JEE Main 2021 · 20 July · evening · Single correct · +4 / −1
Metallic sodium does not react normally with :
- (a) gaseous ammonia
- (b) But-2-yne
- (c) Ethyne
- (d) tert-butyl alcohol
Answer and solution
Answer (b) But-2-yne
Solution
Chemistry ma’am · 3 steps
Sodium needs an acidic hydrogen to replace. Find the one compound that has none to offer.
- What sodium does. Sodium gives away its electron easily, so it replaces an acidic hydrogen and releases H₂ gas. Hydrogen on N, on O, or on a triple-bonded carbon is acidic enough.
Compound Acidic H? Reaction with Na NH₃ (gas) Yes, N–H 2Na + 2NH₃ → 2NaNH₂ + H₂ on heating But-2-yne, CH₃-C≡C-CH₃ No, both triple-bond carbons carry CH₃ groups no reaction Ethyne, HC≡CH Yes, H on sp carbon 2HC≡CH + 2Na → 2HC≡CNa + H₂ tert-Butyl alcohol, (CH₃)₃COH Yes, O–H 2(CH₃)₃COH + 2Na → 2(CH₃)₃CONa + H₂, slowly - Why but-2-yne fails. But-2-yne is an internal alkyne. Its C–H bonds are only on the CH₃ groups, and those sp³ hydrogens are far too weakly acidic for sodium to remove.
- So. Sodium does not react with but-2-yne, option (b).
The idea to keep. Sodium reacts with H on N, on O, or on a terminal alkyne carbon and gives off H₂. An internal alkyne has no such hydrogen, so sodium leaves it alone.
Answer from the NTA final answer key. Solution by PrepWiser.