College Level Organic Chemistry

Page 140

oxygen molecule. There are common names for ethers, with the most obvious being diethyl ether, which is colloquially known as “ether”. Others are named for each side chain plus “ether” at the end of the term (like butyl methyl ether). These involve using the alkanes in alphabetical order. Cyclic ethers or heterocycles have at least one carbon atom replaced by an oxygen atom. In naming these molecules, the prefix “oxa” is used to indicate that oxygen is replacing a carbon atom. They are numbered starting with the oxygen molecule as being “1” and rotating around the ring. An example is 1-oxacyclopentane, which is a 4-carbon, 1oxygen ring. The reference “1” in the name is not truly necessary because the oxygen molecule is automatically going to be number one. When it comes to priority, alcohol has priority over the ether as well as over any halide. The ether also has priority over the halide with the numbering starting with the end that has the side chain at the highest priority. The ring structure with two carbon atoms and an oxygen molecule is called 1-oxirane or oxirane.

PHYSICAL PROPERTIES OF ETHERS Ethers have oxygen atoms but no hydrogen atom associated with them. This leads to less intermolecular hydrogen bonding between molecules; it means that the boiling points tend to be low—nearly the same as that of alkanes. Boiling point increases with molecular mass but does not increase much because the oxygen alone does not cause an increase in intermolecular bonding. Because ether molecules have an oxygen atom, there will be hydrogen bonding with water molecules. This leads to an ether that has about the same solubility in water as the comparable alcohol. It means that ethanol and dimethyl ether have about the same solubility in water; however, diethyl ether has four carbon atoms associated with it and is nearly insoluble in water.

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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

0
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

0
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

0
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

0
page 46

Ketones

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page 45

Quiz

2min
pages 34-37

Alcohols

1min
page 42

Key Takeaways

0
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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