1. Figure Number: 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.

2. Figure Number: 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.

3. Figure Number: UN
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.

4. Figure Number: 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.

5. Figure Number:
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.

6. Figure Number: UN
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.

7. Figure Number: UN
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.

8. Figure Number: UN
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.

9. Figure Number:
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).