College Level Organic Chemistry

Page 18

like ionic compound with a high melting point, while methane, being non-salt-like, has a boiling point of -161 degrees Celsius. Methane or CH4 is mainly a covalently-bonded molecule. There is little electrostatic attraction between methane molecules (they are nonpolar) so that they boil at a very low temperature to become a gas. Hydrogen fluoride boils, on the other hand, 200 degrees higher than methane gas. This is because it is more ionic and has connections between the Hydrogen and Fluorine atoms through not only ionic bonding but also with hydrogen bonding between the HF molecules in chains and rings. This makes the boiling point higher. Because methane is nonpolar, it is inert to almost all reagents that could remove the hydrogen ion under anything but the most extreme conditions. It is therefore difficult to generate a CH3+ or CH3- ion, as these would be very reactive and just wouldn’t last long. In other words, you couldn’t make CH4 plus HF to make CH3F plus H2. This would require a cation of CH3+, which is not very stable in nature.

ORBITAL THEORIES While there are many ways to describe and write covalent bonds (which will be described later in this chapter), there are some concrete theories about how covalent bonds exist in organic molecules. While there is ionic bonding in organic chemistry, the most important bonding in this type of chemistry involves covalent bonds. You may have learned that covalent bonding involves the sharing of electrons but you may not know exactly how this happens. This introduces the topic of the valence bond theory, which describes how bonding happens in covalent molecules. According to this theory, there are two atomic orbitals around a pair of atoms—each orbital of which contains one electron. In sharing orbitals, the orbital pair will contain a stable set of two electrons. The H2 molecule is the simplest case of a covalently-bonded molecule. There are two spherical orbitals (1s orbitals) in each hydrogen atom, each with one electron in it. In the bonding of the two atoms, the electrons no longer are anywhere within the sphere but spend more time in that part of each sphere between the two nuclei, which holds the

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Steroids

1min
pages 237-238

Quiz

3min
pages 240-243

Terpenes

0
page 236

Phospholipids

0
page 234

Quiz

3min
pages 227-230

Prostaglandins

0
page 235

Micelles

0
page 233

Quiz

3min
pages 213-216

Key Takeaways

0
page 226

Reactions of Amino Acids

1min
page 221

Key Takeaways

0
page 212

Glycosides

1min
page 206

Reducing Sugars

1min
page 207

Key Takeaways

0
page 198

Quiz

3min
pages 199-202

Reduction of Nitrogenous Compounds

2min
pages 192-193

Nitrosation of Amines

1min
pages 196-197

Preparing Amides

0
page 195

Alkylation of Ammonia

0
page 191

Quiz

2min
pages 183-186

Synthesis of Sulfides

1min
pages 180-181

Sulfides

1min
page 179

Key Takeaways

0
page 182

Physical Properties of Nitrogenous Compounds

2min
pages 189-190

Thiols

1min
page 178

Oxidation of Alcohols using DMSO

1min
page 177

Quiz

3min
pages 170-173

The Haloform Reaction

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page 163

Michael Addition Reaction

1min
page 168

The Aldol Reaction of Aldehydes

1min
page 165

The Aldol Reaction of Ketones

1min
page 166

Conjugate Reactions

1min
page 167

Alkylation of Enolates

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page 164

Key Takeaways

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page 169

Basic Alpha-Halogenation of Ketones and Aldehydes

1min
page 162

Quiz

3min
pages 153-156

Esters

4min
pages 145-147

Epoxides

2min
pages 143-144

Reactions with Ethers

1min
pages 141-142

Physical Properties of Ethers

1min
page 140

Quiz

2min
pages 135-138

Key Takeaways

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page 134

Glycols

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page 133

Reactivity of Alcohols

1min
page 128

Alcohol Dehydration

3min
pages 129-130

Quiz

3min
pages 120-123

Friedel-Crafts Reaction

3min
pages 116-118

Key Takeaways

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page 119

Sulfonation of Benzene

1min
page 115

Nitration of Benzene

1min
page 114

Halogenation of Benzene

1min
page 113

Aromatic Reactions

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page 112

Benzene Chemistry

3min
pages 109-111

Nomenclature of Aromatics

5min
pages 105-108

Quiz

2min
pages 101-103

Properties of Carboxylic Acids

1min
page 99

Carboxylic Acids

2min
pages 96-97

Natural Occurrence of Ketones and Aldehydes

0
page 95

Reactivity of Aldehydes and Ketones

3min
pages 93-94

Quiz

3min
pages 82-85

The Carbonyl Group

2min
pages 91-92

Naming Ketones

2min
pages 89-90

Naming Aldehydes

1min
page 88

Chapter 5: Aldehydes, Ketones, and Carboxylic Acids

2min
pages 86-87

Physical Properties of Alkenes

1min
page 77

Alkenes

4min
pages 74-76

Alkyne Reactivity

2min
pages 79-80

Cycloalkanes

1min
page 73

Chemical Properties of Alkanes

1min
page 72

Alkyl Groups

1min
page 70

Alkoxides or Alkoxy Groups

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page 71

Key Takeaways

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page 65

Solvation

3min
pages 63-64

Nonpolar Solvents

7min
pages 58-62

Quiz

2min
pages 66-68

Quiz

2min
pages 54-56

Key Takeaways

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page 53

Enantiomer

1min
pages 51-52

Diastereomerism

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page 50

Stereochemistry and Isomers

1min
page 49

Functional Groups

1min
page 48

Carboxylic Acids

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page 46

Ketones

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page 45

Quiz

2min
pages 34-37

Alcohols

1min
page 42

Key Takeaways

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page 33

Orbital Theories

4min
pages 18-20

Writing Organic Molecular Structures

1min
page 24

Organic Molecular Charges

2min
pages 28-29

Resonance Chemistry

2min
pages 30-32

Bonding Trends in Organic Chemistry

2min
pages 25-26

Constitutional Isomers

1min
page 27

Preface

7min
pages 12-15

Carbon Hybridization

2min
pages 21-22
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