Which of the following solvents are reasonable choices for a Grignard reaction? Justify your choices. [Hint: Carbonyls are good electrophiles.]

Predict the products of the following reactions.

(d) product of (c) + cyclopentylmagnesium bromide, then acidic hydrolysis

Predict the product of the following reactions.

(a)

You might expect that aldehydes and ketones could undergo the addition/elimination mechanism. With strong nucleophiles, however, nucleophilic addition is the only outcome. Why?

Beginning with an amide, two different pathways produce the same compound. Predict the product of these two pathways.

A student, when solving the following 'predict-the-product' question, made a common mistake by writing the answer shown here. Explain why this reaction would not work as written.

Dimerization is a side reaction that occurs during the preparation of a Grignard reagent. Propose a mechanism that accounts for the formation of the dimer.

List three different sets of reagents (each set consisting of a carbonyl compound and a Grignard reagent) that could be used to prepare each of the following tertiary alcohols:

a.

A student added an equivalent of 3,4-epoxy-4-methylcyclohexanol to a solution of methylmagnesium bromide in diethyl ether, and then added dilute hydrochloric acid. He expected that the product would be 1,2-dimethyl-1,4-cyclohexanediol. He did not get any of the expected product. What product did he get?