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Answer in Organic Chemistry for Siddharth Gedam #122270

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April 21st, 2023

The three key limitations of Friedel-Crafts alkylation are:

  1. Carbocation Rearrangement – Only certain alkylbenzenes can be made due to the tendency of cations to rearrange.
  2. Compound Limitations – Friedel-Crafts fails when used with compounds such as nitrobenzene and other strong deactivating systems.
  3. Polyalkylation – Products of Friedel-Crafts are even more reactive than starting material. Alkyl groups produced in Friedel-Crafts Alkylation are electron-donating substituents meaning that the products are more susceptible to electrophilic attack than what we began with. For synthetic purposes, this is a big dissapointment.
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