--- title: "Hydroboration–oxidation Template – Chemistry Diagram | MolDraw" url: https://www.moldraw.com/templates/hydroboration-oxidation/ description: "Hydroboration–oxidation template: BH₃ adds H and B in one four-centre step, B on the less hindered carbon; HOO⁻ adds to boron, the alkyl shifts to oxygen and…" 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/) › Hydroboration–oxidation [Name reactions](https://www.moldraw.com/templates/name-reactions/)Premium # Hydroboration–oxidation template ![Hydroboration–oxidation template: BH₃ adds H and B in one four-centre step, B on the less hindered carbon; HOO⁻ adds to boron, the alkyl shifts to oxygen and hydrolysis gives propan-1-ol.](https://www.moldraw.com/templates/hydroboration-oxidation.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). BH₃ adds H and B in one four-centre step, B on the less hindered carbon; HOO⁻ adds to boron, the alkyl shifts to oxygen and hydrolysis gives propan-1-ol. ## Mechanism step by step Anti-Markovnikov, syn addition of H and OH across C=C 1. **Hydroboration** – B adds to the CH₂ end, H to the CH, on one face 2. **Hydroperoxide adds** – HOO⁻ attacks the empty p orbital of B 3. **1,2-Shift** – The alkyl group moves from B to O; HO⁻ leaves 4. **Hydroxide adds** – Attack on boron 5. **Alkoxide leaves** – B–O bond breaks 6. **Protonation** – Propan-1-ol ## Key points - Anti-Markovnikov: OH ends up on the less substituted carbon. - Syn addition, and the C–B → C–O step keeps the configuration. - No carbocation, so no rearrangements (unlike acid-catalysed hydration). - In practice BH₃ adds three times (R₃B); every alkyl group becomes an alcohol. Drawn with 75 atoms, 16 arrows, 10 shapes – every one editable in MolDraw. ## Sources - [Brown & Subba Rao, J. Am. Chem. Soc. 1956, 78, 5694](https://doi.org/10.1021/ja01602a063) 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 Hydroboration–oxidation template free? You can preview the Hydroboration–oxidation 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 Hydroboration–oxidation 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 [**Hydroboration–oxidation: reaction guide**Mechanism, conditions and exam notes](https://www.moldraw.com/reaction/hydroboration-oxidation/)[**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**72 templates](https://www.moldraw.com/templates/name-reactions/)[**All chemistry templates**370 templates in 29 categories](https://www.moldraw.com/templates/) MolDraw Pro Download all 370 templates - Export the 291 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. 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