12. Alcohols, Ethers, Epoxides and Thiols

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

(d)

Show how you would synthesize the following:

c. cyclohexylmethanol from an alkyl halide using an S_N2 reaction

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.)