Alcohols and Ethers


Substrate: (R/S)-1-phenyl-2-propanol

Reagent: H2SO4. Rearrangement, Zaitsev rule, (Z/E) products.

Substrate: (R/S)-2-phenyl-3-butanol

Reagent: HCl. Rearrangement, (R/S) products.

Substrate: 1-methyl-cyclohexanol

Reagent: HBr. Temperature effect on elimination-substitution competition.

Substrate: cyclohexyl-methyl-methanol

Reagent: HBr. Rearrangement, (R/S) products.

Substrate: 3-methyl-2-butanol

Reagent: HBr. Rearrangement, (R/S) products.

Substrate: 3-methyl-2-butanol

Reagent: HBr. Temperature effect on elimination-substitution competition

Substrate: (R/S)-4,4-dimethyl-3-pentanol

Reagent: H2SO4. Rearrangement, Zaitsev rule, (Z/E) products.

Substrate: (R/S)4-ethyl-4-methyl-3-pentanol

Reagent: H2SO4. Rearrangement, Zaitsev rule, (Z/E) products.

Substrate: 2, 2-dimethyl-1-pentanol

Reagent: HBr. Hindered primary alcohol SN1, rearrangement.

Substrate : 3, 3-dimethyl-1-pentanol

Reagent: HBr. primary alcohol SN2.

Substrate: (R/S)-1,1-diphenyl-1,2-ethanediol

Reagent: H2SO4. Pinacol-arrangement, protonation competition, (R/S)product

Substrate: (R/S)-2-methyl-1,1-diphenyl-1,2-ethanediol

Reagent: H2SO4. Pinacol-arrangement, competition in protonation and migration, (R/S)product.

Substrate: (R/S)-1,2-dimethyl-2-phenyl-1,2-ethanediol

Reagent: H2SO4. Pinacol-arrangement, competition in protonation and migration, (R/S)product

Substrate: 2,3-dimethyl-2,3-butanediol

Reagent: H2SO4. symmetrical pinacol-arrangement.

Substrate: (R/S)-1,2-dimethyl-1,2-diphenyl-1,2-ethanediol

Reagent: H2SO4. Pinacol-arrangement, migration competition.

Substrate: (R/S)-1,2-dimethyl-1,2-cyclohexanediol

Reagent: H2SO4. Depending on the substrate config, faster reaction leads to 6-member ring and slower one leads to 5-member ring.

Substrate: (R/S)-2,5-hexanediol

Reagent: H2SO4. E1, Zaitsev rule, (Z/E)product

Substrate: (R/S)-3-methyl-2,4-pentanediol

Reagent: H2SO4. E1, carbocation rearrangement, Zaitsev rule, (Z/E)product

Substrate: (R/S)-2,2-dimethyl-4-methyl-3-pentanol

Reagent: H2SO4. E1, carbocation rearrangement, Zaitsev rule, (R/S)product.

Substrate: (R/S)-2,2-dimethylcyclohexanol

Reagent: H2SO4. E1, carbocation rearrangement, Zaitsev rule, (R/S)product

Substrate: 2-cyclobutyl-2-propanol

Reagent: H2SO4. E1, carbocation rearrangement, Zaitsev rule, (R/S)product.

Substrate: (R/S)-1,2-epoxy-3-methyl-pentane

Reagent: phenol. Catalyst: acid. Inversion at chiral center.

Substrate: (R/S)-2,3-epoxy-pentane

Reagent: HCl. Inversion at one of two chiral centers.

Substrate: (R/S)-1,2-epoxy-butane

Reagent: water. Catalyst: acid. Inversion at chiral center.

Substrate: (R/S)-1,2-epoxy-pentane

Reagent: CH3OH. Catalyst: acid. Inversion at chiral center.

Substrate: (R/S)-1,2-epoxy-pentane

Reagent: HCN. No inversion at chiral center.

Substrate: (R/S)-2,3,4-trimethyl-3-hexanol

Reagent: H2SO4. Three elimination products. Stereochemistry.

Substrate: (R/S)-1,2-epoxy-butane

Reagent: Grignard reagent (then water). This is a two step reaction. Regioselectivity and stereochemistry.

Substrate: (R/S)-3-bromo-2-butanol

Reagent: HBr or HI. Stereochemistry.

Substrate: (R/S)-2-bromo-1-butanol

Reagent: HBr or HI. Regioselectivity, Inversion at the chiral center.

(R/S)-3-bromo-2-pentanol

Reagent: HBr or HI. Regioselectivity and stereochemistry.