Friedel-Crafts acylation with an anhydride

The same reaction with an anhydride as the acyl donor, releasing the carboxylic acid.

mechanism writtenBalanced: every atom is accounted for

What it needs, and what it gives

Reaction class: Electrophilic aromatic substitution
Typical conditions: A stoichiometric Lewis acid; the released acid consumes a further equivalent.
Mass balance: balanced — the co-products are written out, not dropped
Mechanism: Electrophilic aromatic substitution, 2 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 ring gives up its aromaticity for one step to attack the electrophile, then loses a proton to get it back.

The ring attacks the electrophile
A base takes the proton and the ring comes back

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 Electrophilic aromatic 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 electrophilic aromatic substitution transformations

Electrophilic aromatic halogenation

A halogen replaces a hydrogen on an aromatic ring, releasing the hydrogen halide.