--- title: "Oxymercuration–demercuration Template | MolDraw" url: https://www.moldraw.com/templates/oxymercuration-demercuration/ description: "Oxymercuration–demercuration template: Hg(OAc)⁺ forms a mercurinium ion with propene, water opens it at the more substituted carbon, and NaBH₄ replaces…" 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/) › Oxymercuration–demercuration [Mechanisms](https://www.moldraw.com/templates/mechanisms/)Premium # Oxymercuration–demercuration template ![Oxymercuration–demercuration template: Hg(OAc)⁺ forms a mercurinium ion with propene, water opens it at the more substituted carbon, and NaBH₄ replaces mercury by hydrogen to give propan-2-ol.](https://www.moldraw.com/templates/oxymercuration-demercuration.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). Hg(OAc)⁺ forms a mercurinium ion with propene, water opens it at the more substituted carbon, and NaBH₄ replaces mercury by hydrogen to give propan-2-ol. ## Mechanism step by step Markovnikov hydration without a free carbocation, so without rearrangement 1. **Mercurinium ion** – The π bond attacks Hg⁺ (from Hg(OAc)₂ losing AcO⁻): a bridged cation 2. **Water opens the ring** – Anti attack at the more substituted carbon 3. **Deprotonation** – An organomercury alcohol 4. **Demercuration** – NaBH₄ replaces Hg by H (a radical reaction, arrows not shown) ## Key points - Markovnikov orientation: OH goes to the more substituted carbon. - The bridged mercurinium ion never opens to a free carbocation, so no hydride or methyl shifts occur. - In alcohol instead of water (alkoxymercuration) the product is an ether. - Anti-Markovnikov alcohols come from hydroboration–oxidation instead. Drawn with 75 atoms, 11 arrows, 8 shapes – every one editable in MolDraw. ## Sources - [Clayden, Greeves & Warren, Organic Chemistry, 2nd ed., OUP 2012, ch. 19](https://openlibrary.org/isbn/9780199270293) Textbook - [Smith, March's Advanced Organic Chemistry, 8th ed., Wiley 2020, ch. 15](https://openlibrary.org/isbn/9781119371809) Textbook - [Brown & Geoghegan, J. Am. Chem. Soc. 1967, 89, 1522](https://doi.org/10.1021/ja00982a043) 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 Oxymercuration–demercuration template free? You can preview the Oxymercuration–demercuration 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 Oxymercuration–demercuration 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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