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Results tagged with enolate-chemistry
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user 41686
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
Can R-3-methyl-4-heptanone be enantioselectively synthesised from 4-heptanone?
Enders SAMP/RAMP hydrazone chemistry will do this(1).
The Wikipedia article on this technique is a good introduction:
(1): Corey, E. J.; Enders, D. (1976). "Applications of N,N-dimethylhydrazones …
- 23k
1
vote
How would I synthesize ethyl 2‐oxocyclohexane‐1‐carboxylate from cyclohexanone?
As you will see if you look at the reference mentioned by @Mathew-Mahindaratne, the standard conditions for this transformation is NaH/KH in THF at reflux with diethyl carbonate (EtOCOOEt) with an a …
- 23k
2
votes
Why can't the N- end of the nitrile anion attack the alkyl halide in an SN2 fashion during a...
It can.
According to this JACS paper here steric effects are a major factor in whether the ketenimine is formed or the C-alklyated product - the more hindered the nitrile, the more N-alkylation.
- 23k
1
vote
Acidity of alpha hydrogens in enolate formation
The two deprotonated species are in equilibrium (along with the neutral parent molecule). The deprotonation you suggest will occur, but the forward reaction cannot because it would be forming a [4] ri …
- 23k
8
votes
Accepted
Role of NaI in Formation of Silyl Enol Ethers using Chloro(trimethyl)silane
The use of $\ce{NaI}$ in $\ce{MeCN}$ (a solvent in which $\ce{NaI}$ is quite soluble) is forming $\ce{Me3SiI}$ from the $\ce{Me3SiCl}$. The reason for doing this is $\ce{Me3SiI}$ is significantly more …
- 23k
2
votes
Accepted
Nucleophilicity of sterically hindered enolates
The permethylation of cyclohexanone with KH/MeI is described here JOC paper. The yield quoted is 96% and other ketones are also exemplified.
- 23k
3
votes
Accepted
how is the esterification of amino acid carried on in this reaction
I think you need a protection strategy and there are several choices. This one uses O'Donnell's benzophenone imine strategy details here.
First you prepare glycine ethyl ester hydrochloride from glyci …
- 23k
2
votes
Accepted
Mechanism of deprotection of enol thioether
Mechanism: 1 -hydroxide anion adds to the =CHSBu carbon in a Michael addition giving the enolate anion of the carbonyl and -CHOH(SBu).
2- The enolate anion deprotonates the newly arrived -OH group to …
- 23k