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JEE Advanced levelSingle correct optionDifficulty 3 of 3o2043

Propene reacts with DBr in the presence of peroxide (D = deuterium). The major product is

A $CH X_{2} Br - CHD - CH X_{3}$
B $CH X_{2} D - CHBr - CH X_{3}$
C $CH X_{2} Br - CH X_{2} - CH X_{2} D$
D $CHDBr - CH X_{2} - CH X_{3}$

Answer: A

Br \cdot

adds to the terminal carbon giving the secondary radical

BrCH X_{2} - CH \cdot - CH X_{3}

. This radical abstracts D from DBr, so D ends on C-2. The product is

BrCH X_{2} - CHD - CH X_{3}

. The ionic route would give

CH X_{2} D - CHBr - CH X_{3}

.

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