--- title: "Schmidt reaction Template – Chemistry Diagram | MolDraw" url: https://www.moldraw.com/templates/schmidt-reaction/ description: "Schmidt reaction template: In concentrated H₂SO₄, HN₃ adds to the protonated ketone; loss of water gives an iminodiazonium ion, and the group anti to N₂⁺…" lang: en publisher: Scidart Academy generated: 2026-11-13 --- [MolDraw](https://www.moldraw.com/) › [Templates](https://www.moldraw.com/templates/) › [Name reactions](https://www.moldraw.com/templates/name-reactions/) › Schmidt reaction [Name reactions](https://www.moldraw.com/templates/name-reactions/)Premium # Schmidt reaction template ![Schmidt reaction template: In concentrated H₂SO₄, HN₃ adds to the protonated ketone; loss of water gives an iminodiazonium ion, and the group anti to N₂⁺ migrates to nitrogen as N₂ leaves. Water traps the nitrilium ion and tautomerisation gives the amide. Carboxylic acids react the same way to give amines with loss of CO₂.](https://www.moldraw.com/templates/schmidt-reaction.webp) [Edit in MolDraw](https://www.moldraw.com/)Download with Pro Premium template. Preview and edit it free in MolDraw; downloading and exporting it is part of [MolDraw Pro](https://www.moldraw.com/pricing). In concentrated H₂SO₄, HN₃ adds to the protonated ketone; loss of water gives an iminodiazonium ion, and the group anti to N₂⁺ migrates to nitrogen as N₂ leaves. Water traps the nitrilium ion and tautomerisation gives the amide. Carboxylic acids react the same way to give amines with loss of CO₂. ## Mechanism step by step Hydrazoic acid inserts NH next to a carbonyl: ketone → amide, acid → amine 1. **Protonation** – The acid activates the carbonyl 2. **HN₃ adds** – Azide N attacks C (HN₃ drawn as H–N⁻–N⁺≡N) 3. **Dehydration** – Acid-catalysed loss of water: the iminodiazonium ion 4. **Migration** – The phenyl anti to N₂⁺ moves to N as N₂ leaves 5. **Water adds** – Attack on the nitrilium carbon 6. **Tautomerisation** – Proton transfers give the amide 7. **Carboxylic acids** – Acylium ion + HN₃, R migrates (isocyanate), water: the amine and CO₂ ## Key points - The group anti to the N₂⁺ leaving group migrates (as in the Beckmann rearrangement); for aryl alkyl ketones that is usually the aryl group. - Cyclic ketones give lactams (cyclohexanone → ε-caprolactam), the same products as the Beckmann route. - RCOOH → RNH₂ + CO₂ in one pot, with retention at a migrating stereocentre (compare Curtius and Hofmann). - HN₃ is made in situ from NaN₃ and H₂SO₄; it is very toxic and explosive. Drawn with 181 atoms, 17 arrows, 11 shapes – every one editable in MolDraw. ## Sources - [Kürti & Czakó, Strategic Applications of Named Reactions in Organic Synthesis, Elsevier 2005, Schmidt reaction](https://openlibrary.org/isbn/9780124297852) Textbook - [Smith, March's Advanced Organic Chemistry, 8th ed., Wiley 2020, ch. 18](https://openlibrary.org/isbn/9781119371809) Textbook ## How to use this template 1. Press **Edit in MolDraw**. The template opens on the canvas of the free MolDraw editor. 2. Change anything: move structures, edit atoms and labels, recolour highlights or delete what you do not need. 3. Add your own structures, arrows and text next to it, or combine several templates on one page. 4. Export the drawing as PNG, SVG or PDF for slides, worksheets, theses and papers. ## Frequently asked questions ### Is the Schmidt reaction template free? You can preview the Schmidt 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 Schmidt 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. ## More name reactions templates [**Fischer esterification**Free · Name reactions](https://www.moldraw.com/templates/fischer-esterification/)[**Grignard addition to a ketone**Free · Name reactions](https://www.moldraw.com/templates/grignard-addition/)[**Michael addition**Free · Name reactions](https://www.moldraw.com/templates/michael-addition/)[**Diels–Alder reaction**Premium · Name reactions](https://www.moldraw.com/templates/diels-alder/)[**Friedel–Crafts acylation**Premium · Name reactions](https://www.moldraw.com/templates/friedel-crafts-acylation/)[**Claisen condensation**Premium · Name reactions](https://www.moldraw.com/templates/claisen-condensation/)[**Friedel–Crafts alkylation**Premium · Name reactions](https://www.moldraw.com/templates/friedel-crafts-alkylation/)[**Cannizzaro reaction**Premium · Name reactions](https://www.moldraw.com/templates/cannizzaro-reaction/) ## Related pages [**Curved Arrow Mechanism Worksheet**Free printable worksheet](https://www.moldraw.com/educational-materials/curved-arrow-mechanism-worksheet/)[**Predict the Product Worksheet: Organic Reactions**Free printable worksheet](https://www.moldraw.com/educational-materials/predict-the-product-worksheet/)[**All Name reactions templates**93 templates](https://www.moldraw.com/templates/name-reactions/)[**All chemistry templates**525 templates in 31 categories](https://www.moldraw.com/templates/) MolDraw Pro Download all 525 templates - Export the 437 premium templates as PNG, SVG or PDF - AI chemistry assistant - Structure scanning from images - Cloud save and teaching slides [See Pro plans](https://www.moldraw.com/pricing) Free templates stay free. Every template can be opened and edited in MolDraw.