21. Aldehydes and Ketones: Nucleophilic Addition

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

(f) CH₃(CH₂)₅CN

Show how the following transformations may be accomplished in good yield. You may use any additional reagents that are needed.

(a) bromobenzene → propiophenone

(b) CH₃CH₂CN → heptan-3-one

Show how each transformation may be accomplished by using a nitrile as an intermediate. You may use any necessary reagents.

(c) octan-1-ol → decan-2-one

Show how each transformation may be accomplished by using a nitrile as an intermediate. You may use any necessary reagents.

(b) cyclohexanecarboxamide → cyclohexyl ethyl ketone

Show how you would add a Grignard reagent to an ester or a nitrile to synthesize

(c) pentan-2-one.

A ketone can be prepared from the reaction of a nitrile with a Grignard reagent. Describe the intermediate formed in this reaction, and show how it can be converted to a ketone.