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Chapter 12
Reactions of Alcohols, Ethers, Epoxides, and Sulfur-Containing Compounds

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12-00CO
Title
Methanol
Caption
Electrostatic potential map of methanol.
Notes
Alcohols have poorer leaving groups (OH–) than halides (X–), and are therefore less reactive than alkyl halides in substitution and elimination reactions.
Keywords
methanol, electrostatic, potential, map
12-01
Title
Figure 12.1
Caption
Reaction coordinate diagram for the dehydration of a protonated alcohol.
Notes
The major product is the more stable alkene because the transition state leading to its formation is more stable.
Keywords
figure 12.1, reaction coordinate, diagram, dehydration, protonated, alcohol
12-01-05UN
Title
Dehydration vs. Substitution
Caption
E2 dehydration mehanism and SN2 substitution mechanism forming products from ethanol catalyzed by sulfuric acid.
Notes
Primary alcohols undergo dehydration by an E2 pathway with SN2 substitution competing. Secondary and tertiary alcohols undergo dehydration by an E1 pathway with SN1 substitution competing.
Keywords
dehydration, substitution, ethanol, E1, E2, SN1, SN2
12-02
Title
Figure 12.2
Caption
Reaction coordinate diagrams for the nucleophilic attack of hydroxide ion on ethylene oxide and on diethyl ether.
Notes
Ring strain in ethylene oxide destabilizes the reactant relative to the transition state and results in greater reactivity of ethylene oxide.
Keywords
figure, 12.2, reaction coordinate, diagrams, nucleophilic, attack, hydroxide, ethylene, oxide, diethyl, ether
12-02-016
Title
Benzene and Benzene Oxide
Caption
Electrostatic potential maps of benzene and benzene oxide.
Notes
Benzene is converted into benzene oxide by cytochrome P450 in the liver.
Keywords
benzene, oxide, potential, maps
12-02-035UN
Title
Crown Ethers
Caption
Electrostatic potential maps of [12]-crown-4, [15]-crown-5, and [18]-crown-6.
Notes
Crown ethers can be used to bind cations in their centers, forming tight ion-pair complexes with the corresponding anions, and which are soluble in benzene. They thus provide a means of dissolving ionic substances in nonpolar solvents.
Keywords
crown, ethers, [12]-crown-4, [15]-crown-5, [18]-crown-6, potential, maps
12-02-036UN
Title
Crown Ethers
Caption
Electrostatic potential maps of [12]-crown-4, [15]-crown-5, and [18]-crown-6.
Notes
Crown ethers can be used to bind cations in their centers, forming tight ion-pair complexes with the corresponding anions, and which are soluble in benzene. They thus provide a means of dissolving ionic substances in nonpolar solvents.
Keywords
crown, ethers, [12]-crown-4, [15]-crown-5, [18]-crown-6, potential, maps
12-02-037UN
Title
Crown Ethers
Caption
Electrostatic potential maps of [12]-crown-4, [15]-crown-5, and [18]-crown-6.
Notes
Crown ethers can be used to bind cations in their centers, forming tight ion-pair complexes with the corresponding anions, and which are soluble in benzene. They thus provide a means of dissolving ionic substances in nonpolar solvents.
Keywords
crown, ethers, [12]-crown-4, [15]-crown-5, [18]-crown-6, potential, maps
12-02-053
Title
Methyllithium and Methyl Chloride
Caption
Electrostatic potential maps of methyllithium and methyl chloride.
Notes
Note that the carbon in methyl chloride is electron-deficient, whereas the carbon in methyllithium is electron-rich. Alkyllithium reagents are convenient tools for carrying out reactions which require carbanionlike reactants (i.e., carbon acting as a nucleophile or a base).
Keywords
methyllithium, methyl, chloride, potential, maps

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