The Hell Volhard Zelinsky reaction demonstrates a method for alpha addition with a carboxylic acid. The gist of the method is to convert the. Carboxylic acids can be brominated in the alpha position with a mixture of Br2 and PBr3 in a reaction called the Hell-Volhard-Zelinskii reaction. The classical method to convert carboxylic acids into α-haloacyl halides using phosphorus(III) halide is known as the Hell-Volhard-Zelinsky.

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This was a question where AJ needed to make some reacton in offering a solution. The reaction is named after three chemists, the German chemists Carl Magnus von Hell — and Jacob Volhard — and the Russian chemist Nikolay Zelinsky — Substitution reactions Halogenation reactions Name reactions. Chemistry Stack Exchange works best with JavaScript enabled. Retrieved from ” https: Raoul Kessels 3, 2 This page was last edited on 29 Augustat The users who voted to close gave this specific reason: If an aqueous solution is desirable, a full molar equivalent of PBr 3 must be used as the catalytic chain is disrupted.


The phosphorus halides hell-volhare-zelinsky the acyl halides readily because phosphorus has a huge affinity for oxygen.

Sometimes, phosphorus tribromide is not enough to form the acyl halide but, since there is also bromine in the media, phosphorus pentabromide is formed which can form acyl halides even of solid acids. In practice a molar equivalent of PBr 3 is often used anyway to overcome the slow reaction kinetics.

Hell-Volhard-Zelinsky Reaction | Chem-Station Int. Ed.

The reaction is initiated by addition of a catalytic amount of PBr 3after which one molar equivalent of Br 2 is added. However, I hope it will serve others as well. This question appears to be off-topic. From Wikipedia, the free encyclopedia.

Hell-Volhard-Zelinsky reaction

The mechanism for the exchange between an alkanoyl bromide and a carboxylic acid is below. By using our site, you acknowledge that you have read and understand our Cookie PolicyPrivacy Policyand our Terms of Service.

Home Questions Tags Users Unanswered. How do I ask homework questions on Chemistry Stack Exchange? Reason behind conversion of acid to acid bromide in Hell-Volhard-Zelinsky reaction [closed] Ask Question. In other projects Wikimedia Commons.


How do you think the alpha-bromine is incorporated into the acyl bromide? Acyl halides lack the carboxylic acid hydrogen. By using this site, you agree to the Terms of Use and Privacy Policy. Views Read Edit View history.

Google is your friend! For help asking a good homework question, see: PBr 3 replaces the carboxylic OH with a bromide, resulting in a carboxylic acid bromide. Unlike other halogenation reactions, this reaction takes place in the absence of a halogen carrier.