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Darzens glycidic ester condensation template
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Ethoxide removes the acidic α-H of ethyl chloroacetate; the enolate adds to benzaldehyde and the alkoxide displaces chloride inside the molecule, closing the epoxide.
Mechanism step by step
An α-chloro ester and an aldehyde with base give an α,β-epoxy ester
- Enolate – Ethoxide removes the α-H, made acidic by C=O and Cl
- Aldol-type addition – The carbanion adds to the aldehyde carbon
- Ring closure (SN2) – The alkoxide displaces chloride from the next carbon: the epoxide
Key points
- Glycidic esters hydrolyse and decarboxylate to aldehydes or ketones with one more carbon.
- The ring closure is an intramolecular SN2: O and Cl must be anti, which sets the epoxide stereochemistry.
- Usually gives mainly the trans epoxide (aryl and ester on opposite sides).
- Bases: NaOEt, NaNH₂ or KOtBu; ketones also work.
Drawn with 119 atoms, 10 arrows, 9 shapes – every one editable in MolDraw.
Sources
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Frequently asked questions
Is the Darzens glycidic ester condensation template free?
You can preview the Darzens glycidic ester condensation 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 Darzens glycidic ester condensation 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.