In the reaction, phenyl benzoate reacts with the nitronium ion: C_6H_5-O-CO-C_6H_5 + NO_2^ + A The product A is: [J & K CET 2004]

JEE Main Chemistry question

In the reaction, phenyl benzoate reacts with the nitronium ion:

-O-CO- + A

The product is: [J & K CET 2004]

(A) (nitro on the acyl-bearing ring, para to C=O)
(B) (nitro on the O-bearing ring, ortho to O)
(C) (nitro on the O-bearing ring, para to O)Correct
(D) (dinitro, one on each ring, both para)

Answer: (C)

Solution

In phenyl benzoate, , the ring attached through oxygen is activated for electrophilic aromatic substitution because the oxygen lone pair is donated into that ring by resonance, making it -directing, whereas the ring attached to the carbonyl carbon is deactivated

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Question ID VK-150190