Question

Discuss the mechanism of alkaline hydrolysis of methyl bromide.

Answer 1

Alkaline hydrolysis of methyl bromide:

1. It uses the S_N2 mechanism, which is bimolecular nucleophilic substitution.
2. \[\ce{CH3Br + KOH -> CH3OH + KBr}\]
3. This is a one-step reaction in which bond formation and bond breaking at carbon occur simultaneously.
4. To avoid steric repulsion or hindrance with the departing group, there is a backside attack of nucleophiles.
5. This is a single-step reaction. As a result, there is only one transition state. The transition state has penta-coordinate carbon with three sigma bonds in one plane and the remaining two perpendicular to this plane.
6. The backwise assault causes complete inversion, similar to flipping an umbrella.

Mechanism of Reaction: