--- title: "Birch reduction Template – Chemistry Diagram | MolDraw" url: https://www.moldraw.com/templates/birch-reduction/ description: "Birch reduction template: Solvated electrons add to benzene one at a time; each anion takes a proton from ethanol. The second protonation happens at the…" 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/) › Birch reduction [Name reactions](https://www.moldraw.com/templates/name-reactions/)Premium # Birch reduction template ![Birch reduction template: Solvated electrons add to benzene one at a time; each anion takes a proton from ethanol. The second protonation happens at the centre of the pentadienyl anion, so the product is the non-conjugated 1,4-diene.](https://www.moldraw.com/templates/birch-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). Solvated electrons add to benzene one at a time; each anion takes a proton from ethanol. The second protonation happens at the centre of the pentadienyl anion, so the product is the non-conjugated 1,4-diene. ## Mechanism step by step Sodium in liquid ammonia with an alcohol reduces benzene to cyclohexa-1,4-diene 1. **Electron transfer** – A solvated electron from Na in NH₃ adds: a radical anion 2. **Protonation** – Ethanol protonates the anion: a cyclohexadienyl radical 3. **Second electron** – Another electron: a pentadienyl anion with most charge at the centre 4. **Protonation at the centre** – The middle carbon takes H⁺: the 1,4-diene, not the conjugated 1,3-diene ## Key points - The blue colour of Na in liquid NH₃ comes from solvated electrons. - Electron-donating groups (OMe) end up on a C=C; electron-withdrawing groups (CO₂H) end up on an sp³ carbon. - The alcohol is a proton source more acidic than NH₃ but weak enough not to destroy the electrons quickly. - Anisole gives 1-methoxycyclohexa-1,4-diene, which hydrolyses to cyclohex-2-enone: a route to enones. Drawn with 74 atoms, 9 arrows, 6 shapes – every one editable in MolDraw. ## Sources - [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 Birch reduction template free? You can preview the Birch 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 Birch 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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