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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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Most popular questions from this chapter

Give the structure corresponding to each name:

(a) sec-butyl ethyl ketone

(b) methyl vinyl ketone

(c) p-ethylacetophenone

(d) 3-benzoyl-2-benzylcyclopentanone

(e) 6,6-dimethylcyclohex-2-enone

(f) 3-ethylhex-5-enal

Label each compound as an acetal, a hemiacetal, or an ether.

a.

b.

c.

d.

Rank the following compounds in order of increasing reactivity in nucleophilic addition

Hydroxy aldehydes A and B readily cyclize to form hemiacetals. Draw the stereoisomersformed in this reaction from both A and B. Explain why this process gives an opticallyinactive product mixture from A, and an optically active product mixture from B.

Draw a stepwise mechanism for the following reaction
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