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Amines are well known to be stronger bases and nucleophiles than alkenes. Why do enamines, such as 1-dimethylaminocyclopentene, reacts with electrophiles at a double bond carbon rather than at nitrogen?

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The nitrogen is sterically hindered by alkyl substituents

Nitrogen is more electronegative than carbon

The carbocation formed by electrophilic attack at C-2 is stabilized by pi-bonding with the lone pair of electrons on nitrogen.

Ammonium cations are less stable than carbocations

answer is D.

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Detailed Solution

This is because of the formation of a stable carbocation.

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