12. Alcohols, Ethers, Epoxides and Thiols

Predict the product of each of the following alcohol synthesis reactions.

(b)

Show how you would synthesize the following alcohol from appropriate alkene.

(d)

Suggest a reagent and a reactant that could be combined to make each of the following alcohols.

(d)

Show how you would synthesize the following alcohol from appropriate alkene.

(a)

Show how you would synthesize the following:

c. cyclohexylmethanol from an alkyl halide using an S_N2 reaction

Starting from bromobenzene and any other reagents and solvents you need, show how you would synthesize the following compounds. Any of these products may be used as starting materials in subsequent parts of this problem.

a. 1-phenylpropan-1-ol

The Baylis-Hillman reaction is a DABCO (1,4-diazabicyclo[2.2.2]octane) catalyzed reaction of an α,β-unsaturated carbonyl compound with an aldehyde to form an allylic alcohol. Propose a mechanism for the reaction. (Hint: DABCO serves as both a nucleophile and as a base in the reaction.)

Suggest a reagent and a reactant that could be combined to make each of the following alcohols.

(c)

Predict the product of each of the following alcohol synthesis reactions.

(c)

a. Show the reagents required to form the primary alcohol in each of the following reactions.