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Hunsdieker reaction

Reaction-Hunsdieker reaction

silver salts of carboxylic Acid react with halogen to give RX .

  • RCOOAg + X2 RX + AgX + CO2
  • (X2 = Cl2 or Br2)

Reaction Mechanism of Hunsdieker reaction

The mechanism is uncertain but probably in the first step acyl hypohalite is formed which then decomposes into free radicals.
RCOOAg + X2 RCOOX + AgX
RCOOX  RCOO∙ + X∙
RCOO∙  R∙ + CO2
R∙ + X2  RX + X∙
R∙ + RCOOX  RX + RCOO∙ etc.
In Hunsdieker reaction, Br2 in CCl4 gives better yield than Cl2 in CCl4.
The yield and ease of formation of R -X is
1°RX > 2°RX > 3°RX
If I2 is used in Hunsdieker reaction in CCl4, then a ester is formed. This is known as Birnbaum−Simonini Reaction.
Hunsdieker reaction
But if acids are used with I2 and red mercuric oxide, alkyl iodides are obtained.
2RCO2H + 2I2 + HgO  2RI + 2CO2 + HgI2 + H2O

List of Name Reaction of Organic Chemistry consist of detail Reaction Mechanism of all name reactions of Organic Chemistry.

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