JEE Main 2023 · 1 February · morning · Single correct · +4 / −1

But-2-yne is reacted separately with one mole of Hydrogen as shown below :
B ←(Na) CH₃-C≡C-CH₃ →(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. Br₂ adds easily to B than A.
Identify the incorrect statements from the options given below :

  1. (a) A and B only
  2. (b) A, C & D only
  3. (c) B, C & D only
  4. (d) C and D only
Answer and solution

Answer (d) C and D only

Solution

Chemistry ma’am · 3 steps

Name A and B first: the metal surface gives cis, sodium in ammonia gives trans. Then test each statement.

  1. Identify A. With H₂ on Pd/C, both H atoms add from the catalyst surface on the same side (syn addition). With one mole of H₂, A is cis-but-2-ene.
  2. Identify B. Na in liquid NH₃ adds the two H atoms from opposite sides (anti addition). So B is trans-but-2-ene.
    StatementFactVerdict
    A: A more soluble than Bcis has a net dipole and trans has none, so cis is more solublecorrect
    B: A has higher bp and lower mpcis boils higher (about 4 vs 1 °C) but melts lower, because trans packs better in the solidcorrect
    C: A more polar since its dipole moment is zerothe dipole moment of cis is not zero. It is trans whose bond dipoles cancel to zeroincorrect
    D: Br₂ adds more easily to Bcis is less stable because its two methyl groups crowd each other, so cis reacts fasterincorrect
  3. So. The incorrect statements are C and D, which is option (d).

The idea to keep. A metal catalyst gives the cis alkene and Na in liquid ammonia gives trans. Cis is more polar, boils higher, melts lower and reacts faster. Trans has zero dipole and packs better.

Answer from the NTA final answer key. Solution by PrepWiser.

Study Hydrocarbons — Alkenes & Alkynes

Asked about 90 times in JEE Main since 2020. This question is from 2023.