Which of the following leaving groups, when attached to a 2,4-dinitrophenyl ring, would exhibit a faster rate of substitution with compared to a standard bromide () leaving group?

Question

Which of the following leaving groups, when attached to a 2,4-dinitrophenyl ring, would exhibit a faster rate of $S_NAr$ substitution with $CH_3O^-$ compared to a standard bromide ($-Br$) leaving group?

Prashant Kotian · Accepted Answer

Correct answer: A,C,D. In , the rate-determining step is the initial addition of the nucleophile, which is accelerated by strongly electronegative leaving groups that polarize the target carbon atom. The reactivity order for halogens is . The diazonium group () is also an exceptionally excellent leaving group due to the formation of highly stable gas. Therefore, , , and react faster than .

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