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Pinacol rearrangement template
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Pinacol is protonated, loses water to a tertiary cation, a methyl shifts and loss of a proton gives pinacolone.
Mechanism step by step
A 1,2-diol loses water and a group shifts: the diol becomes a ketone
- Protonation – One OH is protonated
- Loss of water – A tertiary carbocation forms
- 1,2-Methyl shift – The new cation is stabilised by the OH oxygen
- Deprotonation – Water removes the O–H proton: C=O forms
Key points
- The OH that leaves is the one giving the more stable carbocation.
- Migratory aptitude: H ≈ aryl > alkyl.
- The shifted cation is really an oxocarbenium ion: the step is downhill.
- Semipinacol rearrangements use the same 1,2-shift with other leaving groups.
Drawn with 82 atoms, 11 arrows, 6 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.
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Frequently asked questions
Is the Pinacol rearrangement template free?
You can preview the Pinacol 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 Pinacol 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.