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JEE Main 2023 · 25 Jan · Shift 2

JEE Main 2023 Chemistry question on Haloalkanes and Haloarenes

The isomeric deuterated bromide with molecular formula C4H8DBrC_4H_8DBr having two chiral carbon atoms is
  1. A.
    2−Bromo−1−deutero−2−methylpropane2 - \text{Bromo} - 1 - \text{deutero} - 2 - \text{methylpropane}
  2. B.
    2−Bromo−3−deuterobutane2 - \text{Bromo} - 3 - \text{deuterobutane}
  3. C.
    2−Bromo−1−deuterobutane2 - \text{Bromo} - 1 - \text{deuterobutane}
  4. D.
    2−Bromo−2−deuterobutane2 - \text{Bromo} - 2 - \text{deuterobutane}
Show answer and solution

Correct option: B

Solution

2-Bromo-3-deuterobutane has the structure CH₃-CHBr-CHD-CH₃. Carbon 2 bears H, Br, CH₃, and CHD-CH₃ — all four substituents are different, making it chiral. Carbon 3 bears H, D, CH₃, and CHBr-CH₃ — again all four substituents are different (H ≠ D isotopically, and the two carbon chains differ), making it chiral as well. Thus this compound possesses two chiral centers, satisfying the requirement.

[JEE Main 2023 · 25 Jan · Shift 2]

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