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Carbocation rearrangement template
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3-Methylbutan-2-ol with HBr: protonation, loss of water, 1,2-hydride shift and bromide capture give the tertiary bromide.
Mechanism step by step
A 1,2-hydride shift turns a secondary cation into a more stable tertiary one
- Protonation – OH becomes a good leaving group
- Loss of water – A secondary carbocation forms
- 1,2-Hydride shift – H moves with its electron pair: 2° → 3° cation
- Bromide capture – Br⁻ adds to the tertiary cation
Key points
- Cation stability: 3° > 2° > 1° > methyl (hyperconjugation and inductive donation).
- A neighbouring H (hydride shift) or alkyl group (methyl shift) moves with its bonding pair.
- Expect rearranged products in SN1, E1 and acid-catalysed additions.
- Neopentyl systems give a 1,2-methyl shift for the same reason.
Drawn with 64 atoms, 10 arrows, 6 shapes – every one editable in MolDraw.
Sources
How to use this template
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Frequently asked questions
Is the Carbocation rearrangement template free?
You can preview the Carbocation 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 Carbocation 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.
What is a curly-arrow mechanism template?
A ready-made drawing of a reaction mechanism in which curved arrows show where electron pairs move in each step. You can open it in MolDraw, change the substrate and reuse it.