JEE Main 2022 · 27 June · morning · Single correct · +4 / −1

'A' and 'B' respectively are:
A →((1) O₃) Ethane-1,2-dicarbaldehyde + Glyoxal/Oxaldehyde; B →((1) O₃) 5-oxohexanal

  1. (a) 1-methylcyclohex-1,3-diene & cyclopentene.
  2. (b) Cyclohex-1,3-diene & cyclopentene
  3. (c) 1-methylcyclohex-1,4-diene & 1-methylcyclopent-1-ene
  4. (d) Cyclohex-1,3-diene & 1-methylcyclopent-1-ene
Answer and solution

Answer (d) Cyclohex-1,3-diene & 1-methylcyclopent-1-ene

Solution

Chemistry ma’am · 4 steps

Cut every C=C, put an O on each end, then match the fragments to the products given.

  1. Ozonolysis rule. O₃ followed by Zn/H₂O breaks each C=C and turns both of its carbons into C=O. A carbon carrying H becomes CHO, and a carbon carrying an alkyl group becomes a ketone. In a ring, the cut opens the ring instead of splitting off a piece.
  2. Finding A. Two products means two C=C. In cyclohexa-1,3-diene, cutting C1=C2 and C3=C4 frees C2–C3 as OHC–CHO (glyoxal). The rest, C4–C5–C6–C1, becomes OHC–CH₂CH₂–CHO, which is ethane-1,2-dicarbaldehyde.
  3. Finding B. 5-oxohexanal is CH₃CO(CH₂)₃CHO, a single open chain with one ketone end and one aldehyde end. That comes from a ring with one C=C whose carbons carry a methyl and an H. In 1-methylcyclopent-1-ene, C1 (with the methyl) becomes CH₃C=O and C2 becomes CHO.
    AlkeneOzonolysis productsMatches?
    Cyclohexa-1,3-dieneOHC–CHO and OHC–CH₂CH₂–CHOA
    1-methylcyclopent-1-ene5-oxohexanal, CH₃CO(CH₂)₃CHOB
    Cyclopentenepentanedial, OHC–(CH₂)₃–CHOno
    1-methylcyclohexa-1,3-dieneOHC–CHO and 4-oxopentanal, CH₃COCH₂CH₂CHOno
  4. So. A is cyclohexa-1,3-diene and B is 1-methylcyclopent-1-ene, which is option (d).

The idea to keep. In ozonolysis, every C=C becomes two C=O. A ring with one double bond opens into one chain, and a substituent on a double-bond carbon turns that end into a ketone instead of an aldehyde.

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

Study d & f Block Elements

Asked about 170 times in JEE Main since 2020. This question is from 2022.