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Hydrocarbons question

2012 · Shift 0 · Q3
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Hydrocarbons question

2012 · Shift 0 · Q3

JEE MainChemistryHydrocarbonsMCQ+4 / −1
2–Hexyne gives trans–2–Hexene on treatment with :
  1. A
    Pt/H2H_2H2​
  2. B
    Li/NH3NH_3NH3​
  3. C
    Pd/BaSO4BaSO_4BaSO4​
  4. D
    LiAlH4LiAlH_4LiAlH4​
View written solutionFree

Correct answer: B

  1. Identify the transformation

We need to convert 2-hexyne (an alkyne) into trans-2-hexene (a trans-alkene).

So this is a case of partial reduction of an alkyne.


  1. Recall the reagents for alkyne reduction

For an alkyne:

  • Catalytic hydrogenation with Pt/H2\mathrm{Pt/H_2}Pt/H2​ gives complete reduction to the alkane.
  • Dissolving metal reduction with Li/NH3\mathrm{Li/NH_3}Li/NH3​ gives the trans-alkene.
  • Poisoned catalyst such as Pd/BaSO4\mathrm{Pd/BaSO_4}Pd/BaSO4​ (similar to Lindlar-type partial hydrogenation conditions) gives cis-alkene, not trans.
  • LiAlH4\mathrm{LiAlH_4}LiAlH4​ does not reduce an alkyne to an alkene in this manner.

  1. Check each option

Option A: Pt/H2\mathrm{Pt/H_2}Pt/H2​

This causes full hydrogenation:

2-Hexyne→Pt/H2Hexane\mathrm{2\text{-}Hexyne \xrightarrow[ ]{Pt/H_2} Hexane}2-HexynePt/H2​​Hexane

So it does not stop at trans-2-hexene.

❌ Incorrect

Option B: Li/NH3\mathrm{Li/NH_3}Li/NH3​

This is dissolving metal reduction of an alkyne, giving anti addition of hydrogen and hence the trans-alkene:

2-Hexyne→Li/NH3trans-2-Hexene\mathrm{2\text{-}Hexyne \xrightarrow[ ]{Li/NH_3} trans\text{-}2\text{-}Hexene}2-HexyneLi/NH3​​trans-2-Hexene

✅ Correct

Option C: Pd/BaSO4\mathrm{Pd/BaSO_4}Pd/BaSO4​

This is a poisoned catalyst used for partial hydrogenation to alkene, generally giving syn addition, hence cis-alkene.

So from 2-hexyne it would give cis-2-hexene, not trans-2-hexene.

❌ Incorrect

Option D: LiAlH4\mathrm{LiAlH_4}LiAlH4​

This reagent is not used for converting alkynes to trans-alkenes.

❌ Incorrect


  1. Final conclusion

The reagent that converts 2-hexyne to trans-2-hexene is:

Li/NH3\boxed{\mathrm{Li/NH_3}}Li/NH3​​

So the correct option is B.


  1. Comparison with stored correct answer

Stored correct answer: B

My derived answer: B

They match.

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