Which of the following is the most reactive c | vedclass

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(A) The reactivity of acyl chlorides towards nucleophilic substitution is governed by two main factors: the electrophilicity of the carbonyl carbon an

Vedclass · Accepted Answer

$CH_3-COCl$

Vedclass · Answer

(A) The reactivity of acyl chlorides towards nucleophilic substitution is governed by two main factors: the electrophilicity of the carbonyl carbon and steric hindrance. $1$. The electrophilicity of the carbonyl carbon is reduced by the $+I$ (inductive) effect of the alkyl group attached to it. As the size of the alkyl group increases,the $+I$ effect increases,making the carbonyl carbon less positive and thus less reactive. $2$. Steric hindrance increases as the bulkiness of the alkyl group increases,which hinders the approach of the nucleophile. Comparing the options: $A$ $(CH_3-COCl)$: Smallest alkyl group,least $+I$ effect,least steric hindrance. $B$ $(CH_3-CH_2-COCl)$: Larger alkyl group,more $+I$ effect. $C$ $(CH_3-CH(CH_3)-COCl)$: Branched alkyl group,higher $+I$ effect and steric hindrance. $D$ $(CH_3-C(CH_3)_2-COCl)$: Most branched alkyl group,highest $+I$ effect and steric hindrance. Therefore,$CH_3-COCl$ is the most reactive. Order of reactivity: $CH_3-COCl > CH_3-CH_2-COCl > (CH_3)_2CH-COCl > (CH_3)_3C-COCl$.

Which of the following is the most reactive compound toward a nucleophile?

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