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Hydrocarbons question

2024 · 6 Apr · Shift 1 · Q21
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Hydrocarbons question

2024 · 6 Apr · Shift 1 · Q21

JEE MainChemistryHydrocarbonsNumerical+4 / −1
The major product of the following reaction is P. CH3C≡C−CH3→ (ii) dil. KMnO4273 K (i) Na /liq. NH3\mathrm{CH}_3 \mathrm{C}\equiv\mathrm{C}-\mathrm{CH}_3\xrightarrow[\substack{\text { (ii) dil. } \mathrm{KMnO}_4 \\ 273 \mathrm{~K}}]{\text { (i) } \mathrm{Na} \text { /liq. } \mathrm{NH}_3}CH3​C≡C−CH3​ (i) Na /liq. NH3​ (ii) dil. KMnO4​273 K​​ 'P' Number of oxygen atoms present in product 'P\mathrm{P}P' is ‾\underline{\hspace{2cm}}​. (nearest integer)
Numerical answer
View written solutionFree

Correct answer: 2

  1. Identify the starting compound

    The given alkyne is: CH3−C≡C−CH3\mathrm{CH_3-C\equiv C-CH_3}CH3​−C≡C−CH3​ This is but-2-yne.

  2. First reagent: Na/liquid NH3\mathrm{Na/liquid\ NH_3}Na/liquid NH3​

    This is the dissolving metal reduction of an alkyne.

    Rule:

    • Alkyne →Na/NH3(l)\xrightarrow{\mathrm{Na/NH_3(l)}}Na/NH3​(l)​ trans-alkene

    Therefore, CH3−C≡C−CH3→Na/NH3(l)trans-CH3−CH=CH−CH3\mathrm{CH_3-C\equiv C-CH_3} \xrightarrow{Na/NH_3(l)} \mathrm{trans\text{-}CH_3-CH=CH-CH_3}CH3​−C≡C−CH3​Na/NH3​(l)​trans-CH3​−CH=CH−CH3​ i.e. trans-but-2-ene.

  3. Second reagent: dilute KMnO4\mathrm{KMnO_4}KMnO4​ at 273 K273\,K273K

    Cold dilute alkaline/neutral KMnO4\mathrm{KMnO_4}KMnO4​ adds two hydroxyl groups across the double bond to form a vicinal diol.

    So, CH3−CH=CH−CH3→273 Kdil. KMnO4CH3−CH(OH)−CH(OH)−CH3\mathrm{CH_3-CH=CH-CH_3} \xrightarrow[273\,K]{dil.\ KMnO_4} \mathrm{CH_3-CH(OH)-CH(OH)-CH_3}CH3​−CH=CH−CH3​dil. KMnO4​273K​CH3​−CH(OH)−CH(OH)−CH3​

    Product PPP is butane-2,3-diol.

  4. Count oxygen atoms in PPP

    In CH3−CH(OH)−CH(OH)−CH3\mathrm{CH_3-CH(OH)-CH(OH)-CH_3}CH3​−CH(OH)−CH(OH)−CH3​, there are two −OH\mathrm{-OH}−OH groups.

    Hence, number of oxygen atoms =2= 2=2.

  5. Final answer

    2\boxed{2}2​

  6. Comparison with stored answer

    Stored correct answer = 2.

    Our derived answer matches the stored answer.

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