--- title: "E2 in chairs: menthyl vs neomenthyl chloride Template | MolDraw" url: https://www.moldraw.com/templates/stereo-e2-anti-periplanar-menthyl/ description: "E2 in chairs: menthyl vs neomenthyl chloride template: Neomenthyl chloride has Cl axial in its stable chair, with an axial H anti on both neighbours, so with…" lang: en publisher: Scidart Academy generated: 2026-11-13 --- [MolDraw](https://www.moldraw.com/) › [Templates](https://www.moldraw.com/templates/) › [Stereochemistry](https://www.moldraw.com/templates/stereochemistry/) › E2 in chairs: menthyl vs neomenthyl chloride [Stereochemistry](https://www.moldraw.com/templates/stereochemistry/)Premium # E2 in chairs: menthyl vs neomenthyl chloride template ![E2 in chairs: menthyl vs neomenthyl chloride template: Neomenthyl chloride has Cl axial in its stable chair, with an axial H anti on both neighbours, so with NaOEt it eliminates fast to menth-3-ene (Zaitsev, about 75 %) and menth-2-ene. Menthyl chloride must flip to the chair with all three groups axial; only C2–H is then anti, so it gives only menth-2-ene, about 200 times more slowly.](https://www.moldraw.com/templates/stereo-e2-anti-periplanar-menthyl.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). Neomenthyl chloride has Cl axial in its stable chair, with an axial H anti on both neighbours, so with NaOEt it eliminates fast to menth-3-ene (Zaitsev, about 75 %) and menth-2-ene. Menthyl chloride must flip to the chair with all three groups axial; only C2–H is then anti, so it gives only menth-2-ene, about 200 times more slowly. ## What the template shows - E2 needs the H and the leaving group anti-periplanar; in a cyclohexane chair that means both axial (trans-diaxial) - Which H is anti-periplanar to Cl? - Neomenthyl chloride: Cl axial in the stable chair (fast) - two axial H (red) anti to the axial Cl - NaOEt, EtOH - menth-3-ene - trisubstituted (Zaitsev) - menth-2-ene - neomenthyl chloride - Menthyl chloride: all equatorial, must flip first (about 200 × slower) - ring flip - Cl equatorial: no anti H, no E2 - minor chair, all axial: only the C2 H (red) is anti; the C4 H (blue) is equatorial - menthyl chloride - green = Cl · red H = axial, anti-periplanar to Cl · blue H = equatorial · red dashes join each anti pair - In E2 the C–H and C–LG bonds must be anti-periplanar (180°) so σ(C–H) overlaps σ*(C–Cl). On a chair only trans-diaxial pairs qualify; equatorial H or Cl never do. - Neomenthyl chloride: Cl is axial in the stable chair (isopropyl and CH₃ equatorial) and both neighbouring carbons have an axial H, so it reacts fast and mostly gives the more substituted menth-3-ene (about 75 : 25). - Menthyl chloride: every group is equatorial, so it must ring-flip to the all-axial chair (a tiny fraction) to react; the C4 H is then equatorial and only the C2 H is anti: menth-2-ene only, about 200 times slower. - Conformation beats Zaitsev’s rule: the alkene formed is set by which β-H can lie anti to the leaving group (Hughes and Ingold, NaOEt in EtOH). - Wedge = toward you, hash = away from you · every part of this figure is editable Drawn with 52 atoms, 99 shapes – every one editable in MolDraw. ## Sources - [Clayden, Greeves & Warren, Organic Chemistry, 2nd ed., OUP 2012, ch. 17](https://openlibrary.org/isbn/9780199270293) Textbook - [Eliel & Wilen, Stereochemistry of Organic Compounds, Wiley 1994, ch. 11](https://openlibrary.org/isbn/9780471016700) Textbook - [Smith, March's Advanced Organic Chemistry, 8th ed., Wiley 2020, ch. 17](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 E2 in chairs: menthyl vs neomenthyl chloride template free? You can preview the E2 in chairs: menthyl vs neomenthyl chloride 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 E2 in chairs: menthyl vs neomenthyl chloride 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. ### Are the R/S labels in the stereochemistry templates checked? Yes. Every R/S and E/Z descriptor is computed with RDKit from the drawn structure, so the labels match the wedges and dashes. ## More stereochemistry templates [**Assigning R and S**Free · Stereochemistry](https://www.moldraw.com/templates/stereo-rs-assignment/)[**Newman projections: butane**Free · Stereochemistry](https://www.moldraw.com/templates/stereo-newman-butane/)[**Cyclohexane chair and ring flip**Free · Stereochemistry](https://www.moldraw.com/templates/stereo-chair-ring-flip/)[**CIP priority rules**Premium · Stereochemistry](https://www.moldraw.com/templates/stereo-cip-rules/)[**E/Z and cis/trans alkenes**Premium · Stereochemistry](https://www.moldraw.com/templates/stereo-ez-alkenes/)[**Enantiomers and diastereomers**Premium · Stereochemistry](https://www.moldraw.com/templates/stereo-enantiomers-diastereomers/)[**Meso compounds: 2,3-dibromobutane**Premium · Stereochemistry](https://www.moldraw.com/templates/stereo-meso-dibromobutane/)[**Tartaric acid stereoisomers**Premium · Stereochemistry](https://www.moldraw.com/templates/stereo-tartaric-acid/) ## Related pages [**Chirality & R/S Configuration Worksheet**Free printable worksheet](https://www.moldraw.com/educational-materials/chirality-rs-worksheet/)[**Structural Isomers & Stereoisomers Worksheet**Free printable worksheet](https://www.moldraw.com/educational-materials/isomers-worksheet/)[**All Stereochemistry templates**19 templates](https://www.moldraw.com/templates/stereochemistry/)[**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. 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