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Dieckmann condensation template
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Diethyl adipate cyclises with ethoxide to ethyl 2-oxocyclopentanecarboxylate; deprotonation of the product drives the equilibrium.
Mechanism step by step
An intramolecular Claisen condensation: a diester closes to a cyclic β-keto ester
- Enolate – Ethoxide removes an α-H
- Ring closure – Attack on the other ester: a five-membered ring
- Elimination – Ethoxide is expelled
- Deprotonation – The doubly activated C–H (pKa 11) drives the reaction
- Work-up – Acid gives the neutral β-keto ester
Key points
- Best for five- and six-membered rings (1,6- and 1,7-diesters).
- A full equivalent of base is needed: the product is deprotonated.
- Hydrolysis and decarboxylation then give the cyclic ketone (cyclopentanone).
- The alkoxide matches the ester to avoid transesterification.
Drawn with 173 atoms, 16 arrows, 7 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.
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Frequently asked questions
Is the Dieckmann condensation template free?
You can preview the Dieckmann 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 Dieckmann 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.