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The nitro substituent was introduced in the meta position of the methyl benzoate

ID: 815135 • Letter: T

Question

The nitro substituent was introduced in the meta position of the methyl benzoate. Why does it preferentially occur at meta, other than para or ortho? Show structures to prove your reasoning. (Be aware that it preferentially goes to meta, which means that the other reactions are not totally excluded.)

The nitro substituent was introduced in the meta position of the methyl benzoate. Why does it preferentially occur at meta, other than para or ortho? Show structures to prove your reasoning. (Be aware that it preferentially goes to meta, which means that the other reactions are not totally excluded.)

Explanation / Answer

The acyl group in the ester is a meta director as are all other groups with a double bond conjugated to the ring

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