UPSC Combined Geo-Scientist, Mains · 2018 · Mains Paper III
Q6(e). Double Michael addition and Dieckmann closure
Question
Benzylamine reacts with excess methyl acrylate on heating to I, then NaOMe/MeOH to J.
Answer in brief
I is BnN(CH₂CH₂CO₂Me)₂; J is methyl 1-benzyl-4-oxopiperidine-3-carboxylate after neutral workup.
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CoversDouble Michael additionDieckmann closureRing synthesis
All parts of Question 6
- 6(a) Epoxidation and anti opening4 marks
- 6(b) Conjugate addition and dehydrogenation4 marks
- 6(c) Houben–Hoesch acylation4 marks
- 6(d) Pyrrole: formylation and expansion4 marks
- 6(e) Double Michael addition and Dieckmann closure4 marks
- 6(f) Sequential electrocyclic reactions4 marks
- 6(g) Benzyne trapped by isoindole4 marks
- 6(h) Pinacol rearrangement pathways4 marks
- 6(i) Rearranged alkylation and Birch reduction4 marks
- 6(j) Hydroboration–oxidation4 marks