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Chapter 21: 24P (page 817)

What two enamines are formed when 2-methylcyclohexanone is treated with (CH3)2NH?

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01

Enamines

Enamines are the organic compounds formed by the reaction of carbonyl compounds with secondary amines.

The intermediate iminium ion would not have a proton on the N atom which is removed to form the C=C double bond. The position of the double bond would depend on the availability of the alpha hydrogen atoms.

02

Formation of enamines

N, N-dimethylamine attacks the carbonyl carbon forming the iminium ion. In order to stabilize the cation, an alpha hydrogen from either carbon atom is removed.

2-methylcyclohexanone reacts with N,N-dimethylamine to form a mixture of enamines.

Reaction of 2-methylcyclohexanone with N, N-dimethylamine

03

Products

The required enamines are as follows:

Deprotonation to form enamines

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