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.

CoversSN2 reactionpolar aprotic solventDMSOsolvent effectsnucleophilicity
All parts of Question 1
- 1(a) Pyridine versus imidazole5 marks
- 1(b) Cyanide addition to a hindered enone5 marks
- 1(c) Tracing the nitrile carbon5 marks
- 1(d) Dichlorocarbene trapping5 marks
- 1(e) Substituent effects on aryl negative charge5 marks
- 1(f) Why DMSO accelerates many SN2 reactions5 marks
- 1(g) Rearrangement during silver-assisted solvolysis5 marks
- 1(h) Organolithium and Baeyer–Villiger sequence5 marks