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Hell Mechanism - Nucleophilic Attack of the Enol on the Br...

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Hell-Volhard-Zelinski Reaction Mechanism The Hell-Volhard-Zelinski reaction places a bromide on the carbon next door (alpha, α ) to a carboxylic acid. This α -bromo carboxylic acid can then be used as an electrophile for a number of reactions that involve S N 2 attack at the α -position. OH O P/ Br 2 OH O Br P + Br 2 P Br 3 OH O + P Br 3 OH O P Br Br Br Br H O O P Br 2 Br O H Br O H Br OH H - H Br OH Formation of an Acid Bromide Acid Catalyzed Enol Formation
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Unformatted text preview: Nucleophilic Attack of the Enol on the Br 2 Electrophile + Br Br Br O Br- Br H- H Br O Br Bromide - Hydroxide Exchange Br O Br + HO O Br O Br H O O O H O O Br Br OH O Br + Br O Product Ready to Cycle back through Hell Application of the Hell-V-Z reaction: OH O P/ Br 2 OH O Br CN OH O N H 2 O/H OH O O OH- NH 3...
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