Problem 615

Problem # 615

Let's go through a benzyne reaction (also called elimination-addition).

In the reaction below, the strong base (NaNH₂) will form a benzyne intermediate, which when forms either ortho nitroaniline or meta nitroaniline.

Used curved arrows to show the formation of each intermediate and the final products.

Solution

First the ^-NH₂ acts as a base to eliminate a leaving group and form Benzyne. Then the ^-NH₂ acts as a nucleophile and attacks the benzyne, and the "leaving group" is the triple bond.

Problem Details

MendelSet practice problem # 615 submitted by Matt on July 10, 2011.

Subject: Organic Chemistry

Subject Topic(s): Nucleophilic Aromatic Substitution and Benzyne

Question Type: Mechanism (show a mechanism using curved arrows..)

Keyword(s): benzyne

Problem 615

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