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Enolates are anions derived from the deprotonation of carbonyl compounds. This tag must be used while dealing with the enolates or its derivatives including its resonance forms.

3 votes
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stereoselectivity in aldol reactions

I do not have the recent or the fifth edition of Advanced Organic Chemistry: Part B but have the forth edition (Ref.1) to answer this question. First, this book is not for for studying stereochemistry …
Mathew Mahindaratne's user avatar
3 votes

Nucleophilicity of sterically hindered enolates

Although Ben Norris has given excellent explanation for why the steric hindrence is not playing the role in the reaction of cyclohexanone with excess methyl iodide to give tetramethylated cyclohexanon …
Mathew Mahindaratne's user avatar
3 votes
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Acidity of alpha hydrogens in enolate formation

I'm interested in the OP's curiosity. I'd agree with Waylander about disfavoring to make 4-membered rings. Yet, it is possible to have two six-membered ring products. The first $\alpha$-proton abstrac …
Mathew Mahindaratne's user avatar
2 votes
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Grignard reagent will act as a base or a nucleophile

As most of us chemists have understood and experienced, the Grignard reagent have undergone the many reactions with suitable substrates. Yet, the most familiar and probably the most used reaction is t …
Mathew Mahindaratne's user avatar
4 votes
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Enolate ion opening an epoxide?

Never say never! :-) Here is the answer for your question (Ref.1): Abstract: We report here that (1) enolate anions of five- to seven-membered cycloalkanones nucleophilically open cyclopentene and …
Mathew Mahindaratne's user avatar