MolDraw › Templates › Name reactions › Simmons–Smith reaction
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Simmons–Smith reaction template
Premium template. Preview and edit it free in MolDraw; downloading and exporting it is part of MolDraw Pro.
Zinc inserts into CH₂I₂ to form the carbenoid ICH₂ZnI; it delivers CH₂ to both alkene carbons in one step (a butterfly transition state), so the alkene geometry is kept.
Mechanism step by step
CH₂I₂ and zinc–copper couple turn an alkene into a cyclopropane
- Carbenoid – Zinc inserts into a C–I bond: iodomethylzinc iodide
- CH₂ transfer – One concerted step: both new C–C bonds form on the same face; ZnI₂ leaves
Key points
- Stereospecific: a cis-alkene gives a cis-disubstituted cyclopropane, a trans-alkene a trans one.
- No free carbene forms, so there are no C–H insertion side products.
- A nearby OH group binds zinc and directs CH₂ to its own face (allylic alcohols).
- Furukawa modification: Et₂Zn with CH₂I₂ is faster and more reproducible.
Drawn with 48 atoms, 6 arrows, 9 shapes – every one editable in MolDraw.
Sources
How to use this template
- Press Edit in MolDraw. The template opens on the canvas of the free MolDraw editor.
- Change anything: move structures, edit atoms and labels, recolour highlights or delete what you do not need.
- Add your own structures, arrows and text next to it, or combine several templates on one page.
- Export the drawing as PNG, SVG or PDF for slides, worksheets, theses and papers.
Frequently asked questions
Is the Simmons–Smith reaction template free?
You can preview the Simmons–Smith reaction 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 Simmons–Smith reaction 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.
Which name reactions are included?
Over seventy, covering the reactions most often asked in school-leaving exams (A-level, IB, CBSE, JEE and NEET) and first-year university courses, including condensations, rearrangements, oxidations, reductions and aromatic substitutions.