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JEE Advanced levelSingle correct optionDifficulty 3 of 3hx035

2-Bromo-2-methylbutane is heated with alcoholic $KOH$ and the major organic product is isolated. This product is then treated with $HBr$ in the presence of a peroxide. The major final product is

A2-bromo-3-methylbutane
B2-bromo-2-methylbutane
C1-bromo-3-methylbutane
D1-bromo-2-methylbutane

Answer: A

E2 elimination follows Zaitsev's rule, giving the more substituted alkene 2-methylbut-2-ene,

(CH X_{3}) X_{2} C = CH - CH X_{3}

. Peroxide-induced addition of

HBr

puts

Br

on the less substituted alkene carbon (giving the tertiary radical):

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

, 2-bromo-3-methylbutane.

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