JEE Advanced 2019 · Paper 2 · Chemistry Q6

ChemistryMultiple correct+4 / -1Question 24 of 54

Choose the correct option(s) that give(s) an aromatic compound as the major product

Answer and worked solution

Official answer: A, B

(A) Alcoholic KOH then $\ce{NaNH2}$ gives propyne. In a red-hot iron tube it trimerises to mesitylene, 1,3,5-trimethylbenzene, which is aromatic. ✓
(B) NaOMe deprotonates cyclopentadiene (pKa about 16) to the cyclopentadienyl anion, which is planar with 6π electrons, so aromatic. ✓
(C) Elimination from 3-bromocyclobutene would give cyclobutadiene, which is antiaromatic. ✗
(D) UV-initiated radical addition gives hexachlorocyclohexane (BHC), which is not aromatic. ✗

(A), (B)

JEE Advanced 2019 · Paper 2, Chemistry question 6