JEE Main 2021 · 20 July · evening · Single correct · +4 / −1

Metallic sodium does not react normally with :

  1. (a) gaseous ammonia
  2. (b) But-2-yne
  3. (c) Ethyne
  4. (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.

  1. 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.
    CompoundAcidic H?Reaction with Na
    NH₃ (gas)Yes, N–H2Na + 2NH₃ → 2NaNH₂ + H₂ on heating
    But-2-yne, CH₃-C≡C-CH₃No, both triple-bond carbons carry CH₃ groupsno reaction
    Ethyne, HC≡CHYes, H on sp carbon2HC≡CH + 2Na → 2HC≡CNa + H₂
    tert-Butyl alcohol, (CH₃)₃COHYes, O–H2(CH₃)₃COH + 2Na → 2(CH₃)₃CONa + H₂, slowly
  2. 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.
  3. 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.

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Asked about 130 times in JEE Main since 2020. This question is from 2021.