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Chapter 18: 21 P (page 702)

Which of the following compounds undergo Friedel–Crafts alkylation with CH3Cland AlCl3? Draw the products formed when a reaction occurs.

Short Answer

Expert verified

Friedel-Craft alkylation substitutes the alkyl group at the ortho and para positions of the substrate having an electron-donating group.

Step by step solution

01

Friedel-Craft reaction

Friedel-Craft alkylation substitutes the alkyl group at the ortho and para positions of the substrate having an electron-donating group.

02

Effect of substituents

Friedel-Crafts reactions do not occur in the presence of strongly deactivating substituents such as NO2,NH2 ,NR2 , NHR groups.

03

Explanation

a. The SO3Hcompound is highly deactivating. Therefore, Friedel-Craft alkylation does not occur.


b. The Cl compound is also electron-donating. Therefore, Friedel-Craft alkylation gives ortho and para products.


c. The NCH32compound is also highly deactivating. Therefore, Friedel-Craft alkylation does not occur.


d. The NHCOCH3 compound is electron-withdrawing, but the ring is sufficient for Friedel-Craft alkylation. Therefore, Friedel-Craft alkylation gives ortho and para products.


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