Indian Forest Service (Mains), Chemistry optional · 2023 · Paper II

Q3(d). Racemization during alpha bromination

5 marks
Topic: Reaction mechanisms
Question only

Question

Why does base-catalysed bromination of an optically active ketone give racemization?

Model answer

The free solution for 2023 answers questions 1, 2, 5, 6 and 7, 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: carbonyl additions and condensations, with every Civil Services, IFoS and Geo-Scientist PYQ →

Topic notes: stereochemistry and conformational analysis (R/S, E/Z, Fischer and Newman projections, cyclohexane chair), with every Civil Services, IFoS and Geo-Scientist PYQ →

Coversracemizationenolate intermediatealpha brominationbase-catalysed halogenationkinetic evidence

All parts of Question 3

3(a) Hydrogen bromide addition to a conjugated diene5 marks
3(b)(i) Nitration of p-bromoanisole3 marks
3(b)(ii) Nitration of p-chloroanisole2 marks
3(c) Solvolysis and antiaromatic destabilization5 marks
3(d) Racemization during alpha bromination5 marks
3(e) Self-condensation of diethyl succinate10 marks
3(f) Six-pi electrocyclic switching10 marks