Questions tagged [esters]

For questions about the synthesis, properties, and reactions of ester compounds, both organic and inorganic.

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17
votes
1answer
4k views

Why are lactones more acidic than esters?

Lactones ($\mathrm pK_\mathrm a \sim 25$) tend to be more acidic than esters ($\mathrm pK_\mathrm a \sim 30$). I know that the lactone is fixed in a (E)-conformation, due to the ring: and that in ...
9
votes
2answers
1k views

Why are peroxides unstable but disulfide bridges considered stable? Why are esters stable but thiolesters are unstable?

I can not understand why a peroxide $\ce{R-O-O-R}$ is considered reactive and unstable. Going down one row on the periodic table, a disulfide bridge ($\ce{R-S-S-R}$) is apparently super stable and ...
1
vote
1answer
2k views

Naming ester as a substituent to carboxylic acid

Can carboxylic acid functional group -COOH and ester's functional group R-COO-R' be in one structure? If yes, carboxylic acid will be the parent chain and ester will be the substituent as c.a. is ...
6
votes
2answers
718 views

How is the configuration of an ester enolate double bond assigned according to CIP?

Two principal modern methods for enantioselective aldol reactions — the Evans aldol and the Masamune aldol — use a carboxylic-acid derived enolate rather than a ketone enolate as e.g. in the Paterson ...
11
votes
1answer
256 views

Which electronic effects are responsible for the reduction of nucleophilicity of a hydroxy group orthogonal to an ester?

I am facing a similar synthetic problem as Boekman Jr. et al noted in their synthesis of Tetronolide.[1] I will quote their’s rather than disclosing my actual synthetic problem, but note that the key ...
3
votes
1answer
745 views

Why aqueous hydroxide is slippery (beyond just saponification)

A recent question mentions: Bases are soapy to touch because of soap formation on contact with lipids present on our skin. This is always the reasoning I hear, as well, and searching the internet ...
4
votes
1answer
152 views

Why does a carbonyl reform in ester reactions

I have noticed that frequently whenever esters react with a nucleophile, the nucleophile will attack the carbonyl carbon and eventually in order for the carbonyl to reform the other oxygen will leave ...
4
votes
1answer
3k views

Are all esterification reactions reversible? What is their general mechanism?

For example the reaction of ethanoic acid with ethanol is reversible, however is this true for all esters? I'm not quite whether it is as easy for a reversible reaction to occur both ways. Is there a ...
2
votes
1answer
203 views

Ester as a side product in the synthesis of bromoalkane from alcohol. Is it correct?

About 5 months ago, I answered a very interesting question albeit a very simple one. Why do we need sulfuric acid in creating alkyl bromide and not in creating alkyl iodide from alcohol and ...
1
vote
1answer
77 views

Which are the radicals containing phosphorus in ATP?

The ATP molecule contains 3 $\ce P$ atoms linked through esteric bonds. The IUPAC name of triphosphate adenosine is "[[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-...