--- title: "Mitsunobu reaction Template – Chemistry Diagram | MolDraw" url: https://www.moldraw.com/templates/mitsunobu-reaction/ description: "Mitsunobu reaction template: PPh₃ adds to DEAD; the betaine deprotonates benzoic acid, the alcohol attacks phosphorus and benzoate displaces Ph₃P=O to give…" 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/) › Mitsunobu reaction [Name reactions](https://www.moldraw.com/templates/name-reactions/)Premium # Mitsunobu reaction template ![Mitsunobu reaction template: PPh₃ adds to DEAD; the betaine deprotonates benzoic acid, the alcohol attacks phosphorus and benzoate displaces Ph₃P=O to give the inverted ester.](https://www.moldraw.com/templates/mitsunobu-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). PPh₃ adds to DEAD; the betaine deprotonates benzoic acid, the alcohol attacks phosphorus and benzoate displaces Ph₃P=O to give the inverted ester. ## Mechanism step by step PPh₃ and DEAD activate an alcohol for SN2 by a carboxylate, with inversion 1. **Betaine** – PPh₃ adds to the N=N of DEAD 2. **Deprotonation** – The betaine takes the acid proton 3. **Alcohol activation** – O attacks P; the hydrazide leaves 4. **Proton transfer** – The alkoxyphosphonium ion 5. **SN2 with inversion** – Benzoate attacks from the back; Ph₃P=O leaves ## Key points - Clean inversion at the alcohol carbon: (R)-alcohol → (S)-ester. - The nucleophile needs pKa < ~13 (carboxylic acids, phenols, imides, HN₃). - By-products Ph₃P=O and the hydrazine dicarboxylate can be hard to remove. - Hydrolysis of the ester gives the inverted alcohol. Drawn with 231 atoms, 16 arrows, 7 shapes – every one editable in MolDraw. ## Sources - [Mitsunobu & Yamada, Bull. Chem. Soc. Jpn. 1967, 40, 2380](https://doi.org/10.1246/bcsj.40.2380) Original paper - [Mitsunobu, Synthesis 1981, 1](https://doi.org/10.1055/s-1981-29317) Review - [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 Mitsunobu reaction template free? You can preview the Mitsunobu 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 Mitsunobu 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 [**Mitsunobu reaction: reaction guide**Mechanism, conditions and exam notes](https://www.moldraw.com/reaction/mitsunobu-reaction/)[**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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