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.

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.

Figure Number: 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.

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.

Figure Number: 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.

Figure Number: 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.

Figure Number: 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.

Figure Number: 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.

Figure Number: 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).