The isomeric deuterated bromide with molecular formula $\mathrm{C}_{4}\mathrm{H}_{8}\mathrm{DBr}$ having two chiral carbon atoms is

(D) 2-Bromo-1-deutero-2-methylpropane

JEE Main · 2023 · 25 Jan 2023 · Shift 2 · General Organic Chemistry

The isomeric deuterated bromide with molecular formula

C_{4} H_{8} DBr

having two chiral carbon atoms is

(A)2-Bromo-1-deuterobutane
(B)2-Bromo-2-deuterobutane
(C)2-Bromo-3-deuterobutane✓ Correct
(D)2-Bromo-1-deutero-2-methylpropane

Answer: (C)

Solution

Two stereocentres require two carbons each bonded to four different groups. In 2-bromo-3-deuterobutane,

C H_{3} - CHBr - CHD - C H_{3}

, the second carbon holds bromine, hydrogen, a methyl and the

CHD - C H_{3}

group, while the third carbon holds deuterium, hydrogen, a methyl and the

CHBr - C H_{3}

group, so each is bonded to four different groups. The other bromides each possess at most one such carbon. The isomer with two chiral carbons is 2-bromo-3-deuterobutane.

JEE Main · 2023 · 25 Jan 2023 · Shift 2 · Single correct option

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