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JEE Advanced levelOne or more correct optionsDifficulty 3 of 3hx017

2-Methylpropene is treated with $HBr$ under two sets of conditions. Which statements are correct?

AWith $HBr$ and a peroxide the major product is 2-bromo-2-methylpropane.
BWith $HBr$ and no peroxide the major product is 2-bromo-2-methylpropane.
CWith $HBr$ and a peroxide the major product is 1-bromo-2-methylpropane.
DThe major product in either case is chiral.

Answer: B, C

Without peroxide the ionic Markovnikov path goes through the tertiary cation to give

(CH X_{3}) X_{3} C - Br

. With peroxide the radical path puts

Br

on the terminal carbon, giving the tertiary radical and

(CH X_{3}) X_{2} CH - CH X_{2} Br

. Neither product has a stereocentre, so neither is chiral.

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