Problems and exercisesNucleophilicity and Solvation
1. Protic and aprotic
Classify these solvents: water, methanol, ethanol, DMF, DMSO, acetone and acetonitrile.
2. Halides as nucleophiles
Order the nucleophilicity of F−, Cl−, Br− and I− in methanol. Does the order change in DMF?
3. Charge
Why is the methoxide ion, CH3O−, a better nucleophile than methanol?
4. HS− versus HO−
In protic solvents HS− is a better nucleophile than HO−, although it is less basic. Why?