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Hydrocarbons question

2018 · Shift 0 · Q8
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Hydrocarbons question

2018 · Shift 0 · Q8

JEE MainChemistryHydrocarbonsMCQ+4 / −1
The trans-alkenes are formed by the reduction of alkynes with
  1. A
    Sn - HCl
  2. B
    H2H_2H2​ – Pd/C, BaSO4BaSO_4BaSO4​
  3. C
    NaBH4NaBH_4NaBH4​
  4. D
    Na/liq. NH3NH_3NH3​
View written solutionFree

Correct answer: D

  1. Identify the reaction asked

    We need the reagent that reduces an alkyne to a trans-alkene.

  2. Recall standard reductions of alkynes

    There are two important partial reductions of alkynes:

    • Catalytic hydrogenation with poisoned catalyst (Lindlar catalyst) gives cis-alkene.
    • Dissolving metal reduction using sodium in liquid ammonia gives trans-alkene.
  3. Check each option

    A: Sn−HCl\mathrm{Sn-HCl}Sn−HCl
    This is generally used as a reducing agent for other functional groups (for example nitro groups), not for selective reduction of alkynes to trans-alkenes.
    So, A is incorrect.

    B: H2−Pd/C,BaSO4\mathrm{H_2 - Pd/C, BaSO_4}H2​−Pd/C,BaSO4​
    This corresponds to a poisoned palladium catalyst (Lindlar-type reduction). Such reduction adds hydrogen syn, producing a cis-alkene, not trans.
    So, B is incorrect.

    C: NaBH4\mathrm{NaBH_4}NaBH4​
    Sodium borohydride reduces carbonyl compounds, but it does not reduce alkynes to alkenes under normal conditions.
    So, C is incorrect.

    D: Na/liquid NH3\mathrm{Na/liquid\ NH_3}Na/liquid NH3​
    This is the dissolving metal reduction of alkynes. It proceeds via anti addition of hydrogen and gives the trans-alkene.
    So, D is correct.

  4. Conclusion

    The reagent that forms trans-alkenes from alkynes is:

    Na/liquid NH3\boxed{\mathrm{Na/liquid\ NH_3}}Na/liquid NH3​​

  5. Comparison with stored answer

    Stored correct answer: D
    Derived answer: D
    Hence, they agree.

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