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Q.(i) Complete the reaction: CH3-C≡CH + H2O --(Hg2+/H+, 333K)--> ? [1 mark]

(ii) Explain ozonolysis with example. [2 marks] OR
(i) Write the name and structural formula of the alkane used for the preparation of toluene by the process of 'aromatization'. [1 mark]
(ii) What happens when 1,2-Dichloroethane is treated with alcoholic KOH followed by reaction with sodamide? [2 marks]
Haryana BsehBoard of School Education Haryana (Senior Secondary Part-I / Class 11) 2025Subjective· 3mImportance★★★★★
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Mercury-catalysed acidic hydration of a terminal alkyne always follows Markovnikov addition, giving a methyl ketone after tautomerisation; ozonolysis is the classic double-bond-cleaving reaction used to pinpoint where a C=C bond was located.

(i) CH3−C≡CH+H2O→Hg2+/H+, 333K?CH_3-C\equiv CH + H_2O \xrightarrow{Hg^{2+}/H^+,\ 333K} ?

This is the acid-catalysed, Hg2+^{2+}-catalysed hydration of an alkyne (propyne), which proceeds by Markovnikov's rule: the −OH-OH group adds to the MORE substituted carbon of the triple bond (C-2 here), giving first an unstable enol:

CH3−C≡CH+H2O→Hg2+/H+CH3−C(OH)=CH2 (enol)CH_3-C\equiv CH + H_2O \xrightarrow{Hg^{2+}/H^+} CH_3-C(OH)=CH_2 \ (\text{enol})

The enol immediately tautomerises (keto-enol tautomerism) to the more stable keto form:

CH3−C(OH)=CH2⟶CH3−CO−CH3 (acetone, propan-2-one)CH_3-C(OH)=CH_2 \longrightarrow CH_3-CO-CH_3\ (\text{acetone, propan-2-one})

(ii) Ozonolysis:

Ozonolysis is the reaction of an alkene with ozone (O3O_3) to form a cyclic intermediate called an ozonide, which is then decomposed (usually with Zn/H2OZn/H_2O, a mild reductive workup) to give two smaller carbonyl compounds (aldehydes and/or ketones), with the C=C double bond completely cleaved.

Example: …

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