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Mannich reaction template
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Dimethylamine and formaldehyde give an iminium ion; the enol of acetone attacks it to give the Mannich base.
Mechanism step by step
An enol attacks an iminium ion from an amine and formaldehyde: a β-amino ketone
- Amine adds – Attack on formaldehyde
- Proton transfer – A hemiaminal
- Protonation – OH becomes a leaving group
- Iminium ion – The N lone pair pushes out water
- C–C bond – The enol of acetone attacks the iminium carbon
- Deprotonation – The Mannich base
Key points
- Three components in one pot: enolisable carbonyl, formaldehyde, amine.
- The iminium ion is a better electrophile than formaldehyde itself.
- Robinson’s tropinone synthesis (1917) is a double Mannich reaction.
- Mannich bases eliminate the amine on heating to give enones.
Drawn with 97 atoms, 20 arrows, 8 shapes – every one editable in MolDraw.
Sources
How to use this template
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Frequently asked questions
Is the Mannich reaction template free?
You can preview the Mannich reaction 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 Mannich reaction 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.