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Which of the following leaving groups, when attached to a 2,4-dinitrophenyl ring, would exhibit a faAromatic Hydrocarbons Chemistry Question

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?

Answer: A,C,D

💡 Solution & Explanation

In $S_NAr$, 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 $F > Cl > Br > I$. The diazonium group ($-N_2^+$) is also an exceptionally excellent leaving group due to the formation of highly stable $N_2$ gas. Therefore, $F$, $Cl$, and $-N_2^+$ react faster than $Br$.

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