Ester hydrolysis

Water splits an ester back into a carboxylic acid and an alcohol.

mechanism writtenBalanced: every atom is accounted for

What it needs, and what it gives

Reaction class: Hydrolysis
Typical conditions: Aqueous acid or base, heating.
Mass balance: balanced — the co-products are written out, not dropped
Mechanism: Nucleophilic acyl substitution, 3 steps

Conditions are what the literature ordinarily uses, recorded so you can see whether yours are in the usual range. They are not a procedure and they are not scaled to your flask.

How it is thought to happen

The nucleophile adds to the carbonyl, the carbon holds four groups for a moment, and the leaving group is pushed out as the double bond comes back.

The nucleophile attacks the carbonyl carbon
The carbonyl comes back and the leaving group goes
A base takes the proton

This is the pathway taught for the class, not a record of what was observed. On the platform it is drawn on the structures you supply, with the curly arrows on the atoms that actually move.

Read the Nucleophilic acyl substitution mechanism

Try it on your own structures

Enter your reactants in the Reaction Lab. If this transformation matches what you drew, it is applied and the outcome is shown next to the records that back it — with the count of documented reactions doing the same thing on substrates like yours, rather than a confidence score.

Open the Reaction Lab Browse recorded reactions

Other hydrolysis transformations

Hydrolysis of an amide

Water splits an amide into the carboxylic acid and the amine.

Ester hydrolysis

What it needs, and what it gives

How it is thought to happen

Try it on your own structures

Other hydrolysis transformations

Hydrolysis of an amide

Where to next

All transformations

Mechanisms

Questions