13. Alcohols and Carbonyl Compounds

Addition to an epoxide occurs via an S_N2 reaction, but the stereochemistry of the epoxide is retained in the following reaction. Why?

Show how you would synthesize the following:

f. 2,5-dimethylhexane from a four-carbon alkyl halide

Predict the products of the following reactions.

(a) allyl bromide + cyclohexyl magnesium bromide

Show how the reaction of an allylic halide with a Grignard reagent might be used to synthesize the following hydrocarbons.

c. 1-cyclopentylpent-2-ene