Indian Forest Service (Mains), Chemistry optional · 2021 · Paper II

Q7(c)(i). Solvolysis of a tertiary allylic bromide

5 marks
Topic: Substitution reactions
Question only

Question

Predict products and mechanism when the drawn 1-bromo-1-ethylcyclohex-2-ene reacts with ethanol. [structure given in the paper]

Model answer

The free solution for 2021 answers questions 1, 2, 3, 5 and 6, the ones picked in its time plan. This part is not answered on the site yet. New answers are announced on Telegram.

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Topic notes: nucleophilic substitution (SN1, SN2, SNi, neighbouring group participation, solvent effects, rearrangement), with every Civil Services, IFoS and Geo-Scientist PYQ →

CoversSN1 solvolysisallylic carbocationSN1′allylic rearrangementethanolysis

All parts of Question 7

7(a)(i) A beta-chloroamine and sulfonyl chloride5 marks
7(a)(ii) Hydration followed by oxidation5 marks
7(b) Ireland–Claisen rearrangement of an allylic acetate10 marks
7(c)(i) Solvolysis of a tertiary allylic bromide5 marks
7(c)(ii) Ring expansion of vinylcyclobutane5 marks
7(d) Stability of triarylmethyl radicals5 marks
7(e) State-dependent diene chemistry and photo-Fries rearrangement5 marks