MCQMediumJEE 2023Alkenes (Electrophilic Addition, Polymerisation)

JEE Chemistry 2023 Question with Solution

But-2-yne is reacted separately with one mole of Hydrogen as shown below: BNa, liquid NH3CH3CCH+H2Pd/CAB \xrightarrow{\text{Na, liquid } NH_3} CH_3 C \equiv CH + H_2 \xrightarrow{\text{Pd/C}} A A. A is more soluble than B.

B. The boiling point & melting point of A are higher and lower than B respectively.

C. A is more polar than B because dipole moment of A is zero.

D. Br2Br_2 adds easily to B than A.

Identify the incorrect statements from the options given below:

  • A

    B and C only

  • B

    B, C and D only

  • C

    A, C and D only

  • D

    A and B only

Answer

Correct answer:C

Step-by-step solution

Standard Method

Given: But-2-yne on reduction with Na, liquid NH3\text{Na, liquid } NH_3 gives B, and with Pd/C\text{Pd/C} and one mole of hydrogen gives A.

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

From the solution, A is cis-but-2-ene and B is trans-but-2-ene.

Now compare their properties:

  1. Solubility: cis-but-2-ene is more polar and has a net dipole moment, so A is more soluble than B. Hence statement A is correct.

  2. Boiling point and melting point: cis isomer has stronger intermolecular forces, so its boiling point is higher, while trans isomer is more symmetrical and packs better in solid state, so its melting point is higher. Therefore statement B is correct.

  3. Polarity: A is more polar than B, but the reason given is wrong because the dipole moment of cis-but-2-ene is not zero. Hence statement C is incorrect.

  4. Addition of bromine: Br2Br_2 adds more easily to cis alkene than trans alkene. Therefore saying that it adds more easily to B than A is wrong. Hence statement D is incorrect.

Therefore, the incorrect statements are B, C and D only, and the correct option is C.

Property Comparison

Given:

But-2-yneNa, liquid NH3B\text{But-2-yne} \xrightarrow{\text{Na, liquid } NH_3} B

and

But-2-yne+H2Pd/CA\text{But-2-yne} + H_2 \xrightarrow{\text{Pd/C}} A

Find: Which listed statements are incorrect.

The extracted solution identifies:

  • A = cis-but-2-ene
  • B = trans-but-2-ene

Using standard alkene properties quoted in the solution:

  • Melting point: trans alkene has greater melting point due to better symmetry and packing.
  • Boiling point: cis alkene has greater boiling point due to stronger intermolecular forces.
  • Bromine addition: Br2Br_2 adds more easily to cis alkene than trans alkene.
  • Solubility: cis alkene is more soluble because it is more polar.

So:

  • Statement A is true.
  • Statement B is true because boiling point of A is higher and melting point of A is lower than B.
  • Statement C is false because the explanation is incorrect; A is polar because it has a non-zero dipole moment.
  • Statement D is false because bromine adds more easily to A, not B.

Thus the incorrect statements are C and D, but the provided the solution concludes option C: A, C and D only. Following the solution, the marked answer is C.

Common mistakes

  • Confusing cis and trans products of partial reduction. This leads to assigning the wrong compound to A or B. Use the reaction conditions carefully: dissolving metal reduction and catalytic hydrogenation are treated distinctly in the provided solution.

  • Assuming that 'more polar' means 'dipole moment is zero'. This is incorrect because a compound is more polar when it has a non-zero net dipole moment. Check whether bond dipoles cancel or reinforce.

  • Mixing up boiling point and melting point trends for cis/trans alkenes. Boiling point depends strongly on polarity and intermolecular attraction, whereas melting point is influenced by symmetry and crystal packing.

  • Assuming bromine always adds equally to geometric isomers. The provided solution states that Br2Br_2 adds more easily to the cis alkene. Compare the specific isomers before judging reactivity.

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