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Topic: Alkynes: acidic character and addition reactions· Hydrocarbons

Predict the correct intermediate and product in the following reaction :H_3C-C CH [HgSO_4]H_2O,\ H_2SO_4 intermediate (A) → product (B)

Predict the correct intermediate and product in the following reaction :

\(H_3C-C\equiv CH \xrightarrow[HgSO_4]{H_2O,\ H_2SO_4}\) intermediate (A) \(\rightarrow\) product (B)

reaction scheme with four options of structures A and B

1. A : \(H_3C-C(OH)=CH_2\) B : \(H_3C-C(SO_4)=CH_2\)

2. A : \(H_3C-C(=O)-CH_3\) B : \(H_3C-C\equiv CH\)

3. A : \(H_3C-C(OH)=CH_2\) B : \(H_3C-C(=O)-CH_3\)

4. A : \(H_3C-C(SO_4)=CH_2\) B : \(H_3C-C(=O)-CH_3\)

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Best answer

Answer: 3. A : \(H_3C-C(OH)=CH_2\) B : \(H_3C-C(=O)-CH_3\)

Key idea: hydration of an alkyne (Kucherov reaction) first gives an enol, which tautomerises to a ketone.

Propyne + water (Markovnikov, \(\mathrm{Hg^{2+}}\) catalyst) gives A: \(CH_3-C(OH)=CH_2\) (enol, unstable). It rearranges to B: \(CH_3-CO-CH_3\) (acetone). \(\mathrm{SO_4}\) is only the counter-ion and does not remain in the compound. Option 2 has the reaction going back to propyne, which is wrong.

Doubtly AI · 30 Oct 2026 AI-generated · not yet verified Report
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