Question

The reaction mechanism of the Hunsdiecker reaction is believed to involve _______ intermediates.

• A. carboanion
• B. carbocation
• C. organic radicals
• D. all of these

Answer 1

The correct option is C organic radicals

Hunsdiecker reaction is a halogenation reaction. The reaction mechanism of the Hunsdiecker reaction is believed to involve organic radical intermediates. The silver salt of the carboxylic acid 1 will quickly react with bromine to form acyl hypohalite intermediate 2. Formation of the diradicalpair 3 allows for radical decarboxylation to form the diradical pair 4, which will quickly recombine to form the desired organic halide 5. The trend in the yield of the resulting halide is primary > secondary > tertiary.