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Chemistry

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Organic Chemistry

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α-Carbon Chemistry: Enols, Enolates, and Enamines

Making α-Bromo Carboxylic Acids

Description

The Hell–Volhard–Zelinski reaction makes α-brominated carboxylic acids. It uses a mixture of phosphorus tribromide and bromine. This method is a standard way to add bromine at the alpha position of a carboxylic acid.

Phosphorus tribromide can be used directly in the reaction. It can also be forme...

Transcript

Hell–Volhard–Zelinsky reaction is a method to convert carboxylic acids bearing α hydrogen to α-brominated carboxylic acids in the presence of a mixture of phosphorus tribromide and bromine, followed by hydrolysis.

Phosphorus tribromide acts as a catalyst—it is either added directly or generated in situ by the reaction of red phos...

Tags

Alpha Bromination Carboxylic AcidsPhosphorus Tribromide CatalysisAcid Bromide FormationEnolization MechanismNucleophilic Enol AttackAlpha Bromo Acid BromideHydrolysis StepRed Phosphorus BromineIn Situ Catalyst