--- title: "Knoevenagel condensation Template – Chemistry Diagram | MolDraw" url: https://www.moldraw.com/templates/knoevenagel-condensation/ description: "Knoevenagel condensation template: Piperidine deprotonates malononitrile; the anion adds to benzaldehyde and E1cB loss of hydroxide gives…" 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/) › Knoevenagel condensation [Name reactions](https://www.moldraw.com/templates/name-reactions/)Premium # Knoevenagel condensation template ![Knoevenagel condensation template: Piperidine deprotonates malononitrile; the anion adds to benzaldehyde and E1cB loss of hydroxide gives benzylidenemalononitrile.](https://www.moldraw.com/templates/knoevenagel-condensation.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). Piperidine deprotonates malononitrile; the anion adds to benzaldehyde and E1cB loss of hydroxide gives benzylidenemalononitrile. ## Mechanism step by step An active methylene compound condenses with an aldehyde under mild base 1. **Carbanion** – Two C≡N groups make the CH₂ acidic (pKa 11) 2. **Addition** – Attack on the aldehyde 3. **Protonation** – The piperidinium ion gives back its proton 4. **Carbanion** – The remaining acidic C–H is removed 5. **Elimination (E1cB)** – Hydroxide leaves; C=C forms in conjugation ## Key points - Needs two electron-withdrawing groups on the CH₂ (malononitrile, malonates, cyanoacetates, β-keto esters). - A weak amine base is enough, so the aldehyde does not self-condense. - Doebner modification: malonic acid in pyridine also decarboxylates, giving cinnamic acid. - Piperidine can also act through an iminium ion of the aldehyde. Drawn with 179 atoms, 16 arrows, 7 shapes – every one editable in MolDraw. ## Sources - [Knoevenagel, Ber. Dtsch. Chem. Ges. 1898, 31, 2596](https://doi.org/10.1002/cber.18980310308) 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 Knoevenagel condensation template free? You can preview the Knoevenagel condensation 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 Knoevenagel condensation 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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