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Question

Bring out the following conversions: Acetic acid to Malonic acid.


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Solution

Conversion of Acetic acid to Malonic acid:

  • The conversion of acetic acid to malonic acid takes place in two steps:

Step 1: Hell-Volhard-Zelinsky reaction

  • In this reaction, acetic acid CH3COOHis treated with chlorine, and an alpha chloro-acetic acid is obtained. this reaction is known as the Hell-Volhard-Zelinsky reaction.
  • This reaction takes place in the presence of red phosphorus which helps in the formation of necessary intermediates.
  • The chemical reaction can be depicted as:

CH3COOH+Cl2RedPCH2(Cl)COOH+POCl3+HCl(Aceticacid)(Chlorine)(Chloro-aceticacid)(Phosphorusocychloride)(Hydrochloricacid)

Step 2: Conversion of alpha chloroacetic acid to malonic acid

  • An alpha chloroacetic acid is treated with potassium cyanide in the presence of ethanol which results in the formation of malonic acidCOOH-CH2-COOH
  • The reaction can be depicted as:

CH2(Cl)COOH+KCNCH2(CN)COOH+KCl(Chloro-aceticacid)(Potassiumcyanide)(Cyanoaceticacid)(Potassiumchloride)CH2(CN)COOHH3O+/H+COOHCH2COOH(Cyanoaceticacid)(Malonicacid)


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