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13.23     Out of benzene, m–dinitrobenzene and toluene which will undergo nitration most easily and why?

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Nitration is occurred by an electrophilic substitution reaction, in which an electron rich species is attacked by an electron deficient molecule known as an electrophile. In nitration NO_{2}^+ is used as an electrophile. Here methyl group is electron donating group and the nitro group is electron withdrawing group. So, benzene ring attached with the -CH_{3} group has high electron density and the ring which is attached with the nitro group has least electron density. Hence toluene undergoes nitration most easily. 

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