Chemistry - Hydrocarbon Question with Solution | TestHub

NBS brominates the three allylic positions: the methyl group and the two ring CH2 groups next to the double bond.
Direct products: 1-(bromomethyl)cyclopentene (1) and 3-bromo- and 5-bromo-1-methylcyclopentene (2 enantiomers each).
Allylic rearrangement also gives 2-bromo-1-methylenecyclopentane and 1-bromo-1-methylcyclopent-2-ene (2 enantiomers each).
Total = 1 + 2 + 2 + 2 + 2 = 9.