Identify the major product formed when 2-Methylhexan-3-ol is heated with concentrated sulphuric acid.

Identify the major product formed when 2-Methylhexan-3-ol is heated with concentrated sulphuric acid.




Solution

Dehydration of 2-methylhexan-3-ol with concentrated $\mathrm{H_2 SO_4}$ proceeds via an E1 mechanism. Protonation of the hydroxyl group forms an oxonium ion, which loses water to yield a secondary carbocation at C3.

To enhance stability, a 1,2-hydride shift occurs from the adjacent carbon, converting the secondary carbocation into a tertiary carbocation at C2: $\mathrm{CH_3-C+(CH_3)-CH_2-CH_2-CH_2-CH_3}$.

Elimination follows Zaitsev's rule, favoring formation of the most substituted alkene. Deprotonation from C3 generates the trisubstituted alkene 2-methylhex-2-ene: $\mathrm{CH_3-C(CH_3)=CH-CH_2-CH_2-CH_3}$, which corresponds to option A.

The final answer is $\boxed{A}$.

Asked in: MHT CET 2025 (21 April Shift 1)

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