Predict the products of the following reactions.
(a) allyl bromide + cyclohexyl magnesium bromide

A variety of organometallics, which as strong nucleophiles can react with epoxides, are introduced in Chapter 16. Predict the product of these reactions. [Hint: Assume the carbon–metal bond in each is ionic, with the carbon possessing the negative charge.]

(b)

Predict the product of the following epoxide addition reactions.

(b)

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

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

We discuss the reaction of Grignard reagents (organomagnesium compounds) to ketones in Chapter 17. Mechanistically, the reaction proceeds by the nucleophilic addition of a methyl carbanion to the electrophilic carbon of the carbonyl, breaking the C―Oπ bond, resulting in an alkoxide intermediate that is subsequently protonated to produce the 3° alcohol.

(a) Why does this reaction produce a racemic mixture of 3° alcohols?