21. Aldehydes and Ketones: Nucleophilic Addition

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:

Identify the bonds broken and formed in the following addition reaction.

(a) Would you expect this reaction to be favored based on entropy?

(b) Based on enthalpy [qualitatively]?

(c) Overall?

The following reaction is known as the benzoin condensation. The reaction does not take place if sodium hydroxide is used instead of sodium cyanide. Propose a mechanism for the reaction and explain why the reaction does not occur if hydroxide ion is the base.

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

(k) sodium cyanide

Suggest a carbonyl to react with NaCN/HCN to produce the following cyanohydrins.

(a)

How would you synthesize the cyanohydrin shown?

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