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In Clayden, the increased rate of electrophillic aromatic substitution is explained by the stabilization of the intermediate through sigma conjugation. In Solomon & Frhyle, the same is explained through inductive effects.

Both the factors oppose each other in the following compounds: toluene, ethylbenzene, isopropylbenzene, and t-butylbenzene, respectively.

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My question:

What should be the order of electrophillic aromatic substitution for the above molecules ?

Gaurang Tandon
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Avyansh Katiyar
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  • Can you cite the relevant chapters, page numbers, and the exact paragraph written in the books, to support your first paragraph? That will also give potential answer posters some additional insight into what the books might have meant. Thanks! – Gaurang Tandon Feb 24 '18 at 04:51
  • Hyperconjugation is more generally effective than inductive effects, I guess. – Apoorv Potnis Feb 24 '18 at 10:21
  • @Apoorv see this https://chemistry.stackexchange.com/questions/88752/why-is-the-rate-of-reaction-of-polar-eas-favored-by-inductive-effects-and-the-ra – Avyansh Katiyar Feb 24 '18 at 10:21
  • I was thinking too simplistically. – Apoorv Potnis Feb 24 '18 at 10:43

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