JEE Main 2025 · 28 January · evening · Single correct · +4 / −1

Identify product [A], [B] and [C] in the following reaction sequence.
CH₃-C ≡ CH →(Pd / C)[A] →((i) O₃)[ B]+[C]

  1. (a) [A]: CH₃—CH=CH₂, [B]: CH₃CHO, [C]: CH₃CH₂OH
  2. (b) [A]: CH₃—CH=CH₂, [B]: CH₃CHO, [C]: HCHO
  3. (c) [A]: CH₃CH₂CH₃, [B]: CH₃CHO, [C]: HCHO
  4. (d) [A]: CH₂=CH₂, [B]: H₃C-C(∥(O))-CH₃, [C]: HCHO
Answer and solution

Answer (b) [A]: CH₃—CH=CH₂, [B]: CH₃CHO, [C]: HCHO

Solution

Chemistry ma’am · 4 steps

Stop at the alkene with one H₂, then cut the C=C in two and put an oxygen on each half.

  1. Partial hydrogenation. Propyne takes one mole of H₂ over the Pd catalyst, and the triple bond becomes a double bond. So [A] is propene, CH₃-CH=CH₂. It has to be an alkene, because the next step, ozonolysis, needs a C=C to attack.
  2. Reductive ozonolysis. Ozone adds across the C=C and forms an ozonide. Zn and H₂O break the ozonide and remove the extra oxygen, so each carbon of the old double bond ends up as a C=O group. Aldehydes stay as aldehydes. They are not oxidised to acids or reduced to alcohols.

    CH₃-CH=CH₂ →((i) O₃, (ii) Zn, H₂O) CH₃CHO + HCHO

  3. Check carbons. Propene has 3 carbons. Cutting it at the double bond gives a 2-carbon piece, ethanal (CH₃CHO), and a 1-carbon piece, methanal (HCHO). That gives 2 + 1 = 3, so no carbon is lost.
  4. So. [A] is CH₃-CH=CH₂, [B] is CH₃CHO and [C] is HCHO, which is option (b).

The idea to keep. For ozonolysis, find each C=C, cut it, and put =O on both ends. With Zn/H₂O you get aldehydes and ketones only, and the carbons of the pieces always add up to the alkene's carbons.

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 2025.