21. Aldehydes and Ketones: Nucleophilic Addition

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

b.

Draw structures of the following derivatives.

(a) the 2,4-dinitrophenylhydrazone of benzaldehyde

Show how you would synthesize octanal from each compound. You may use any necessary reagents.

(f) octanoic acid

Show how you would accomplish the following syntheses.

(b) benzonitrile → propiophenone

For each compound,

1. name the functional group.

2. show what compound(s) result from complete hydrolysis.

(h)

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

Show what amines and carbonyl compounds combine to give the following derivatives.

(d)

Which of the following secondary alcohols can be prepared by the reaction of methyl formate with excess Grignard reagent?

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

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

(c) cyclohexanone + aniline

Which ketone forms the most hydrate in an aqueous solution?

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

(b)

For each compound,

1. name the functional group.

2. show what compound(s) result from complete hydrolysis.

(b)

Show a complete mechanism for this equilibrium established in diethyl ether with HCl gas as catalyst.

Rank the following compounds from largest K_eq to smallest K_eq for hydrate formation: