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Schotten–Baumann reaction template
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Aniline adds to benzoyl chloride, chloride is expelled and hydroxide removes the N–H proton to give benzanilide.
Mechanism step by step
Acylation of an amine by an acyl chloride in aqueous base
- Addition – The amine attacks the acyl chloride
- Elimination – Chloride is expelled
- Deprotonation – NaOH neutralises the acid formed
Key points
- The base removes HCl, which would otherwise protonate (deactivate) the amine.
- Two phases: the acyl chloride stays in the organic layer, away from hydroxide.
- Also acylates alcohols and phenols (benzoylation).
- Pyridine is the usual base in a single organic phase.
Drawn with 129 atoms, 10 arrows, 5 shapes – every one editable in MolDraw.
Sources
- Schotten, Ber. Dtsch. Chem. Ges. 1884, 17, 2544 Original paper
- Baumann, Ber. Dtsch. Chem. Ges. 1886, 19, 3218 Original paper
- Clayden, Greeves & Warren, Organic Chemistry, 2nd ed., OUP 2012 Textbook
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Frequently asked questions
Is the Schotten–Baumann reaction template free?
You can preview the Schotten–Baumann 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 Schotten–Baumann 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.