JEE Main 2021 · 24 Feb · Shift 1 · Chemistry Q44

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ChemistrySingle correct+4 / -1Question 44 of 90

What is the final product (major) 'A' in the given reaction ?

Scheme: 1-(2-methylcyclohexyl)ethanol treated with HCl gives 'A' (major product).

1-(1-Chloroethyl)-2-methylcyclohexane

Option A: cyclohexane with CH3 and an adjacent CH(Cl)CH3 group.

1-Methyl-2-vinylcyclohexane

Option B: cyclohexane with CH3 and an adjacent CH=CH2 group.

1-Ethylidene-2-methylcyclohexane

Option C: cyclohexane bearing CH3, with an exocyclic C=CH-CH3 on the adjacent ring carbon.

1-Chloro-1-ethyl-2-methylcyclohexane

Option D: cyclohexane with CH3 and, on the adjacent ring carbon, both Cl and CH2CH3.

Answer and worked solution

Official answer: D

Carbocation route. Loss of water gives a secondary cation next to the ring; a hydride shift from the ring carbon gives the more stable tertiary ring cation, which takes Cl⁻: 1-chloro-1-ethyl-2-methylcyclohexane.

(D)

Topics:Alcohols Reactive intermediates

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JEE Main 2021 · 24 Feb · Shift 1, Chemistry question 44