IIT-JEE 2011 · Paper 1 · Chemistry Q16

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ChemistrySingle correct+3 / -1Question 16 of 69

Passage

Paragraph for Question Nos. 15 and 16

An acyclic hydrocarbon P, having molecular formula $\ce{C6H10}$ , gave acetone as the only organic product through the following sequence of reactions, in which Q is an intermediate organic compound.

P (C₆H₁₀) → [(i) dil. H₂SO₄/HgSO₄; (ii) NaBH₄/ethanol; (iii) dil. acid] → Q → [(i) conc. H₂SO₄ (catalytic amount) (−H₂O); (ii) O₃; (iii) Zn/H₂O] → 2 acetone.

The structure of the compound Q is

\ce{(CH3)2CH-CH(OH)-CH2CH3}

\ce{(CH3)3C-CH(OH)-CH3}

\ce{(CH3)2CH-CH2-CH(OH)-CH3}

\ce{CH3CH2CH2CH(OH)CH2CH3}

Answer and worked solution

Official answer: B

Q is the alcohol $\ce{(CH3)3C-CH(OH)-CH3}$ (3,3-dimethylbutan-2-ol), formed by HgSO₄ hydration of the alkyne to the methyl ketone and NaBH₄ reduction.

(B)

Topics:Alcohols Alkynes

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IIT-JEE 2011 · Paper 1, Chemistry question 16