MCQMediumJEE 2026Isomerism (Structural, Stereoisomerism)

JEE Chemistry 2026 Question with Solution

But-2-yne and hydrogen (one mole each) are separately treated with (i) Pd/C and (ii) Na/liq.NH₃ to give the products X and Y respectively.

Reaction scheme showing but-2-yne reacting with H2; upper arrow Pd/C gives product X and lower arrow Na over liquid NH3 gives product Y.

Identify the incorrect statements.

A. X and Y are stereoisomers.

B. Dipole moment of X is zero.

C. Boiling point of X is higher than Y.

D. X and Y react with O₃/Zn + H₂O to give different products.

Choose the correct answer from the options given below :

  • A

    A and B Only

  • B

    A and C Only

  • C

    B and C Only

  • D

    B and D Only

Answer

Correct answer:D

Step-by-step solution

Standard Method

Given: But-2-yne is treated separately with H2H_2 and Pd/C to form XX, and with Na/liq.NH3Na/\text{liq.}\,NH_3 to form YY.

Find: The incorrect statements among A, B, C and D.

Alkynes undergo stereoselective partial reduction depending on the reagent used.

But-2-yneone mole H2Pd/Ccis-but-2-ene=X\text{But-2-yne} \xrightarrow[\text{one mole } H_2]{\text{Pd/C}} \text{cis-but-2-ene} = XBut-2-yneNa/liq. NH3trans-but-2-ene=Y\text{But-2-yne} \xrightarrow{Na/\text{liq. }NH_3} \text{trans-but-2-ene} = Y

Now evaluate each statement:

  1. Statement A: cis-but-2-ene and trans-but-2-ene are geometrical isomers, hence stereoisomers. So A is true.
  2. Statement B: cis-but-2-ene has a non-zero dipole moment, so the statement "Dipole moment of X is zero" is false. Thus B is incorrect.
  3. Statement C: The cis isomer is more polar and generally has a higher boiling point than the trans isomer. So C is true.
  4. Statement D: Ozonolysis of both cis-but-2-ene and trans-but-2-ene gives the same carbonyl product, namely acetaldehyde.
CH3CH=CHCH3Zn+H2OO32CH3CHOCH_3CH=CHCH_3 \xrightarrow[Zn + H_2O]{O_3} 2\,CH_3CHO

Therefore D is incorrect.

So, the incorrect statements are B and D only. The correct option is D.

Statement-wise Analysis

Given:

  • Pd/C partial reduction gives syn-addition product.
  • Na/liq.NH3Na/\text{liq.}\,NH_3 gives anti-addition product.

Find: Which listed statements are incorrect.

Step 1: Identify XX and YY.

For an alkyne, partial hydrogenation with Pd/C gives the cis alkene, while reduction with Na/liq.NH3Na/\text{liq.}\,NH_3 gives the trans alkene.

Hence:

  • X=X = cis-but-2-ene
  • Y=Y = trans-but-2-ene

Step 2: Check stereochemistry.

Since cis and trans forms differ only in spatial arrangement, they are stereoisomers. So A is correct.

Step 3: Check dipole moment.

In cis-but-2-ene, bond dipoles do not cancel completely, therefore μ0\mu \ne 0. In trans-but-2-ene, symmetry causes dipole cancellation, so μ=0\mu = 0 for YY, not for XX. Hence B is incorrect.

Step 4: Compare boiling points.

Because cis-but-2-ene is more polar, intermolecular attraction is stronger, so its boiling point is higher than that of trans-but-2-ene. Thus C is correct.

Step 5: Ozonolysis products.

Both geometrical isomers have the same carbon skeleton. On ozonolysis, each double-bond carbon becomes an aldehyde carbon.

CH3CH=CHCH32CH3CHOCH_3CH=CHCH_3 \rightarrow 2\,CH_3CHO

Thus both XX and YY give the same product, not different products. Therefore D is incorrect.

Conclusion: The incorrect statements are B and D only, so the correct option is D.

Common mistakes

  • Assuming Pd/C always gives complete hydrogenation to an alkane is incorrect here because the solution explicitly treats it as partial hydrogenation to an alkene. First identify the intended reaction condition from the given solution, then assign cis-but-2-ene as X.

  • Assigning zero dipole moment to the cis isomer is wrong because dipoles do not cancel completely in cis-but-2-ene. Use molecular symmetry to check dipole cancellation; the zero dipole moment belongs to the trans isomer.

  • Thinking that cis and trans alkenes must give different ozonolysis products is incorrect. Ozonolysis depends on cleavage of the same double bond framework, so both geometrical isomers of but-2-ene produce the same carbonyl compound, acetaldehyde.

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