JEE Chemistry 2023 Question with Solution

Given: The deuterated bromide has molecular formula $\mathrm{C_4H_9DBr}$ and it must have two chiral carbon atoms.

Find: Which option gives the isomer having two chiral carbon atoms.

The solution states that the correct answer is 2-Bromo-3-deuterobutane.

In 2-Bromo-3-deuterobutane, the second and third carbon atoms are each attached to four different groups, so both are chiral centres.

Therefore, the correct option is C.

Given: A four-carbon deuterated bromide is required to contain two chiral carbon atoms.

Find: The correct isomer.

From the extracted solution text: the bromine is attached to the second carbon and the deuterium is attached to the third carbon. This gives 2-Bromo-3-deuterobutane.

Here, carbon-2 is bonded to Br, H, CH3, and the remaining substituted carbon chain. Carbon-3 is bonded to D, H, CH3, and the remaining substituted carbon chain. Since each of these carbons has four different substituents, both are chiral.

Hence, the compound with two chiral carbon atoms is 2-Bromo-3-deuterobutane, so the correct option is C.