Questions tagged [esters]

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

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Routes of formation of esters with highest yield

Esters can be formed in two ways according to the syllabus I'm following: (1) Mixing an alcohol with a carboxylic acid in the presence of sulfuric acid; and (2) Mixing an alcohol with an acid ...
8
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1answer
276 views

How can rotamers of alpha-keto esters be named to distinguish between different geometries?

When talking about free rotation it is often helpful to determine about which geometric arrangement one is referring to. For example in the case of butane we talk about several eclipsed or staggered ...
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1answer
113 views

How would I go about making an ethyl ester from vegetable oil?

I'm teaching myself how to make lotion and a lot of lotions contain esters like isopropyl myristate or isopropyl palmitate. I'd like to make an ethyl ester from a popular skin-care oil (olive, apricot ...
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1answer
12k views

What is the difference between the esterification and transesterification?

What is the difference between an esterification and a transesterification. Esterification objective is the formation of an ester by reacting an alcohol and a carboxylic acid. I am more concerned ...
6
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1answer
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Protonation of ketone and ester

If there is a ketone and ester functional group in the same compound and I want to protonate with $\ce{HCl}$, which one will protonate first? Is it the carbonyl group in the ketone or the carbonyl ...
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1answer
753 views

Acid catalyzed hydrolysis of ester

During acid catalyzed hydrolysis of ester why does the carbonyl oxygen attack the $\ce{H^{+}}$ ? Why doesn't the alkoxy oxygen which is more electron rich and less electronegative not attack the $\ce{...
8
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1answer
5k views

Is it possible to oxidize ether to ester?

Is it possible to synthesize an ester from an ether in a single step? For example if I had an ether $\ce{(R-CH2-OR')}$, can I oxidize it so it will be an ester $\ce{(R-CO-OR')}$.
11
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1answer
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Mechanism for formation of amide by reaction of amine with ester

This is the mechanism given in my lecture handout: I have a problem with the third species along. Surely the negatively charged oxygen would protonate before the other oxygen would. Also, why does ...
7
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2answers
617 views

Why can you not make a compound with a quaternary alpha carbon using malonic ester?

So my textbook tells me that using a malonic ester to make a quaternary alpha carbon is impossible (I get that this might be hyperbole). However, it doesn't explain why and I don't understand why. ...
6
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1answer
234 views

Electrophilicities of carboxylic acid derivatives

I would like to ask about the rate of hydrolysis for 4-hydroxyphenyl acetate (A), N-(4-hydroxyphenyl)acetamide (B), 4-hydroxyphenyl chloroacetate (C), and methyl 4-hydroxybenzoate (D). I know that ...
8
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1answer
346 views

No chlorate esters? Why?

Why are there no chlorate esters? Or are they just undocumented or too unstable? I've seen perchlorate esters, but google "chlorate esters" and only perchlorate esters come up.
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2answers
37k views

Why do esters actually smell?

We all know the very famous esterification reaction, where a carboxylic acid and an alcohol react to give an ester and water. But why do they actually smell? What is the reason behind its aromatic ...
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1answer
674 views

Differences between alkyl halides and alkyl tosylates

What are the functional differences between alkyl halides alkyl tosylates? Both halides and tosylates are good leaving groups, yes. But is there chemistry that one will do and the other won't? Etc.? I'...
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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 ...
4
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1answer
337 views

Formation of methyl esters

Can't we perform Fischer esterification using methanol to make a methyl ester from a carboxylic acid? If so, why might we use diazomethane? Would the release of nitrogen gas confer an entropic ...
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Reaction of Grignard reagents with esters

Suppose I have a phenyl Grignard and methyl benzoate. If I react the two, can I expect benzophenone and a triphenylmethoxide ion as my products? I ask because I know that Grignards react with ...
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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 ...
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2answers
1k views

Oxidation numbers for esters?

How do I find the oxidation numbers for ester? My main issue is about finding the numbers for ester groups. /O\ - || R -- O -- C -- R' - I ...
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1answer
2k views

How many grams of each substance will be present at equilibrium in the reaction of ethanol and ethanoic acid?

In the following reaction, $K_c=4.0$: $$\ce{C2H5OH + CH3COOH <=> CH3COOC2H5 + H2O}$$ A reaction is allowed to occur in a mixture of $\pu{17.2 g}$ $\ce{C2H5OH}$, $\pu{23.8 g}$ $\ce{CH3COOH}...
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Resonance stability: ester vs. thioester

My problem set solution cites: "Although sulfur is less electronegative than oxygen, overlap is a more important consideration. Sulfur is a member of the third period. As a consequence, a ...
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4answers
2k views

During the development of aspartame, why was the methyl ester chosen?

One frequent argument against the safety of the synthetic sweetener aspartame is that it can be hydrolyzed, with one of the hydrolysis products being methanol, which is known to be toxic. Of course, ...

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