--- title: "Wolff–Kishner reduction Template – Chemistry Diagram | MolDraw" url: https://www.moldraw.com/templates/wolff-kishner-reduction/ description: "Wolff–Kishner reduction template: The hydrazone of acetophenone is deprotonated and protonated on carbon, then loses N₂ to a carbanion that is protonated to…" lang: en publisher: Scidart Academy generated: 2026-10-28 --- [MolDraw](https://www.moldraw.com/) › [Templates](https://www.moldraw.com/templates/) › [Name reactions](https://www.moldraw.com/templates/name-reactions/) › Wolff–Kishner reduction [Name reactions](https://www.moldraw.com/templates/name-reactions/)Premium # Wolff–Kishner reduction template ![Wolff–Kishner reduction template: The hydrazone of acetophenone is deprotonated and protonated on carbon, then loses N₂ to a carbanion that is protonated to ethylbenzene.](https://www.moldraw.com/templates/wolff-kishner-reduction.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). The hydrazone of acetophenone is deprotonated and protonated on carbon, then loses N₂ to a carbanion that is protonated to ethylbenzene. ## Mechanism step by step Hydrazone + strong base at high temperature: C=O becomes CH₂ with loss of N₂ 1. **Deprotonation** – The hydrazone (from C=O + N₂H₄) loses an N–H; the charge moves to C 2. **C-Protonation** – Water protonates carbon: a diimide 3. **Loss of N₂** – Deprotonation releases N₂ and a carbanion 4. **Protonation** – Water gives the alkane ## Key points - Loss of N₂ gas makes the reduction irreversible. - Strongly basic: the complement to the acidic Clemmensen reduction (Zn/Hg, HCl). - Huang-Minlon: one pot in ethylene glycol, water distilled off. - Base-sensitive groups (esters, alkyl halides) do not survive. Drawn with 107 atoms, 15 arrows, 8 shapes – every one editable in MolDraw. ## Sources - [Wolff, Justus Liebigs Ann. Chem. 1912, 394, 86](https://doi.org/10.1002/jlac.19123940107) Original paper - [Kürti & Czakó, Strategic Applications of Named Reactions in Organic Synthesis, Elsevier 2005](https://openlibrary.org/isbn/9780124297852) Textbook - [Clayden, Greeves & Warren, Organic Chemistry, 2nd ed., OUP 2012](https://openlibrary.org/isbn/9780199270293) 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 Wolff–Kishner reduction template free? You can preview the Wolff–Kishner reduction 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 Wolff–Kishner reduction 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? 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