Questions tagged [enolate-chemistry]

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1answer
26 views

Regioselective enolate formation, choosing major and minor products

This question came in my organic chem assignment. The options highlighted are the answers. The end carbon(adjacent to the carbonyl group) should have more acidic alpha-hydrogen and the alkene formed ...
2
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1answer
75 views

Mechanism of acid-catalyzed Robinson annulation?

My professor posed my organic chemistry class a challenge problem for bonus points and I've been racking my brain over the last three days trying to work it out and I want to know if my solution is ...
0
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1answer
51 views

how is the esterification of amino acid carried on in this reaction

i was asked to synthesis this compound from this amino acid, i first alkylated the alpha carbon using enolate alkylating method then i esterficated the amino acid but i'm doubtful that my steps are ...
3
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0answers
60 views

Help with mechanism similar to Robinson Annulation

I need to figure out a mechanism for this reaction. All I know is that it is supposed to have a similar mechanism to Robinson Annulation. This is the best I could come up with, but I've been told it ...
0
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1answer
199 views

Grignard reagent will act as a base or a nucleophile [duplicate]

R- from grignard reagent (RMgBr) and gilmann's reagent (R2CuLi) although being a strong base reduces the carbonyl group and does not act as a base. Why can't it abstract the alpha hydrogen forming an ...
0
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1answer
191 views

How would I synthesize ethyl 2‐oxocyclohexane‐1‐carboxylate from cyclohexanone? [closed]

I thought the 1st step would be deprotonation of a H atom to form the enolate. Then an aldol reaction, but the product I end up with is the alcohol, not the ketone.
2
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1answer
76 views

Can R-3-methyl-4-heptanone be enantioselectively synthesised from 4-heptanone?

I wonder if it is possible to do the following reaction with its enantioselectivity: I am trying to do it via enolate, but I don't know how to make only the R product or if it's even possible to ...
3
votes
1answer
210 views

Role of NaI in Formation of Silyl Enol Ethers using Chloro(trimethyl)silane

I am forming silyl enol ethers using Chloro(trimethyl)silane (TMSCl), and below is an experimental protocol I am following Silyl Enol Ether Synthesis In an oven-dried 100 mL three-necked ...
4
votes
1answer
392 views

Enolate ion opening an epoxide?

Does anyone know if it is possible to open an epoxide and do a 2-C extension using an enolate ion, say, of acetone? Here's an example of what I mean: Based on what I know of enolate chemistry, this ...
0
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0answers
113 views

Alkylation of acetophenone

When the NaOH deprotonates the hydrogen off the carbon, I thought there would be a resonance structure, with the negative charge being on both the oxygen and carbon. Since the oxygen is more stable ...
-2
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2answers
1k views

Less substituted vs more substituted alkene [closed]

In general, more substituted alkenes are more thermodynamically stable. However, in certain cases such as enamine alkylation, the less substituted double bond is favored. How do we know that which is ...
3
votes
1answer
363 views

How does base size affect the ratio of kinetic/thermodynamic enolate?

One of the factors that favor kinetic products is bulky bases. So, I'd expect that, for a certain substrate, the use of a more bulky base to favor even more the kinetic product. However, in the table ...
3
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0answers
126 views

Claisen-like condensation with acid chloride

In the Claisen condensation, an ester enolate attacks an ester, with an alkoxide anion leaving subsequently to give a $\beta$-keto ester. Is it possible for a typical enolate of an aldehyde or ketone ...
5
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0answers
50 views

Increasing C-alkoxycarbonylation of enolates

I am working with N-tosyl-2-piperidone and attempts to use the lithium enolate of this compound to perform an nucleophilic acyl substitution reaction on an several chloroformate esters in THF has lead ...
2
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0answers
134 views

Does the amine used to generate the enolate affect the selectivity of an Evans aldol reaction?

In an Evans aldol reaction, the enolate is typically generated by addition of a boron Lewis acid (e.g. $\ce{(n-Bu)2BOTf}$) and an amine, which acts as a weak base. I'd like to know whether there's any ...