the-reaction-of-1-2-dimethylcyclohexene-with-nbs-under-uv-light-produces-a-mixtu

Question

The reaction of 1,2-dimethylcyclohexene with NBS under UV light produces a mixture of two products.
However, the reaction of cyclopentene with NBS only produces one product despite the generation of a resonance-stabilized radical. Explain why this reaction does not yield a second product.

Accepted Answer

The two allylic radicals formed from cyclopentene are equivalent.

Answer

Multiple products are formed but there is only one major product.

Answer

Since one mole of NBS is used, there can only be a single allylic brominated product.

Answer

Cycloalkenes with odd number of carbon atoms only produce single products in allylic bromination reactions.