21. Aldehydes and Ketones: Nucleophilic Addition

Propose mechanisms for the following reactions.

(e)

Show how the following compounds can be synthesized from cyclohexanol.

a. b. c.

Propose a mechanism for the hydrolysis of benzaldehyde methyl imine just shown.

Give the expected products of the following acid-catalyzed reactions.

(d) cyclohexanone + piperidine

Propose mechanisms for the following reactions.

(e)

Which of the following are a. hemiacetals? b. acetals? c. hydrates?

4.

Predict the major products of the following reactions.

(h)

How would you synthesize the cyanohydrin shown?

Propose a mechanism for the acid-catalyzed hydrolysis of cyclohexanone ethylene acetal.

Show how you would synthesize octan-2-one from each compound. You may use any necessary reagents.

(b) oct-1-yne

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

(e) propane-1,3-diol, H⁺

Propose a mechanism for the acid-catalyzed hydrolysis of the acetal given in Problem 18-26(f).

(a) Outline the syntheses indicated in Solved Problem 18-2, beginning with aldehydes and alkyl halides.

(b) Both of these syntheses of 1-phenylbuta-1,3-diene form the central double bond. Show how you would synthesize this target molecule by forming the terminal double bond.

Propose mechanisms for the following reactions.

(b)