21. Aldehydes and Ketones: Nucleophilic Addition

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

(d) cyclohexanone + piperidine

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

(c) cyclohexanone + aniline

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

(b) acetophenone + dimethylamine

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

(a) acetophenone + methylamine

Propose a mechanism for the acid-catalyzed reaction of cyclohexanone with pyrrolidine.

Which of the following amino acid side chains can form an imine with a substrate?

Propose a mechanism for each of the following reactions:

b.

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

(e)

Propose mechanisms for the following reactions.

(b)

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

Depending on the reaction conditions, two different imines of formula C₈H₉N might be formed by the reaction of benzaldehyde with methylamine. Explain, and give the structures of the two imines.

For each compound,

1. name the functional group.

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

(g)

For each compound,

1. name the functional group.

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

(h)

Show how you would synthesize the following derivatives from appropriate carbonyl compounds.

(b)

Identify A through O: