Question

Ester hydrolysis is appreciated in which medium? Basic or acidic .. give a possible explanation.

Answer 1

Ester hydrolysis occurs in both acidic and basic medium, but basic hydrolysis is preferred because the reaction goes to completion.

Explanation:

Hydrolysis in acid medium

The reaction is:

`"RCOOR'" + "H"_2"O" ⇌ "RCOOH" + "HOR'"`

The reaction is an equilibrium process, so the reaction does not go to completion.

Hydrolysis in basic medium

In this case, the carboxylic acid is neutralized by the base as fast as it is formed.

According to Le Châtelier's Principle, this pulls the position of equilibrium to the right.

The equations are

`color(white)(mmmll)"RCOOR'" + color(red)(cancel(color(black)("H"_2"O"))) ⇌ color(red)(cancel(color(black)("RCOOH"))) + "HOR'"`
`color(white)(mmml)ul(color(red)(cancel(color(black)("RCOOH"))) + "OH"^"-" → "RCOO"^"-" + color(red)(cancel(color(black)("H"_2"O"))))`
Overall: `"RCOOR'" + "OH"^"-" → "RCOO"^"-" + "HOR'"`

Thus, the theoretical yield is 100 %.

The carboxylic acid is regenerated by acidifying the product mixture.

`"RCOO"^"-" + "H"_3"O"^"+" → "RCOOH" + "H"_2"O"`