) The nucleophile, H −, is a weak nucleophile.
26)
Which is (are) the product(s) of the following reaction?
A) Only I and II B) Only I and III C) Only II and III D) I, II, and III
27)
Which of the following products do not form in the following reaction?
A) Only I B) Only II C) Only III and IV D) Only I and II
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28)
What is (are) the product(s) of the following reaction?
A) Only I B) Only II C) Only III D) Only I and II
29)
Determine the product of the following reaction, ignoring stereochemistry.
A) I B) II C) III D) IV
30)
What is (are) the product(s) of the following reaction?
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A) I B) II C) III D) IV
31)
What is the reagent required to accomplish the following transformation?
A) LiA1H 4 B) [1] OsO 4; [2] NaHSO 3, H 2O C) RCO 3H, H 2O/HO − D) PCC/CH 2Cl 2
32)
What is the reagent required to accomplish the following transformation?
A) [1] OsO 4; [2] NaHSO 3, H 2O B) KMnO 4, H 2O/HO − C) RCO 3H/H 2O/HO − D) PCC/CH 2Cl 2
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33)
Determine the product of the following reaction.
A) I B) II C) III D) IV
After ozonolysis and treatment of the unstable ozonide with CH3SCH3, compound A was 34) converted to the compound below. What is the structure of compound A?
A) I B) II C) III D) IV
35)
What is the starting material in the following sequence of reactions?
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A) I B) II C) III D) IV
36)
Which of the following is (are) formed by ozonolysis of compound A?
A) Only I B) Only II C) Only I and II D) I, II, and III
37)
Which of the following is (are) formed by ozonolysis of compound A?
A) Only I B) Only II C) I and II D) I, II, and III
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38)
Which of the following is (are) formed by ozonolysis of the following alkyne?
A) Only I and II B) Only III and IV C) Only I and IV D) Only II and III
39)
Which of the following is (are) formed by ozonolysis of the following alkyne?
A) Only I B) Only II C) I and II D) I, II, and III
40)
Determine the product of the following reaction.
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A) I B) II C) III D) IV
41)
Determine the product of the following reaction.
A) I B) II C) III D) IV
42)
What is the product of the following reaction?
A) I B) II C) III D) IV
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43)
Predict the major product of the following reaction.
A) I B) II C) III D) IV
44)
Predict the major product of the following reaction.
A) I B) II C) III D) IV
45)
What is the starting material in the following reaction?
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A) I B) II C) III D) IV
46)
What is the starting material in the following reaction?
A) I B) II C) III D) IV
47)
What reagents are necessary to perform the following reaction?
A) H 2, Lindlar's B) Na, NH 3 C) O 3 D) KMnO 4
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48)
What is the major product of the following reaction?
A) I B) II C) III D) IV
49)
What reagents are necessary to perform the following reaction?
A) LiAlH 4, H 2O B) O 2 C) KMnO 4 D) PCC
50)
What is the major product of the following reaction?
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A) Only I B) Only I and IV C) OnlyII D) Only III
51)
What reagents are necessary to perform the following reaction?
A) PCC B) K 2Cr 2O 7, H 2SO 4, H 2O C) LiAlH 4, H 2O D) Na, NH 3
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Answer Key Test name: Chap 11_6e 1) D 2) A 3) A 4) B 5) A 6) B 7) A 8) B 9) A 10) A 11) D 12) B 13) C 14) A 15) D 16) B 17) D 18) B 19) D 20) C 21) D 22) A 23) D 24) B 25) A 26) A Version 1
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27) C 28) D 29) C 30) C 31) B 32) C 33) D 34) A 35) B 36) C 37) C 38) A 39) A 40) D 41) D 42) B 43) A 44) A 45) A 46) A 47) B 48) B 49) A 50) B 51) A
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CHAPTER 12 1)
Which of the following dienes contain conjugated double bonds?
A) Only I and II B) Only II and III C) Only I and III D) Only II and IV
2)
Which of the following dienes contain isolated double bonds?
A) Only I and II B) Only II and III C) Only I and III D) Only II and IV
3)
Which of the following statements about resonance structures is true?
A) The placement of atoms is different. B) The placement of p bonds is different. C) The placement of s bonds is different. D) The placement of nonbonded electrons is the same.
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4)
What is the hybridization around the indicated carbon atom in the following anion?
A) sp3 B) sp2 C) sp D) p
5)
What is the hybridization around the indicated oxygen atom in the following anion?
A) sp3 B) sp2 C) sp D) p
6)
Which of the following is (are) conjugated dienes?
A) Only I B) Only II C) Only I and II D) I, II, and III
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7)
Which of the following compounds is conjugated?
A) I B) II C) III D) IV
8)
Which of the following conjugated dienes represent two conformations?
A) Only I and II B) Only I and III C) Only II and III D) None of the choices
9) Rank the following dienes in order of decreasing heat of hydrogenation, putting the diene with the highest heat of hydrogenation first.
A) I > II > III B) III > II > I C) II > I > III D) III > I > II
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10) first.
Rank the following compounds in order of increasing stability, putting the least stable
A) I < II < III B) III < II < I C) II < I < III D) III < I < II
11) What is the reactive intermediate in the reaction of 1,3-diene with HBr, resulting in 1,4addition?
A) Allylic radical B) Cyclic bromonium C) Dienophile D) Allylic carbocation
12) Which of the following is the appropriate term for the mechanism of the addition of HBr to 1,3-dienes?
A) Nucleophilic addition B) Electrophilic addition C) Free radical addition D) Conjugate addition
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13)
What is (are) the major product(s) of the following reaction?
A) Only I B) Only II and IV C) Only I and III D) Only I, II, and III
14)
What is (are) the major product(s) of the following reaction?
A) Only I B) Only I and III C) Only II and IV D) Only I, II, and III
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15)
What is (are) the major product(s) of the following reaction?
A) Only I B) Only II C) Only I and II D) I, II, and III
16) Which of the following is not a product obtained from the addition of 1 equivalent of HBr to ( E)-1,3-pentadiene?
A) ( E)-4-Bromo-2-pentene B) ( E)-1-Bromo-2-pentene C) 3-Bromo-1-pentene D) ( E)-3-Bromo-2-pentene
17) What is the thermodynamic product obtained from the addition of 1 equivalent of HBr to 1,3-butadiene?
A) 3-Bromo-1-butene B) 1-Bromo-2-butene C) 2-Bromo-2-butene D) 2-Bromo-1-butene
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18) What is the kinetic product obtained from the addition of 1 equivalent of HBr to 1,3butadiene?
A) 3-Bromo-1-butene B) 1-Bromo-2-butene C) 2-Bromo-2-butene D) 2-Bromo-1-butene
19)
Which of the following statements about kinetic vs. thermodynamic products is true?
A) The product that is formed faster is the thermodynamic product. B) The kinetic product predominates at low temperature. C) The product that predominates at equilibrium is the kinetic product. D) The thermodynamic product is less stable.
20) true?
Which of the following statements about the mechanism of the Diels-Alder reaction is
A) Three π bonds break; two σ bonds and one π bond form. B) Three π bonds break; one σ bond and two π bonds form. C) Two π bonds break; one σ bond and one π bond form. D) Two π bonds break; two σ bonds and one π bond form.
21)
Which of the following is not a feature of the Diels-Alder reaction?
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A) They are initiated by peroxides. B) They form new six-membered rings. C) Three π bonds break. D) They are concerted.
22) Rank the following dienes in order of increasing reactivity in a Diels-Alder reaction, listing the least reactive first.
A) I< II < III B) III < I < II C) II < I < III D) I < III < II
23)
Which of the following is the least reactive diene in a Diels-Alder reaction?
A) I B) II C) III D) IV
24)
Which of the following statements about the Diels-Alder reaction is true?
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A) The diene can react only when it adopts the s-trans conformation. B) Electron-withdrawing substituents in the diene increase reaction rate. C) Electron-donating substituents in the dienophile increase the reaction rate. D) The stereochemistry of the dienophile is retained in the product.
25) Rank the following dienophile in order of increasing reactivity in a Diels-Alder reaction, listing the least reactive first.
A) I < II < III B) III < I < II C) II < I < III D) III < II < I
26) Which of the following compounds is the least reactive dienophile in a Diels-Alder reaction?
A) I B) II C) III D) IV
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27) Which of the following compounds is the most reactive dienophile in a Diels-Alder reaction?
A) I B) II C) III D) IV
28)
Which of the following is the most reactive diene in a Diels-Alder reaction?
A) I B) II C) III D) IV
29)
Which of the following is the least reactive diene in a Diels-Alder reaction?
A) I B) II C) III D) IV
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30)
What is the major organic product of the following reaction?
A) I B) II C) III D) IV
31)
What is the major organic product of the following reaction?
A) Only I B) Only II C) Only III D) Only I and III
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32)
What is the major organic product of the following reaction?
A) Only I B) Only II C) Only III D) Only I and II
33)
What is the major organic product of the following reaction?
A) Only I B) Only I and II C) Only II and III D) I, II, and III
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13)
What is the major organic product of the following reaction?
A) I B) II C) III D) IV
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14)
What is the major organic product of the following reaction?
A) I B) II C) III D) IV
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36) What diene and dienophile are used in a Diels-Alder reaction to prepare the following compound?
A) I B) II C) III D) IV
37)
Rank the following anions from most to least stable, listing the most stable first.
A) I> II > III B) III > II > I C) I > III > II D) III > I > II
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38)
How would you favor the formation of the kinetic product of the following reaction?
A) Excess HBr B) Long reaction time C) Low temperature D) High pressure
39)
Which of the following is an example of a bridged bicyclic system?
A) I B) II C) III D) IV
40)
Why would the compound below not react with a dienophile in a Diels-Alder reaction?
A) The compound is not a conjugated diene. B) There are no electron withdrawing groups on the compound. C) There are no electron donating groups on the compound. D) The compound cannot adopt the s-cis conformation.
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41)
Which of the following is not a resonance structure of acetic anhydride?
A) I B) II C) III D) IV
42)
Which triene has the largest heat of hydrogenation?
A) I B) II C) III D) IV
43)
Which triene has the smallest heat of hydrogenation?
A) I B) II C) III D) IV
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44)
Which triene absorbs the longest wavelength of UV light?
A) I B) II C) III D) IV
45)
Which of the following is a major resonance contributor to the first structure?
A) I B) II C) III D) IV
46)
What is the major product of the following reaction?
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A) I B) II C) III D) IV
47)
What is the major product of the following reaction?
A) I B) II C) III D) IV
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48)
What is the major product of the following reaction?
A) I B) II C) III D) IV
49)
What is the major product of the following reaction?
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A) I B) II C) III D) IV
50)
Which of the following molecules is a naturally occurring conjugated diene?
A) Ethylene B) Acetylene C) Isoprene D) None of these are correct.
51)
Which of the following molecules contains the shortest carbon carbon bond length?
A) Ethylene B) Ethyne C) Ethane D) Butane
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Answer Key Test name: Chap 12_6e 1) C 2) D 3) B 4) B 5) B 6) B 7) D 8) C 9) D 10) A 11) D 12) B 13) B 14) D 15) C 16) D 17) B 18) A 19) B 20) A 21) A 22) B 23) D 24) D 25) B 26) D Version 1
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27) C 28) D 29) C 30) D 31) C 32) D 33) A 34) B 35) D 36) D 37) B 38) C 39) C 40) D 41) C 42) D 43) A 44) A 45) C 46) B 47) A 48) B 49) A 50) C 51) B
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CHAPTER 11 1)
What is the name of the general reaction type that aldehydes and ketones undergo?
A) Electrophilic addition B) Nucleophilic addition C) Nucleophilic substitution D) Electrophilic substitution
2) What is the name of the general reaction type that carboxylic acids, esters, and amides undergo?
A) Electrophilic acyl addition B) Nucleophilic acyl addition C) Nucleophilic acyl substitution D) Electrophilic acyl substitution
3)
What are the two steps in a nucleophilic addition mechanism?
A) Nucleophilic attack followed by protonation B) Nucleophilic attack followed by deprotonation C) Nucleophilic attack followed by substitution D) Nucleophilic attack followed by elimination
4)
Which of the following terms explain why aldehydes are more reactive than ketones?
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A) Electronegativity and resonance B) Hybridization and resonance C) Electronegativity and hybridization D) Sterics and electronics
5)
Why are ketones less reactive than aldehydes?
A) Ketones are more sterically hindered B) Ketones are less electron deficient due to donation from the two alkyl groups C) The statement is false; ketones are more reactive than aldehydes D) Both Ketones are more sterically hindered and Ketones are less electron deficient due to donation from the two alkyl groups
6)
If a compound is reduced, what is the result?
A) Fewer C-H bonds B) Increased number of C-H bonds C) Fewer C-Z bonds D) Both increased number of C-H bonds and fewer C-Z bonds
7) Rank the following compounds in order of decreasing reactivity in nucleophilic addition reactions, starting with the most reactive compound.
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A) III > I > IV > II B) II > IV > I > III C) IV > II > III > I D) II > IV > III > I
8) Rank the following compounds in order of increasing reactivity in nucleophilic acyl substitution reactions, starting with the least reactive compound.
A) III < II < I B) II < III < I C) III < I < II D) II < I < III
9)
What is the product of the following reaction?
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A) I B) II C) III D) IV
10)
What is the product of the following reaction?
A) I B) II C) III D) IV
11)
What is the starting material in the following reaction?
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A) I B) II C) III D) IV
12)
Which reagent can be used to reduce the alkene in cyclopentenone?
A) NaBH 4 B) LiAlH 4 C) H 2and Pd-C D) DIBAL-H
13)
Which reagent can be used to reduce the carbonyl in methyl vinyl ketone?
A) NaBH 4/CH 3OH B) H 2and Pd-C C) FeCl 3 D) NaH
14)
Which reagent can be used to reduce an acid chloride to an aldehyde?
A) NaBH 4 B) LiAlH(O tBu) 3 C) LiAlH 4 D) FeCl 3
15)
What reagent would be used to reduce an amide to an amine?
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A) NaBH 4 B) LiAlH(OtBu) 3 C) LiAlH 4 D) FeCl 3
16)
What is the product of the following reaction?
A) I B) II C) III D) IV
17)
What is the product of the following reaction?
A) I B) II C) III D) IV
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18)
What will be the product of the following reaction (before any aqueous work-up)?
A) I B) II C) III D) IV
19)
Why would the alcohol in the following compound need to be protected before reaction?
A) If it isn't protected, the product will be a carboxylic acid. B) The Grignard reagent will react with the alcohol before the ketone. C) Magnesium is Lewis acidic and will coordinate with the alcohol. D) There is no need to protect the alcohol.
20)
What is the purpose of a silyl ether?
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A) To protect esters from organometallic reagents and other reagents B) To protect ketones from organometallic reagents and other reagents C) To protect alcohols from organometallic reagents and other reagents D) To prevent the formation of carboxylic acids
21)
What reagent can be used to cleave a silyl ether protecting group?
A) NaOMe B) MeMgBr C) Bu 4NF D) Pd/C
22)
What is the product of the following reaction?
A) Only I B) Only II C) Only III D) Only I and II
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23)
What is the major organic product of the following reaction?
A) I B) II C) III D) IV
24)
What is the major organic product of the following reaction?
A) I B) II C) III D) IV
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25)
What is the major organic product of the following reaction?
A) I B) II C) III D) IV
26)
What is the major organic product of the following reaction?
A) I B) II C) III D) IV
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27)
What is the major organic product of the following reaction?
A) I B) II C) III D) IV
28)
What is the major organic product of the following reaction?
A) I B) II C) III D) IV
29) Rank the carbon-metal bond in the following organometallic reagents in order of decreasing polarity, starting with the most polar.
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A) II > I > III B) II > III > I C) III > I > II D) III > II > I
30)
Which of the following statements about organometallic reagents is not true?
A) Organometallic reagents contain a carbon atom bonded to a metal. B) The more polar the carbon-metal bond, the more reactive the organometallic reagent. C) Organometallic reagents react as bases and nucleophiles. D) Organometallic reagents are strong acids that readily donate a proton to water.
31)
What is the product of the following reaction?
A) I B) II C) III D) IV
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32)
What is the product of the following reaction?
A) I B) II C) III D) IV
33)
What is the major organic product of the following reaction?
A) Only I B) Only II C) Only III D) Only I and II
34)
What carbonyl compound and Grignard reagent could be used to prepare 2-butanol?
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A) Only I B) Only II C) Only III D) Only I and II
35)
What is the major organic product in the following sequence of reactions?
A) I B) II C) III D) IV
36)
What is the major organic product of the following reaction?
A) I B) II C) III D) IV
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37)
What is the major organic product of the following reaction?
A) I B) II C) III D) IV
38)
What is the major organic product in the following sequence of reactions?
A) I B) II C) III D) IV
39)
What is the missing reagent in the reaction below?
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A) [1] Mg, [2] CO 2, [3] acidic work-up B) [1] CO 2, [2] NaOH C) [1] CO 2, [2] acidic work-up D) LiAlH 4
40)
What is the major organic product of the following reaction?
A) I B) II C) III D) IV
41)
What is the major organic product of the following reaction?
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A) I B) II C) III D) IV
42)
What is the major organic product of the following reaction?
A) I B) II C) III D) IV
43)
What is the missing reagent in the reaction below?
A) Et 2CuLi then H 2O B) EtMgBr then H 2O C) NaBH 4/CH 3OH D) H 2, Pd-C
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44)
What is the missing reagent in the reaction below?
A) PhMgBr then H 2O B) Benzene, AlCl 3 C) Ph 2CuLi then H 2O D) PhLi then H 2O
45)
What is the missing reagent in the reaction below?
A) NaBH 4/CH 3OH B) H 2, Pd-C C) LiAlH 4then H 2O D) MeMgBr then H 2O
46)
What is the starting material in the reaction below?
A) Bromobenzene B) Benzyl bromide C) Benzoic acid D) Lithium benzoate
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47)
What is the missing reagent in the reaction below?
A) NaBH 4/CH 3OH B) DIBAL-H C) H 2, Pd-C D) LiAlH 4then H 2O
48) Rank the following compounds in order of increasing reactivity toward the nucleophilic hydride reagent, NaBH4.
A) I < II < III B) III < II < I C) II < III < I D) II < I < III
49) A carbonyl group, C=O, and an alkene, C=C, double bonds are both sp2hybridized. However, the chemistry of these two functional groups is very different. This can be explained by which of the following statements?
A) The bond angle of the carbonyl is larger than the bond angle of the alkene. B) The electronegative oxygen of the C=O group makes this bond polar. C) The bond of the C=C is longer that the bond of the C=O. D) There is more steric crowding in the carbonyl than in the alkene.
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50) true?
Both LiAlH 4and NaBH 4are reducing agents. Which statement about these reagents is
A) Both reagents contain polar metal-hydrogen bonds. The polarity of the B-H bond is greater than the polarity of the Al-H bond, so LiAlH 4is the stronger reducing agent. B) Both reagents contain polar metal-hydrogen bonds. The polarity of the B-H bond is greater than the polarity of the Al-H bond, so LiAlH 4is the weaker reducing agent. C) Both reagents contain polar metal-hydrogen bonds. The polarity of the B-H bond is less than the polarity of the Al-H bond, so LiAlH 4is the stronger reducing agent. D) Both reagents contain polar metal-hydrogen bonds. The polarity of the B-H bond is less than the polarity of the Al-H bond, so LiAlH 4is the weaker reducing agent.
51) If the starting material has no stereogenic centers, when carbonyl compounds are reduced with a reagent such as LiAlH 4or NaBH 4and a new stereogenic center is formed, what will the composition of the product mixture be?
A) Forms a racemic mixture of the two possible enantiomers B) Forms more of one enantiomer than another because of steric reactions around the carbonyl C) Forms more of one enantiomer than another depending on the temperature of the reaction D) Forms different products depending on the solvent used
52) Rank the following compounds in order of increasing reactivity (least to most reactive) with respect to acyl substitution. I. methyl benzoate II. benzoylchloride III. benzamide
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A) III< I < II B) II < I < III C) II < III < I D) I < III < II
53) The behavior of acid chlorides is different from that of aldehydes in a reaction with a nucleophile because
A) the acid chloride contains a better leaving group B) the aldehyde is more easily oxidized C) the carbonyl of the aldehyde is more positive D) the carbonyl of the aldehyde is less hindered
54)
What is the missing reagent in the reaction below?
A) [1] LiAlH 4, [2] H 2O B) [1] CH 3MgBr (excess), [2] H 2O C) [1] (CH 3) 2CuLi (excess), [2] H 2O D) [1] DIBAL-H, [2] H 2O
55)
What is the missing reagent in the reaction below?
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A) [1] LiAlH 4, [2] H 2O B) [1] CH 2=CHLi, [2] H 2O C) [1] (CH 2=CH) 2CuLi, [2] H 2O D) [1] DIBAL-H, [2] H 2O
56)
What is the major product from the following reaction?
A) I B) II C) III D) IV
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57)
What is the major product from the following reaction?
A) I B) II C) III D) IV
58)
What is the major product from the following reaction?
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A) I B) II C) III D) IV
59)
What is the major product from the following reaction?
A) I B) II C) III D) IV
60) The reduction of 2-butanone with sodium borohydride will result in a product with the following type of stereochemistry:
A) A mix of diastereomers B) A racemic mixture C) An enantiomeric excess of one enantiomer D) A meso compound
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Answer Key Test name: Chap 13_6e 1) B 2) C 3) A 4) D 5) D 6) D 7) B 8) D 9) B 10) C 11) D 12) C 13) A 14) B 15) C 16) B 17) C 18) C 19) B 20) C 21) C 22) D 23) B 24) A 25) B 26) A Version 1
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27) D 28) C 29) A 30) D 31) B 32) C 33) D 34) D 35) B 36) A 37) B 38) D 39) A 40) D 41) A 42) A 43) A 44) C 45) C 46) B 47) D 48) D 49) B 50) C 51) A 52) A 53) A 54) B 55) B 56) B Version 1
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57) D 58) C 59) C 60) B
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CHAPTER 14 1)
Which is the most reactive carbonyl compound?
A) I B) II C) III D) IV
2)
What is the IUPAC name for the following compound?
A) Pivaldehyde B) 2,2-Dimethylpropanal C) Tert-butyl aldehyde D) 2,2-Dimethylpentanal
3)
What is the structure of 3-methylcyclohexanone?
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A) I B) II C) III D) IV
4)
What is the structure of 2-trifluoromethyl-2-methoxybutanal?
A) I B) II C) III D) IV
5)
What is the structure of benzophenone?
A) I B) II C) III D) IV
6) Using IR spectroscopy, how can you tell the difference between a ketone and an aldehyde?
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A) A ketone has no carbonyl stretch at 1720 cm −1. B) An aldehyde has a carbonyl stretch at 1820 cm −1. C) An aldehyde has two C-H stretches between 2700-2850 cm −1. D) A ketone has no C-H stretches.
7) Which of the following will have the highest wave number for the carbonyl stretch in the IR spectrum?
A) I B) II C) III D) IV
8) Using 1H NMR spectroscopy, how can you tell the difference between an aldehyde and a ketone? A) An aldehyde has a C-H stretch (one or two) between 2700–2830 cm −1. B) An aldehyde has a proton signal between 9–10 ppm. C) A ketone has signals around 2–3 ppm. D) A ketone has a signal around 200 ppm.
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9)
What compound is consistent with the following 1H NMR spectrum?
A) Acetone B) Propanal C) Cyclobutanone D) 2-butanone
10)
Which of the following oxidants would work for the following reaction?
A) H 2Cr 2O 7 B) FeCl 3 C) I 2 D) Ag 2O
11)
What is the first step in nucleophilic addition under acidic conditions?
A) Protonation of the nucleophile B) Addition of the nucleophile C) Loss of water D) Protonation of the carbonyl
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12) Why can't you use acidic conditions (such as aqueous hydrochloric acid) for the addition of a Grignard reagent to a ketone?
A) Because the Grignard reagent will react with the acid and be quenched B) Because the ketone will be protonated and thus unreactive C) Because the ketone will form an unreactive enol D) Because the Grignard reagent won't dissolve in aqueous solutions
13)
What is the major organic product obtained from the following sequence of reactions?
A) I B) II C) III D) IV
14)
Is the following reaction reversible and, if so, under what conditions?
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A) No B) Yes, under acidic conditions C) Yes, using Pd/C D) Yes, under basic conditions
15)
What would you use to prepare the following ylide from the starting phosphonium salt?
A) Butyl lithium B) 1-Bromo-2-methylpropane C) Triphenylphosphine D) Acetic acid
16)
What is the driving force for the Wittig reaction?
A) The formation of an alkene B) The deprotonation of a phosphonium salt C) The elimination of triphenylphosphine oxide D) The formation of a phosphonium salt
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17)
What is the product of the following reaction?
A) I B) II C) III D) IV
18)
Why are strongly acidic conditions not used in the formation of enamines and imines?
A) The carbonyl will be protonated. B) The amine will be completely protonated. C) The product is not stable to strong acid. D) An enol will be formed.
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19)
What is the product of the following reaction?
A) I B) II C) III D) IV
20)
What is the product of the following reaction?
A) I B) II C) III D) IV
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21)
What needs to be done to make the following reaction proceed?
A) Heat the reaction. B) Add an acid catalyst only. C) Add a base catalyst only. D) Heat the reaction and add an acid catalyst.
22)
What needs to be done to make the following reaction go to starting materials?
A) Heat the reaction. B) Add aqueous acid. C) Add aqueous base. D) Add water.
23)
What sequence of reactions is required for the following transformation?
A) [1] NaOMe, [2] acetone B) [1] Ph 3P, [2] acetone C) [1] Ph 3P, [2] KO tBu, [3] acetone D) Acetone, heat
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24)
What is the product?
A) I B) II C) III D) IV
25)
What is the product of the following reaction?
A) I B) II C) III D) IV
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26)
What is (are) the product(s) of the following reaction?
A) I only B) II only C) III only D) II and III
27)
What is the product of the following reaction?
A) I B) II C) III D) IV
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28)
What is (are) the product(s) of the following reaction?
A) I only B) II only C) III only D) II and III
29)
What is the product of the following reaction?
A) I B) II C) III D) IV
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30)
What is the product of the following sequence of reactions?
A) I B) II C) III D) IV
31)
What is the missing reagent in the reaction below?
A) Ethyl amine, mild acid B) Diethylamine, mild acid C) Diethylamine, strong acid D) Diethylamine, NaOMe
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32)
What is the missing reagent in the reaction below?
A) I B) II C) III D) IV
33) What is the cyclic hemiacetal product formed from intramolecular cyclization of the following hydroxy aldehyde?
A) I B) II C) III D) IV
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34)
What is the missing reagent in the reaction below?
A) Methanol, acid B) Ethanol, acid C) NaOEt D) NaOMe
35) Which of the following products is (are) formed by Wittig reaction of CH3CH2CH2CHO with Ph3P CHCH3?
A) Only I B) Only II C) Only III D) Only I and II
36)
What is the IUPAC for the following compound?
A) 1-Formyl-2-nitropropane B) 1-Formyl-3-nitrobutane C) 2-Nitrobutanal D) 3-Nitrobutanal
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37)
What is the product of the following reaction?
A) I B) II C) III D) IV
38) How would the following compounds be distinguishable using IR and 1H NMR spectroscopy?
A) The 1H NMR spectrum of compound I will have two singlets. B) The C=O absorption in the IR spectrum of compound I will be at a higher wave number than that of compound II. C) The 1H NMR spectrum of compound II will have one triplet at a chemical shift of about 4. D) The 1H NMR spectrum of compound I will have two singlets AND the C=O absorption in the IR spectrum of compound I will be at a higher wave number than that of compound II.
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39)
Name the following aldehyde.
A) 1-Methylcyclopentanal B) 2-Methylcyclopentanal C) 2-Methylcyclopentanecarbaldehyde D) 1-Methylcyclopentanylcarbaldehyde
40) Butanal (MW= 72) has a boiling point of 76 °C while butanol (MW= 74) has a boiling point of 118 °C. What accounts for this difference in boiling points?
A) Butanol is polar while butanal is not polar. B) Butanol can exhibit dipole-dipole interactions while butanal cannot. C) Butanol can hydrogen bond and butanal cannot hydrogen bond. D) Butanal is less sterically hindered than butanol.
41)
Identify how you could synthesize an enamine.
A) React a ketone or an aldehyde with a secondary amine. B) React a ketone or an aldehyde with a primary amine. C) React a ylide with a primary amine. D) React a ylide with a secondary amine.
42) When an aldehyde is reacted with excess ethanol with an acid as a catalyst, what is the product called?
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A) Hemiacetal B) Di-ether C) Di-alkoxy alkane D) Acetal
43) Cyclic acetals are used as protecting groups for ketones or aldehydes because they are inert to all of the following reagents except
A) aqueous acid. B) aqueous base. C) oxidizing reagents. D) reducing reagents.
44)
Which of the following statements about carbohydrates is not true?
A) Carbohydrates are sugars and starches. B) Carbohydrates often contain acetals and hemiacetals. C) In solution, glucose is in the cyclic acetal form only. D) Glucose can form a cyclic hemiacetal from the acyclic polyhydroxy aldehyde.
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45)
What is the product of the following reaction?
A) I B) II C) III D) IV
46)
What product is formed when the following acetal is hydrolyzed with aqueous acid?
A) I B) II C) III D) IV
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47)
What product is formed when the following compound is hydrolyzed with aqueous acid?
A) I B) II C) III D) IV
48)
Give the IUPAC name for the following compound.
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A) R-3-methylcyclohexanone B) S-3-methylcyclohexanone C) R-5-methylcyclohexanone D) S-5-methylcyclohexanone
49)
Give the IUPAC name for the following compound.
A) R-3-bromobutanal B) S-3-bromobutanal C) R-2-bromobutan-4-al D) S-2-bromobutan-4-al
50)
Give the IUPAC name for the following compound.
A) R-4-bromo-2-pentanone B) S-4-bromo-2-pentanone C) R-2-bromo-4-pentanone D) S-2-bromo-4-pentanone
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51)
Give the IUPAC name for the following compound.
A) R-3-hydroxybutanal B) S-3-hydroxybutanal C) R-2-hydroxybutan-4-al D) S-2-hydroxybutan-4-al
52)
Give the IUPAC name for the following compound.
A) R-4-hydroxy-2-pentanone B) S-4-hydroxy-2-pentanone C) R-2-hydroxy-4-pentanone D) S-2-hydroxy-4-pentanone
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53)
What is the major product of the following reaction?
A) I B) II C) III D) IV
54)
What is the major product of the following reaction?
A) I B) II C) III D) IV
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Answer Key Test name: Chap 14_6e 1) A 2) B 3) B 4) D 5) B 6) C 7) A 8) B 9) C 10) A 11) D 12) A 13) C 14) D 15) A 16) C 17) A 18) B 19) D 20) A 21) D 22) B 23) C 24) B 25) A 26) D Version 1
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27) C 28) A 29) A 30) A 31) B 32) C 33) B 34) B 35) D 36) D 37) B 38) D 39) C 40) C 41) A 42) D 43) A 44) C 45) B 46) C 47) A 48) A 49) A 50) B 51) A 52) B 53) B 54) B
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CHAPTER 15 1)
What is the hybridization of the carbon atom in a carboxy group?
A) sp B) sp2 C) sp3 D) p
2) Why is the C-O single bond of a carboxylic acid shorter than the C-O single bond of an alcohol? A) The carbon in the alcohol is sp2hybridized and has a higher percent s-character that lengthens the C-O bond in the alcohol. B) The carbon in the carboxylic acid is sp3hybridized and has a lower percent scharacter that shortens the C-O bond in the carboxylic acid. C) The carbon in the carboxylic acid is sp hybridized and has a higher percent scharacter that shortens the C-O bond in the carboxylic acid. D) The carbon in the carboxylic acid is sp2hybridized and has a higher percent scharacter that shortens the C-O bond in the carboxylic acid.
3)
What two groups make up the carboxylic acid group (RCOOH)?
A) Carbon dioxide and hydrogen B) Carbonyl and hydroxyl C) Carbon monoxide and hydroxyl D) Carbonyl oxide and hydrogen
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4)
What is the correct IUPAC name of the following compound?
A) 4-Isopropyl-3-methylbutanoic acid B) 2,4-Dimethylhexanoic acid C) 3,5-Dimethylhexanoic acid D) 3,5-Dimethy-1-hexanoic acid
5)
What is the correct IUPAC name of the following compound?
A) 3,5,5-Trimethylcyclohexanecarboxylic acid B) 3,3,5-Trimethylcyclohexanecarboxylic acid C) 3,3,5-Trimethylcyclohexanoic acid D) 3,5,5-Trimethylcyclohexanoic acid
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6)
What is the correct IUPAC name of the following compound?
A) 2- sec-Butyl-4,4-dimethylnonanoic acid B) 4,4-Dimethyl-2-isobutylnonanoic acid C) 4,4-Dimethyl-2- sec-butylnonanoic acid D) 2-Isobutyl-4,4-dimethylnonanoic acid
7)
What is the correct IUPAC name of the following compound?
A) 3,4-Dimethylcyclohexanoic acid B) 3,4-Dimethylcyclohexanecarboxylic acid C) 4,5-Dimethylcyclohexanecarboxylic acid D) 1,2-Dimethylcyclohexanecarboxylic acid
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8)
What is the common name of the following compound?
A) a-Methylbutyric acid B) a-Propylpropionic acid C) a-Methylvaleric acid D) a-Methylcaproic acid
9)
What is the common name of the following compound?
A) a,b-Dimethoxyvaleric acid B) 2,3-Dimethoxyvaleric acid C) 2,3-Dimethoxycaproic acid D) a,b-Dimethoxycaproic acid
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10)
What is the common name of the following compound?
A) b,b-Dimethyl-a-fluorobutyric acid B) a-Fluoro-b,b-dimethylbutyric acid C) a-Fluoro-b,b,b-trimethylpropionic acid D) a-Fluoro-b,b,b-trimethylbutyric acid
11)
What is the common name of the following compound?
A) Propanedioic acid B) 1,3-Propanedicarboxylic acid C) Malonic acid D) Succinic acid
12)
What is the correct IUPAC name of the following compound?
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A) ( E)-2-Hexenoic acid B) ( Z)-2-Hexenoic acid C) ( E)-4-Hexenoic acid D) ( Z)-4-Hexenoic acid
13)
What is the correct IUPAC name of the following compound?
A) 2-Methoxypentanoic acid B) 2-Methoxybutanoic acid C) 4-Methoxybutanoic acid D) 4-Methoxypentanoic acid
14)
Which of the following is the structure of oxalic acid?
A) I B) II C) III D) IV
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15)
Which of the following is the correct IUPAC name for the following structure?
A) Potassium propanoate B) Butanoic potassium C) Potassium propanoic D) Potassium butanoate
16)
Which of the following is the most polar organic compound?
A) CH 3CH 2CH 2CH 3 B) CH 3CH 2CHO C) CH 3CH 2CH 2OH D) CH 3COOH
17) Arrange the following compounds in order of increasing boiling point, putting the compound with the lowest boiling point first.
A) I < II < III < IV B) I < IV < II < III C) III < II < IV < I D) II < IV < I < III
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18) Arrange the following compounds in order of decreasing water solubility, putting the most soluble compound first.
A) I > II > III > IV B) I > IV > II > III C) I > II > IV > III D) IV > III > II > I
19) Arrange the following compounds in order of increasing water solubility, putting the least soluble compound first.
A) I < II < III < IV B) II < I < III < IV C) I < III < II < IV D) IV < II < III < I
20)
What two strong absorptions are characteristic of the IR spectrum of carboxylic acids? A) A C=O absorption at 1710 cm −1and a C-H absorption at 3000 cm −1. B) A C=O absorption at 1710 cm −1and an O-H absorption at 2500–3500 cm −1. C) A C=O absorption at 1600 cm −1and an O-H absorption at 2500–3000 cm −1. D) A C-O absorption at 1500 cm −1and an O-H absorption at 2500–3500 cm −1.
21)
Where do the two noteworthy peaks of carboxylic acids appear in 1HNMR spectra?
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A) Between 10 and 12 ppm for the OH proton and 2–2.5 ppm for the protons on the a carbon to the carboxy group. B) Between 6 and 9 ppm for the OH proton and 2–2.5 ppm for the protons on the a carbon to the carboxy group. C) Between 10 and 12 ppm for the OH proton and 1–1.5 ppm for the protons on the a carbon to the carboxy group. D) Between 6 and 9 ppm for the OH proton and 1–1.5 ppm for the protons on the a carbon to the carboxy group.
22)
Why is pure acetic acid often called glacial acetic acid?
A) Because it freezes just below 0°C, forming white crystals B) Because it freezes just below 100°C, forming white crystals C) Because it freezes just below room temperature, forming white crystals D) Because it freezes just above room temperature, forming white crystals
23)
Which of the following reagents can accomplish the transformation below?
A) PCC, CH 2Cl 2 B) [1] LiAlH 4, THF; [2] H 2O C) [1] O 3; [2] H 2O D) K 2Cr 2O 7, H 2SO 4, H 2O
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24)
What is the other product formed in the oxidation of the following terminal alkyne?
A) HCOOH B) HCOH C) CO 2 D) CO
25)
Which of the following cannot be the starting material for the following reaction?
A) I B) II C) III D) IV
26) In the presence of strong acids, which of the oxygen atoms on the carboxyl group is preferentially protonated and why?
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A) Protonation occurs at the carbonyl oxygen because the resulting conjugate acid is stabilized by resonance. B) Protonation occurs at the carbonyl oxygen because the resulting conjugate base is stabilized by the inductive effect. C) Protonation occurs at the hydroxyl oxygen because the resulting conjugate acid is stabilized by resonance. D) Protonation occurs at the hydroxyl oxygen because the resulting conjugate base is stabilized by the inductive effect.
27) Which of the following structures is the major contributor to the resonance hybrid of the phenoxide anion?
A) I B) II C) III D) IV
28) first.
Arrange the following compounds in order of increasing acidity, putting the least acidic
A) I < II < III < IV B) IV < III < II < I C) III < IV < II < I D) IV < II < III < I
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29) 3CH
Which of the following bases are strong enough to significantly deprotonate ethanol, CH 2OH ( pKa = 16)?
A) NaOCH 3 B) NaOH C) NaH D) NaOCH 2CH 3
Rank the labeled protons (Ha-Hd) in order of increasing acidity, starting with the least 30) acidic.
A) Ha < Hb < Hc < Hd B) Hb < Hc < Ha < Hd C) Hd < Ha < Hc < Hb D) Hb < Hc < Hd < Ha
31) first.
Rank the following compounds in order of decreasing acidity, putting the most acidic
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A) IV > III > I > II B) IV > II > I > III C) II > I > IV > III D) II > I > III > IV
32) first.
Rank the following compounds in order of increasing acidity, putting the least acidic
A) II < III < I < IV B) II < I < III < IV C) IV < III < I < II D) IV < I < II < III
33) first.
Rank the following compounds in order of increasing acidity, putting the least acidic
A) III < II < IV < I B) III < IV < II < I C) I < IV < II < III D) I < II < III < IV
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34) first.
Rank the following compounds in order of decreasing acidity, putting the most acidic
A) IV > III > II > I B) IV > I > III > II C) I > II > III > IV D) IV > II > III > I
35) first.
Rank the following compounds in order of increasing acidity, putting the least acidic
A) I < II < III < IV B) III < II < I < IV C) IV < I < II < III D) I < IV < III < II
36) first.
Rank the following compounds in order of decreasing acidity, putting the most acidic
A) III > IV > I > II B) IV > III > I > II C) I > II > III > IV D) IV > III > II > I
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37) What physical property and reaction type are used by extraction as useful techniques to separate and purify mixtures of compounds?
A) Physical property = solubility differences; reaction type = acid-base reaction B) Physical property = boiling point; reaction type = acid-base reaction C) Physical property = solubility differences; reaction type = oxidation-reduction D) Physical property = density; reaction type = oxidation-reduction
What would happen if a mixture of benzoic acid (C 6H 5COOH) and NaCl is added to a 38) separatory funnel containing H 2O and CH 2Cl 2?
A) The benzoic acid would dissolve in the water layer and the NaCl would dissolve in the organic layer. B) The benzoic acid would dissolve in the organic layer and the NaCl would dissolve in the water layer. C) Both benzoic acid and NaCl would dissolve in the organic layer. D) Both benzoic acid and NaCl would dissolve in the water layer.
What would happen if a mixture of benzoic acid and cyclohexanol dissolved in CH 2Cl 39) 2is treated with aqueous NaOH solution?
A) Benzoic acid would remain in the CH 2Cl 2layer, and cyclohexanol would dissolve in the aqueous layer. B) Benzoic acid would dissolve in the aqueous layer while cyclohexanol would remain in the CH 2Cl 2layer. C) The salt of benzoic acid would dissolve in the aqueous layer while cyclohexanol would remain in the CH 2Cl 2layer. D) The salt of benzoic acid would remain in the CH 2Cl 2layer while cyclohexanol would dissolve in the aqueous layer.
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40)
What is the overall charge of the amino acid, alanine, at pH = 2?
A) + 1 B) − 1 C) No overall charge D) + 2
41)
What is the overall charge of the amino acid, alanine, at pH = 10?
A) + 1 B) − 1 C) No overall charge D) − 2
42)
What is the overall charge of the amino acid, alanine, at pH = 7?
A) + 1 B) − 1 C) No overall charge D) + 2
43) As applied to the chemistry of amino acids, what is the definition for the isoelectric point?
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A) The pH at which the amino acid exists primarily in its acidic form. B) The pH at which the amino acid exists primarily in its basic form. C) The pH at which the amino acid exists as a mixture of isomers. D) The pH at which the amino acid exists primarily in its neutral form.
44)
Which of the following compounds is most basic?
A) I B) II C) III D) IV
45)
Which of the following compounds is least basic?
A) I B) II C) III D) IV
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46)
Give the IUPAC name for the following compound.
A) (E,R)-2-bromo-3-pentenoic acid B) (Z,R)-2-bromo-3-pentenoic acid C) (E,S)-2-bromo-3-pentenoic acid D) (Z,S)-2-bromo-3-pentenoic acid
47)
Give the IUPAC name for the following compound.
A) (E,R)-2-bromo-3-pentenoic acid B) (Z,R)-2-bromo-3-pentenoic acid C) (E,S)-2-bromo-3-pentenoic acid D) (Z,S)-2-bromo-3-pentenoic acid
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48)
Give the IUPAC name of the following compound.
A) R-2-methylpentanenitrile B) S-2-methylpentanenitrile C) R-2-nitrilehexane D) S-2-nitrilehexane
49)
Give the IUPAC name for the following compound.
A) (E,R)-2-methyl-3-pentenenitrile B) (E,S)-2-methyl-3-pentenenitrile C) (Z,R)-2-methyl-3-pentenenitrile D) (Z,S)-2-methyl-3-pentenenitrile
50)
What reagents are necessary to perform the following reaction?
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A) H 2O, H + B) LiAlH 4, H 2O C) DIBAL-H, H 2O D) CH 3MgBr, H 2O
51)
What reagents are necessary to perform the following reaction?
A) H 2O, H + B) LiAlH 4, H 2O C) DIBAL-H, H 2O D) CH 3MgBr, H 2O
52)
What reagents are necessary to perform the following reaction?
A) H 2O, H + B) LiAlH 4, H 2O C) DIBAL-H, H 2O D) CH 3MgBr, H 2O
53)
What reagents are necessary to perform the following reaction?
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A) H 2O, H + B) LiAlH 4, H 2O C) DIBAL-H, H 2O D) CH 3MgBr, H 2O
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Answer Key Test name: Chap 15_6e 1) B 2) D 3) B 4) C 5) B 6) A 7) B 8) C 9) D 10) B 11) C 12) B 13) D 14) B 15) D 16) D 17) B 18) C 19) D 20) B 21) A 22) C 23) D 24) C 25) B 26) A Version 1
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27) D 28) B 29) C 30) B 31) D 32) B 33) C 34) A 35) C 36) D 37) A 38) B 39) C 40) A 41) B 42) C 43) D 44) D 45) B 46) C 47) B 48) A 49) A 50) A 51) B 52) C 53) D
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CHAPTER 16 1)
Which of the following is a lactam?
A) I B) II C) III D) IV
2)
Why is an amide less reactive to nucleophilic acyl substitution than an acid chloride?
A) Nitrogen is a better leaving group. B) Chloride is a better leaving group. C) Nitrogen donates more electron density into the carbonyl. D) The amide anion is less basic.
3)
What is the IUPAC name for the following compound?
A) Methyl 3-methylbutanamide B) 5-Methylhexanamide C) N-Methyl 3-methylhexanamide D) N-Methyl 3-methylbutanamide
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4)
What is the IUPAC name for the following compound?
A) 4-Fluoro-3-methylbenzoate B) 4-Fluoro-3-methylbenzoic acid C) 3-Methyl-4-fluorobenzoic acid D) 4-Fluoro-5-methylbenzoic acid
5)
What is the structure for acetic propanoic anhydride?
A) I B) II C) III D) IV
6)
What is the structure for ethyl 4-chlorobenzoate?
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A) I B) II C) III D) IV
7)
What is the structure for 3-cyanocyclopentanone?
A) I B) II C) III D) IV
8)
What is the IUPAC name for the following compound?
A) 2-fluorobutanonitrile B) 2-fluoropentanonitrile C) 3-fluoropentanonitrile D) 2-fluorobutylcyanide
9)
Where is the carbonyl absorption found in the IR spectrum of a simple ester?
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A) 2.5 ppm B) 2250 cm −1 C) 3800 cm −1 D) 1740 cm −1
10)
Which of the following peaks would you see in the IR spectrum of a carboxylic acid?
A) A flat line (carboxylic acids are not IR active) B) A sharp line at 2250 cm −1 C) A broad peak from 3800-2800 cm −1 D) A broad peak from 800-600 cm −1
11) You see an absorption at 2250 cm −1in the IR spectrum of a compound. What kind of functional group is present?
A) A ketone B) An aldehyde C) An ester D) A nitrile
12) Where do the carbonyl signals appear in the 13C NMR spectrum of carboxylic acid derivatives? A) 1700 cm −1 B) 180−160 ppm C) 2.5−3.0 ppm D) 100−80 ppm
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13)
Which structure is consistent with the following 1H NMR spectrum?
A) Ethyl acetate B) 2-Propanone C) 3,3-Dimethyl-2-pentanone D) Ethyl 2,2-dimethylpropionate
14)
What is the first step in the general mechanism for nucleophilic acyl substitution?
A) Protonation of the carbonyl B) Removal of an a-proton C) Addition of the nucleophile to the carbonyl D) Loss of the leaving group
15)
Why doesn't nucleophilic acyl substitution stop at the tetrahedral intermediate?
A) The nucleophile is too basic. B) Reforming the carbonyl is energetically favorable. C) The leaving group is unstable and wants to be negatively charged. D) There is no tetrahedral intermediate.
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16)
Will the following reaction occur?
A) Yes B) No
17)
Will the following reaction occur?
A) Yes B) No
18)
Will the following reaction occur?
A) Yes B) No
19)
Why is pyridine included in the reaction of an acid chloride and an amine or alcohol?
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A) Pyridine will deprotonate the amine or alcohol, making it a better nucleophile. B) Pyridine will neutralize the acid by-product of the reaction. C) Pyridine will protonate the carbonyl of the acid chloride, making it more reactive. D) Pyridine will absorb the heat of the reaction.
20)
What is the product of the following reaction?
A) I B) II C) III D) IV
21)
What is the product of the following reaction?
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A) I B) II C) III D) IV
22)
How can you convert a carboxylic acid into an ester?
A) Heat with an alcohol and catalytic acid. B) Deprotonate with a base and react with an alcohol. C) Deprotonate with a base and react with an alkyl halide. D) Both heat with an alcohol and catalytic acid and deprotonate with a base and react with an alkyl halide. E) Both heat with an alcohol and catalytic acid and deprotonate with a base and react with an alcohol.
23)
How can you convert a carboxylic acid into an acid chloride?
A) Heat with hydrochloric acid. B) React with thionyl chloride (SOCl 2). C) React with sodium chloride. D) React with Cl 2and FeCl 3.
24)
What is the product of the following reaction?
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A) I B) II C) III D) IV
25)
What is the direct product of the base-promoted hydrolysis of an ester?
A) A nitrile B) A carboxylic acid C) An amide D) A carboxylic acid salt
26)
Which of the following two amides will react more readily with a nucleophile? Why?
A) I, because it is less hindered B) II, because it is less hindered C) I, because it is more strained D) II, because it is more strained
27)
What is the structure for the compound whose IUPAC name is pentyl 2-methylbutanoate?
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A) I B) II C) III D) IV
28)
What is the IUPAC name for the following compound?
A) Propionyl phenol B) Phenyl propanoate C) Phenol propanoate D) Phenyl acetate
29)
What is the product of the following reaction?
A) I B) II C) III D) IV
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30)
What is the product of the following reaction?
A) I B) II C) III D) IV
31)
What is the product of the following reaction?
A) I B) II C) III D) IV
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32)
What is the product of the following reaction?
A) I B) II C) III D) IV
33)
What is the product of the following reaction?
A) I B) II C) III D) IV
34)
What is the missing reagent in the reaction below?
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A) Acetic acid B) NaOMe C) SOCl 2 D) Pyridine
35)
Which of the following reaction conditions can be used to synthesize an ester (RCOOR')?
A) RCOCl + R'NH 2+ pyridine B) RCOOH + R'OH + H + C) RCOOH + R'OH + OH − D) RCONH 2+ R'OH
36) Rank the following compounds in order of increasing reactivity in nucleophilic acyl substitution.
A) I < II < III B) III < II < I C) II < III < I D) III < I < II
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37)
Draw the structure of N-phenyl acetamide.
A) I B) II C) III D) IV
38) Which of the following substrates cannot be used as an immediate precursor to synthesize an ester?
A) I B) II C) III D) IV
39)
From the list below, pick the compound that does not react with acetyl chloride.
A) Isopropyl alcohol B) Benzoic acid C) Ammonia D) Triethyl amine
40)
Which of the following statements about amides is true?
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A) Amides react with methyl alcohol in the presence of an acid catalyst to form an ester. B) Amides are hydrolyzed in acid or base to form carboxylic acids or carboxylate anions. C) Amides react with thionyl chloride to form the acid chloride. D) Amides do not react under any conditions. They are inert compounds.
41) An unknown compound has a sharp, medium peak at 2250 cm −1. The unknown compound is probably
A) an alkane. B) an aldehyde. C) an alkene. D) a nitrile.
42)
All of the following contain sp2hybridized atoms in their functional group except
A) a carboxylic acid. B) a nitrile. C) an aldehyde. D) an anhydride.
43)
What is the product formed by hydrolysis of the following lactone with acid?
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A) I B) II C) III D) IV
44)
What is the product formed by hydrolysis of the following lactone with acid?
A) I B) II C) III D) IV
45) Which of the following compounds will have the lowest frequency for carbonyl absorption in IR spectroscopy?
A) I B) II C) III D) IV
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46)
Give the IUPAC name for the following compound.
A) R-3-methoxybutanoyl chloride B) S-3-methoxybutanoyl chloride C) R-2-methoxy-4-butanoyl chloride D) S-2-methoxy-4-butanoyl chloride
47)
Give the IUPAC name for the following compound.
A) Butyl ethanoate B) Ethyl butanoate C) 4-hexanoate D) 3-hexanoate
48)
What reagents are necessary to perform the following reaction?
A) EtOH, H + B) CH 3CH 2NH 2, DCC C) SOCl 2 D) Heat
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49)
What reagents are necessary to perform the following reaction?
A) EtOH, H + B) CH 3CH 2NH 2, DCC C) SOCl 2 D) Heat
50)
What reagents are necessary to perform the following reaction?
A) EtOH, H + B) CH 3CH 2NH 2, DCC C) SOCl 2 D) Heat
51)
What reagent(s) would be needed to complete the following organic reaction?
I. CH3NH2 II. NH4Cl III. NH3 IV. H2O
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A) I B) II C) III D) IV
52)
Acetyl coenzyme A is commonly used to perform the following type of organic reaction:
A) Acyl transfer reaction B) Wittig reaction C) Oxidation D) Reduction
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Answer Key Test name: Chap 16_6e 1) A 2) C 3) D 4) B 5) A 6) D 7) B 8) C 9) D 10) C 11) D 12) B 13) D 14) C 15) B 16) B 17) A 18) B 19) B 20) C 21) B 22) D 23) B 24) C 25) D 26) C Version 1
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27) A 28) B 29) C 30) A 31) D 32) C 33) D 34) C 35) B 36) B 37) C 38) B 39) D 40) B 41) D 42) B 43) B 44) A 45) B 46) A 47) B 48) A 49) B 50) C 51) C 52) A
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CHAPTER 17 1)
Which is the more stable form of acetophenone?
A) Only I B) Only II C) Only III D) I and II are equally stable
2)
Which is the most stable form of 1,3-cyclohexanedione?
A) I B) II C) III D) IV
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3)
Which of the following is an enol form of the following compound?
A) I B) II C) III D) IV
4)
Why is the enolate of acetone less basic than the allyl anion derived from propene?
A) Because there are more atoms in acetone B) Because there are more resonance structures for the enolate of acetone C) It isn't; the allyl anion is less basic. D) One of the resonance structures for the enolate places the negative charge on the more electronegative oxygen.
5)
Which of the following four compounds is the most acidic?
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A) I B) II C) III D) IV
6)
Will acetone be completely deprotonated by potassium tert-butoxide?
A) Yes B) No
7)
Will acetophenone be completely deprotonated by lithium diisopropylamide (LDA)?
A) Yes B) No
8)
Which is the kinetic enolate of 2-methylcyclohexanone?
A) I B) II C) III D) IV
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9)
If you want to form a thermodynamic enolate, you want to
A) keep the reaction as cold as possible. B) use an aprotic solvent such as THF. C) use a protic solvent such as ethanol. D) use a carboxylic acid.
10)
If you want to form a kinetic enolate, you want to
A) use a strong, non-nucleophilic base such as LDA. B) use a protic solvent. C) use a low temperature. D) both use a strong, non-nucleophilic base such as LDA and use a low temperature.
11) Which of the following is the intermediate for halogenation of ketones under acidic conditions?
A) An enolate B) An enol C) A tautomer D) An epimer
12) Why is it difficult to stop the halogenation of ketones under basic conditions at the monohalogenated stage?
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A) The ketone undergoes a Bayer-Villigar oxidation. B) The ketone is reduced. C) The ketone undergoes an Aldol reaction. D) The bromine helps to stabilize the second enolate, making the product more acidic than the starting material.
13)
Why can't you prepare 2-tert-butylcyclohexanone by the following reaction?
A) Because tert-butyl bromide is too basic. B) Because tert-butyl bromide cannot undergo an S N2 reaction. C) Because tert-butyl bromide is a nucleophile. D) Because tert-butyl bromide is not a stable compound.
14)
What are the three steps in the malonic ester synthesis?
A) Deprotonation, alkylation, hydrolysis/decarboxylation B) Hydrogenation, alkylation, deprotonation C) Alkylation, hydrolysis/decarboxylation. hydrogenation D) Hydrolysis/decarboxylation, deprotonation, alkylation
15)
What is the missing reagent for the following reaction?
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A) Br 2/HOAc B) Br 2/KOH C) Cl 2/FeCl 3 D) Br 2/FeBr 3
16)
Starting with cyclohexanone, how could you prepare the diketone below?
A) Treat cyclohexanone with a base under thermodynamic conditions. B) Hydrogenate cyclohexanone with Raney nickel. C) Convert cyclohexanone into the a-bromoketone and then react this with the enolate of cyclohexanone. D) Convert cyclohexanone into an enamine with diethylamine and then react this with more cyclohexanone.
17)
What is the product of the following reaction?
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A) I B) II C) III D) IV
18)
What is the product of the following reaction?
A) I B) II C) III D) IV
19)
What is (are) the product(s) of the following reaction?
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A) Only I B) Only II C) Only III D) Only I and III
20)
What is the missing reagent in the reaction below?
A) Br 2/AcOH B) I 2/KOH C) I 2 D) KOH
21)
What is the starting material in the following reaction?
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A) I B) II C) III D) IV
22)
What is the starting material for the following reaction?
A) I B) II C) III D) IV
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23)
Which of the following compounds is an enol of compound X drawn below?
A) Only I B) Only II C) Only III D) Only I and II
24)
Which of the following are enol forms of ethyl acetoacetate drawn below?
A) Only I B) Only II C) Only III D) Only I and II
25) For most compounds with a single keto group in the molecule, equilibrium favors the keto form over the enol form of the compound. This is due largely to what?
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A) The C=O bond is much stronger than the C=C bond. B) The C=C bond is much stronger than the C=O bond. C) The keto form can undergo intramolecular hydrogen bonding. D) The enol form can undergo intramolecular hydrogen bonding.
26) It has been found that b-dicarbonyl compounds have a greater concentration of the enol form over the keto form. This can be explained by
A) the C=C of the enol is conjugated with the carbonyl group. B) the -OH of the enol can hydrogen bond to the oxygen of the nearby carbonyl group. C) Both of these choices are true. D) None of the choices are true.
27) The reaction below is a direct enolate alkylation. It has been found that this reaction only works well with unhindered methyl and 1° alkyl halides. Pick the statement that best explains this observation.
A) The nucleophilic enolate requires a reaction center that has a positive charge. B) Hindered alkyl halides do not undergo S N1 reactions. C) Hindered alkyl halides do not undergo S N2 reactions. D) Methyl and 1° alkyl halides can form carbocations that can readily react with the nucleophilic enolate.
28)
The following molecule is called
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A) a 1,3-diketopentanoate. B) a diethyl malonate. C) an ethyl acetoacetate. D) a b-keto ester.
29) A simple chemical test to distinguish between acetone and 3-pentanone would be the reaction of the compounds with
A) bromine with acetic acid. B) bromine and aqueous hydroxide ion. C) THF, LDA at −78 °C followed by reaction with bromine. D) base and methyl bromide.
30)
Which is the thermodynamic enolate of 2-methylcyclohexanone?
A) I B) II C) III D) IV
31)
Which of the following compounds is the most acidic?
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A) Ethyl acetoacetate B) 2-Butanone C) 1-Butanol D) 3-Pentanone
32)
Which is the most acidic proton in the following compound?
A) I B) II C) III D) IV
33)
Which is the most acidic proton in the following compound?
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A) I B) II C) III D) IV
34) Which of the following bases will completely convert 1,4-cyclohexandione into an enolate?
A) Sodium hydroxide B) Sodium methoxide C) Sodium tert-butoxide D) Sodium hydride
35) Which of the following compounds would undergo racemization in the presence of a base?
A) I B) II C) III D) IV
36)
Which of the following ketones will give a positive iodoform test?
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A) 3-Heptanone B) 2-Pentanone C) 3-Hexanone D) Cyclohexanone
37)
What is the major product of the following reaction?
A) I B) II C) III D) IV
Treatment of 2-hexanone with NaOCH2CH3 followed by CH3Br affords compound X 38) (C7H14O) as the major product. X shows a strong absorption in the IR spectrum at 1713 cm−1, and its 1H NMR data is given below. What is the structure of X?
Signal #
Shift (ppm)
Multiplicity
Integration
1
0.96
triplet
3H
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2
1.16
doublet
3H
3
1.33
multiplet
2H
4
1.53
multiplet
2H
5
2.09
singlet
3H
6
2.52
multiplet
1H
A) I B) II C) III D) IV
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39) The malonic ester synthesis can be adapted to synthesize a-amino acids by using diethyl acetamidomalonate as the starting material. Select the structure of the amino acid produced by the following synthesis.
A) I B) II C) III D) IV
40)
Select the appropriate sequence of reactions to accomplish the following synthesis.
A) [1] Br 2, CH 3CO 2H; [2] Li 2CO 3, LiBr, DMF; [3] CH 3CH 2CH 2CH 2Br B) [1] Br 2, CH 3CO 2H; [2] Mg, Et 2O; [3] CH 3CH 2CH 2CH 2Br C) [1] LDA; [2] BrCH 2CH 2CH 2CH 2Br; [3] NaOEt D) [1] NaOEt; [2] BrCH 2CH 2CH 2CH 2Br; [3] LDA
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41)
What is the starting material required to accomplish the following transformation?
A) I B) II C) III D) IV
42) Vitamin C is a stable enediol. Which is the structure of a possible keto form in equilibrium with the enediol form?
A) I B) II C) III D) IV
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43)
What is the structure of X, product of the following reaction?
A) I B) II C) III D) IV
44)
Which of the following is a possible enol form of 2-butanone?
A) I B) II C) III D) II and III
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45)
Which of the following is the most acidic compound?
A) I B) II C) III D) IV
46)
Which of the following is the least acidic compound?
A) I B) II C) III D) IV
47)
Which of the following would undergo racemization under basic conditions?
A) I B) II C) III D) IV
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48) Which of the following compound would most likely undergo racemization under basic conditions?
A) (R)-3-Iodo-2-pentanone B) (R)-4-Iodo-2-pentanone C) (S)-4-Iodo-2-pentanone D) (R)-5-Iodo-5-bromo-2-pentanone
49) Which of the following organic molecules will undergo decarboxylation to form an amine?
A) Histidine B) Pyridine C) Ethyl acetoacetate D) Isoamyl acetate
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Answer Key Test name: Chap 17_6e 1) B 2) A 3) D 4) D 5) C 6) B 7) A 8) C 9) C 10) D 11) B 12) D 13) B 14) A 15) A 16) C 17) C 18) D 19) D 20) B 21) D 22) C 23) D 24) D 25) A 26) C Version 1
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27) C 28) D 29) B 30) D 31) A 32) A 33) C 34) D 35) B 36) B 37) A 38) D 39) A 40) C 41) B 42) C 43) A 44) D 45) B 46) A 47) B 48) A 49) A
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CHAPTER 18 1)
What is the general name for the reaction product formed in an aldol addition reaction?
A) a-Hydroxy carbonyl compound B) b-Hydroxy carbonyl compound C) g-Hydroxy carbonyl compound D) a,b-Hydroxy carbonyl compound
2)
In the correct order, what are the three steps in the mechanism of an Aldol reaction?
A) Protonation, enolate formation, nucleophilic addition B) Enolate formation, protonation, nucleophilic addition C) Enolate formation, nucleophilic addition, protonation D) Nucleophilic addition, enolate formation, protonation
3) Which of the following statements about Aldol reactions with either aldehydes or ketones is true?
A) Equilibrium favors the products with aldehydes; equilibrium favors the starting materials with ketones. B) Equilibrium favors the starting materials with aldehydes; equilibrium favors the products with ketones. C) Equilibrium favors the products with both aldehydes and ketones. D) Equilibrium favors the starting materials with both aldehydes and ketones.
4)
What reaction type is an Aldol reaction?
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A) Nucleophilic substitution B) Electrophilic substitution C) Electrophilic addition D) Nucleophilic addition
5) What is the Aldol addition product formed from reaction of the following compound with itself?
A) I B) II C) III D) IV
What is the Aldol addition product formed from the reaction of (CH3)2CHCH2CHO with 6) itself?
A) I B) II C) III D) IV
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What is the Aldol addition product formed from the reaction of acetone, (CH3)2CO, with 7) itself?
A) I B) II C) III D) IV
8) Which of the following carbonyl compounds will undergo Aldol addition reactions when treated with aqueous sodium hydroxide?
A) I B) II C) III D) None of the choices
9) Which of the following carbonyl compounds does not undergo Aldol addition reactions when treated with aqueous sodium hydroxide?
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A) I B) II C) III D) IV
10)
Why is the Aldol reaction often called an Aldol condensation?
A) The initially formed b-hydroxy carbonyl compound loses a hydroxyl group. B) The initially formed b-hydroxy carbonyl compound loses an oxygen atom. C) The initially formed b-hydroxy carbonyl compound loses a hydrogen atom. D) The initially formed b-hydroxy carbonyl compound loses water.
11) What is the general name for the class of products formed in an Aldol condensation reaction?
A) b,g-Unsaturated carbonyl compound B) a,b-Unsaturated carbonyl compound C) a,g-Unsaturated carbonyl compound D) b-Hydroxy carbonyl compound
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12) Which is the unsaturated carbonyl compound formed by the dehydration of the following b-hydroxy carbonyl compound?
A) I B) II C) I and II D) None of the choices
13) Which is the unsaturated carbonyl compound formed in the dehydration of the following b-hydroxy carbonyl compound?
A) I B) II C) I and II D) None of the choices
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14) What aldehyde or ketone is needed to prepare the following compound by an Aldol reaction?
A) I B) II C) III D) IV
15)
What is the name given to an Aldol reaction between two different carbonyl compounds?
A) Multiple Aldol reaction B) Crossed Aldol reaction C) Differential Aldol reaction D) Versatile Aldol reaction
16)
When is a crossed Aldol reaction said to be synthetically useful?
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A) When both carbonyl compounds have a hydrogens B) When both carbonyl compounds have no a hydrogens C) When one carbonyl compound has no a hydrogens D) When one carbonyl compound has no b hydrogens
17)
In what situation can the yield of a single crossed Aldol product be increased?
A) The electrophilic carbonyl component is relatively unhindered and is used in excess. B) The electrophilic carbonyl carbon component is relatively hindered and is used in limited amount. C) The nucleophilic carbonyl component is relatively unhindered and is used in excess. D) The nucleophilic carbonyl component is relatively hindered and is used in limited amount.
18) What is the cyclic product formed in the intramolecular Aldol condensation when the following compound is treated with aqueous NaOH?
A) I B) II C) III D) IV
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19) What cyclic product is formed in the intramolecular Aldol condensation when the following compound is treated with aqueous NaOH?
A) I B) II C) III D) IV
20)
What is the general name for the reaction product formed in a Claisen reaction?
A) b-Hydroxy ester B) b-Keto ester C) a-Keto ester D) g-Hydroxy ester
21)
What reaction type is a Claisen reaction?
A) Electrophilic addition B) Electrophilic substitution C) Nucleophilic addition D) Nucleophilic substitution
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22)
What type of esters can undergo Claisen reactions?
A) All esters can undergo Claisen reactions. B) Only esters with two hydrogen atoms on the a carbon can undergo Claisen reactions. C) Only esters with three hydrogen atoms on the a carbon can undergo Claisen reactions. D) Only esters with two or three hydrogen atoms on the a carbon can undergo Claisen reactions.
23)
What is the product of the following Claisen reaction?
A) I B) II C) III D) IV
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24)
What is the product of the following Claisen reaction?
A) I B) II C) III D) IV
25)
What is the name given to the Claisen reaction between two different esters?
A) Multiple Claisen reaction B) Differential Claisen reaction C) Crossed Claisen reaction D) Versatile Claisen reaction
26)
When is a crossed Claisen reaction between two different esters synthetically useful?
A) When only one of the esters has a hydrogen atoms B) When both esters have a hydrogen atoms C) When only one of the esters has b hydrogen atoms D) When both esters lack a hydrogen atoms
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27) What is the general name of the product of a crossed Claisen reaction between a ketone and an ester?
A) b-Keto ester B) a,b-Dicarbonyl compound C) g-Dicarbonyl compound D) b-Dicarbonyl compound
28) In the correct order, what are the three general steps in the mechanism of a Claisen reaction?
A) Enolate formation, elimination, nucleophilic addition B) Enolate formation, nucleophilic addition, elimination C) Elimination, enolate formation, nucleophilic addition D) Nucleophilic addition, enolate formation, elimination
29)
What is an intramolecular Claisen reaction called?
A) Michael reaction B) Robinson reaction C) Hoffman reaction D) Dieckmann reaction
30) In a Michael reaction, what is the name given to the a,b-unsaturated carbonyl component?
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A) Michael donor B) Michael enolate C) Michael nucleophile D) Michael acceptor
31) In a Michael reaction, where does the nucleophile attack the a,b-unsaturated carbonyl component?
A) a-Carbon B) b-Carbon C) Carbonyl carbon D) Carbonyl carbon and b-carbon
32)
Which of the following compounds cannot serve as a Michael acceptor?
A) I B) II C) III D) IV
33)
What are the two starting materials for a Robinson annulation?
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A) an a,b-Unsaturated carbonyl compound and an enolate B) a b-Ketoester and an enolate C) a 1,5-Dicarbonyl compound and an enolate D) a 1,3-Dicarbonyl compound and an enolate
34)
What are the names for the two parts of the mechanism in a Robinson annulation?
A) Michael addition and intramolecular Claisen reaction B) Michael addition and intramolecular aldol reaction C) Claisen reaction and intramolecular aldol reaction D) Aldol reaction and intramolecular Claisen reaction
35)
Which of the following compounds can undergo an Aldol with itself?
A) I B) II C) III D) Both I and II
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36)
What is the product of the self-condensation of ethanal (acetaldehyde), shown below?
A) I B) II C) III D) IV
37)
The following reaction is an example of what type of reaction?
A) Claisen condensation B) Mixed Aldol reaction C) Robinson annulation D) Dieckmann condensation
38)
The following reaction is an example of what type of reaction?
A) Michael reaction B) Aldol self-condensation C) Dieckmann condensation D) Robinson annulation
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39) The b-hydroxy carbonyl product of an Aldol reaction is oftentimes not the final isolated product; what is the explanation for this result?
A) It undergoes elimination, since water is a good leaving group. B) The hydroxy group is oxidized to a carbonyl. C) The hydroxy group reacts with the carbonyl to form a ketal. D) Hydroxide is eliminated via an enolate intermediate.
40) Under basic conditions, the Aldol reaction is reversible, but dehydration is not. What is the reason for this difference in reactivity?
A) The initial Aldol product is an alkoxide, so the reaction is not energetically downhill in either direction. B) The initial Aldol product is an alkoxide, so the reaction is energetically downhill going toward the product. C) The initial Aldol product is an alkoxide, so the reaction is energetically downhill going toward the starting materials. D) Water is a stable molecule.
41)
Would this crossed Aldol reaction work well? Why or why not?
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A) Yes, the diketone is significantly more acidic, so this enolate can be formed selectively. B) Yes, the aldehyde is significantly more acidic, so this enolate can be formed selectively. C) No, the aldehyde is significantly more acidic, so this enolate cannot be formed selectively. D) No, the diketone is significantly more acidic, so this enolate cannot be formed selectively.
42) Of the carbonyl compounds; (1) benzaldehyde, (2) acetophenone and (3) dicyclohexyl ketone, which compound has noa-hydrogens?
A) Benzaldehyde B) Acetophenone C) Acetone D) All of these compounds contain a-hydrogens.
43) Complete this statement: A major difference between the Aldol condensation and the Claisen condensation reactions is that
A) the Aldol reaction involves substitution while the Claisen reaction involves addition. B) the Aldol reaction is acid catalyzed while the Claisen reaction is base-catalyzed. C) the Aldol reaction is base catalyzed while the Claisen reaction requires a full equivalent of base. D) the Aldol reaction is base catalyzed while the Claisen reaction is acid-catalyzed.
44) If a Claisen condensation reaction is run using methyl propanoate as the reactant, NaOCH 3 is the ideal base. Why is it important to use NaOCH 3 and not NaOCH 2CH 3?
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A) NaOCH 3 is a stronger base than NaOCH 2CH 3, and this reaction requires a stronger base. B) NaOCH 3 is a weaker base than NaOCH 2CH 3, and this reaction requires a weaker base. C) Transesterfication can occur when esters react, and this transesterfication would result in a mixture of products. D) NaOCH 3 is more soluble than NaOCH 2CH 3 in organic solvents, and this reaction requires a full equivalent of base to proceed. A full equivalent of NaOCH 2CH 3 would not dissolve, so the reaction would not proceed.
45) There are several variations of the Aldol reaction. Which of the following types of reactants leads to only one possible product with the Aldol condensation reaction?
A) Two different aldehydes with a-hydrogens are able to form a single aldol condensation product. B) Two different ketones with a-hydrogens are able to form a single aldol condensation product. C) Any aldehyde and ketone mixed together can react to form a single condensation product. D) Any pair of aldehyde or ketone reactants where one of the reactants has no ahydrogens will lead to a single aldol product.
46) What product (including stereochemistry) is formed in the following intermolecular reaction?
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A) I B) II C) III D) IV
47) What product (including stereochemistry) is formed in the following intermolecular reaction?
A) I B) II C) III D) IV
48) Which of the following bicyclic ring systems can be prepared by an intermolecular Robinson annulation?
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A) I B) II C) III D) IV
49)
What is the major product of the following reaction?
A) I B) II C) III D) IV
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50)
What is the major product of the following reaction?
A) I B) II C) III D) IV
51)
What is the major product of the following reaction?
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A) I B) II C) III D) IV
52) A key step in the biosynthesis of glucose involves the reaction of glyceraldehyde 3phosphate with dihydroxyacetone phosphate to form fructose 1,6-bisphosphate in the presence of an aldolase enzyme. The end product formed from this reaction is
A) an equilibrium between an acyclic form of fructose and a cyclic hemiacetal. B) a single form of fructose in the cyclic hemiacetal form. C) a single form of fructose in the acyclic form. D) a form of critic acid.
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Answer Key Test name: Chap 18_6e 1) B 2) C 3) A 4) D 5) B 6) D 7) A 8) C 9) A 10) D 11) B 12) B 13) A 14) D 15) B 16) C 17) A 18) C 19) A 20) B 21) D 22) D 23) C 24) B 25) C 26) A Version 1
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27) D 28) B 29) D 30) D 31) B 32) B 33) A 34) B 35) C 36) B 37) D 38) A 39) D 40) A 41) A 42) A 43) C 44) C 45) D 46) A 47) A 48) C 49) C 50) B 51) C 52) A
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CHAPTER 19 1)
Which of the following statements about benzene is true?
A) Benzene is a saturated hydrocarbon. B) Benzene undergoes addition reactions. C) Benzene has five degrees of unsaturation. D) Benzene undergoes substitution reactions.
2)
Which of the following statements about the structure of benzene is not true?
A) Benzene is planar. B) Benzene has three short double bonds alternating with three longer single bonds. C) The electrons in the pi bonds are delocalized around the ring. D) Benzene has six pi electrons.
3)
What orbitals are used to form the bond indicated in the following molecule?
A) C sp2¾C sp2 B) C sp2¾ C 2p C) C 2p¾C 2p D) C sp3¾C sp3
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4)
What is the IUPAC name of the following compound?
A) 3,6-Dichloroaniline B) 2,5-Dichloroaniline C) 2,5-Dichloroaminobenzene D) 2,5-Dichloroanisole
5)
What is the IUPAC name of the following compound?
A) 2-Nitro-5-carboxychlorobenzene B) 2-Chloro-4-carboxynitrobenzene C) 2-Chloro-1-nitro-4-benzoic acid D) 3-Chloro-4-nitrobenzoic acid
6)
What is the IUPAC name of the following compound?
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A) 1-Chloro-4-ethyl-3-propylbenzene B) 1-Chloro-4-ethyl-5-propylbenzene C) 4-Chloro-1-ethyl-2-propylbenzene D) 4-Chloro-2-propyltoluene
7)
What is the IUPAC name of the following compound?
A) 3-Bromo-1-chloro-4-toluene B) 2-Bromo-4-chlorotoluene C) 4-Chloro-2-bromo-1-toluene D) 2-Bromo-4-chloroanisole
8)
What is the correct assignment of the names of the following substituted benzenes?
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A) I = Phenol; II = anisole; III = toluene B) I = Benzaldehyde; II = phenol; III = anisole C) I = Benzaldehyde; II = phenol; III = toluene D) I = Phenol; II = anisole; III = styrene
9)
What is the correct assignment of the names of the following substituted benzenes?
A) I = Styrene; II = aniline; III = anisole B) I = Toluene; II = anisole; III = styrene C) I = Styrene; II = anisole; III = phenol D) I = Toluene; II = aniline; III = anisole
10)
How many 13CNMR signals does the following compound exhibit?
A) 4 B) 5 C) 6 D) 8
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What is the structure of a compound of molecular formula C10H14O2 that shows a strong 11) IR absorption at 3150 ¾2850 cm−1 and gives the following 1H NMR absorptions: 1.4 (triplet, 6H); 4.0 (quartet, 4H); and 6.8 (singlet, 4H) ppm?
A) I B) II C) III D) IV
12) What is the correct assignment of the number of signals in the 13C NMR spectra of the following disubstituted benzene derivatives?
A) I = 3 signals; II = 3 signals; III = 2 signals B) I = 3 signals; II = 4 signals; III = 2 signals C) I = 6 signals; II = 6 signals; III = 6 signals D) I = 3 signals; II = 4 signals; III = 3 signals
13)
Which of the following is not one of the Hückel's criteria for aromaticity?
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A) The molecule must be cyclic. B) The molecule must be planar. C) The molecule must be completely conjugated. D) The molecule must have 4n pi electrons.
14)
Which of the following is not a criterion for antiaromaticity?
A) The molecule must be cyclic. B) The molecule must have (4n + 2) pi electrons. C) The molecule must be planar. D) The molecule must be completely conjugated.
15)
What is the correct assignment of the names of the following aromatic heterocycles?
A) I = pyridine; II = pyrimidine; III = furan B) I = pyrimidine; II =pyrrole; III = furan C) I = pyridine; II = pyrrole; III = furan D) I = pyrimidine; II = pyrrole; III = tetrahydrofuran
16)
What is the correct assignment of the names of the following fused aromatic compounds?
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A) I = naphthalene; II = anthracene; III = phenanthrene B) I = naphthalene; II = phenanthrene; III = anthracene C) I = naphthalene; II = phenanthrene; III = benzo[a]pyrene D) I = anthracene; II = naphthalene; III = phenanthrene
17)
Which of the following heterocycles is not aromatic?
A) I B) II C) III D) IV
18)
Which of the following ions is aromatic?
A) I B) II C) III D) IV
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19)
Which of the following molecules has the most acidic hydrogen atoms?
A) I B) II C) III D) IV
20) Rank the following compounds in order of decreasing acidity, starting with the most acidic.
A) I > II > III B) III > II > I C) III > I > II D) I > III > II
21)
Which of the following ions is aromatic?
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A) Only I and II B) Only II and III C) Only III and IV D) Only II and IV
22)
Which of the following statements about the molecular orbital (MO) theory is true?
A) When two p orbitals of similar phase overlap side-by-side, a p* antibonding molecular orbital is formed. B) When two p orbitals of opposite phase overlap side-by-side, a p bonding molecular orbital is formed. C) A p bonding molecular orbital is higher in energy than the two atomic p orbitals from which it is formed. D) A p* antibonding molecular orbital is higher in energy than the two atomic p orbitals from which it is formed.
23)
What orbitals are used to form the indicated bond?
A) sp 3 B) sp 2 C) p D) sp 3 and sp 2
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24)
What orbitals are used to form the indicated bond?
A) sp 3 B) sp 2 C) p D) sp 3 and sp 2
25)
What is the name of the following compound?
A) 2,6-Dimethylbenzene B) 5-Methyltoluene C) Anisole D) 1,3-Dimethylbenzene
26)
What is the name of the following compound?
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A) Meta-bromophenol B) Para-hydroxybenzene C) 3-bromoanisole D) 6-methoxy-2-bromobenzene
27)
What is the correct structure for aniline?
A) I B) II C) III D) IV
28)
What is the correct structure for anisole?
A) I B) II C) III D) IV
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29)
What is the correct structure for toluene?
A) I B) II C) III D) IV
30)
What is the correct structure for 1-bromo-2,4-dimethoxybenzene?
A) I B) II C) III D) IV
31)
Where do the protons in benzene appear in the 1H NMR spectrum? A) Around 1600 cm −1 B) Around 120 ppm C) Around 0 ppm D) Around 7 ppm
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32) How many different proton signals would the following compound show in its 1H NMR spectrum?
A) 1 B) 3 C) 5 D) 6
33)
What compound is consistent with the following 1H NMR spectrum?
A) Phenol B) Anisole C) 4-bromoanisole D) 4-bromotoluene
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34)
What is the correct structure for para-bromotoluene?
A) I B) II C) III D) IV
35)
Which of the following compounds is not aromatic?
A) I B) II C) III D) IV
36)
Which of the following compounds is not aromatic?
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A) I B) II C) III D) IV
37)
Which of the following compounds is aromatic?
A) I B) II C) III D) IV
38)
Which of the following compounds is aromatic?
A) I B) II C) III D) IV
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39)
Why is the following compound not aromatic?
A) It has 4n pi electrons. B) It is not cyclic. C) It has 4n+2 pi electrons. D) The pi electron system is not continuous.
40)
Why is the following compound not aromatic?
A) It has 4n electrons. B) It is not cyclic. C) It has 4n+2 electrons. D) The pi electron system is not continuous.
41)
What is the hybridization of the indicated N atom in the following compound?
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A) p B) sp C) sp2 D) sp3
42)
What is the hybridization of the indicated N atom in the following compound?
A) p B) sp C) sp2 D) sp3
43)
In what type of orbital does the lone pair on the indicated N atom reside?
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A) p B) sp C) sp2 D) sp3
44)
In what type of orbital does the lone pair on the indicated N atom reside?
A) p B) sp C) sp2 D) sp3
45)
What is the IUPAC name of the following compound?
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A) o-nitroanisole B) m-nitroanisole C) p-nitroanisole D) 19nitroaniline
46)
What is the IUPAC name of the following compound?
A) o-nitroanisole B) m-nitroanisole C) p-nitroanisole D) 4-nitroaniline
47)
What is the IUPAC name of the following compound?
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A) o-nitroanisole B) m-nitroanisole C) p-nitroanisole D) 20nitroaniline
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Answer Key Test name: Chap 19_6e 1) D 2) B 3) A 4) B 5) D 6) C 7) B 8) C 9) A 10) C 11) D 12) B 13) D 14) B 15) C 16) A 17) C 18) A 19) C 20) B 21) D 22) D 23) D 24) B 25) D 26) A Version 1
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27) B 28) C 29) D 30) C 31) D 32) B 33) C 34) A 35) B 36) A 37) D 38) B 39) D 40) A 41) C 42) C 43) C 44) A 45) A 46) C 47) B
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CHAPTER 20 1)
What is the first step in the general mechanism for electrophilic aromatic substitution?
A) Protonation of the aromatic ring B) Deprotonation of the aromatic ring C) Addition of the electrophile to the aromatic ring D) Loss of the electrophile from the aromatic ring
2) What is the driving force for losing a proton as the last step in electrophilic aromatic substitution?
A) To neutralize the base that is present B) To make room for the electrophile C) To make the ring more reactive D) To rearomatize the ring system
3)
What is the electrophile in aromatic nitration? A) NO + B) NO 2 + C) NO 3 + D) NO 2H
4)
What is the electrophile in aromatic sulfonation?
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A) H 2SO 3 B) H 2SO 4 C) SO 3 + D) HSO 3 +
5)
Why is sulfuric acid used in aromatic nitration?
A) To keep the reaction from getting too basic B) To form the active electrophile NO 2 + C) To protonate the aromatic ring D) To keep the reaction from getting too acidic
6)
What is the electrophile in the Friedel-Crafts alkylation reaction with tert-butylchloride?
A) The tert-butyl cation B) A complex of tert-butylchloride and aluminum chloride C) A proton D) Aluminum chloride
7) Which of the following halides will not work as an electrophile in a Friedel-Crafts alkylation reaction?
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A) I B) II C) III D) IV
8) What are the two effects that have to be considered to determine the influence a substituent will have on electrophilic aromatic substitution?
A) Steric and electronic B) Inductive and steric C) Inductive and resonance D) Resonance and electronic
9)
Why is the nitro group a meta director?
A) Because it is sterically very large B) Because it adds electron density to the meta position, thus activating it C) Because it stabilizes the intermediate cation D) Because it removes more electron density from the ortho and para positions than the meta position, thus deactivating the meta position less
10)
What is a major problem with Friedel-Crafts alkylation?
A) It requires high temperatures. B) The conditions are too acidic. C) The starting material is frequently over-alkylated. D) The products coordinate with the aluminum chloride.
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11) Which of the following statements about the mechanism of electrophilic aromatic substitution is not true?
A) All electrophilic aromatic substitution reactions occur via a two-step mechanism. B) The transition state of the first step is lower in energy. C) The first step is the rate-determining step. D) The second step is the fast step.
12) What will be the site that leads to the major mono substitution product for an electrophilic aromatic substitution reaction of the following compound?
A) I B) II C) III D) IV
13)
What is the major organic product obtained from the following reaction?
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A) I B) II C) III D) IV
14)
What is the major organic product obtained from the following reaction?
A) I B) II C) III D) IV
15)
What is the major organic product obtained from the following reaction?
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A) I B) II C) III D) IV
16)
What is the major organic product obtained from the following reaction?
A) I B) II C) III D) IV
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17)
What is the major organic product obtained from the following reaction?
A) I B) II C) III D) IV
18)
What is the major organic product obtained from the following reaction?
A) I B) II C) III D) IV
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19)
What is the major organic product obtained from the following reaction?
A) I B) II C) III D) IV
20)
What is the major organic product obtained from the following reaction?
A) I B) II C) III D) IV
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21)
Which of the following substituents are activators in electrophilic aromatic substitution? A) CH 3O ¾ B) Cl ¾ C) NO 2¾ D) HSO 3¾
22) Which of the following substituents are deactivators in electrophilic aromatic substitution?
A) HO ¾ B) CH 3NH ¾ C) CH 3O ¾ D) (CH 3) 3N +¾
23)
Which of the following substituents is an ortho, para director?
A) ¾ CHO B) ¾ COOH C) ¾ NHCOR D) ¾ CN
24)
Which of the following substituents is a meta director?
A) ¾ N(CH 3) 2 B) ¾ OCH 3 C) ¾ NHCOCH 3 D) ¾ SO 3H
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25)
What is (are) the product(s) of the following reaction?
A) Only I B) Only II C) Only III D) Only I and III
26)
What is (are) the product(s) of the following reaction?
A) Only I B) Only II C) Only III D) Only I and II
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27) Rank the following compounds in order of increasing reactivity in electrophilic aromatic substitution.
A) I < II < III < IV B) II < I < IV < III C) III < IV < I < II D) II < I < III < IV
28) Rank the following compounds in order of decreasing reactivity in electrophilic aromatic substitution.
A) II > IV > I > III B) II > III > IV > I C) IV > II > I > III D) IV > I > II > III
29) Rank the following activating groups in order of decreasing strength of activation, listing the most activating first.
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A) IV > II > III > I B) II > III > IV > I C) III > IV > II > I D) II > IV > III > I
30) Rank the following deactivating groups in order of increasing deactivating strength, listing the least deactivating first.
A) I < II < III < IV B) II < III < IV < I C) II < I < III < IV D) IV < III < I < II
31)
What are the product(s) of the following reaction?
A) Only I B) Only II C) Only I and II D) Only III
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32)
What are the product(s) of the following reaction?
A) Only I and II B) Only I and III C) Only II and III D) Only IV
33)
How can polyalkylation be minimized in Friedel-Crafts alkylation?
A) Use a large excess of alkyl halide relative to the aromatic compound. B) Use a large excess of benzene relative to the alkyl halide. C) Use an alkyl halide without a Lewis acid catalyst. D) Use a large excess of the Lewis acid catalyst.
34)
What is the major product of the following reaction?
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A) I B) II C) III D) IV
35)
What is (are) the product(s) of the following reaction?
A) Only I B) Only II C) Only III D) Only I and II
36)
What are the two distinct pathways for nucleophilic aromatic substitution?
A) Addition-substitution and substitution-addition B) Addition-elimination and elimination-addition C) Addition-addition and elimination-elimination D) Elimination-substitution and substitution-elimination
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37) What is the reactive intermediate formed in the addition-elimination mechanism of nucleophilic aromatic substitution?
A) Carbocation B) Radical C) Benzyne D) Carbanion
38) What is the reactive intermediate formed in the elimination-addition mechanism of nucleophilic aromatic substitution?
A) Carbocation B) Radical C) Benzyne D) Carbanion
39)
Which of the following statements about nucleophilic aromatic substitution is not true?
A) Increasing the electronegativity of the halogen increases the reactivity of the aryl halide. B) Increasing the number of electron-withdrawing groups increases the reactivity of the aryl halide. C) Electron-withdrawing groups stabilize the intermediate carbanion, and lower the energy of the transition state. D) When a nitro group is located meta to the halogen, the negative charge of the intermediate carbanion can be delocalized onto the NO 2group, thus stabilizing it.
40)
Which of the following statements about nucleophilic aromatic substitution is true?
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A) For the addition-elimination pathway, the nucleophile may become attached either at the site bearing the leaving group or at the site bearing the ortho hydrogen atom. B) For the elimination-addition pathway, the nucleophile becomes attached only at the site bearing the leaving group. C) The elimination-addition mechanism is not as common as the addition-elimination mechanism. D) In the addition-elimination mechanism, the aromatic ring first accepts a pair of electrons from a nucleophile to form a cationic intermediate.
41) Rank the following compounds in order of increasing reactivity in nucleophilic aromatic substitution.
A) III < II < I B) I < II < III C) III < I < II D) I < III < II
42)
What is the major product of the following reaction?
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A) I B) II C) III D) IV
43)
Which aryl fluoride reacts the fastest with NaOH?
A) I B) II C) III D) IV
44)
In addition to the product shown, what other product is formed in the following reaction?
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A) I B) II C) III D) IV
45)
Which set of reagents would most likely bring about the following transformation?
A) Br 2and FeBr 3 B) NBS and light C) Br 2in CCl 4 D) NaBr and H 2O
46)
What is the product of the following sequence of reactions?
A) I B) II C) III D) IV
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47)
What is the product of the following reaction?
A) I B) II C) III D) IV
48)
What is the product of the following reaction?
A) I B) II C) III D) None of these
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49)
What is the best choice of reagent to bring about the following transformation?
A) [1] LiAlH 4; [2] H 2O B) Zn (Hg), HCl C) NH 3, NaOH D) H 2, Pd-C
50)
What is the best choice of reagent to bring about the following transformation?
A) [1] LiAlH 4; [2]H 2O B) Zn (Hg), HCl C) NH 3, NaOH D) H 2, Pd-C
51)
What is the product of the following reaction?
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A) I B) II C) III D) IV
52)
What is the major product of electrophilic addition of HBr to the following alkene?
A) I B) II C) III D) IV
53) Consider the tetracyclic aromatic compound drawn below, with rings labelled as I, II, III, and IV. Which of the four rings is most reactive in electrophilic aromatic substitution?
A) I B) II C) III D) IV
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54) Consider the tetracyclic aromatic compound drawn below, with rings labelled as I, II, III, and IV. Which of the four rings is least reactive in electrophilic aromatic substitution?
A) I B) II C) III D) IV
55)
What is the structure of compound A?
A) I B) II C) III D) IV
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56)
What is the product of the following monobromonation reaction?
A) Only I B) Only II C) Only III D) Only I and III
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24)
What is the major organic product of the following reaction?
A) I B) II C) III D) IV
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25)
What is the major organic product of the following reaction?
A) I B) II C) III D) IV
59)
What reagents would be necessary to produce the following product from benzene?
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A) CH 3Cl, AlCl 32. HNO 3, H 2SO 43. KMnO 4 B) HNO 3, H 2SO 42. CH 3Cl, AlCl 33. KMnO 4 C) KMnO 42. CH 3Cl, AlCl 33. HNO 3, H 2SO 4 D) KMnO 42. HNO 3, H 2SO 43.CH 3Cl, AlCl 3
60)
What reagents would be necessary to produce the following product from benzene?
A) CH 3CH 2C(O)Cl, AlCl 32. HNO 3, H 2SO 43. Zn(Hg), HCl B) HNO 3, H 2SO 42. CH 3CH 2C(O)Cl, AlCl 33. Zn(Hg), HCl C) CH 3CH 2C(O)Cl, AlCl 32. Zn(Hg), HCl 3. HNO 3, H 2SO 4 D) Zn(Hg), HCl 2. CH 3CH 2C(O)Cl, AlCl 33. HNO 3, H 2SO 4
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Answer Key Test name: Chap 20_6e 1) C 2) D 3) B 4) D 5) B 6) A 7) A 8) C 9) D 10) C 11) B 12) D 13) D 14) B 15) D 16) A 17) B 18) C 19) B 20) C 21) A 22) D 23) C 24) D 25) D 26) A Version 1
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27) B 28) D 29) B 30) C 31) D 32) A 33) B 34) A 35) D 36) B 37) D 38) C 39) D 40) C 41) B 42) D 43) C 44) D 45) B 46) D 47) A 48) D 49) B 50) D 51) B 52) B 53) B 54) A 55) A 56) B Version 1
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57) C 58) C 59) A 60) A
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CHAPTER 21 1)
Which of the following statements about radicals and radical reactions is not true?
A) Most radicals are unstable. B) A radical contains an atom that has an octet of electrons. C) Half-headed arrows are used to show the movement of lone electrons. D) A radical is formed by homolysis of a covalent bond.
2)
Which of the following statements about carbon radicals is not true?
A) Carbon radicals are classified as primary, secondary, tertiary, or quaternary. B) A carbon radical is sp2hybridized. C) The geometry of a carbon radical is trigonal planar. D) The unhybridized p orbital in a carbon radical contains the unpaired electron.
3)
Which of the following statements about radicals is true?
A) Cleavage of a stronger bond forms the more stable radical. B) The stability of a radical increases as the number of alkyl groups bonded to the radical carbon decreases. C) The higher the bond dissociation energy for a C-H bond, the more stable the resulting carbon radical. D) Less stable radicals generally do not rearrange to more stable radicals.
4)
Which of the following compounds contain primary (1°) radical carbons?
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A) Only I B) Only II C) Only III D) Only II and IV
5)
Which of the following compounds contain secondary (2°) radical carbons?
A) Only I B) Only II C) Only III D) Only II and IV
6)
Which of the following compounds contain tertiary (3°) radical carbons?
A) Only I B) Only II C) Only III D) Only II and IV
7)
Which of the following is a radical scavenger?
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A) O 3 B) O 2 C) Vitamin C D) CO 2
8) How many monochlorination products can be formed (constitutional isomers only) from the reaction of (CH 3) 2CHCH 2CH 3with Cl 2and hn?
A) 2 B) 3 C) 4 D) 5
9) How many monochlorination products can be formed (constitutional isomers only) from the reaction of CH 3CH 2CH 2CH 2CH 2CH 3with Cl 2and hn?
A) 3 B) 4 C) 5 D) 6
How many monochlorination products can be formed from the reaction of (CH 3) 3CH 10) with Cl 2and hn?
A) 1 B) 2 C) 3 D) 4
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11)
Which of the following statements about radical reactions is not true?
A) Light or heat provides the energy needed for homolytic bond cleavage to form radicals. B) Breaking the weak O-O bond of peroxides initiates radical reactions. C) The diradical O 2removes radicals from a reaction mixture. D) Radicals rearrange.
12)
Which steps are the rate-determining step in the mechanism of radical halogenation?
A) Initiation B) Propagation C) Termination D) Initiation and propagation
13) Which of the following statements about the propagation steps in the chlorination of ethane is true?
A) Radical chlorination consists of two propagation steps. B) The energy diagram for the propagation steps has three energy barriers. C) The first of the propagation steps is rate-determining because its transition state is at lower energy. D) The second of the propagation steps is rate-determining because its transition state is at higher energy.
14)
Which of the following statements about chlorination and bromination is true?
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A) Bromination is unselective, yielding a mixture of products. B) Chlorination is often selective, yielding one major product. C) Chlorination is faster than bromination. D) Bromination is faster than chlorination.
15)
Which of the following statements about bromination is true?
A) The rate-determining step in bromination is exothermic. B) Both radicals are formed. C) A mixture of products results. D) A single radical halogenation product predominates.
16)
Which of the following statements about chlorination is true?
A) The rate-determining step in chlorination is endothermic. B) The transition state resembles the product. C) The more stable radical is formed faster. D) A mixture of products results.
17)
What is the product in the following sequence of reactions?
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A) I B) II C) III D) IV
18)
What is the product in the following sequence of reactions?
A) I B) II C) III D) IV
19) true?
Which of the following statements about the stereochemistry of halogenation reactions is
A) An achiral starting material always gives an achiral product only. B) An achiral starting material always gives a racemic product only. C) The configuration at a stereogenic center of a product must change even if a reaction does not occur at a stereogenic center. D) An achiral starting material always gives either an achiral or a racemic product.
20) How many monochlorination products (constitutional isomers and stereoisomers) are formed from the reaction of butane with Cl 2and hn?
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A) 2 B) 3 C) 4 D) 5
21) How many monochlorination products (constitutional isomers and stereoisomers) are formed from the reaction of pentane with Cl 2and hn?
A) 2 B) 3 C) 4 D) 5
22)
Rank the following radicals in order of increasing stability, putting the least stable first.
A) III< I < II B) I < II < III C) III < II < I D) I < III < II
23)
Rank the following radicals in order of decreasing stability, putting the most stable first.
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A) II > IV > III > I B) III > II > IV > I C) IV > III > II > I D) IV > III > I > II
24)
What is the product of the following reaction?
A) I B) II C) III D) IV
25)
What is the product of the following reaction?
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A) I B) II C) III D) IV
26) How many allylic halides can be formed when 3-methycyclohexene undergoes allylic halogenation with one equivalent of NBS and light?
A) 1 B) 2 C) 3 D) 4
27)
What is the product of the following reaction?
A) I B) II C) III D) IV
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28)
Identify the monomer used to make the following polymer.
A) I B) II C) III D) IV
29)
Identify the monomer used to make the following polymer.
A) I B) II C) III D) IV
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30)
Identify the monomer used to make the following polymer.
A) I B) II C) III D) IV
31)
Determine the monochlorination product(s).
A) Only I B) Only II C) Only III D) Only I and II
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32)
Determine the product of the following reaction.
A) I B) II C) III D) IV
33)
Determine the product(s) of the following reaction.
A) Only I B) Only II C) Only III D) Only I and II
34) Which of the following statements is (are) true about free radical halogenation of alkanes?
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A) The first of the chain-propagating steps is rate-determining. B) The reaction proceeds by way of a flat sp2hybridized free radical. C) The chain-initiating step involves cleavage of a carbon-hydrogen bond to afford a carbon radical and a hydrogen atom. D) Statements (The first of the chain-propagating steps is rate-determining) and (The reaction proceeds by way of a flat sp2hybridized free radical) are both true.
35) Which of the labeled hydrogens is most easily abstracted in a free radical bromination reaction?
A) H a B) H b C) H c D) H d
36) Which of the indicated hydrogens is most readily abstracted in a free radical halogenation reaction?
A) I B) II C) III D) IV
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37)
A possible reaction of ethane with chlorine is shown below.
This reaction could conceivably occur by the following chain mechanisms [1], [2], and [3]. The chain initiating step(s) is (are) .
A) Only [1] B) Only [2] C) Only [3] D) Only [1] and [2]
38)
A possible reaction of ethane with chlorine is shown below.
This reaction could conceivably occur by the following chain mechanisms [1], [2], and [3]. The chain propagating step(s) is (are) .
A) Only [1] and [2] B) Only [2] and [3] C) Only [1] and [3] D) Only [3]
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15)
A possible reaction of ethane with chlorine is shown below.
This reaction could conceivably occur by the following chain mechanisms [1], [2], and [3]. Determine DH for step [1].
Bond dissociation energies (kcal/mol):
A) −5 kcal/mol B) +58 kcal/mol C) −28 kcal/mol D) None of the choices are correct.
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16)
A possible reaction of ethane with chlorine is shown below.
This reaction could conceivably occur by the following chain mechanisms [1], [2], and [3]. Determine DH for step [2].
Bond dissociation energies (kcal/mol):
A) −5 kcal/mol B) +58 kcal/mol C) −28 kcal/mol D) None of the choices are correct.
41) Select the route that would most likely produce the desired results from the given starting material.
I.(1) H2SO4and heat; (2) HBr II.(1) KOH in ethanol; (2) HBr III.(1) H2SO4and heat; (2) HBr + peroxides IV.(1) potassium tert-butoxide in tert-butanol; (2) HBr + peroxides
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A) I B) II C) III D) IV
42) What type of reactive intermediate is formed in the reaction of propene with Nbromosuccinimide (NBS) to give 3-bromo-1-propene?
A) Cyclic bromonium ion B) Allylic carbocation C) Allylic carbanion D) Allylic radical
43) Which of the following alkenes undergoes allylic bromination to form a single monobrominated product?
A) I B) II C) III D) IV
44) How many monochlorination products, including stereoisomers, are formed from (S,S)1,2-dimethylcyclopropane?
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A) 4 B) 3 C) 6 D) 5
45) How many products, including stereoisomers, are formed when 2-methylpent-2-ene is treated with HBr in presence of peroxides?
A) 1 B) 2 C) 3 D) 4
46) How many products, including stereoisomers, are formed when (R)-2,4-dimethylhex-2ene is treated with HBr in presence of peroxides?
A) 1 B) 2 C) 3 D) 4
47)
Rank the following in order of increasing stability.
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A) I < II < III < IV B) II < I < III < IV C) I < II < IV < III D) IV < III < II < I
48)
What is/are the product(s) of the following monochlorination?
A) I B) II C) III D) All of the choices are correct.
49) For a radical reaction, put the following steps in the correct order: 1. Initiation 2. Propagation 3. Termination
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A) 1, 2, 3 B) 1, 3, 2 C) 2, 3, 1 D) 3, 2, 1
50)
Which of the following would be the fastest to form a radical?
A) I B) II C) III D) IV
51)
Find the major product of the following reaction.
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A) I B) II C) III D) IV
52) The proposed reaction between chlorofluorocarbons and ozone involves what type of mechanism?
A) Radical mechanism B) Substitution mechanism C) Elimination mechanism D) Electrophilic aromatic substitution
53) The proposed reaction of the oxidation of unsaturated lipids involves what type of mechanism?
A) Radical mechanism B) Substitution mechanism C) Elimination mechanism D) Electrophilic aromatic substitution
54)
Which of the following are radical inhibitors?
A) Vitamin E B) BHT C) Both of these choices are correct. D) None of these are correct.
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Answer Key Test name: Chap 21_6e 1) B 2) A 3) D 4) C 5) D 6) A 7) B 8) C 9) A 10) B 11) D 12) B 13) A 14) C 15) D 16) D 17) B 18) A 19) D 20) B 21) C 22) C 23) A 24) D 25) B 26) D Version 1
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27) A 28) A 29) B 30) C 31) D 32) D 33) D 34) D 35) B 36) C 37) A 38) B 39) B 40) A 41) D 42) D 43) A 44) C 45) B 46) B 47) A 48) D 49) A 50) D 51) A 52) A 53) A 54) C
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CHAPTER 22 1)
Which of the following amines are classified as primary (1°) amines?
A) I B) II C) III D) I and II
2)
Which of the following amines are classified as secondary (2°) amines?
A) I B) II C) III D) I and II
3)
Which of the following amines are classified as tertiary (3°) amines?
A) I B) II C) III D) IV
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4) What is the approximate bond angle of the substituents around a nitrogen atom in amines?
A) 90° B) 109.5° C) 120° D) 180°
5) Although an amine nitrogen atom containing an electron pair and bonded to three different groups is technically a stereogenic center, the chirality of the amine nitrogen is often ignored. Why is that?
A) Because four bonds are needed to define a stereogenic center B) Because chirality only exists with the tetrahedral carbon atoms C) Because there is usually slow interconversion between the two isomeric forms at room temperature D) Because there is usually rapid interconversion between the two isomeric forms at room temperature
6) Why should the chirality of an ammonium salt with four different groups on the nitrogen atom not be ignored?
A) Because there is rapid interconversion between the two isomeric forms at room temperature B) Because interconversion cannot occur between the two isomeric forms at room temperature C) Because the compound would be a meso compound D) Because the compound would be a racemic mixture
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7)
What is the common name of the following compound?
A) Isopropylamine B) Sec-butylamine C) 2-Methyl-1-propanamine D) Isobutylamine
8)
What is the common name of the following compound?
A) isopropylamine B) sec-butylamine C) isobutylamine D) tert-butylamine
9)
What is the common name of the following compound?
A) isopropylamine B) 2-methyl-2-propanamine C) tert-butylamine D) isobutylamine
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10)
What is the common name of the following compound?
A) diisopropylamine B) dipropylamine C) diisopropanamine D) dibutylamine
11)
What is the common name of the following compound?
A) dimethylisobutylamine B) butyldimethylamine C) N,N-dimethylbutanamine D) sec-butyldimethylamine
12)
What is the IUPAC name of the following compound?
A) N-propylhexanamine B) N-propylaniline C) N-ethylcyclohexylamine D) N-propylcyclohexanamine
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13)
What is the IUPAC name of the following compound?
A) N-ethyl- N-methylpentylamine B) N-ethyl- N-methyl-1-pentanamine C) N-methyl-3-octanamine D) N-ethyl-2-heptanamine
14)
What is the IUPAC name of the following compound?
A) 3-methyl-1-hexanamine B) 4-methyl-1-hexylamine C) 4-methyl-1-hexanamine D) 3-methyl-6-hexylamine
15)
What is the IUPAC name of the following compound?
A) N-ethyl- N-methylcyclopentanamine B) N-cyclopentyl- N-methylethanamine C) N-methyl- N-ethylcyclopentylamine D) N-ethyl- N-methylpentanamine
16)
What is the IUPAC name of the following compound?
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A) 1-methyl- N-propyl-1-propanamine B) 4-methyl-4-heptanamine C) 2-propyl-3-hexanamine D) N-propyl-2-pentanamine
17)
What is the IUPAC name of the following compound?
A) ( S)-methyl-4-hexanamine B) ( S)-5-methyl-3-hexanamine C) ( R)-2-methyl-4-hexanamine D) ( R)-5-methyl-3-hexanamine
18)
What is the IUPAC name of the following compound?
A) ( Z)-4-hexen-1-amine B) ( E)-4-hexen-1-amine C) ( E)-2-hexen-6-amine D) ( Z)-2-hexen-6-amine
19)
What is the correct assignment of the names of the following aromatic amines?
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A) I = pyrrolidine; II = pyrimidine; III = aniline B) I = pyrrole; II = pyrimidine; III = anisole C) I = pyrrolidine; II = pyridine; III =aniline D) I = pyrrole; II = pyridine; III = aniline
20) Arrange the following compounds in order of decreasing boiling point, putting the compound with the highest boiling point first.
A) I > II > III B) I > III > II C) III > I > II D) III > II > I
21) Arrange the following compounds in order of increasing boiling point, putting the compound with the least boiling point first.
A) I < II < III B) II < I < III C) I < III < II D) II < III < I
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22) Arrange the following amines in order of decreasing water solubility, putting the most soluble amine first.
A) I > II > III B) II > I > III C) III > I > II D) II > III > I
23) The mass spectrum of an amine shows a parent peak with an odd mass for the molecular ion. What does this tell you about the amine?
A) The amine is a primary amine. B) The amine is a secondary amine. C) The amine contains an even number of N atoms. D) The amine contains an odd number of N atoms.
24)
What is a typical characteristic absorption in the IR spectrum of a primary amine? A) Two N-H absorptions at 2500−2600 cm −1 B) One N-H absorption at 2500−2600 cm −1 C) Two N-H absorptions at 3300−3500 cm −1 D) One N-H absorption at 3300−3500 cm −1
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A compound with molecular formula C6H15N exhibits a singlet at d 0.9 (1H), a triplet at d 25) 1.10 (3H), a singlet at d1.15 (9H), and a quartet at d 2.6 (2H) in its 1HNMR spectrum. Its IR spectrum shows one medium absorption band near 3400 cm−1. What is the structure of this compound?
A) I B) II C) III D) IV
26)
What is the name given to naturally occurring amines derived from plant sources?
A) Enamines B) Imines C) Alkaloids D) Alkamines
Why is direct nucleophilic substitution of an alkyl halide with NH 27) method for preparing primary amines?
3
not a very useful
A) NH 3is not a nucleophile. B) Elimination will occur. C) NH 3is too bulky to act as a nucleophile. D) Polyalkylation of the amine will result in multiple products.
28) In the preparation of primary amines, how can direct nucleophilic substitution between NH 3and alkyl halide be made more practical than reacting NH 3and the alkyl halide in a 1:1 ratio? Version 1
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A) Use a large excess of NH 3. B) Use a large excess of alkyl halide. C) Use a limited amount of NH 3. D) Make the alkyl halide sterically hindered.
29)
Why is the N-H bond of an imide especially acidic?
A) The conjugate base is stabilized by electron-donating inductive effect. B) The conjugate base is stabilized by resonance. C) The conjugate acid is stabilized by resonance. D) The conjugate base is stabilized by intramolecular hydrogen bonding.
30) Which of the following alkyl halides cannot be used to prepare primary amines by the Gabriel synthesis?
A) 2-Bromo-2-methylbutane B) 1-Bromo-2-methylbutane C) 2-Bromo-3-methylbutane D) 1-Bromo-3-methylbutane
31)
Predict the product(s) of the following reaction.
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A) I B) II C) III D) None of the choices
32)
What is the major organic product obtained in the following reaction?
A) I B) II C) III D) IV
33)
What is the major organic product obtained in the following reaction?
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A) I B) II C) III D) IV
34)
What is the major organic product obtained in the following reaction?
A) I B) II C) III D) IV
35)
What is the major organic product obtained in the following reaction?
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A) I B) II C) III D) IV
36)
Why are 1°, 2°, and 3° alkylamines more basic than ammonia (NH 3)?
A) Because of the electron-withdrawing inductive effect of the alkyl groups B) Because of the steric hindrance of the alkyl groups C) Because of the resonance delocalization of the alkyl groups D) Because of electron-donating inductive effect of the alkyl groups
37)
Why are alkylamines more basic than arylamines?
A) The lone pair electrons are localized in alkylamines and delocalized in arylamines. B) The lone pair electrons are delocalized in alkylamines and localized in arylamines. C) The lone pair electrons are less readily available in alkylamines. D) The lone pair electrons are more readily available in arylamines.
38) Rank the following compounds in order of increasing basicity, putting the least basic compound first.
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A) III < II < IV < I B) II < III < IV < I C) I < IV < II < III D) III < I < II < IV
39) Rank the following compounds in order of decreasing basicity, putting the most basic compound first.
A) II > I > III > IV B) I > II > III > IV C) I > III > II > IV D) IV > II > III > I
40) first.
Rank the following compounds in order of increasing basicity, putting the least basic
A) II < III < IV < I B) I < II < III < IV C) IV < III < II < I D) II < I < III < IV
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41) first.
Rank the following compounds in order of decreasing basicity, putting the most basic
A) I > II > III > IV B) I > III > II > IV C) IV > III > I > II D) II > I > III > IV
42)
Why is pyrrole much less basic than pyridine?
A) The lone pair of electrons in pyrrole is located on an sp2orbital. B) The lone pair of electrons in pyrrole is part of the aromatic p system. C) The lone pair of electrons in pyrrole is not part of the aromatic p system. D) The pKaof the conjugate acid of pyrrole is much greater than the conjugate acid of pyridine.
43)
Why is piperidine a stronger base than pyridine?
A) The lone pair of electrons in pyridine is part of the delocalized p system. B) Aromatic compounds are always less basic than non-aromatic compounds. C) The lone pair of electrons in piperidine is in an sp 3hybrid orbital; the lone pair of electrons in pyridine is in an sp hybrid orbital. D) The lone pair of electrons in piperidine is in an sp 3hybrid orbital; the lone pair of electrons in pyridine is in an sp 2hybrid orbital.
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44) first.
Rank the following compounds in increasing order of basicity, putting the least basic
A) II < I < IV < III B) I < III < II < IV C) IV < II < III < I D) I < II < III < IV
45) Rank the nitrogen atoms in chloroquine, shown below, in order of decreasing basicity, putting the most basic nitrogen atom first.
A) N1 > N2 > N3 B) N2 > N1 > N3 C) N3 > N2 > N1 D) N3 > N1 > N2
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46) Histamine, a vasodilator, is responsible for a wide variety of physiological effects. Rank the three nitrogen atoms in histamine in increasing order of basicity, putting least basic nitrogen atom first.
A) N2 < N1 < N3 B) N1 < N2 < N3 C) N3 < N1 < N2 D) N3 < N2 < N1
47)
Predict the major organic product of the following reaction.
A) I B) II C) III D) IV
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48)
Predict the major organic product of the following reaction.
A) I B) II C) III D) IV
49)
Predict the major organic product of the following reaction.
A) I B) II C) III D) IV
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50)
Predict the major organic product of the following reaction.
A) I B) II C) III D) IV
51)
Predict the major product of the following reaction.
A) I B) II C) III D) IV
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52)
Predict the major product of the following reaction.
A) I B) II C) III D) IV
53)
Select the reagent(s) required for the following transformation.
A) NaI B) (1) NaNO 2, HCl; (2) NaI C) (1) NaNO 2, HCl; (2) I 2 D) I 2
54)
Select the reagent(s) required for the following transformation.
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A) NaF B) (1) NaNO 2, HCl; (2) F 2 C) (1) NaNO 2, HCl; (2) HBF 4 D) F 2
55)
Select the reagent(s) required for the following transformation.
A) (1) NaNO 2, HCl; (2) H 2 B) (1) NaNO 2, HCl; (2) H 2O C) (1) NaNO 2, HCl; (2) H 3PO 4 D) (1) NaNO 2, HCl; (2) H 3PO 2
56)
Predict the major product of the following reaction.
A) I B) II C) III D) IV
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57)
Predict the major product of the following reaction.
A) I B) II C) III D) IV
58)
What starting materials are required to synthesize the following azo compound?
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A) I B) II C) III D) IV
59)
Consider the following multistep synthesis.
What is the structure of intermediate A?
A) I B) II C) III D) IV
60)
Consider the following multistep synthesis.
What is the structure of intermediate B?
A) I B) II C) III D) IV
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61)
Consider the following multistep synthesis.
What is the structure of intermediate C?
A) I B) II C) III D) IV
62)
What is the IUPAC name for the following compound?
A) (E,R)-4-chloro-3-penten-2-amine B) (E,S)-4-chloro-3-penten-2-amine C) (Z,R)-4-chloro-3-penten-2-amine D) (Z,S)-4-chloro-3-penten-2-amine
63)
What is the IUPAC name for the following compound?
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A) (E,R)-4-chloro-3-penten-2-amine B) (E,S)-4-chloro-3-penten-2-amine C) (Z,R)-4-chloro-3-penten-2-amine D) (Z,S)-4-chloro-3-penten-2-amine
64)
What is the major product of the following reaction?
A) I B) II C) III D) IV
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26)
What is the major product of the following reaction?
A) I B) II C) III D) IV
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27)
What is the major product of the following reaction?
A) I B) II C) III D) IV
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28)
What is the major product of the following reaction?
A) I B) II C) III D) IV
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29)
What is the major product of the following reaction?
A) I B) II C) III D) IV
69)
Which of the following natural dyes can be synthesized?
A) Indigo B) Tyrian purple C) Alizarin D) All of these are correct.
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Answer Key Test name: Chap 22_6e 1) D 2) C 3) B 4) B 5) D 6) B 7) D 8) B 9) C 10) A 11) D 12) D 13) B 14) C 15) A 16) D 17) B 18) B 19) D 20) C 21) D 22) B 23) D 24) C 25) B 26) C Version 1
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27) D 28) A 29) B 30) A 31) B 32) D 33) B 34) A 35) B 36) D 37) A 38) A 39) C 40) B 41) D 42) B 43) D 44) B 45) C 46) A 47) B 48) D 49) A 50) D 51) A 52) B 53) B 54) C 55) D 56) A Version 1
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57) D 58) B 59) B 60) D 61) A 62) C 63) B 64) A 65) D 66) B 67) C 68) A 69) D
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CHAPTER 23 1)
Which of the following compounds is not an amino acid?
A) A B) B C) C D) D
2)
What is the configuration of naturally occurring amino acids?
A) D B) S C) L D) R
3)
Which is the correct structure for serine?
A) A B) B C) C D) D
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4)
Which is the correct structure for the amino acid proline?
A) A B) B C) C D) D
5)
Which is the correct structure for the amino acid cysteine?
A) A B) B C) C D) D
6)
Which is the correct structure for the amino acid valine?
A) A B) B C) C D) D
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7)
Which of the following is the correct structure for alanine at pH = 7?
A) A B) B C) C D) D
8)
Which of the following is the correct structure for aspartic acid at pH = 1?
A) A B) B C) C D) D
9) Which of the following aldehydes would be a good starting material in the Strecker synthesis of phenylalanine?
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A) A B) B C) C D) D
10)
What reagents would you use to convert acetaldehyde into alanine?
A) NH 3 B) HCN C) NaCN, NH 4Cl D) NaNH 2
11)
What is the separation of a racemic mixture into its component enantiomers called?
A) Diastereomers B) Meso C) Resolution D) Neutralization
12) Why does the formation of salts of a racemic mixture of N-acetyl valine with a single enantiomer of a-methylbenzylamine enable the separation of the two enantiomers of N-acetyl valine?
A) They form amides. B) They form diastereomers. C) They form salts. D) They form meso compounds.
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13)
Why can glycine not be resolved into two enantiomers?
A) It has no stereogenic centers. B) It has no nitrogen atoms. C) It has no aromatic rings. D) It cannot be converted into a salt.
14)
What amino acid is at the N-terminus of the following peptide?
A) Valine B) Serine C) Alanine D) Proline
15)
What amino acid is at the C-terminus of the following peptide?
A) Valine B) Serine C) Alanine D) Proline
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16)
Why is the s-trans form of an amide bond more stable?
A) There is no s-cis form in an amide bond. B) The oxygen is hydrogen-bonded with the nitrogen atom. C) The nitrogen is able to be sp 2-hybridized. D) The more sterically bulky groups are farther apart.
17) Why do amide bonds exist as reasonably stable s-cis or s-trans isomers at room temperature?
A) These amide bonds are not stable. B) There is partial double bond character between the carbonyl carbon and the nitrogen atom. C) The oxygen atom is hydrogen-bonded with the nitrogen atom. D) The side-chains can form hydrogen bonds.
18)
Which of the following is the major advantage of the Merrifield synthesis of peptides?
A) It allows for the formation of absolutely no by-products. B) Impurities can be easily washed away. C) Excess reagent can be used. D) It prevents hydrogenation.
19)
What are the basic steps in the Merrifield peptide synthesis?
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A) Coupling and hydrolysis B) Hydrolysis and deprotection C) Deprotection and hydrogenation D) Coupling and deprotection
20)
Which of the following is the structure of the amino acid lysine?
A) A B) B C) C D) D
21)
What is (are) the missing reagent(s) in the reaction below?
A) NH 3 B) HCN C) NaCN, NH 4Cl D) NaNH 2
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22)
What is the major organic product for the following reaction?
A) A B) B C) C D) D
23)
What is the IUPAC or common name for the following compound?
A) Cysteinylalanine B) Alanylcysteine C) Serinylalanine D) Alanylserine
24) Amino acid synthesis is possible by all except one of the pathways listed. Which is not a synthetic pathway for amino acids?
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A) Amination of malonic ester followed by hydrolysis and decarboxylation B) Nucleophilic addition of NH 3 to an aldehyde followed by addition of cyanide to the imine, and, finally, hydrolysis C) S N2 reaction using an a-halo carboxylic acid with ammonia as the nucleophile D) Reaction of NH 4Cl and NaCN with an aldehyde followed by an acidic work-up
25)
Which of the following correctly describes a protein?
A) a dipeptide; two amino acids joined together by one amide bond B) a tripeptide; three amino acids joined together by two amide bonds C) a polymer of more than 40 amino acids joined together by amide bonds D) a polypeptide of any number of amino acids joined together by amide bonds
26)
Which of the following correctly describes a peptide bond?
A) a bond between sp 3-hybridized atoms only B) a bond usually found in the s-cis conformation C) an amide bond D) the result of the formation of the carbonyl group of one amino acid with a R-group from the other amino acid
27)
Which of the following correctly describes the Merrifield synthesis?
A) It uses a solid phase technique for the synthesis of peptides. B) It uses DCC (dicyclohexylcarbodiimide) to form the amide bond in a peptide synthesis. C) It uses BOC ( tert-butoxycarbonyl) as a protecting group for peptide synthesis. D) It uses aqueous phase techniques for the synthesis of large polypeptides.
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28)
Which of the following correctly describes the tertiary structure of a peptide?
A) the three-dimensional conformations of localized regions of a protein B) the particular sequence of amino acids that are joined together by peptide bonds C) the structure is defined by the b-pleated sheet form D) the three-dimensional shape adopted by the entire peptide
29)
What are the only covalent bonds that stabilize the tertiary structure of a peptide?
A) Hydrogen bonds B) Disulfide bonds C) Van der Waal bonds D) Ionic bonds
30)
Which of the following is (are) globular protein(s)?
A) Hemoglobin B) Keratins C) Collagens D) Elastins
31)
Which of the following is (are) fibrous protein(s)?
A) Keratins B) Hormones C) Enzymes D) Antibodies
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32) What is the appropriate sequence of reaction conditions used to synthesize valine from acetamidomalonic ester?
A) (1) NaOH; (2) (CH 3) 2CHBr; (3) Cl 2, H 2O, heat B) (1) NaOCH 2CH 3; (2) (CH 3) 2CH 2CHBr; (3) HCl, H 2O, heat C) (1) NaOCH 2CH 3; (2) (CH 3) 2CHBr; (3) HCl, H 2O, heat D) (1) NaOH; (2) CH 3CH 2CH 2Br; (3) HCl, H 2O, heat
33) Below is a 2D chromatogram that shows the separation of five amino acids. In this technique, the amino acid mixture is first separated by chromatography using a polar solvent system. Then the plate is rotated 90°, and the amino acids are further separated by electrophoresis. Identify the spots obtained from a mixture of Trp, Glu, Lys, Ile and Thr. A table with isoelectric points is included to aid in solving this problem.
amino acid-pI value Trp-5.9 Glu-3.2 Lys-9.7 Ile-6.0 Thr-5.6 Version 1
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A) 1=Lys, 2=Thr, 3=Glu, 4=Trp, 5=Ile B) 1=Glu, 2=Thr, 3=Lys, 4=Trp, 5=Ile C) 1=Lys, 2=Ile, 3=Glu, 4=Trp, 5=Thr D) 1=Glu, 2=Ile, 3=Lys, 4=Trp, 5=Thr
34) Below is a proposed method for resolving a racemic mixture of (R)- and (S)phenylalanine. Upon separation of the products, will this method produce (R)- or (S)phenylalanine?
A) ( R)-Phenylalanine is produced since the acylase only hydrolyzes the amides of Lamino acids. B) ( S)-Phenylalanine is produced since the acylase only hydrolyzes the amides of Lamino acids. C) ( R)-Phenylalanine is produced since the acylase only hydrolyzes the amides of Damino acids. D) ( S)-Phenylalanine is produced since the acylase only hydrolyzes the amides of Damino acids.
35) Give the order (1 st to last) in which the following amino acids would be eluted with a buffer of pH = 4 from a column containing a cationic-exchange resin (Dowex 50): Arg (pI = 10.8), Ser (pI = 5.7), Asp (pI = 2.8) and His (pI = 7.6).
A) His, Ser, Asp, Arg B) Arg, His, Ser, Asp C) His, Ser, Arg, Asp D) Asp, Ser, His, Arg
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36) Reaction of a polypeptide, composed of 12 amino acids, with carboxypeptidase A releases Met (C-terminal amino acid). The polypeptide undergoes partial hydrolysis to give 12 groups of peptides. Use the groups of overlapping amino acids to determine the proper sequence of this polypeptide. Note: Since these lists of peptides are separated by commas, they are not necessarily in the proper sequence. Ser, Lys, Trp-5. Met, Ala, Gly- 9. Lys, Ser Gly, His, Ala-6. Ser, Lys, Val -10. Glu, His, Val Glu, Val, Ser-7. Glu, His-11. Trp, Leu, Glu Leu, Glu, Ser-8. Leu, Lys, Trp-12. Ala, Met A) Met-Ala-Gly-His-Glu-Val-Ser-Lys-Trp-Leu-Glu-Ser B) Met-Ala-Gly-Glu-His-Ser-Val-Lys-Trp-Leu-Glu-Ser C) Ser-Glu-Leu-Trp-Lys-Ser-Val-Glu-His-Gly-Ala-Met D) Ser-Lys-Leu-Trp-Lys-Ser-Val-His-Glu-Gly-Ala-Met
37)
What is formed by the combination of four amino acids?
A) A protein B) A polypeptide C) A tripeptide D) A tetrapeptide
38)
Which of the following amino acids is achiral?
A) Phenylalanine B) Glycine C) Valine D) Alanine
39)
Which of the following amino acids does not have an L-isomer?
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A) Alanine B) Valine C) Glycine D) Leucine
40) Which one of the following naturally occurring amino acids does not have an S configuration?
A) Cysteine B) Alanine C) Tyrosine D) Isoleucine
41) What is the name given to the pH at which the concentration of the zwitterionic form of an amino acid is at a maximum concentration?
A) Electric point B) Dipolar point C) Neutral point D) Isoelectric point
42)
What is the major organic product for the following reaction?
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A) I B) II C) III D) IV
43)
What is the product of the following reaction? (Assume workup to neutralize.)
A) I B) II C) III D) IV
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16)
What is the product of the following reaction? (Assume workup to neutralize.)
A) I B) II C) III D) IV
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17)
What is the product of the following reaction? (Assume workup to neutralize.)
A) I B) II C) III D) IV
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18)
What is the product of the following reaction? (Assume workup to neutralize.)
A) I B) II C) III D) IV
47)
Oxidoreductase performs the following function:
A) Catalyzes oxidation-reduction reactions B) Catalyzes the transfer of a group from one molecule to another C) Catalyzes the hydrolysis of esters, amides, and other functional groups that are cleaved when they react with water D) Catalyzes the conversion of one isomer to another
48)
Transferase performs the following function:
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A) Catalyzes oxidation-reduction reactions B) Catalyzes the transfer of a group from one molecule to another C) Catalyzes the hydrolysis of esters, amides, and other functional groups that are cleaved when they react with water D) Catalyzes the conversion of one isomer to another
49)
Hydrolase performs the following function:
A) Catalyzes oxidation-reduction reactions B) Catalyzes the transfer of a group from one molecule to another C) Catalyzes the hydrolysis of esters, amides, and other functional groups that are cleaved when they react with water D) Catalyzes the conversion of one isomer to another
50)
Iosmerase performs the following function:
A) Catalyzes oxidation-reduction reactions B) Catalyzes the transfer of a group from one molecule to another C) Catalyzes the hydrolysis of esters, amides, and other functional groups that are cleaved when they react with water D) Catalyzes the conversion of one isomer to another
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Answer Key Test name: Chap 23_6e 1) A 2) C 3) C 4) A 5) D 6) C 7) D 8) A 9) A 10) C 11) C 12) B 13) A 14) A 15) C 16) D 17) B 18) B 19) D 20) A 21) A 22) A 23) B 24) A 25) C 26) C Version 1
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27) C 28) D 29) B 30) A 31) A 32) C 33) A 34) B 35) D 36) C 37) D 38) B 39) C 40) A 41) D 42) A 43) A 44) B 45) C 46) D 47) A 48) B 49) C 50) D
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CHAPTER 24 1)
Which of the following compounds is an aldose?
A) A B) B C) C D) D
2)
How many carbons does a pentose sugar have?
A) 2 B) 3 C) 4 D) 5
3)
How many possible stereoisomers are there of the following heptose?
A) 16 B) 21 C) 32 D) 64
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4)
Is the following carbohydrate D or L? Provide an explanation for your answer.
A) It is D because the OH group on C2 is on the right. B) It is L because the OH group on C4 is on the left. C) It is L because the OH group on C3 is on the left. D) It is D because the sugar is not symmetric.
5)
Which of the following compounds is a b anomer?
A) A B) B C) C D) D
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6)
Which is the correct Haworth projection for the aanomer of allose?
A) A B) B C) C D) D
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7)
Which is the correct Haworth projection for the banomer of D-glucose?
A) A B) B C) C D) D
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8) Which is the correct Fischer projection for the open-chain form of the carbohydrate shown below?
A) A B) B C) C D) D
9)
Does a monosaccharide prefer to exist in the open-chain or closed-ring form?
A) Open B) Closed C) Both forms exist in equal ratios.
10)
What is the process called for the interconversion of one anomer to the other?
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A) Racemization B) Mutarotation C) Epimerization D) Enolization
11)
What is the correct chair form for the a anomer of D-mannose?
A) A B) B C) C D) D
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12)
What is the correct chair form for the b anomer of D-glucose?
A) A B) B C) C D) D
13)
Which of the following reagents would convert glucose into ethyl glucopyranoside?
A) EtBr, aq. HCl B) EtOH, aq. HCl C) EtOH, NaOH D) Ag 2O in NH 4OH
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14)
Which of the following is a reducing sugar?
A) A B) B C) C D) D
15)
Which of the following reagents will selectively oxidize an aldose to an aldonic acid?
A) PCC B) Ag 2O in NH 4OH C) FeCl 3 D) HNO 3
16) Which of the following pairs of carbohydrates will afford the same product from a Wohl degradation?
A) Xylose/glucose B) Ribose/arabinose C) Fructose/mannose D) Lyxose/threose
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17)
What are the products of the following reaction?
A) A B) B C) C D) D
18)
Which of the following compounds is not a valid representation for D-glucose?
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A) A B) B C) C D) D E) E
19)
Cellulose is a polysaccharide with
linkages.
A) b-1,4'-glycosidic B) a-1,4'-glycosidic C) b-1,6'-glycosidic D) a-1,6'-glycosidic
20)
Amylose is a polysaccharide with
linkages.
A) b-1,4'-glycosidic B) a-1,4'-glycosidic C) b-1,6'-glycosidic D) a-1,6'-glycosidic
21) The branching units in amylopectin, a polysaccharide, which enable this molecule to be water soluble are connected with linkages.
A) b-1,4'-glycosidic B) a-1,4'-glycosidic C) a-1,6'-glycosidic D) b-1,6'-glycosidic
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22)
What is the composition of lactose?
A) Two glucose units with a a-1,4'-glycoside bond B) One glucose and one fructose unit with a a-glycosidic bond to the 2' carbon of a fructofuranose ring C) One galactose and one glucose unit with a b-1,4'-glycoside bond D) Repeating unit of glucose units joined in a b-1,4'-glycosidic linkage
23)
What is the composition of sucrose?
A) Two glucose units with a a-1,4'-glycoside bond B) One glucose and one fructose unit with a a-glycosidic bond to the 2' carbon of a fructofuranose ring C) One galactose and one glucose unit with a b-1,4'-glycoside bond D) Repeating unit of glucose units joined in a b-1,4'-glycosidic linkage
24)
What is the composition of maltose?
A) Two glucose units with a a-1,4'-glycoside bond B) One glucose and one fructose unit with a a-glycosidic bond to the 2' carbon of a fructofuranose ring C) One galactose and one glucose unit with a b-1,4'-glycoside bond D) Repeating unit of glucose units joined in a b-1,4'-glycosidic linkage
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25)
From the sugars shown below, which one is a non-reducing sugar?
A) A B) B C) C D) D
26)
From the disaccharides listed below, which one will not undergo mutarotation?
A) Sucrose B) Maltose C) Lactose D) Xylobiose
27)
Upon hydrolysis of cellulose, what sugar is formed?
A) Sucrose B) Maltose C) Lactose D) Glucose
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28)
Upon hydrolysis of amylose, what sugar is formed?
A) Sucrose B) Maltose C) Lactose D) Glucose
29)
Upon hydrolysis of amylopectin, what sugar is formed?
A) Sucrose B) Maltose C) Lactose D) Glucose
30) From the sugars shown below, which one will not give a positive test with Tollens reagent?
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A) A B) B C) C D) D
31)
What is the best description of the product formed in the following reaction sequence?
A) The product is an optically active aldonic acid. B) The product is an optically inactive aldonic acid. C) The product is an optically active aldaric acid. D) The product is an optically inactive aldaric acid.
32) The following reaction is an example of a base-catalyzed epimerization reaction in which a ketose is converted to a pair of aldoses. What are the products from this reaction?
A) D-glucose and D-mannose B) D-galactose and D-talose C) D-talose and D-idose D) D-glucose and D-idose
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33)
Which sugar is represented by the line angle structure below?
A) D-fructose B) D-sorbose C) L-psicose D) L-tagatose
34) Oxidation of a D -hexose with nitric acid forms an optically active aldaric acid. A Wohl degradation of the same D -hexose followed by oxidation with nitric acid forms an optically active aldaric acid. What are the three possible D -hexoses that fit this data?
A) D-allose, D-altrose and D-glucose B) D-glucose, D- mannose and D-talose C) D-glucose, D-idose and D-altrose D) D-galactose, D-talose and D-mannose
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35) After a series of Kiliani-Fischer syntheses on D-glyceraldehyde, an unknown sugar was isolated from the reaction mixture. The following experimental data was obtained. What is the structure of this unknown sugar? Data: - Molecular formula: C6H12O6 - Reacts with phenylhydrazine to give an osazone, mp 178°C. - Reacts with HNO3to give an optically active aldaric acid. - Wohl degradation followed by HNO3oxidation gives an optically inactivealdaric acid. - Two Wohl degradations followed by HNO3oxidation give a meso-tartaric acid.
A) A B) B C) C D) D
36)
Which of the following sugars can be classified as an aldohexose?
A) A B) B C) C D) D
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37)
Which of the following sugars can be classified as a ketohexose?
A) A B) B C) C D) D
38)
Which of the following sugars can be classified as a ketotetrose?
A) A B) B C) C D) D
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39)
Which of the following sugars can be classified as a ketopentose?
A) A B) B C) C D) D
40) Which of the following best describes the relationship between D-glucose and Dfructose?
A) Enantiomers B) Epimers C) Anomers D) Constitutional isomers
41)
What is the classification of pyranose forms of monosaccharides?
A) 5-Membered cyclic hemiacetals B) 6-Membered cyclic acetals C) 5-Membered cyclic acetals D) 6-Membered cyclic hemiacetals
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42) What is the Fischer projection of the monosaccharide from which the following glycoside was prepared?
A) I B) II C) III D) IV
43) What is the Fischer projection of the monosaccharide from which the following glycoside was prepared?
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A) I B) II C) III D) IV
44) What is the Haworth projection of the α anomer of a monosaccharide epimeric with Dglucose at C3?
A) I B) II C) III D) IV
45)
Which of the following is D-fructose?
A) I B) II C) III D) IV
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46)
Which of the following is D-sorbose?
A) I B) II C) III D) IV
47)
Which of the following is D-glucose?
A) I B) II C) III D) IV
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48)
Which of the following is D-galactose?
A) I B) II C) III D) IV
49)
Which of the following is a disaccharide?
A) Maltose B) Lactose C) Sucrose D) All of these choices are correct
50)
Which of the following is a polysaccharide?
A) Cellulose B) Starch C) Glycogen D) All of these choices are correct
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51)
What type of linkage is present in chitin?
A) alpha-1,4'-glycosidic linkage B) beta-1,4'-glycosidic linkage C) alpha-1,2'-glycosidic linkage D) beta-1,2'-glycosidic linkage
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Answer Key Test name: Chap 24_6e 1) B 2) D 3) C 4) B 5) C 6) A 7) B 8) C 9) B 10) B 11) B 12) A 13) B 14) D 15) B 16) B 17) D 18) E 19) A 20) B 21) C 22) C 23) B 24) A 25) C 26) A Version 1
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27) D 28) D 29) D 30) C 31) D 32) B 33) C 34) B 35) A 36) B 37) A 38) C 39) D 40) D 41) D 42) B 43) C 44) A 45) A 46) B 47) C 48) D 49) D 50) D 51) B
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CHAPTER 25 1)
Provide a definition of the term lipid.
A) A compound with a carbonyl group B) A compound with an aromatic ring C) A hydrophobic biomolecule D) A water-soluble compound
2)
Which of the following compounds is not a lipid?
A) A B) B C) C D) D
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3)
Which of the following compounds is not a hydrolyzable lipid?
A) A B) B C) C D) D
4)
Evaluate the following statement: The terpene structure shown is a hydrolysable lipid.
A) True, because it contains an alcohol functional group. B) False, because alcohol and aldehyde moieties are not hydrolysable. C) True, because there are three polar groups and only 12 total carbon atoms. D) False, because there is too much steric repulsion from the alcohol and aldehyde moieties.
5)
What happens to the melting point in fatty acids as the unsaturation increases?
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A) It increases B) It decreases. C) There is no direct correlation between unsaturation and melting point. D) The melting point stays the same.
6)
Solid fats are generally from what source?
A) Vegetables B) Starches C) Legumes D) Animals
7)
Liquid oils usually have a higher percentage of what component compared to solid fats?
A) Oxygen B) Hydrogen C) Unsaturation D) Aromatic rings
8)
How can an unsaturated fatty acid be converted into a saturated fatty acid?
A) Hydrogenation B) Hydration C) Ozonolysis D) Hydrolysis
9)
What chemical process causes an oil (such as soybean oil) to become rancid?
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A) Hydrogenation with hydrogen B) Hydration with water C) Oxidation with molecular oxygen D) Bromination with bromine
10)
What is the main cellular function of a triacylglycerol?
A) Signal transduction B) Form cell membranes C) Nerve cell transferal D) Energy storage
11)
Which of the following is a phospholipid?
A) A B) B C) C D) D
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12)
What is the purpose of vitamin K?
A) Energy storage B) Blood clotting C) Photosynthesis D) Hydrogenation
13)
Eicosanoids are derived from what compound?
A) Arachidonic acid B) Cyclohexane C) Cholesterol D) Triacylglycerols
14) What is the first key enzyme required for the synthesis of prostaglandins from arachidonic acid?
A) Protein Kinase C B) Synthase C) Transferase D) COX (cyclic oxygenase)
15)
What is (are) the basic subunits of terpenes?
A) Cyclohexane B) Triacylglycerols C) Isoprene D) Carbonyls
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16)
How many isoprene units are in the following molecule?
A) 1 B) 2 C) 3 D) 4
17)
How many isoprene units are contained in the following molecule?
A) 5 B) 4 C) 3 D) 2
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18)
Which of the following compounds is a steroid?
A) A B) B C) C D) D
19) What is (are) the biological precursor(s) for the formation of the steroid skeleton found in cholesterol?
A) Cyclohexane B) Squalene C) Triacylglycerols D) Arachadonic acid
20)
Which structure represents the lowest energy conformation of a trans-decalin?
A) A B) B C) C D) D
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21) Which of the following sequences shows a reasonable series of 1,2-rearrangements as might be found in the biosynthesis of a steroid?
A) A B) B C) C D) D
22)
Which of the following is not one of the three main categories of hydrolyzable lipids?
A) Waxes B) Steroids C) Triacylglycerols D) Phospholipids
23)
Which of the following classes of molecules is not a nonhydrolyzable lipid?
A) Steroids B) Terpenes C) Phospholipids D) Eicosanoids
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24) All except one of the statements below are true about the molecule given. Which statement is not correct?
A) This molecule is a phospholipid and is generally found in fruits, vegetables, fish, liver, and dairy products. B) This molecule is a phospholipid that composes the main fabric of the insoluble barrier that protects the cell. C) This molecule contains two fatty acids and has at least one stereogenic center. D) This molecule is a phospholipid and belongs to the general category of lecithins.
25)
From the statements below, pick out the one that is not correct for fat-soluble vitamins.
A) Fat-soluble vitamins are classified as lipids. B) Fat-soluble vitamins are a group of biologically active compounds containing 20 carbon atoms. C) Fat-soluble vitamins are required in small quantities for normal metabolism. D) Fat-soluble vitamins are stored in fat cells for use when they are needed.
26)
What is the result of the oxidation of arachidonic acid with O 2by cyclooxygenase?
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A) It results in the synthesis of prostaglandins, thromboxanes, and prostacyclins. B) It results in the synthesis of fat-soluble vitamins from sphingomyelins. C) It results in the synthesis of phosphoacylglycerols. D) It is an important step in the synthesis of lipids that form the lipid bilayer.
Triacylglycerol A yields compound B when treated with excess H2, Pd-C. Ozonolysis of 27) A affords three molecules of compound C and one molecule of compound D. What is the structure of A?
Choices for Triglycerol A:
A) A B) B C) C D) D
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28)
Patchouli alcohol is an example of a terpene. How is this molecule classified?
A) Monoterpene B) Diterpene C) Triterpene D) Sesquiterpene
29) The stereoselective introduction of the C15 OH group on the w side chain of prostaglandins has presented a challenge for synthetic chemists. Recently, Mulzer and coworkers demonstrated a new route in which the w side chain is synthesized independently and then attached to the bicyclic counterpart. What is the appropriate sequence of reagents for the following synthesis?
A) (1) PBr 3; (2) Grubbs' catalyst, Reagent X; (3) KOC(CH 3) 3 B) (1) PCC; (2) Ph 3P=CH 2; (3) Grubbs' catalyst, Reagent X C) (1) PBr 3; (2) Ph 3P=CH 2; (3) Grubbs' catalyst, Reagent X D) (1) TsCl, pyridine; (2) Grubbs' catalyst, Reagent X; (3) KOC(CH 3) 3
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30) Norethindrone is a synthetic steroid that is better than progesterone in suppressing ovulation. What reagents (1–3) are required to convert norethindrone to the derivatives shown below?
A) (1) H 2, Pd-C; (2) (CH 3) 2CHCH 2NH 2, NaBH 3CN; (3) a. O 3, b. Zn, DMS B) (1) H 2, Pd-C; (2) (CH 3) 2CHCH 2NH 2, mild acid; (3) a. O 3, b. Zn, DMS C) (1) a. LiAlH 4, b. H 2O; (2) (CH 3) 2CHCH 2NH 2, NaBH 3CN; (3) a. OsO 4, b. NaHSO 3 D) (1) a. LiAlH 4, b. H 2O; (2) (CH 3) 2CHCH 2NH 2, mild acid; (3) a. OsO 4, b. NaHSO 3
31) Sphingomyelins are a major component of the myelin sheath. Damage to the myelin sheath results in such diseases as multiple sclerosis. Which compound below corresponds to a sphingomyelin?
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A) A B) B C) C D) D
32)
Which of the following are complex lipids?
A) Steroids B) Terpenes C) Waxes D) Protaglandins
33)
Which of the following are simple lipids?
A) Steroids B) Terpenes C) Waxes D) Prostaglandins
34)
Which of the following correctly describes waxes?
A) Long chain alcohols B) Long chain esters C) Long chain ethers D) Long chain fatty acids
35)
What is the correct classification of the following compound? CH3(CH2)15COOH
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A) Saturated triglyceride B) Simple lipid C) Wax D) Saturated fatty acid
36)
Which of the following fatty acids has the highest melting point?
A) Palmitic acid B) Arachidic acid C) Stearic acid D) Lauric acid
37)
Which of the following fatty acids has the lowest melting point?
A) Palmitic acid B) Arachidic acid C) Stearic acid D) Lauric acid
38)
Which of the following fatty acids has the highest melting point?
A) Linoleic acid B) Oleic acid C) Arachidonic acid D) Palmitoleic acid
39)
Which of the following fatty acids has the lowest melting point?
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A) Linoleic acid B) Oleic acid C) Arachidonic acid D) Palmitoleic acid
40)
Which of the following fatty acids is not present in natural fats and oils?
A) Hexadecanoic acid B) Heptadecanoic acid C) Octadecanoic acid D) None of the choices
41)
What is the name of the reaction of triglycerides with a base?
A) Esterification B) Transesterification C) Ozonolysis D) Saponification
42) What is the structure of a cortisone derivative that has a C=C between C6 and C7, methyl group at C8 and chlorine at C12? The configuration of C8 is S and the configuration at C12 is R.
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A) I B) II C) III D) IV
43)
How many isoprene units can be found in the following compound?
A) 1 B) 4 C) 8 D) 9
44)
Which state about waxes is not true?
A) Waxes are esters B) Waxes are formed from a high molecular weight alcohol and a fatty acid C) Waxes are water soluble D) Waxes are the simplest hydrolysable lipid
45)
Which of the following is a fat soluble vitamin?
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A) Vitamin A B) Vitamin D 3 C) Vitamin K D) All of these choices are correct
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Answer Key Test name: Chap 25_6e 1) C 2) B 3) C 4) B 5) B 6) D 7) C 8) A 9) C 10) D 11) B 12) B 13) A 14) D 15) C 16) D 17) B 18) C 19) B 20) D 21) A 22) B 23) C 24) A 25) B 26) A Version 1
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27) C 28) D 29) B 30) A 31) C 32) C 33) A 34) B 35) D 36) B 37) D 38) B 39) C 40) B 41) D 42) C 43) B 44) C 45) D
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CHAPTER 26 1)
Which base is found in DNA or RNA, but not both?
A) Uracil B) Cytosine C) Adenine D) Guanine
2)
Which choice is a polynucleotide that is a polymer of ribonucleotides?
A) DNA B) RNA C) Both DNA and RNA D) Neither DNA nor RNA
3)
What is the name of the nucleoside shown?
A) Hydroadenine B) Deoxyadenosine C) Deoxyguanosine D) Hydroguanine
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4)
What is the base present in the nucleoside below?
A) Purine B) Pyrimidine C) Phenol D) Aniline
5)
What is the name of the nucleoside shown?
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A) Uridine B) Uridosine C) Oxyuridine D) Oxyuridosine
6)
Which nucleotide abbreviation is not valid?
A) dAMP B) AMP C) dUMP D) CMP
7) Which of the following is the name of the nucleoside formed from D-ribose and cytosine?
A) Ribosine B) Cytose C) Cytidine D) Cytamine
8)
Which structure represents a nucleotide?
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A)
B)
C)
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D)
9)
What is a nucleoside?
A) A monosaccharide + a base B) A polymer of ribonucleotides C) The monosaccharides ribose and deoxyribose D) A monosaccharide + a base + phosphate
10) The combination of a monosaccharide like ribose or deoxyribose, a base like purine or pyrimidine, and a phosphate unit is called .
A) a polysaccharide B) a nucleoside C) a nucleotide D) a polyamide
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11)
What is the abbreviation of the structure shown below?
A) GMP B) AMP C) CMP D) TMP
12)
Which is the structure of ATP?
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A)
B)
C)
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D)
13)
A polynucleotide contains
.
A) one free phosphate group at the 5' end B) a backbone of alternating sugar and base groups C) one free phosphate group at the 1' end D) one free OH group at the 5' end
14)
What is the abbreviation of the polynucleotide shown?
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A) TAC B) CAT C) CGT D) TGC
15)
Which base is at the 3' end of the structure shown?
A) Adenine B) Cytosine C) Guanine D) Thymine E) Uracil
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16)
Which base is at the 5' end of the structure shown?
A) Adenine B) Cytosine C) Guanine D) Thymine E) Uracil
17)
Which sequence has a purine base at the 3' end?
A) TCTAG B) AUCCT C) GUGCCU D) CCTTC
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18)
Which sequence is not possible?
A) GAGAA B) TAGGG C) UTAGA D) CCCCC
19) How many different trinucleotides can be formed from one guanine, one uracil, and one adenine?
A) 1 B) 3 C) 6 D) 18 E) 27
20)
How many hydrogen bonds form between a G–C base pair in a DNA double helix?
A) 1 B) 2 C) 3 D) 4
21)
What is the complementary strand for the DNA strand 5'–AAGGTAGC–3'?
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A) 3'–CGATGGAA–5' B) 3'–AAGGTAGC–5' C) 3'–TTCCATCG–5' D) 5'–TTCCATCG–3' E) 5'–CGATGGAA–3'
22)
What is the process by which DNA makes a copy of itself when a cell divides?
A) Transcription B) Replication C) Duplication D) Cloning
23) What step in the synthesis of proteins involves the genetic message contained in mRNA specifying the specific amino acid sequence of a protein?
A) Elongation B) Directed synthesis C) Translation D) Protein hydrolysis
24)
Which statement concerning the replication of DNA is not true?
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A) The first step in replication is unwinding the DNA to expose the bases on each strand. B) A new phosphodiester bond is formed between the 5'-phosphate of the nucleoside triphosphate and the 3'-OH group of the new DNA strand. C) Replication occurs in only one direction on the template strand, from the 5' end to the 3' end. D) In replication, the lagging strand is synthesized in small fragments which are then joined together by a DNA ligase enzyme.
25)
Which is not a type of RNA molecule?
A) mRNA B) dRNA C) tRNA D) rRNA
26)
Which is the smallest type of RNA?
A) mRNA B) dRNA C) tRNA D) rRNA
27)
Which statement about RNA codons is not true?
A) It is possible for two different codons to code for the same amino acid. B) There are 64 different codons. C) Three codons are "stop" codons, signaling the termination of protein synthesis. D) Three codons are "start" codons, signaling the start of protein synthesis.
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28) Which amino acid sequence is coded for by the mRNA sequence 5' AAG GCU AGU GGC 3'?
A) Thr–His–Asn–Asp B) Lys–Ala–Ser–Gly C) Asp–Asn–His–Thr D) Gly–Ser–Ala–Lys
29) Which amino acid sequence is coded for by the mRNA sequence 5' CCA AAC UGG GUA 3'?
A) Pro-Asn-Trp-Val B) Gln-Lys-Cys-Asp C) Pro-Ser-Tyr-Val D) Leu-Ile-Leu-Asp
30)
Which mRNA sequence codes for the amino acid sequence Leu–Gly–Asp–Arg?
A) 5' CUA GGU GAU AGC 3' B) 5' CUA CAG GAU AGA 3' C) 5' AGA GAU GGA UUA 3' D) 5' UUA GGA GAU AGA 3'
31)
Which codon does not code for alanine?
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A) GCG B) GCU C) GCC D) GCA E) GAC
32)
Which is not a stop codon?
A) UAA B) UGA C) UAG D) UGC
33)
Each individual tRNA contains
.
A) a base sequence that is identical to the informational strand of DNA B) the sequence of codons that determines the order of amino acids in the protein C) an anticodon of three nucleotides that is complementary to the codon in mRNA and identifies individual amino acids D) an anticodon complementary to any of the three stop codons
34) What polypeptide would be synthesized from the following template strand of DNA: 3' CGG AGA CGG ACG 5'? A) Ala–Ser–Ala–Cys B) Arg–Arg–Arg–Cys C) Gln–Lys–Gln–Met D) Ala–Ser–Ala–Thr E) Cys–Ala–Ser–Ala
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35)
How many different mRNA sequences code for the dipeptide Leu–Ile?
A) 1 B) 2 C) 9 D) 18
36) Which is not one of the elements needed to amplify DNA by polymerase chain reaction (PCR)?
A) Two primers—short polynucleotides that are complementary to the two ends of the segment to be amplified B) A restriction endonuclease enzyme that cleaves DNA at specific locations C) The segment of DNA that must be copied D) A DNA polymerase enzyme that will catalyze the synthesis of a complementary strand of DNA from a template strand E) Nucleoside triphosphates that serve as the source of the nucleotides A, T, C, and G needed in the synthesis of the new strands of DNA
37)
Which statement concerning the biomolecules DNA is incorrect?
A) DNA stands for diribonucleic acid. B) DNA stores the genetic information of an organism and transmits that information from one generation to another. C) DNA molecules are located in the nucleus of a cell. D) Four common bases are found in DNA: adenine, cytosine, guanine, and thymine.
38) DNA is a double-stranded nucleic acid that exists as a double helix. Which is responsible for holding the double helix of DNA together? Version 1
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A) Phosphodiester bonds between complementary base pairs on each strand B) β-N-glycosidic linkages between the sugar-phosphate backbone of each strand C) Disulfide bonds between the cysteine residues on each strand D) Hydrogen bonding between complementary bases on each strand
39)
Which of the following best describes the primary function of mRNA in a cell?
A) To serve as a coenzyme in the enzyme-catalyzed hydrolysis of proteins B) To serve as the template strand in the synthesis of DNA C) To transcribe the instructions for protein synthesis from DNA and carry this information to the ribosomes D) To transport amino acids to the ribosomes for protein synthesis
40)
How are the correct amino acids brought to the ribosomes for protein synthesis?
A) By reduced coenzymes that match the codons found on the DNA template strand B) By the transport protein coenzyme A C) By tRNA molecules that contain the complementary sequence of an mRNA codon in their anticodon loop D) Amino acids are synthesized at the ribosomes by the hydrolysis of proteins
41)
Which structure correctly represents the dinucleotide sequence GU that is found in RNA?
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A)
B)
C)
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D)
42)
Which component is not part of a nucleotide?
A) A nitrogen-containing base B) A monosaccharide C) An amino acid D) A phosphate group
43)
PCR stands for
A) polymer chain reduction. B) polymer chain reaction. C) polymerase chain reaction. D) polymerase chain reduction.
44) The correct order of steps in each cycle of the polymerase chain reaction are: I. The DNA sample is heated to unwind the double helix into two single stands. II. Primers are added to form a short segment of double-stranded DNA on each strand III. DNA polymerase is used to add nucleotides to lengthen the DNA segment
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A) I II III B) II I III C) III I II D) II III I
45)
A virus lacks which of the following molecules?
A) Enzymes B) Free Nucleotides C) DNA D) Two of these are correct.
46)
A virus that contains RNA is called a
A) retrovirus. B) RNA virus. C) AZT. D) reverse transcription.
47)
Which of the following is an example of a virus?
A) Common cold B) Influenza C) Herpes D) All of these are correct.
48)
Which of the following part of cocktail of drugs used to fight HIV?
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A) PCR B) DNA C) RNA D) AZT
49) For the DNA segment 3'–ACCTGCCTACCCG–5', the sequence of the mRNA molecule synthesized is?
A) 5'–UGGACGGAUGGGC–3' B) 3'–UGGACGGAUGGGC–5' C) 3'–ACCTGCCTACCCG–5' D) 5'–ACCTGCCTACCCG–3'
50)
In the transcription "cartoon" shown, the direction of transcription is from
A) left to right. B) right to left. C) top to bottom. D) bottom to top.
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51)
The "cartoon" shown below is an example of an
A) tRNA cloverleaf. B) mRNA cloverleaf. C) rRNA cloverleaf. D) DNA cloverleaf.
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Answer Key Test name: Chap 26_6e 1) A 2) B 3) B 4) A 5) A 6) C 7) C 8) B 9) A 10) C 11) B 12) D 13) A 14) B 15) D 16) B 17) A 18) C 19) C 20) C 21) C 22) B 23) C 24) C 25) B 26) C Version 1
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27) D 28) B 29) A 30) D 31) E 32) D 33) C 34) A 35) D 36) B 37) A 38) D 39) C 40) C 41) A 42) C 43) C 44) A 45) D 46) A 47) D 48) D 49) A 50) A 51) A
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CHAPTER 27 1)
Which is the sum of all of the chemical reactions that take place in an organism?
A) Anabolism B) Metabolism C) Catabolism D) Citric acid cycle
2)
Which is the first stage of catabolism?
A) Digestion B) Citric acid cycle C) Fatty acid oxidation D) Glycolysis E) Formation of acetyl CoA
3)
Which is the second stage of catabolism?
A) Digestion B) Citric acid cycle C) Fatty acid oxidation D) Glycolysis E) Formation of acetyl CoA
4)
Which is the third stage of catabolism?
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A) Digestion B) Citric acid cycle C) Fatty acid oxidation D) Glycolysis E) Formation of acetyl CoA
5)
Where does the hydrolysis of carbohydrates to monosaccharides begin?
A) In the stomach B) In the saliva C) In the liver D) In the small intestines
6)
Which is the abbreviated structure of acetyl CoA?
A)
B)
C)
D)
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7)
Which molecule contains the largest amount of stored energy?
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A)
B)
C)
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D)
8) The addition of a phosphate group to ADP, forming ATP, is an example of what type of reaction?
A) Hydration B) Hydrolysis C) Phosphorylation D) Reduction E) Decarboxylation
9)
Which is not true about coenzymes?
A) Many reactions in metabolic pathways involve coenzymes. B) When a coenzyme gains hydrogen atoms the coenzyme is an oxidizing agent. C) Many coenzymes are involved in oxidation and reduction reactions. D) The coenzyme nicotinamide adenine dinucleotide, NAD +, is a common biological reducing agent.
10) Which coupled reaction properly indicates the role of the coenzyme as an oxidizing agent?
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A)
B)
C)
D)
11) Which functional group is not contained in coenzyme A, whose structure is shown below?
A) Alcohol B) Sulfhydryl C) Phosphoester D) Amide E) Aldehyde
12)
How many molecules of CO 2are produced for each turn of the citric acid cycle?
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A) 1 B) 2 C) 4 D) 8
13)
How many molecules of GTP are produced for each turn of the citric acid cycle?
A) 1 B) 2 C) 4 D) 8
14) How many molecules of ATP are produced for each unit of GTP formed in the citric acid cycle?
A) 4 B) 3 C) 2 D) D1
15) How many molecules of reduced coenzymes are produced for each turn of the citric acid cycle?
A) 2 B) 4 C) 16 D) 32
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16)
How many reactions make up the citric acid cycle?
A) 3 B) 4 C) 6 D) 8
17)
What is the classification of the reaction shown?
A) Redox B) Isomerization C) Decarboxylation D) Hydrolysis
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18)
What is the classification of the reaction shown?
A) Oxidation B) Reduction C) Decarboxylation D) Hydrolysis E) Isomerization
19)
How many carbons enter into the citric acid cycle with each new Acetyl CoA?
A) 1 B) 2 C) 4 D) 6
20) Which steps of the citric acid cycle generate reduced coenzymes necessary in the production of ATP?
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A) Steps 2, 3, 4, and 7 B) Steps 1, 4, 7, and 8 C) Steps 3, 4, 5, and 7 D) Steps 3, 4, 6, and 8
21)
Which steps of the citric acid cycle generate CO 2?
A) Steps 2 and 3 B) Steps 3 and 4 C) Steps 4 and 5 D) Steps 5 and 6
22) How much ATP is generated for each acetyl CoA during stages [3] and [4] of catabolism?
A) 4 molecules of ATP B) 5 molecules of ATP C) 8 molecules of ATP D) 10 molecules of ATP E) 16 molecules of ATP
23)
In which stage of metabolism are biomolecules degraded into two-carbon acetyl units?
A) Stage [1] B) Stage [2] C) Stage [3] D) Stage [4]
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24)
Which is the primary energy-carrying molecule in metabolic pathways?
A) AMP B) ATP C) NADH D) Acetyl CoA E) FADH 2
25)
Which is an oxidizing agent? A) Fe 2+ B) NAD + C) FADH 2 D) ATP
26) Which statement best describes what occurs with a substrate is oxidized using FAD to product FADH 2?
A) FAD is a reducing agent, and FADH 2is its oxidized form. B) FAD is a reducing agent, and FADH 2is its reduced form. C) FAD is an oxidizing agent, and FADH 2is its oxidized form. D) FAD is an oxidizing agent, and FADH 2is its reduced form.
27)
Which intermediate in the citric acid cycle is a secondary alcohol?
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A)
B)
C)
D) E) Two of the intermediates are secondary alcohols.
28)
Which intermediate in the citric acid cycle contains two chirality centers?
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A)
B)
C)
D)
29)
How many reactions in the citric acid cycle generate FADH 2?
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A) 0 B) 1 C) 3 D) 8
30)
How many reactions in the citric acid cycle generate NAD +?
A) 0 B) 1 C) 3 D) 8
31)
Which product(s) of the citric acid cycle are funneled into the electron transport chain?
A) ATP B) NAD +and FAD C) NADH, FADH 2, and H + D) NADH, FADH 2, H +, and ATP
32)
Which is the major product of stage [2] of catabolism?
A) NADH B) Acetyl CoA C) GTP D) CO 2
33)
Which is the enzyme that hydrolyzes triacylglycerols?
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A) Acetyl CoA B) Protease pepsin C) Amylase D) Lipase
34)
Which statement concerning the digestion of food groups is incorrect?
A) Carbohydrates are ultimately broken down to glucose and other monosaccharides. B) Triacylglycerols are ultimately broken down by lipases into glycerol and fatty acids. C) Proteins are ultimately broken down by proteases into amino acids. D) Polysaccharides are ultimately broken down to nucleotides.
35)
What is the primary function of the citric acid cycle in metabolism?
A) To break down food molecules into smaller components so they can be absorbed by the blood B) To synthesize ATP from the energy produced in the hydrolysis of citric acid C) To provide the enzymes necessary to aid in the hydrolysis of carbohydrates, proteins, and lipids D) To convert acetyl groups to CO 2molecules and provide reduced coenzymes for the electron transport chain
36)
At which stage of metabolism is the most energy in the form of ATP produced?
A) Electron transport chain and oxidative phosphorylation B) Digestion C) Citric acid cycle D) Transcription
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37) Which best describes the function of the coenzymes NAD +and FAD in catabolic pathways?
A) Competitive inhibitors of the enzymes present in each pathway B) Noncompetitive inhibitors of the enzymes present in each pathway C) Oxidizing agents that accept electrons and hydrogen ions from molecules undergoing oxidation D) Transport molecules that carry acetyl units to or from the different stages of metabolism
38) The primary function of the electron transport chain and oxidative phosphorylation is which of the following?
A) To provide electrons and energy for the phosphorylation of ATP B) To synthesize the reduced coenzymes necessary for digestion C) To oxidize the reduced coenzymes NADH and FADH 2, and provide energy for the synthesis of ATP D) To transport electrons from ATP to ADP, and synthesize acetyl CoA molecules
39)
Each NADH that enters the electron transport chain will result in the formation of units of ATP.
A) 10 B) 2.5 C) 1.5 D) 32 E) 7.3
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40)
Each FADH 2that enters the electron transport chain will result in the formation of units of ATP.
A) 7.3 B) 10 C) 1.5 D) 2.5 E) 32
41) Which statement best describes how the interconversion of ATP and ADP is responsible for storing and providing energy for cellular reactions?
A) The energy stored in ADP is released when ATP is synthesized. B) The energy required to phosphorylate ADP is stored in ATP, and released when ATP undergoes hydrolysis. C) The energy released in the phosphorylation of ADP can be coupled with unfavorable reactions within the cell. D) The energy required to hydrolyze ATP comes from the energy producing reactions in the cell; the energy lost is then stored in ATP.
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42) Oxaloacetate is the starting material in the first step of the citric acid cycle and the product of the last step. The last step of the citric acid cycle, the oxidation of malate to oxaloacetate, is shown. What is the structure of oxaloacetate?
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A)
B)
C)
D)
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43) The second step of the citric acid cycle, the isomerization of citrate to isocitrate, is shown. What is the structure of isocitrate?
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A)
B)
C)
D)
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44) Step 7 of the citric acid cycle is shown. Which statement best describes what occurs in this step?
A) Fumarate undergoes hydrolysis with the aid of the enzyme fumarase. B) Fumarate undergoes reduction with the aid of the cofactor fumarase. C) Fumarate undergoes hydrogenation with hydrogens and electrons provided by the enzyme fumarase. D) Fumarate undergoes hydration with the aid of the enzyme fumarase.
45) Step 6 of the citric acid cycle is shown. Which statement best describes the role of FAD in this reaction?
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A) FAD causes the reduction of succinate to form fumarate. B) FAD causes succinate to undergo hydration to form fumarate. C) FAD causes the oxidation of succinate to form fumarate. D) FAD causes the isomerication of succinate to form fumarate.
46) Since more energy is released from the hydrolysis of creatine phosphate than is needed for the phosphorylation of ADP, the coupling of these two reactions results in the formation of
A) ATP. B) ADP. C) AMP. D) ATP and ADP.
47) The conversion of Fe 3+to Fe 3+acting as a (an) agent.
2+
in the electron transport chain is an example of Fe
A) oxidizing B) reducing C) catalytic D) oxidizing and reducing
48)
NAD +is the abbreviation for
A) nicotinamide adenine dinucleotide. B) nicotine amino dinucleotide. C) nitrogen adenine dinucleotide. D) nitrogen amino dinucleotide.
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49)
FAD is the abbreviation for
A) fluorine adenine dinucleotide. B) flavin amino dinucleotide. C) flavin adenine dinucleotide. D) fluorine amino dinucleotide.
50)
How many electrons are donated by each NADH in the electron transport chain?
A) 0 B) 1 C) 2 D) 3
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Answer Key Test name: Chap 27_6e 1) B 2) A 3) E 4) B 5) B 6) C 7) D 8) C 9) D 10) B 11) E 12) B 13) A 14) D 15) B 16) D 17) A 18) E 19) B 20) D 21) B 22) D 23) B 24) B 25) B 26) D Version 1
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27) E 28) B 29) B 30) A 31) C 32) B 33) D 34) D 35) D 36) A 37) C 38) C 39) B 40) C 41) B 42) A 43) C 44) D 45) C 46) D 47) A 48) A 49) C 50) C
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CHAPTER 28 1) Organocuprate reagents (R 2CuLi) react with several compounds. Which listed reaction is not correct?
A) Acid chlorides react with organocuprate reagents to form ketones. B) Epoxides react with organocuprate reagents to form alcohols. C) Alkyl halides react with organocuprate reagents to form coupling products containing a new carbon-carbon bond. D) Carbon dioxide reacts with organocuprate reagents to form carboxylic acids.
2) Which class of compounds listed below does not react with organocuprate reagents to form a coupling product that contains a new carbon-carbon bond?
A) 1° Alkyl halides B) 3° Alkyl halides C) Vinyl halides D) Aryl halides
3) Which statement below best explains what is meant by the statement, "An organocuprate reaction with a vinyl halide is stereospecific"?
A) The reaction of a specific stereoisomer with the R 2CuLi reagent will yield that particular stereoisomer as the product. B) The reaction of a vinyl halide with the R 2CuLi reagent will only yield the cis product. C) The reaction of a vinyl halide with the R 2CuLi reagent will only yield the trans product. D) The reaction of a vinyl halide with the R 2CuLi reagent will only yield one enantiomer product—either R or S configuration.
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4) Coupling reactions with vinyl halides are stereospecific. Which choice below best describes the expected product when trans-1-bromo-1-hexene reacts with (CH 3) 2CuLi?
A) The reaction will only yield a trans-alkene. B) The reaction will only yield a cis-alkene. C) The reaction will only yield one enantiomeric product with R configuration. D) The reaction will only yield one enantiomeric product with S configuration.
5)
What is the major organic product of the following reaction?
A) I B) II C) III D) IV
6)
What is the major organic product of the following reaction?
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A) I B) II C) III D) IV
7)
What is the major organic product of the following reaction?
A) I B) II C) III D) IV
8)
What is the missing reactant in the following reaction?
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A) I B) II C) III D) IV
9)
Identify the products of the following reaction.
A) I B) II C) III D) IV
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10)
Identify the products of the following reaction.
A) I B) II C) III D) IV
11)
Which of the reactions listed below is not stereospecific?
A) Suzuki reaction B) Organocuprate coupling reaction C) Heck reaction D) Simmons-Smith reaction
12)
Choose the statement below that is not true about the Suzuki reaction.
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A) The product of the Suzuki reaction is completely stereospecific. B) The Suzuki reaction involves both an organoborane reagent and an organopalladium catalyst. C) The Suzuki reaction forms more highly substituted alkenes. D) The Suzuki reaction involves an oxidative addition followed by a reductive elimination.
13)
Which of the following is not a step in the Suzuki reaction?
A) Oxidative addition of R-X to the palladium catalyst B) Substitution of the R group to the palladium catalyst C) Transfer of the alkyl group from the organoborane to palladium D) Reductive elimination of R-R, forming the new C-C bond
14) What do the Suzuki reaction, the Heck reaction, and the organocuprate reaction all have in common when they react with an alkyl halide?
A) All reactions form new carbon-carbon bonds. B) They all use palladium as a catalyst in one step of the reaction. C) They are all stereospecific reactions. D) They all require harsh conditions.
15)
Which of the following statements is not true about the Simmons-Smith reaction?
A) The Simmons-Smith reaction involves the formation of a free carbene. B) The Simmons-Smith reaction uses the reagents zinc-copper couple. C) The Simmons-Smith reaction is stereospecific. D) The Simmons-Smith reaction involves CH 2I 2reacting with a copper-activated zinc reagent.
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16)
Which of the following is true about the use of the Grubbs catalyst?
A) The Grubbs catalyst is used in carbon-carbon coupling reactions. B) The Grubbs catalyst is used in alkene metathesis. C) The Grubbs catalyst is used in carbene formation. D) The Grubbs catalyst is used with palladium as a co-catalyst.
17)
What products are formed when diazomethane is heated?
A) Methane gas and nitrogen gas B) Propene gas and nitrogen gas C) Methyl radical and nitrogen gas D) Methylene and nitrogen gas
18)
Which of the following descriptions does not apply to methylene? A) Methylene is sp 2hybridized. B) Methylene is a neutral, reactive intermediate. C) Methylene is a radical intermediate. D) The formula of methylene is :CH 2.
19)
Which of the following statements is not true about a carbene?
A) A carbene is a neutral reactive intermediate. B) A carbene contains a divalent carbon. C) A carbene is sp 3hybridized. D) A carbene is surrounded by six electrons.
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20)
Which of the following correctly describes a reaction yielding a dichorocarbene?
A) The reaction of chloroform with KOC(CH 3) 3 B) The reaction of chloroform with Zn(Cu) C) The reaction of chloroform with (CH 3) 2CuLi D) The reaction of diazomethane with KOC(CH 3) 3
21) Dichlorocarbene reacts with an alkene to form a cyclopropane derivative. In this reaction the dichlorocarbene acts as a(n)
A) Lewis base. B) electrophile. C) nucleophile. D) Brønsted-Lowry base.
22)
Why is the Grubbs catalyst synthetically important?
A) Because it only requires dilute concentrations of the reactants B) Because it produces only stereospecific products C) Because it produces only stereoselective products D) Because it provides a synthetic pathway for ring-closing metathesis reactions
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23) What would be the starting material for the following product that was made via a Grubbs catalyst?
A) I B) II C) III D) IV
24) Identify the starting material that would be used to form the following product in a ringclosing metathesis reaction utilizing a Grubbs catalyst?
A) I B) II C) III D) IV
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25)
Identify the major organic product of the following reaction.
A) I B) II C) III D) IV
26)
What would be the major organic product of the following Heck reaction?
A) I B) II C) III D) IV
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27)
Identify the major organic product of the following reaction.
A) I B) II C) III D) IV
28)
Identify the major organic product of the following reaction.
A) I B) II C) III D) IV
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29)
Identify the structure of the organic product Y formed in the following reaction sequence.
A) I B) II C) III D) IV
30)
What is the name for the type of intermediate X formed in the reaction sequence below?
A) A carbocation B) A carbanion C) A free radical D) A carbene
31) As shown below, when cis-2-butene reacts with dichlorocarbene, only the cis-1,1dichloro-2,3-dimethylcyclopropane is formed. What can we conclude about the nature of the reaction mechanism?
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A) The mechanism is an S N1 mechanism. B) The mechanism is a concerted. C) The mechanism proceeds through a radical intermediate. D) The mechanism is an E2 mechanism.
32)
What is the major organic product of the following reaction?
A) I B) II C) III D) IV
33)
What is the major organic product of the following reaction?
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A) I B) II C) III D) None of the choices is correct.
34)
Identify the structure of the organic product Y formed in the following reaction sequence.
A) I B) II C) III D) IV
35) Many of the reactions studied in this chapter are stereospecific. Why are stereospecific reactions important?
A) When a reaction produces a mixture of enantiomers, it is often very difficult to separate them. A mixture of products is often not useful. B) Often stereoisomers of a particular compound will have very different biological effects on an organism. Only one isomer is biologically helpful, and the other may be harmful. C) Often only one stereoisomer is biologically active, and coupling reactions are often used for the production of biological materials. D) All of the choices are true.
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36) What starting material could yield the following compound if Simmons-Smith conditions were used?
A) I B) II C) III D) IV
37) What starting material could yield the following compound if Simmons-Smith conditions were used?
A) I B) II C) III D) IV
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38) Identify the structure of the major organic product that results from the following reaction.
A) I B) II C) III D) IV
39) Compound X can be synthesized via a ring-closing metathesis reaction when treated with a Grubbs' catalyst. What is a possible structure of the starting material for this reaction?
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A) I B) II C) III D) IV
40) What is the appropriate sequence of reagents that will produce the target molecule shown below from ethylbenzene?
A) (1) HBr, H 2O 2; (2) KOC(CH 3) 3; (3) MCPBA; (4) CH 2=CPh 2 B) (1) NBS, hn ; (2) KOC(CH 3) 3; (3) CHBr 3, KO(CH 3) 3; (4) a. LiCuPh 2, b. H 2O
C) (1) H 2SO 4(aq.), D ; (2) MCPBA; (3) CHBr 3, KO(CH 3) 3; (4) CH 2=CPh 2 D) (1) Br 2, FeBr 3; (2) MCPBA; (3) CHBr 3, KO(CH 3) 3; (4) Ph 2COCl
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41) What is the appropriate sequence of starting material and reagents that will produce the target molecule shown below?
A) I B) II C) III D) IV
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42) Identify the structure of the major organic product that results from the following reaction.
A) I B) II C) III D) IV
43) Identify the structure of the major organic product that results from the following reaction.
A) I B) II C) III D) IV
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44)
What is the major product of the following reaction?
A) I B) II C) III D) IV
45) What reactant would be necessary to produce the product indicated in the following reaction?
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A) I B) II C) III D) IV
46) Starting with chloroform, what reactions order and reagents are necessary to produce the following product and its enantiomer?
A) [1] KOC(CH 3) 3,[2] trans-2-butene B) [1] KOC(CH 3) 3,[2] cis-2-butene C) [1] trans-2-butene, [2] KOC(CH 3) 3 D) [1] cis-2-butene, [2] KOC(CH 3) 3
47) Starting with chloroform, what reactions order and reagents are necessary to produce the following product?
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A) [1] KOC(CH 3) 3,[2] trans-2-butene B) [1] KOC(CH 3) 3,[2] cis-2-butene C) [1] trans-2-butene, [2] KOC(CH 3) 3 D) [1] cis-2-butene, [2] KOC(CH 3) 3
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Answer Key Test name: Chap 28_6e 1) D 2) B 3) A 4) A 5) A 6) B 7) D 8) C 9) B 10) A 11) C 12) C 13) B 14) A 15) A 16) B 17) D 18) C 19) C 20) A 21) B 22) D 23) B 24) C 25) A 26) C Version 1
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27) D 28) B 29) C 30) D 31) B 32) C 33) A 34) A 35) D 36) C 37) D 38) B 39) A 40) B 41) D 42) A 43) B 44) B 45) B 46) A 47) B
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CHAPTER 29 1)
Which of the following statements about pericyclic reactions is true?
A) Pericyclic reactions occur by way of ionic intermediates. B) Pericyclic reactions occur by way of radical intermediates. C) Pericyclic reactions involve multiple steps. D) Reactive intermediates are not formed in pericyclic reactions.
2)
Which of the following statements about pericyclic reactions is true?
A) In pericyclic reactions, bonds are broken and formed in multiple steps. B) In pericyclic reactions, all bonds are broken and formed in a single step. C) One intermediate has been identified in pericyclic reactions. D) The transition state in a pericyclic reaction is acyclic.
3)
Which of the following statements about pericyclic reactions is not true?
A) Pericyclic reactions are concerted reactions. B) Pericyclic reactions proceed through a cyclic transition state. C) Pericyclic reactions are not stereospecific. D) Pericyclic reactions require light or heat.
4)
Which of the following is a type of pericyclic reaction?
A) electrocyclic reactions B) acyclic reactions C) cycloelimination reactions D) electrophilic reactions
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5)
Which of the following is not a type of pericyclic reactions? A) cycloadditions B) nucleophilic reactions C) electrocyclic reactions D) sigmatropic rearrangements
6)
Which of the following statements about electrocyclic ring closure is not true?
A) It is an intramolecular reaction. B) It requires heat or light. C) The cyclic product contains one more s bond and one fewer p bond than the reactants. D) The cyclic product contains one more p bond and one fewer s bond than the reactants.
7) true?
Which of the following statements about an electrocyclic ring-opening reaction is not
A) An electrocyclic ring-opening reaction is an intramolecular reaction. B) An electrocyclic ring-opening reaction requires a source of energy (heat or light). C) The product of an electrocyclic ring-opening reaction contains one fewer p bond than the reactant. D) The product of an electrocyclic ring-opening reaction contains one more p bond than the reactant.
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8)
What is the organic product of the following electrocyclic reaction?
A) I B) II C) III D) IV
9)
Which of the following statements about cycloaddition reactions is true?
A) Cycloaddition reactions occur only intermolecularly. B) Cycloaddition reactions occur only intramolecularly. C) Cycloaddition reactions form a cyclic product with two new p bonds. D) Cycloaddition reactions can be intramolecular or intermolecular.
10)
Which of the following statements about sigmatropic reactions is true?
A) The reactants contain one more p bond than the product. B) The product contains one more p bond than the reactant. C) A p bond is broken in the reactant. D) A s bond is broken in the reactant.
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11)
What is the correct classification of the following reaction?
A) Cycloaddition reaction B) Electrocyclic reaction C) Electrophilic reaction D) Sigmatropic reaction
12)
What is the correct classification of the following reaction?
A) Cycloaddition reaction B) Electrocyclic reaction C) Electrophilic reaction D) Sigmatropic reaction
13)
What is the correct classification of the following reaction?
A) Cycloaddition reaction B) Electrophilic reaction C) Electrocyclic reaction D) Sigmatropic reaction
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14)
What is the correct classification of the following reaction?
A) Cycloaddition reaction B) Electrophilic reaction C) Electrocyclic reaction D) Sigmatropic reaction
15)
Which of the following statements about porbitals is true? A) p orbitals are formed by the linear combination of two sp3orbitals. B) p orbitals are formed by the linear combination of two sp2orbitals. C) p orbitals are formed by the linear combination of two sp orbitals. D) p orbitals are formed by the linear combination of two p orbitals.
16)
Which of the following statements about molecular orbitals is true?
A) The number of molecular orbitals formed is different from the number of atomic orbitals used. B) The number of molecular orbitals formed is equal to the number of atomic orbitals used. C) The number of molecular orbitals formed is equal to twice the number of atomic orbitals used. D) The number of molecular orbitals formed is equal to half the number of atomic orbitals used.
17)
Which of the following statements about a p-bonding molecular orbital is true?
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A) A p-bonding molecular orbital is formed when two p orbitals of similar phase overlap. B) A p-bonding molecular orbital is lower in energy than a s-bonding molecular orbital. C) A p-bonding molecular orbital is formed when two p orbitals of opposite phase overlap. D) Both the statements a p-bonding molecular orbital is formed when two p orbitals of similar phase overlap and a p-bonding molecular orbital is lower in energy than a s-bonding molecular orbital are true.
18)
Which of the following statements about a p* antibonding molecular orbital is true?
A) A p* antibonding molecular orbital is formed when two p orbitals of similar phase overlap. B) A p* antibonding molecular orbital is formed when two p orbitals of opposite phase overlap. C) A p* antibonding molecular orbital is a higher-energy molecular orbital than a p bonding molecular orbital. D) Both the statements a p* antibonding molecular orbital is formed when two p orbitals of opposite phase overlap and a p* antibonding molecular orbital is a higher-energy molecular orbital than a p bonding molecular orbital are true.
19)
How many p molecular orbitals are present in 1,3,5-hexatriene?
A) 3 B) 4 C) 5 D) 6
20)
How many bonding molecular orbitals are present in 1,3,5-hexatriene?
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A) 3 B) 4 C) 5 D) 6
21)
How many p molecular orbitals are present in 1,3,5,7,9-decapentaene?
A) 4 B) 5 C) 10 D) 12
22)
How many bonding molecular orbitals are present in 1,3,5,7,9-decapentaene?
A) 4 B) 5 C) 10 D) 12
23)
How many nodes are present in Y5of 1,3,5,7,9-decapentaene?
A) 2 B) 3 C) 4 D) 5
24)
Which of the following statements about electrocyclic reactions is true?
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A) An electrocyclic reaction is generally irreversible. B) Generally, an acyclic triene is favored over a six-membered ring at equilibrium. C) Generally, a four-membered ring is favored over an acyclic diene at equilibrium. D) An electrocyclic reaction is generally reversible.
25)
Predict the major organic product(s) of the following electrocyclic reaction.
A) Only I B) Only II C) Only III D) Only I and II
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26)
Predict the major organic product(s) of the following electrocyclic reaction.
A) Only I B) Only II C) Only III D) Only I and II
27)
Predict the major organic product(s) of the following electrocyclic reaction.
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A) Only I B) Only II C) Only III D) Only I and II
28)
Predict the major organic product(s) of the following electrocyclic reaction.
A) Only I B) Only II C) Only III D) Only I and II
29)
Which of the following statements about thermal electrocyclic reactions is not true?
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A) The number of s bonds in the conjugated polyene determines whether rotation is conrotatory or disrotatory. B) Thermal electrocyclic reactions occur in a disrotatory fashion for a conjugated polyene with an odd number of p bonds. C) Thermal electrocyclic reactions occur in a conrotatory fashion for a conjugated polyene with an even number of p bonds. D) In thermal reactions, we consider the orbitals of the HOMO of the ground state electronic configuration to determine the course of the reaction.
30) true?
Which of the following statements about photochemical electrocyclic reactions is not
A) In photochemical reactions, we consider the orbitals of the HOMO of the excited state to determine the course of the reaction. B) Photochemical electrocyclic reactions occur in a conrotatory fashion for a conjugated polyene with an odd number of p bonds. C) Photochemical electrocyclic reactions occur in a disrotatory fashion for a conjugated polyene with an even number of p bonds. D) In photochemical reactions, we consider the orbitals of the LUMO of the excited state to determine the course of the reaction.
31)
Which of the following statements about cycloaddition reactions is not true?
A) Cycloaddition reactions form a cyclic product with two new s bonds. B) The course of the reaction is determined by the symmetry of the molecular orbitals of the products. C) Cycloaddition reactions are concerted. D) Cycloaddition reactions are stereospecific.
32)
Which of the following statements about cycloaddition reactions is true?
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A) Cycloaddition reactions can be initiated by heat only. B) Cycloaddition reactions can be initiated by light only. C) Cycloaddition reactions can be initiated by heat or light. D) Cycloaddition reactions are identified by the number of p electrons in the two products.
33)
Why is the Diels-Alder reaction called a thermal [4+2] cycloaddition?
A) Because the reaction is initiated by heat; the diene has four p electrons and the dienophile has two p electrons. B) Because the reaction is initiated by light; the diene has four p electrons and the dienophile has two p electrons. C) Because the reaction is initiated by heat; the dienophile has four p electrons and the diene has two p electrons. D) Because the reaction is initiated by light; the dienophile has four p electrons and the diene has two p electrons.
34) Which of the following statements about [2+2] cycloaddition reactions between two alkenes is true?
A) The reaction is initiated by heat. B) The reaction is initiated by light. C) The product is a cyclopentane derivative. D) Each reactant contains two s electrons that participate in the formation of new bonds.
35)
What type of cycloaddition reaction is shown below?
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A) [2+2] B) [4+2] C) [4+4] D) [0+2]
36)
What type of cycloaddition reaction is shown in the following equation?
A) [2+2] B) [4+2] C) [4+4] D) [0+2]
37)
What are the two modes of bond formation in cycloaddition reactions?
A) Suprafacial and antarafacial bond formations B) Superfacial and antifacial bond formations C) Suprafacial and synfacial bond formations D) Synfacial and antifacial bond formations
38) true?
Which of the following statements about orbital symmetry and cycloaddition reactions is
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A) Thermal cycloadditions involving an even number of p bonds proceed by a suprafacial pathway. B) Thermal cycloadditions involving an odd number of p bonds proceed by a suprafacial pathway. C) Photochemical cycloadditions involving an odd number of p bonds proceed by a suprafacial pathway. D) Photochemical sycloadditions involving an even number of p bonds proceed by an antarafacial pathway.
39) true?
Which of the following statements about orbital symmetry and cycloaddition reactions is
A) Thermal cycloadditions involving an even number of p bonds proceed by a suprafacial pathway. B) Thermal cycloadditions involving an odd number of p bonds proceed by an antarafacial pathway. C) Photochemical cycloadditions involving an even number of p bonds proceed by an antarafacial pathway. D) Photochemical cycloadditions involving an even number of p bonds proceed by a suprafacial pathway.
40)
Which of the following statements about sigmatropic reactions is not true?
A) A sigmatropic reaction is an intramolecular pericyclic reaction. B) In a sigmatropic reaction, s bond is broken in one of the reactants. C) The p bonds rearrange in a sigmatropic reaction. D) The number of p bonds in the reactants and product differs in a sigmatropic reaction.
41)
Which of the following is not a correct designation for a sigmatropic rearrangement?
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A) [1,3] B) [1,5] C) [3,3] D) [3,1]
42)
What type of sigmatropic rearrangement is illustrated below?
A) [1,3] B) [1,4] C) [3,3] D) [1,5]
43)
What type of sigmatropic rearrangement is illustrated below?
A) [1,3] B) [1,4] C) [3,3] D) [1,5]
44)
What type of sigmatropic rearrangement is illustrated below?
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A) [1,3] B) [1,4] C) [3,3] D) [1,5]
45) Which of the following statements about sigmatropic rearrangements and orbital symmetry is not true?
A) Reactions involving six atoms or fewer must take place by suprafacial pathways. B) In a suprafacial rearrangement, the new s bond forms on the opposite side of the p system as the broken s bond. C) In an antarafacial rearrangement, the new s bond forms on the opposite side of the p system as the broken s bond. D) In a suprafacial rearrangement, the new s bond forms on the same side of the p system as the broken s bond.
46)
Which of the following statements about the Cope rearrangement is not true?
A) The Cope rearrangement involves the rearrangement of a 1,5-diene to an isomeric 1,5-diene. B) The Cope rearrangement takes place readily in a suprafacial pathway under photochemical conditions. C) The Cope rearrangement involves three electron pairs; two in p bonds and one in a s bond. D) The Cope rearrangement takes place readily in a suprafacial pathway, when heated.
47)
Which of the following statements about the Claisen rearrangement is true?
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A) The Claisen rearrangement occurs readily in a suprafacial pathway under photochemical conditions. B) The Claisen rearrangement occurs readily in an antarafacial pathway under thermal conditions. C) The Claisen rearrangement involves three electron pairs; two in p bonds and one in a s bond. D) The Claisen rearrangement involves the rearrangement of an unsaturated ether to a b,g-unsaturated carbonyl compound.
48)
What is the major organic product of the following Cope rearrangement?
A) I B) II C) III D) IV
49)
What is the major organic product of the following oxy-Cope rearrangement?
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A) I B) II C) III D) IV
50)
What is the major organic product of the following Claisen rearrangement?
A) I B) II C) III D) IV
51)
What is the major organic product of the following Claisen rearrangement?
A) I B) II C) III D) IV
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52) Which of the following statements about a thermal reaction involving an even number of electron pairs is true?
A) A thermal reaction involving an even number of electron pairs is conrotatory or antarafacial. B) A thermal reaction involving an even number of electron pairs is disrotatory or suprafacial. C) A thermal reaction involving an even number of electron pairs is conrotatory or suprafacial. D) A thermal reaction involving an even number of electron pairs is disrotatory or antarafacial.
53) Consider the following reaction sequence. What is the correct classification of the first reaction in the sequence?
A) [1,3] Sigmatropic rearrangement B) [1,5] Sigmatropic rearrangement C) [3,3] Sigmatropic rearrangement D) [5,5] Sigmatropic rearrangement
54) Consider the following reaction sequence. What is the correct classification of the second reaction in the sequence?
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A) [2 + 2] Cycloaddition B) [6 + 4] Cycloaddition C) [4 + 4] Cycloaddition D) [4 + 2] Cycloaddition
55)
How many pi electrons are in the ground state HOMO for buta-1,3-diene?
A) 0 B) 2 C) 4 D) 6
56)
How many pi electrons are in the ground state LUMO for buta-1,3-diene?
A) 0 B) 2 C) 4 D) 6
57)
How many pi electrons are in the excited state HOMO for buta-1,3-diene?
A) 0 B) 1 C) 2 D) 3
58)
How many pi electrons are in the excited state LUMO for buta-1,3-diene?
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A) 0 B) 1 C) 2 D) 3
59)
How many pi electrons are in the ground state HOMO for hexa-1,3,5-triene?
A) 0 B) 2 C) 4 D) 6
60)
How many pi electrons are in the ground state LUMO for hexa-1,3,5-triene?
A) 0 B) 2 C) 4 D) 6
61)
How many pi electrons are in the excited state HOMO for hexa-1,3,5-triene?
A) 0 B) 1 C) 2 D) 3
62)
How many pi electrons are in the excited state LUMO for hexa-1,3,5-triene?
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A) 0 B) 1 C) 2 D) 3
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Answer Key Test name: Chap 29_6e 1) D 2) B 3) C 4) A 5) B 6) D 7) C 8) B 9) D 10) D 11) B 12) A 13) C 14) D 15) D 16) B 17) D 18) D 19) D 20) A 21) C 22) B 23) C 24) D 25) B 26) A Version 1
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27) D 28) C 29) A 30) D 31) B 32) C 33) A 34) B 35) A 36) B 37) A 38) B 39) D 40) D 41) D 42) D 43) C 44) A 45) B 46) B 47) C 48) B 49) D 50) B 51) B 52) A 53) B 54) D 55) B 56) A Version 1
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57) B 58) A 59) B 60) A 61) B 62) A
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CHAPTER 30 1)
Which of the following monomers yields the polymer shown below?
A) A B) B C) C D) D
2)
Which of the following is the repeating unit in polyvinyl chloride (PVC)?
A) A B) B C) C D) D
3) Which of the following is (are) addition polymer(s)? I. polypropylene II. Teflon III. nylon
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A) Only I B) Only II C) Only III D) Both I and II
4) Which of the following is (are) condensation polymer(s)? I. polypropylene II. Teflon III. nylon A) Only I B) Only II C) Only III D) Both II and III
5)
Which one of the following monomers undergoes cationic polymerization most readily?
A) H 2C=CH 2 B) H 2C=CHCH 3 C) H 2C=C(CH 3) 2 D) H 2C=CHCN
6)
Which one of the following monomers undergoes anionic polymerization most readily?
A) H 2C=CH 2 B) H 2C=CHCH 3 C) H 2C=C(CH 3) 2 D) H 2C=CHCN
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7) In which type of polymer are the chains packed less tightly together, resulting in lower melting points and a softer texture?
A) Isotactic polymers B) Syndiotactic polymers C) Atactic polymers D) Cross-linked polymers
8)
Which of the following best describes the polymer chain shown below?
A) Atactic polypropylene B) Isotactic polypropylene C) Syndiotactic polypropylene D) Cross-linked polypropylene
9)
Which of the following is used to make Teflon?
A) Fluoroethene B) 1,1,4,4-Tetrafluorobutadiene C) 1,2-Difluoroethene D) Tetrafluoroethylene
10)
Which of the following best describes the polymer chain shown below?
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A) Atactic polypropylene B) Isotactic polypropylene C) Syndiotactic polypropylene D) Cross-linked polypropylene
11) The monomer used to make superglue is shown below. Which of the following methods of polymerization is most suitable for this type of monomer?
A) Free-radical chain-growth B) Cationic chain-growth C) Anionic chain-growth D) Acid-catalyzed step-growth
12) Which type of polymerization process uses benzoyl peroxide (or other peroxides) as an initiator?
A) Free-radical chain-growth B) Cationic chain-growth C) Anionic chain-growth D) Acid-catalyzed step-growth
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13)
Which of the following is the monomer that gives the polymer shown below?
A) A B) B C) C D) D
14) What modification occurs when a small amount of p-divinylbenzene is added to the polymerization reaction of styrene to form polystyrene? (Recall that the vinyl group is —CH=CH 2.)
A) Cross-linking of the polystyrene B) Isotactic stereochemistry of the polystyrene C) Syndiotactic stereochemistry of the polystyrene D) "Softening" of the polystyrene by a plasticizer
15)
Identify the repeating unit in the polymer formed from the following reaction sequence.
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A) A B) B C) C D) D
16) The acid-catalyzed dimerization of isobutylene gives a mixture of two isomeric alkenes, A and B. Hydrogenation of this mixture gives a single C8H18hydrocarbon. What is the structure of this hydrocarbon?
A) 2,2,4-Trimethylpentane B) 2,3,4-Trimethylpentane C) 2,4-Dimethylhexane D) 2,5-Dimethyhexane
17) The repeating unit of poly(methyl methacrylate) is shown below. Which one of the following is the monomer used to make poly(methyl methacrylate)?
A) A B) B C) C D) D
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18)
Which of the following monomers is used to make the polymer carbowax, shown below?
A) A B) B C) C D) D
19)
Which of the following initiators can be used for anionic chain-growth polymerization?
A) Benzoyl peroxide B) CH 3CH 2CH 2CH 2Li C) BF 3 D) Al(CH 2CH 3) 3, TiCl 4
20) Which of the following initiators can be used for free radical chain-growth polymerization?
A) Benzoyl peroxide B) CH 3CH 2CH 2CH 2Li C) BF 3 D) Al(CH 2CH 3) 3, TiCl 4
21)
Which of the following initiators is used to make isotactic polypropylene?
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A) Benzoyl peroxide B) CH 3CH 2CH 2CH 2Li C) BF 3 D) Al(CH 2CH 3) 3, TiCl 4
22)
The repeating unit of a polymer is shown below. This polymer is formed by
A) addition of ethylene. B) addition of trans-2-butene. C) 1,2 addition of butadiene. D) 1,4 addition of butadiene.
23) Vulcanization is the process of cross-linking polymer chains in rubber using what chemical?
A) Sulfur B) Formaldehyde C) Benzoyl peroxide D) Ethylene glycol
24)
What monomer(s) would be used to make the polyester shown below?
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A) Butanedioic acid B) 4-Hydroxybutanal C) 4-Hydroxybutanoic acid D) Butanedioic acid and 1,4-butanediol
25) Which of the following is the repeating unit of the polymer formed in the polymerization of p-hydroxybenzoic acid?
A) A B) B C) C D) D
26)
Identify the monomer(s) needed to make the following polyester.
A) 3-Hydroxybutanoic acid B) Butanedioic acid C) Butanedioic acid and ethylene glycol D) Butanedioic acid and ethanol
27)
Which of the following is (are) repeating unit(s) of step-growth polymers?
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A) Only I B) Only II C) Only III D) I and II
28) Bakelite is formed by the acid-catalyzed polymerization of phenol with formaldehyde. What is (are) the product(s) of the first step in this polymerization, shown below? (Note: in the answers below the hydroxymethyl group is -CH2OH.)
A) Ortho and para-hydroxybenzaldehyde B) Meta-hydroxybenzaldehyde C) Ortho and para-(hydroxymethyl)phenol D) Meta-(hydroxymethyl)phenol
29)
What is the purpose of plasticizers?
A) To harden plastics B) To soften plastics C) To initiate polymerizations D) To cross-link polymer chains
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30) Which of the following is the repeating unit of the polymer formed in the polymerization reaction shown below?
A) A B) B C) C D) D
31)
What is the name given to polymers that soften when heated and harden when cooled?
A) Cross-linked polymers B) Copolymers C) Thermosetting polymers D) Thermoplastics
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What is the structure of the polymer which results when styrene is reacted with BF3and 32) H2O?
A) A B) B C) C D) D
33) Rank the following monomers (X, Y and Z) in order of increasing ability to undergo anionic polymerization, starting with the least reactive monomer.
A) Y< X < Z B) Z < Y < X C) X < Y < Z D) Y < Z < X
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34) Melamine and formaldehyde combine to form the polymer, Melmac®. How is Melmac®classified, and what physical characteristics are consistent with its structure?
A) Polycarbonate, transparent B) Polyurethane, elastic C) Thermosetting, rigid D) Thermoplastic, can be melted and molded into new shapes
35) Which monomer and which type of initiator would you use to synthesize the following polymer?
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A) A B) B C) C D) D E) E
36)
Which of the following sets of products results if nylon 66 is treated with sulfuric acid?
A) A B) B C) C D) D
37) What is the classification of the following polymer in which X and Y represent repeating units?
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A) Block copolymer B) Homopolymer C) Alternating copolymer D) Random copolymer
38) What is the classification of the following polymer in which X and Y represent repeating units?
A) Block copolymer B) Homopolymer C) Alternating copolymer D) Random copolymer
39) What is the classification of the following polymer in which X and Y represent repeating units?
A) Block copolymer B) Homopolymer C) Alternating copolymer D) Random copolymer
40)
What is the name given to polymers with single monomers?
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A) Homopolymers B) Copolymers C) Block polymers D) Random polymers
41)
What is the name given to polymers with two or more different monomers?
A) Homopolymers B) Copolymers C) Block polymers D) Random polymers
42) What are the structures of the three monomers needed to synthesize the following polymer?
A) I B) II C) III D) IV
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43)
What type of polymer is Lexan?
A) Epoxy B) Polyurethane C) Polycarbonate D) Polyamide
44)
What type of polymer is Nylon?
A) Epoxy B) Polyurethane C) Polycarbonate D) Polyamide
45)
What type of polymer is Spandex?
A) HDPE B) Polyurethane C) Polycarbonate D) Polyamide
46) Which of the following polymers can be made at least in part from glucose derived from a renewable plant source?
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A) Teflon B) Polyethylene C) Sorona D) Polypropylene
47)
Which of the following polymers can be recycled into floor mats?
A) PVC B) LDPE C) PET D) HDPE
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Answer Key Test name: Chap 30_6e 1) B 2) A 3) D 4) C 5) C 6) D 7) C 8) B 9) D 10) C 11) C 12) A 13) D 14) A 15) B 16) A 17) B 18) D 19) B 20) A 21) D 22) D 23) A 24) C 25) A 26) C Version 1
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27) D 28) C 29) B 30) B 31) D 32) B 33) D 34) C 35) A 36) D 37) A 38) C 39) D 40) A 41) B 42) A 43) C 44) D 45) B 46) C 47) A
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