Alkylation of enolates
Description: Enolates of carbonyl compounds will react with alkyl halides in SN2 reactions to give alkylation products.
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Real-Life Example:
Org. Synth. 1936, 16, 60
DOI Link: 10.15227/orgsyn.016.0060
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Org. Synth. 1948, 28, 8
DOI Link: 10.15227/orgsyn.028.0008
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Org. Synth. 1948, 28, 8
DOI Link: 10.15227/orgsyn.021.0099
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There’s just a little different: the last quiz shows ID:1781 on the front but ID:1781 on the back.
Thank you for showing so many examples.
That’s really helpful.
Thank you for spotting the typo. Don’t stop!
Why in the fourth reaction was formed the least substituted enolate? More substituted enolate (and pi bond) wouldn’t be more stable?
Great site!
Great question. Lithium diisopropyl amide (LDA) is a bulky base and forms the least substituted enolate upon deprotonation. https://www.masterorganicchemistry.com/2011/08/05/reagent-friday-lithium-di-isopropyl-amide-lda/