UPSC Combined Geo-Scientist, Mains · 2018 · Mains Paper III
Q6(i). Rearranged alkylation and Birch reduction
Question
Anisole reacts with isobutyl chloride/AlCl₃ to Q, then Li/liquid NH₃/EtOH/ether to R.
Answer in brief
Q is predominantly p-tert-butylanisole; R is its Birch-reduced 1,4-diene with methoxy and tert-butyl on unsaturated carbons.
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The full model answer
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CoversRearranged alkylationBirch reductionAromatic reactions
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