Consider the reaction, CH3CH2CH2Br + NaCN CH3CH2CH2CN + NaBr The reaction will be the fastest in
- ethanol
- methanol
- N,N-dimethylformamide (DMF)
- water
Answer
(3) N,N-dimethylformamide (DMF)
Solution
1-Bromopropane is a 1° halide ⇒ the substitution by CN- follows the SN2 mechanism.
Protic solvents (water, methanol, ethanol) solvate CN- by H-bonding ⇒ its nucleophilicity falls.
DMF is a polar aprotic solvent ⇒ dissolves NaCN but leaves CN- almost free (unsolvated) ⇒ SN2 is fastest.
Answer: (3)