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 ?

  • $\begingroup$ 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! $\endgroup$ Feb 24, 2018 at 4:51
  • $\begingroup$ Hyperconjugation is more generally effective than inductive effects, I guess. $\endgroup$ Feb 24, 2018 at 10:21
  • $\begingroup$ @Apoorv see this chemistry.stackexchange.com/questions/88752/… $\endgroup$ Feb 24, 2018 at 10:21
  • $\begingroup$ I was thinking too simplistically. $\endgroup$ Feb 24, 2018 at 10:43


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