Q8(d). Ozonolysis, then intramolecular aldol condensation
Identify the products X and Y in the following reaction sequence. Explain the mechanism of conversion of X to Y: [structure of the cycloalkene, atoms numbered 1–7, given in the paper], O₃/Me₂S → X; MeONa/MeOH → Y.
Model answer
The free solution for 2024 answers questions 1, 4, 5, 6, 7 and 9, the ones picked in its time plan. Question 8 is answered in full in the Geo-Scientist Chemistry Paper III, 2021 to 2025 book, with every part of every paper.
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UPSC Combined Geo-Scientist (Main) Chemistry Paper III: Model Answers 2021 to 2025
- All ten questions of each paper, with the question printed above its answer
- Instruments drawn as labelled diagrams, numericals worked with units
- Topic-wise weightage and a topic-wise index
Coversozonolysisintramolecular aldol condensationE1cBketo-aldehyde1-acetylcyclohexene
All parts of Question 8
- 8(a)(i) 2-Acetylbenzaldehyde with KCN: internal hydride shift to a lactone5 marks
- 8(a)(ii) Hydroboration–oxidation of norbornene: exo-norborneol5 marks
- 8(b) Photolysis of two ketones: Norrish Type II and Type I5 marks
- 8(c) Hexane-2,5-dione with acid: Paal–Knorr furan synthesis5 marks
- 8(d) Ozonolysis, then intramolecular aldol condensation10 marks