--- title: "Nucleophilic aromatic substitution (SNAr) Template | MolDraw" url: https://www.moldraw.com/templates/snar-meisenheimer/ description: "Nucleophilic aromatic substitution (SNAr) template: Hydroxide adds to 1-chloro-2,4-dinitrobenzene at the carbon bearing Cl; the anion is delocalised onto the…" 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/) › Nucleophilic aromatic substitution (SNAr) [Mechanisms](https://www.moldraw.com/templates/mechanisms/)Premium # Nucleophilic aromatic substitution (SNAr) template ![Nucleophilic aromatic substitution (SNAr) template: Hydroxide adds to 1-chloro-2,4-dinitrobenzene at the carbon bearing Cl; the anion is delocalised onto the nitro groups, then chloride leaves to give 2,4-dinitrophenol.](https://www.moldraw.com/templates/snar-meisenheimer.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). Hydroxide adds to 1-chloro-2,4-dinitrobenzene at the carbon bearing Cl; the anion is delocalised onto the nitro groups, then chloride leaves to give 2,4-dinitrophenol. ## Mechanism step by step Addition–elimination through the Meisenheimer complex; nitro groups ortho and para hold the charge 1. **Addition (slow)** – OH⁻ attacks the C–Cl carbon; aromaticity is lost 2. **Meisenheimer complex** – The negative charge spreads onto a nitro oxygen 3. **Elimination** – Chloride leaves; aromaticity returns ## Key points - Needs strong electron-withdrawing groups ortho or para to the leaving group; a meta-NO₂ cannot take the charge. - Addition is the slow step, so Ar–F reacts fastest (F ≫ Cl ≈ Br > I): Sanger’s reagent, 2,4-dinitrofluorobenzene, labels the N-terminus of peptides. - Plain aryl halides do not do SN1 or SN2: the ring blocks backside attack and aryl cations are very unstable. - In NaOH the phenol is present as its phenoxide; acid work-up gives 2,4-dinitrophenol. Drawn with 112 atoms, 10 arrows, 7 shapes – every one editable in MolDraw. ## Sources - [Clayden, Greeves & Warren, Organic Chemistry, 2nd ed., OUP 2012, ch. 22](https://openlibrary.org/isbn/9780199270293) Textbook - [Smith, March's Advanced Organic Chemistry, 8th ed., Wiley 2020, ch. 13](https://openlibrary.org/isbn/9781119371809) Textbook - [Meisenheimer, Justus Liebigs Ann. Chem. 1902, 323, 205](https://doi.org/10.1002/jlac.19023230205) Original paper - [Bunnett & Zahler, Chem. Rev. 1951, 49, 273](https://doi.org/10.1021/cr60153a002) Review ## 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 Nucleophilic aromatic substitution (SNAr) template free? You can preview the Nucleophilic aromatic substitution (SNAr) 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 Nucleophilic aromatic substitution (SNAr) 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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