Explain two different ways to introduce an alkyl group on a benzene ring ?

Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Andrei Straumanis
Chapter19: Eas: Electrophilic Aromatic Substitution
Section: Chapter Questions
Problem 36E
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Explain two different ways to introduce an alkyl group on a benzene ring ?

Expert Solution
Step 1:(1) Friedel Crafts alkylation:

In a Friedel crafts alkylation the alkyl group is introduced on to the benzene ring ring in presence of anhydrous AlCl3.

When an alkyl halide is treated with a benzene ring in presence of anhydrous AlCl3 results in the formation of alkylated benzene ring.

The reaction is as follows:

Chemistry homework question answer, step 1, image 1

Mechanism:

Anhydrous AlCl3 is a Lewis base and try to abstract the halogen of the alkyl halide which results in the formation of a carbocation.

Now the formed carbocation will be attacked by the electron density of the benzene ring which results in substitution of one of the hydrogens on benzene ring with the alkyl group.

The substituted H+ will now be attacked by the chlorine atom present in anhydrous AlCl4+ thus leaving the AlCl3 and HCl.

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