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Cope and oxy-Cope rearrangements template
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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
- Cope [3,3] shift – The C3–C4 σ bond breaks as C1–C6 forms: six electrons in a chair
- Anionic oxy-Cope – A potassium alkoxide at C3 (KH, 18-crown-6) speeds the shift up to 10¹⁷-fold
- 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
How to use this template
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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).