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

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asked Oct 13, 2017 in Chemistry by jisu zahaan (28,760 points) 28 435 1064

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

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answered Oct 13, 2017 by sforrest072 (157,439 points) 63 447 1245
selected Nov 5, 2017 by sarthaks
 
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The ease of nitration depends on the presence of electron density on the compound to form nitrates. Nitration reactions are examples of electrophilic substitution reactions where an electron-rich species is attacked by a nitronium ion (NO2). Now, CH3 group is electron donating and NO2 is electron withdrawing. Therefore, toluene will have the maximum electron density among the three compounds followed by benzene. 

On the other hand, m– Dinitrobenzene will have the least electron density. Hence, it will undergo nitration with difficulty. Hence, the increasing order of nitration is as follows: 

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