JEE Main · 2022 · 29 Jul 2022 · Shift 2 · Haloalkanes and Haloarenes

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Compound 'A' undergoes following sequence of reactions to give compound 'B'. The correct structure and chirality of compound 'B' is:
[where Et is

- C_{2} H_{5}

]

(A)(see structure)
(B)(see structure)
(C)(see structure)
✓ Correct
(D)(see structure), Achiral

Answer: (C)

Solution

The reaction sequence shows compound A undergoing (i)

Br X_{2} / CCl X_{4}

(bromination), (ii) alc. KOH (dehydrohalogenation to form alkene), and (iii)

m CPBA

(epoxidation). Starting from the given structure, bromination adds Br across the double bond, elimination with alcoholic KOH regenerates a double bond, and mCPBA converts the alkene to an epoxide. The product is a chiral epoxide as shown in option (C), which contains an asymmetric carbon center.

JEE Main · 2022 · 29 Jul 2022 · Shift 2 · Single correct option

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