Question

Benzene undergoes electrophilic aromatic substitution with anhydrides, compounds having the general structure (RCO}$_2$O, in a reaction that resembles Friedel-Crafts acylation. Draw a stepwise mechanism for the reaction of benzene with glutaric anhydride in the presence of AICl$_3$.

Name: Problem 62, Chapter 18: Organic Chemistry
Uploaded: 2019-05-30T04:44:35-08:00
Duration: 4 min 36 s
Channel: Nima Gharibi
Description: Benzene undergoes electrophilic aromatic substitution with anhydrides, compounds having the general structure (RCO2O, in a reaction that resembles Friedel-Crafts acylation. Draw a stepwise mechanism for the reaction of benzene with glutaric anhydride in the presence of AICl3.

   Benzene undergoes electrophilic aromatic substitution with anhydrides, compounds having the general structure (RCO}$_2$O, in a reaction that resembles Friedel-Crafts acylation. Draw a stepwise mechanism for the reaction of benzene with glutaric anhydride in the presence of AICl$_3$.

Organic Chemistry

Janice Gorzynski… 4th Edition

Chapter 18, Problem 62

Instant Answer

Solved by Expert Nima Gharibi

05/30/2019

Step 1

The oxygen in the glutaric anhydride attacks the AlCl$_3$ due to its lone pair of electrons. This results in the formation of a complex with a positive charge on the oxygen and a negative charge on the AlCl$_3$. \[ \begin{array}{ccc} \text{RCO}_2\text{O} + Show more…

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Benzene undergoes electrophilic aromatic substitution with anhydrides, compounds having the general structure (RCO}$_2$O, in a reaction that resembles Friedel-Crafts acylation. Draw a stepwise mechanism for the reaction of benzene with glutaric anhydride in the presence of AICl$_3$.