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3-Methyl-pent-2-ene on reaction with HBr in presence of peroxide forms an addition product. The number of possible stereoisomers for the product is:

1. Six
2. Zero
3. Two
4. Four

Correct answer: Four

Solution

HBr with peroxide gives anti-Markovnikov addition: Br adds to C2, giving 2-bromo-3-methylpentane (CH3-CHBr-CH(CH3)-CH2CH3). Both C2 and C3 are stereocentres and are different, so 2^2 = 4 stereoisomers are possible.

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