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JEE Advanced levelSingle correct optionDifficulty 3 of 3hx016

Propene is heated with $Cl X_{2}$ at 773 K to give compound P. P is then treated with $HBr$ in the presence of a peroxide. The major final product is

A1,2-dichloropropane
B1,3-dibromopropane
C1-bromo-3-chloropropane
D2-bromo-1-chloropropane

Answer: C

At high temperature

Cl X_{2}

substitutes the allylic hydrogen: P is

CH X_{2} = CH - CH X_{2} Cl

(3-chloroprop-1-ene). With peroxide,

HBr

adds anti-Markovnikov, placing

Br

on the terminal carbon:

BrCH X_{2} - CH X_{2} - CH X_{2} Cl

.

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