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Chapter 21: 25P (page 817)

What carbonyl compound and amine are formed by the hydrolysis of each compound?

a.

b.

c.

Short Answer

Expert verified

a.

b.

c.

Step by step solution

01

Hydrolysis of imines and enamines

Imines and enamines are hydrolyzed to form their corresponding carbonyl compounds in a reversible manner in the presence of an acid.

During the hydrolysis of enamines, the carbonyl carbon comes from the hybridized carbon bonded to the N atom.

02

Formation of carbonyl compound

Consider the hydrolysis of the given intermediates,

a. The hydrolysis of the given imine would give a molecule of benzaldehyde and cyclopentamine.

b. The hydrolysis of the given enamine would yield a molecule of cyclopentanone and N-methyl benzyl amine.

c. The hydrolysis of this intermediate gives N,N-dimethylamine and 2-methylpropanone.

03

Products

Hydrolysis of compound a.

The given enamine would give a molecule of cyclopentanone and N-methylbenzyl amine on hydrolysis.

Hydrolysis of compound b.

c. The given enamine would give a molecule of 2-methylpropanal and N,N-dimethylamine on hydrolysis.

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Most popular questions from this chapter

What 1° amine and carbonyl compound are needed to prepare each imine?

a.

b.

Brevicomin, the aggregation pheromone of the western pine bark beetle, contains a bicyclic bridged ring system and is prepared by the acid-catalyzed cyclization of 6,7-dihydroxynonan-2-one.

a. Suggest a structure for brevicomin.

b. Devise a synthesis of 6,7-dihydroxynonan-2-one from 6-bromohexan-2-one. You may also use three-carbon alcohols and any required organic or inorganic reagents.

Give the IUPAC name for each aldehyde.

a.

b.

c

What Wittig reagent and carbonyl compound are needed to prepare each alkene? When two routes are possible, indicate which route, if any, is preferred.

a.

b.

c.

What carbonyl compound and amine or alcohol are needed to prepare each product?

a.

b.

c.

d.
See all solutions

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