21. Aldehydes and Ketones: Nucleophilic Addition

Draw structures of the following derivatives.

(b) the semicarbazone of cyclobutanone

Draw structures of the following derivatives.

(c) cyclopropanone oxime

Predict the products formed when cyclohexanone reacts with the following reagents.

(e) phenylhydrazine and weak acid

Draw a mechanism for the reaction of propanoyl chloride with 2 moles of phenylmagnesium bromide.

What are the products of the following reactions?

b.

Suggest a series of steps involving a cuprate reagent that would convert the reactant on the left to the product on the right. The ideal number of steps is shown.

(b)

Predict the product of the following reaction sequences.

(b)

Give the nitrile and organometallic reagent you would use to make the following ketones. There are two possible answers for both.

(a)

Give the nitrile and organometallic reagent you would use to make the following ketones. There are two possible answers for both.

(b)

Draw a mechanism for the acidic hydrolysis of the magnesium salt shown below to acetophenone.

What is the best set of reagents to use for the synthesis?

What is the best set of reagents to use for the synthesis?

2.

What carbonyl compound and what phosphonium ylide are needed to synthesize the following compounds?

b.

Show how you would accomplish the following synthetic conversions efficiently and in good yield. You may use any necessary additional reagents and solvents.

(a)

Show how you would accomplish the following synthetic conversions efficiently and in good yield. You may use any necessary additional reagents and solvents.

(d)