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18. Reactions of Aromatics:EAS and Beyond - Part 3 of 5!

19. Reactions of Aromatics: EAS and Beyond / Benzyne / Problem 14

Problem 14

When 1-chloro-2-methylbenzene is treated with sodium amide in ammonia, it undergoes nucleophilic aromatic substitution to form a mixture of two products. Write the products and the mechanism that accounts for the formation of two products.

A

Mechanism of nucleophilic aromatic substitution of 1-chloro-2-methylbenzene with sodium amide.

B

Detailed mechanism showing products from nucleophilic aromatic substitution of 1-chloro-2-methylbenzene.

C

Illustration of nucleophilic aromatic substitution mechanism with 1-chloro-2-methylbenzene and sodium amide.

D

Nucleophilic aromatic substitution mechanism for 1-chloro-2-methylbenzene, showing two product formation.