--- title: "Cope and oxy-Cope rearrangements Template | MolDraw" url: https://www.moldraw.com/templates/pericyclic-cope-oxy-cope/ description: "Cope and oxy-Cope rearrangements template: 3-Methylhexa-1,5-diene rearranges to hepta-1,5-diene; with an alkoxide at C3 the anionic oxy-Cope is very fast and…" lang: en publisher: Scidart Academy generated: 2026-10-28 --- [MolDraw](https://www.moldraw.com/) › [Templates](https://www.moldraw.com/templates/) › [Pericyclic reactions](https://www.moldraw.com/templates/pericyclic-reactions/) › Cope and oxy-Cope rearrangements [Pericyclic reactions](https://www.moldraw.com/templates/pericyclic-reactions/)Free # Cope and oxy-Cope rearrangements template ![Cope and oxy-Cope rearrangements template: 3-Methylhexa-1,5-diene rearranges to hepta-1,5-diene; with an alkoxide at C3 the anionic oxy-Cope is very fast and the enolate gives a ketone.](https://www.moldraw.com/templates/download/pericyclic-cope-oxy-cope.svg) [Edit in MolDraw](https://www.moldraw.com/)[Download SVG](https://www.moldraw.com/templates/download/pericyclic-cope-oxy-cope.svg) Free template. Download it, or open it in MolDraw to change it first. 3-Methylhexa-1,5-diene rearranges to hepta-1,5-diene; with an alkoxide at C3 the anionic oxy-Cope is very fast and the enolate gives a ketone. ## Mechanism step by step The [3,3]-sigmatropic shift of a 1,5-diene through a chair transition state 1. **Cope [3,3] shift** – The C3–C4 σ bond breaks as C1–C6 forms: six electrons in a chair 2. **Anionic oxy-Cope** – A potassium alkoxide at C3 (KH, 18-crown-6) speeds the shift up to 10¹⁷-fold 3. **Protonation** – The enolate takes a proton on work-up: the ketone ## Key points - A [3,3]-sigmatropic shift: σ bond 1–1′ moves to 3–3′, suprafacial on both allyl fragments, thermally allowed (six electrons). - FMO picture: two allyl radicals whose SOMOs (ψ2) overlap in phase at both ends of a chair. - Stereospecific: the chair transition state sets the geometry of the new alkene (mostly E) and transfers stereocentres along the chain. - Reversible for the Cope; the oxy-Cope is pulled forward because the enol or enolate gives a C=O. Drawn with 63 atoms, 13 arrows, 5 shapes – every one editable in MolDraw. ## Sources - [Woodward & Hoffmann, Angew. Chem. Int. Ed. Engl. 1969, 8, 781](https://doi.org/10.1002/anie.196907811) Review - [Fleming, Molecular Orbitals and Organic Chemical Reactions, Wiley 2010](https://openlibrary.org/isbn/9780470746585) Textbook - [Clayden, Greeves & Warren, Organic Chemistry, 2nd ed., OUP 2012, ch. 35](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 Cope and oxy-Cope rearrangements template free? Yes. The Cope and oxy-Cope rearrangements template is one of the free MolDraw templates: open it in the editor or download it from this page as SVG or PNG and use it in your slides, worksheets and notes. ### Can I edit the Cope and oxy-Cope rearrangements 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. ### Do the pericyclic templates show orbital symmetry? They show the curly arrows, the stereochemical outcome and the Woodward–Hoffmann rule that predicts it (conrotatory or disrotatory, endo or exo). ## More pericyclic reactions templates [**Diels–Alder reaction: the endo rule**Free · Pericyclic reactions](https://www.moldraw.com/templates/pericyclic-diels-alder-endo/)[**Diels–Alder regiochemistry**Free · Pericyclic reactions](https://www.moldraw.com/templates/pericyclic-diels-alder-regio/)[**Claisen rearrangement**Premium · Pericyclic reactions](https://www.moldraw.com/templates/pericyclic-claisen/)[**Electrocyclic ring closure**Premium · Pericyclic reactions](https://www.moldraw.com/templates/pericyclic-electrocyclic/)[**1,3-Dipolar cycloaddition**Premium · Pericyclic reactions](https://www.moldraw.com/templates/pericyclic-dipolar-cycloaddition/) ## Related pages [**Curved Arrow Mechanism Worksheet**Free printable worksheet](https://www.moldraw.com/educational-materials/curved-arrow-mechanism-worksheet/)[**All Pericyclic reactions templates**6 templates](https://www.moldraw.com/templates/pericyclic-reactions/)[**All chemistry templates**370 templates in 29 categories](https://www.moldraw.com/templates/) MolDraw Pro Download all 370 templates - Export the 291 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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