--- title: "Benzyne mechanism Template – Chemistry Diagram | MolDraw" url: https://www.moldraw.com/templates/benzyne-mechanism/ description: "Benzyne mechanism template: NaNH₂ removes the H next to Cl in chlorobenzene, chloride leaves to give benzyne, NH₂⁻ adds and NH₃ protonates the aryl anion to…" lang: en publisher: Scidart Academy generated: 2026-11-13 --- [MolDraw](https://www.moldraw.com/) › [Templates](https://www.moldraw.com/templates/) › [Mechanisms](https://www.moldraw.com/templates/mechanisms/) › Benzyne mechanism [Mechanisms](https://www.moldraw.com/templates/mechanisms/)Premium # Benzyne mechanism template ![Benzyne mechanism template: NaNH₂ removes the H next to Cl in chlorobenzene, chloride leaves to give benzyne, NH₂⁻ adds and NH₃ protonates the aryl anion to give aniline.](https://www.moldraw.com/templates/benzyne-mechanism.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). NaNH₂ removes the H next to Cl in chlorobenzene, chloride leaves to give benzyne, NH₂⁻ adds and NH₃ protonates the aryl anion to give aniline. ## Mechanism step by step Elimination–addition: a very strong base makes a benzyne, which the amide ion then attacks 1. **Deprotonation** – NH₂⁻ removes the H ortho to Cl 2. **Benzyne** – The carbanion pushes out Cl⁻: a strained triple bond 3. **Addition** – NH₂⁻ attacks either end of the triple bond 4. **Protonation** – NH₃ protonates the aryl anion ## Key points - The extra π bond of benzyne uses sp² orbitals in the ring plane: poor overlap, so it is weak and very reactive. - ¹⁴C-labelled chlorobenzene gives aniline with NH₂ half on the labelled carbon, half on its neighbour (Roberts, 1953). - Substituted aryl halides can give mixtures: the nucleophile ends up on the carbon that carried the halogen (ipso) or on its neighbour (cine substitution). - No H ortho to the halogen, no benzyne: such halides do not react. Drawn with 76 atoms, 13 arrows, 6 shapes – every one editable in MolDraw. ## Sources - [Clayden, Greeves & Warren, Organic Chemistry, 2nd ed., OUP 2012, ch. 22](https://openlibrary.org/isbn/9780199270293) Textbook - [Smith, March's Advanced Organic Chemistry, 8th ed., Wiley 2020, ch. 13](https://openlibrary.org/isbn/9781119371809) Textbook - [Roberts, Simmons, Carlsmith & Vaughan, J. Am. Chem. Soc. 1953, 75, 3290](https://doi.org/10.1021/ja01109a523) Original paper ## 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 Benzyne mechanism template free? You can preview the Benzyne mechanism 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 Benzyne mechanism 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. 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