JEE Main 2022 · 28 Jun · Shift 2 · Chemistry Q74

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ChemistrySingle correct+4 / -1Question 74 of 90

The major product (P) of the given reaction is (where, Me is $-\mathrm{CH_3}$ )

Cyclohexane ring with Me on one carbon, OH two carbons away, and two Me groups on the carbon next to the OH carbon; treated with H+ to give P.

3,3,6-Trimethylcyclohex-1-ene

Cyclohexene with Me on one carbon, the ring C=C beside it, and two Me groups on the far end of the double bond's neighbour (gem-dimethyl).

1,2,4-Trimethylcyclohex-1-ene with the double bond away from C2 (1,4,6-trimethylcyclohexene)

Cyclohexene bearing three Me groups, the C=C between a Me-bearing carbon and an unsubstituted ring carbon.

1,2,4-Trimethylcyclohex-1-ene

Cyclohexene with a tetrasubstituted C=C carrying two Me groups, and a third Me two carbons away.

2,4-Dimethyl-1-methylidenecyclohexane

Cyclohexane with two Me groups and an exocyclic =CH2.

Answer and worked solution

Official answer: C

Steps. Loss of water gives a secondary cation next to the $\mathrm{CMe_2}$ carbon; a methyl shift makes it tertiary; loss of H⁺ gives the more substituted (tetrasubstituted) alkene, 1,2,4-trimethylcyclohexene.

(C)

Topics:Alcohols Reactive intermediates

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JEE Main 2022 · 28 Jun · Shift 2, Chemistry question 74