Which of the following amines reacts most rap | vedclass

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(D) The reaction of an amine with $CH_3I$ is a nucleophilic substitution reaction $(S_N2)$ where the lone pair on the nitrogen atom of the amine attac

Vedclass · Accepted Answer

Cyclopentylamine

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(D) The reaction of an amine with $CH_3I$ is a nucleophilic substitution reaction $(S_N2)$ where the lone pair on the nitrogen atom of the amine attacks the methyl carbon of $CH_3I$.The rate of this reaction depends on the nucleophilicity of the amine,which is determined by the availability of the lone pair on the nitrogen atom.$1$. In aromatic amines like aniline,$p$-chloroaniline,and $p$-nitroaniline,the lone pair on the nitrogen is involved in resonance with the benzene ring,making it less available for nucleophilic attack.$2$. Electron-withdrawing groups (like $-Cl$ and $-NO_2$) further decrease the electron density on the nitrogen atom,making them even less nucleophilic.$3$. In contrast,cyclopentylamine is an aliphatic amine. There is no resonance stabilization of the lone pair,and the alkyl group (cyclopentyl) is electron-donating,which increases the electron density on the nitrogen atom,making it more nucleophilic.Therefore,cyclopentylamine is the most nucleophilic and will react most rapidly with $CH_3I$.

Which of the following amines reacts most rapidly with $CH_3I$?

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