Hunsdiecker Reaction Mechanism

Hunsdiecker Reaction Mechanism - CH 2 O O Br Br Product O O...

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Hunsdiecker Reaction Mechanism The Hunsdiecker reaction is a method for cleaving off a carboxylate group and replacing it with a bromide. O OH Ag , OH , Br 2 Br + CO 2 It is a very useful reaction to remove carbons from an organic molecule. The mechanism involves the formation of a silver salt that then is converted to a hypobromite (a very unstable species with a weak O–Br bond). Radical chemistry then ensues. O OH Ag , OH O O Ag O O Ag + Br Br O O Br + AgBr Very weak bond O O Br O O + Br O O CH 2 + O C O Homolytic Cleavage Fast
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Unformatted text preview: CH 2 O O Br + Br Product O O The story continues along radical lines Form a Silver Carboxylate Salt Nucleophilic attack on the electrophile Br 2 Homolytic cleavage of a very weak bond Silver bromide precipitates out of solution to drive this reaction Radical decomposition to lose very stable CO 2 Radical chain process begins as the carbon radical abstracts a Br CO 2 is very stable and will often be the product of a fragmentation radical mechanism +...
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This note was uploaded on 09/25/2009 for the course CH 223 taught by Professor Brown during the Spring '08 term at N.C. State.

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