--- title: "Bromination of phenol and aniline Template | MolDraw" url: https://www.moldraw.com/templates/phenol-aniline-bromination/ description: "Bromination of phenol and aniline template: Phenol with bromine water gives a white precipitate of 2,4,6-tribromophenol with no Lewis acid, aniline gives…" 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/) › Bromination of phenol and aniline [Mechanisms](https://www.moldraw.com/templates/mechanisms/)Premium # Bromination of phenol and aniline template ![Bromination of phenol and aniline template: Phenol with bromine water gives a white precipitate of 2,4,6-tribromophenol with no Lewis acid, aniline gives 2,4,6-tribromoaniline, and acetylating the NH₂ (acetanilide) tames the ring enough to stop at 4-bromoaniline.](https://www.moldraw.com/templates/phenol-aniline-bromination.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). Phenol with bromine water gives a white precipitate of 2,4,6-tribromophenol with no Lewis acid, aniline gives 2,4,6-tribromoaniline, and acetylating the NH₂ (acetanilide) tames the ring enough to stop at 4-bromoaniline. ## Mechanism step by step OH and NH₂ push electrons into the ring so strongly that bromine water substitutes all three ortho/para positions 1. **Attack at C4** – The O lone pair pushes through the ring; the para carbon attacks Br₂ (no FeBr₃ needed) 2. **Loss of H⁺** – The C–H electrons restore the aromatic ring: 4-bromophenol 3. **Both ortho positions** – The same two steps at C2 and C6 4. **Aniline** – NH₂ is even more activating: 2,4,6-tribromoaniline at once (white precipitate) 5. **Acetanilide: one Br** – Acetylation moderates NH₂; bromination goes para; hydrolysis removes the acetyl group ## Key points - OH and NH₂ donate a lone pair into the ring (+M), so the σ-complex for ortho/para attack has a form with every atom an octet; they activate the ring more than a Lewis acid is needed for. - In water, phenol is partly phenoxide (even more activating) and Br₂ is polarised by the solvent: all three o/p positions react. In a non-polar solvent (CS₂ or CHCl₃, about 0 °C) the main product is 4-bromophenol. - In acetanilide the N lone pair is shared with C=O, so the ring is only moderately activated and the bulky NHCOCH₃ group blocks ortho: one Br, para. - Aniline cannot be nitrated or acylated directly (oxidation, or protonation/Lewis-acid binding at N); protecting it as acetanilide solves this too. Drawn with 133 atoms, 16 arrows, 7 shapes – every one editable in MolDraw. ## Sources - [Clayden, Greeves & Warren, Organic Chemistry, 2nd ed., OUP 2012, ch. 21](https://openlibrary.org/isbn/9780199270293) Textbook - [Wade, Organic Chemistry, 8th ed., Pearson 2013, ch. 17](https://openlibrary.org/isbn/9780321768414) Textbook - [Smith, March's Advanced Organic Chemistry, 8th ed., Wiley 2020, ch. 11](https://openlibrary.org/isbn/9781119371809) 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 Bromination of phenol and aniline template free? You can preview the Bromination of phenol and aniline 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 Bromination of phenol and aniline 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. You can open it in MolDraw, change the substrate and reuse it. ## More mechanisms templates [**Aldol addition**Free · Mechanisms](https://www.moldraw.com/templates/aldol-addition/)[**SN2 substitution**Free · Mechanisms](https://www.moldraw.com/templates/sn2-substitution/)[**SN1 substitution**Free · Mechanisms](https://www.moldraw.com/templates/sn1-substitution/)[**E2 elimination**Premium · Mechanisms](https://www.moldraw.com/templates/e2-elimination/)[**E1 elimination**Premium · Mechanisms](https://www.moldraw.com/templates/e1-elimination/)[**Acid-catalysed hemiacetal formation**Premium · Mechanisms](https://www.moldraw.com/templates/hemiacetal-formation/)[**Imine formation**Premium · Mechanisms](https://www.moldraw.com/templates/imine-formation/)[**Ester hydrolysis (saponification)**Premium · Mechanisms](https://www.moldraw.com/templates/ester-saponification/) ## Related pages [**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 Mechanisms templates**59 templates](https://www.moldraw.com/templates/mechanisms/)[**All chemistry templates**525 templates in 31 categories](https://www.moldraw.com/templates/) MolDraw Pro Download all 525 templates - Export the 437 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. Every template can be opened and edited in MolDraw.