Nucleophilic Aromatic Substitution and Benzyne

Problem # 616

Let's go through another way to make benzyne.

First, let's form a Grignard reagent. Then, let's elminate to form benzyne.

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.

Problem # 612

Draw a mechanism for the nucleophilic aromatic substitution (SNAr) reaction below. Show all resonance forms of the intermediate.