Indian Forest Service (Mains), Chemistry optional · 2024 · Paper II

Q2(b)(iii). Rearrangement during solvolytic elimination

5 marks
Topic: Elimination reactions
Answered

Question

Complete the reaction of the drawn secondary alkyl chloride with hot ethanol, explaining the intermediate and major product. [structure given in the paper]

Answer in brief

The principal rearranged alkene is 2,3-dimethylpent-2-ene, (CH₃)₂C=C(CH₃)CH₂CH₃.

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Read the whole 2024 solution 2024 question paper

Topic notes: elimination reactions (E1, E2, E1cB, Saytzeff and Hofmann, anti-periplanar, Chugaev, Cope), with every Civil Services, IFoS and Geo-Scientist PYQ →

CoversE1 elimination1,2-hydride shiftcarbocation rearrangementsolvolysisSaytzeff product

All parts of Question 2

2(a)(i) A para-Claisen crossover experiment5 marks
2(a)(ii) Kinetic and thermodynamic enolates5 marks
2(b)(i) Photolysis of an ortho-methyl diazo compound5 marks
2(b)(ii) Bridgehead carbocation stability5 marks
2(b)(iii) Rearrangement during solvolytic elimination5 marks
2(c)(i) Hofmann elimination10 marks
2(c)(ii) Chugaev elimination5 marks