Amines are well known to be stronger bases and nucleophiles than alkcn – InterviewSolution

1.	Amines are well known to be stronger bases and nucleophiles than alkcnes. Why do enamines, such as 1-dimethylaminocyclopentene, preferentially react with electrophiles at a double bond carbon rather than at nitrogen?
Answer» The NITROGEN is stcrically HINDERED by alkyl subst.ituents. Nitrogen is more elcctoncgativc 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. Solution :

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