MolDraw › Templates › Name reactions › Benzilic acid rearrangement
Name reactionsPremium
Benzilic acid rearrangement template
Premium template. Preview and edit it free in MolDraw; downloading and exporting it is part of MolDraw Pro.
Hydroxide adds to benzil, a phenyl group shifts to the neighbouring carbonyl and proton transfer gives the benzilate anion.
Mechanism step by step
A 1,2-diketone and hydroxide give an α-hydroxy acid
- Hydroxide adds – Attack on one C=O
- 1,2-Phenyl shift – Phenyl migrates as C=O re-forms (slow step)
- Proton transfer – The stable carboxylate (benzilate)
Key points
- One of the oldest known rearrangements (Liebig, 1838).
- The irreversible proton transfer to the carboxylate drives it.
- Cyclic diketones contract by one carbon.
- Alkoxides give the α-hydroxy ester instead.
Drawn with 136 atoms, 11 arrows, 5 shapes – every one editable in MolDraw.
Sources
How to use this template
- Press Edit in MolDraw. The template opens on the canvas of the free MolDraw editor.
- Change anything: move structures, edit atoms and labels, recolour highlights or delete what you do not need.
- Add your own structures, arrows and text next to it, or combine several templates on one page.
- Export the drawing as PNG, SVG or PDF for slides, worksheets, theses and papers.
Frequently asked questions
Is the Benzilic acid rearrangement template free?
You can preview the Benzilic acid rearrangement template here and open and edit it in MolDraw for free. Downloading or exporting it is part of MolDraw Pro, together with the other premium templates.
Can I edit the Benzilic acid rearrangement template?
Yes. It opens as an ordinary MolDraw drawing, so every structure, arrow, label and colour can be changed, and you can add your own content around it.
Is the chemistry checked?
Every structure is checked with RDKit and every curly arrow passes MolDraw’s electron-flow audit. The sources used are listed on this page.
Which name reactions are included?
Over seventy, covering the reactions most often asked in school-leaving exams (A-level, IB, CBSE, JEE and NEET) and first-year university courses, including condensations, rearrangements, oxidations, reductions and aromatic substitutions.