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Indian Forest Service (Mains)

Chemistry optional

  • 2 papers
  • 200 marks each
  • 3 h per paper

Paper II covers organic chemistry and spectroscopy.

Indian Forest Service (Mains), Chemistry optional · 2022 · Paper II

Q1(f). Why DMSO accelerates many SN2 reactions

Question

Why do polar aprotic solvents such as DMSO favour SN2 reactions?

Answer in brief

DMSO dissolves many ionic reagents and strongly solvates cations while leaving anionic nucleophiles relatively reactive.

Key points

  • Its polar S–O group coordinates a counter-cation; it lacks O–H or N–H groups and cannot form hydrogen-bond cages around anions.
  • The less solvated anion attacks the electrophilic carbon more readily, lowering the effective barrier relative to a protic medium.
  • The rate law is v = k[RX][Nu⁻]; backside attack gives inversion at a stereogenic carbon.
  • The effect is most relevant to anionic nucleophiles; substrate crowding and competing elimination still control SN2 feasibility.

The full model answer

As written for the answer booklet: the diagram carries the working, the lines stay short. Read here only; it is not offered as a download.

Model answer to Q1(f), 2022 Paper II: solution pages 7 and 8
Solution pages 7 and 8 of 34

CoversSN2 reactionpolar aprotic solventDMSOsolvent effectsnucleophilicity