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Enolate alkylation with LDA template
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LDA deprotonates cyclohexanone at −78 °C; the lithium enolate attacks iodomethane to give 2-methylcyclohexanone.
Mechanism step by step
A strong, hindered base makes the enolate completely; it then does SN2 on an alkyl halide
- Enolate – LDA removes an α-H (Li⁺ not drawn)
- C-Alkylation (SN2) – The enolate carbon attacks CH₃; iodide leaves
Key points
- LDA (pKa of iPr₂NH ≈ 36) deprotonates a ketone (pKa ≈ 19) completely, so no ketone is left for aldol side reactions.
- Bulky and cold: with an unsymmetrical ketone LDA removes the more accessible H (the kinetic enolate).
- The alkylation is SN2: methyl, primary, allylic and benzylic halides work; secondary halides are sluggish and tertiary halides eliminate.
- NaOH or NaOEt give only a little enolate at equilibrium, so self-condensation competes.
Drawn with 62 atoms, 9 arrows, 6 shapes – every one editable in MolDraw.
Sources
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Frequently asked questions
Is the Enolate alkylation with LDA template free?
You can preview the Enolate alkylation with LDA 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 Enolate alkylation with LDA 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.
What is a curly-arrow mechanism template?
A ready-made drawing of a reaction mechanism in which curved arrows show where electron pairs move in each step. You can open it in MolDraw, change the substrate and reuse it.