Questions tagged [esters]

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

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Formation of (Gamma) Methylparaconic acid

I came across this question recently, I tried to devise a mechanism but I'm struck here, My try - Moreover, I think my mechanism is somewhat inefficient because of formation of some byproducts, ...
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1answer
217 views

Acid hydrolysis of ethyl acetate [closed]

For my chemistry IA, I am planning to determine the reaction rate and activation energy of the acid catalyzed hydrolysis of ethyl acetate. Where can I find literature values for these, so i can ...
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2answers
549 views

Fischer-Speier Esterification: Sulfuric acid removal following creation of ester

I'm a beginning chemistry student, and I was wondering what the best way of removing sulfuric acid was following the creation of benzyl acetate. So far, I have that benzyl alcohol and glacial acetic ...
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1answer
247 views

Mechanism for the intra-molecular exchange of an ester and a nitrile group

When the isolated product 4 is treated with sodium ethoxide in ethanol it rearranges to 5 as shown: My TA says that you need to start with a reverse Claisen at the ketone but I am not quite sure ...
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2answers
321 views

Can the alkyl-oxygen bond in lactones be cleaved in an SN2 reaction?

I understand that nucleophiles typically attack the electrophilic carbonyl carbon of the lactone and open the ring through a nucleophilic acyl substitution. Has there ever been the case where the ...
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176 views

What is first protonated aldehyde or lactone?

In a six membered lactone with carbaldehyde in beta position, which oxygen gets protonated first? the lactone or the aldehyde? (Using concentrated HCl)
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49 views

Confused about enolate chemistry [closed]

I'm not so sure how this mechanism is supposed to go. Could anyone provide some pointers? The answer is supposed to be: In particular, I'm confused about how to break up the two esters.
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121 views

Can an enol acetate be formed through Fischer esterification?

Since acetone is converted into its enol form under acidic conditions, could it participate in Fischer esterification to form an enol acetate? For example, would refluxing acetone, p-TSA, and acetic ...
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1answer
573 views

Which mechanism is not seen during hydrolysis of esters? [closed]

Which mechanism is not seen during the hydrolysis of esters? AAC2 BAC2 AAL2 BAL2 AAC1 I know that hydrolysis of ester is pseudo-first order reaction but I found this question where there are ...
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60 views

How do sulphate esters compare to phosphate esters? [closed]

In particular, the energy released from hydrolysis of the -S-O-S- bonds and how stable are they in aqueous solution compared to phosphate esters?
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1answer
633 views

Deciding more electrophilic centre between ester and thioester for SN type reaction

My question: (though it won't alter the product) Which carbon is attacked first, the one adjacent to sulphur or the one adjacent to oxygen? The solution says that the carbon adjacent to sulphur is ...
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1answer
1k views

Base used in Claisen Condensation

Here's what I read about which base to use in Claisen Condensation reaction (two esters or ester + carbonyl compound forming a beta keto-ester or beta-diketone): The base used must not interfere ...
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1answer
2k views

What type of polyester is most commonly used for clothing?

Many polymers have the name of the monomer in their names, e.g. polyethylene, polyvinyl chloride, polypropylene, polystyrene etc. But the ester in polyester refers to a group of chemicals (having an ...
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1answer
81 views

Residual catalyst leaching from PETE

I am trying to look for healthy options for 5 gallon water jugs. The problem is all the plastic 5 gallon water jugs on the market are either made of #1 PETE (BPA free) or #7 (which contains BPA). It ...
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1answer
450 views

Can citric acid create a polyester?

Citric acid has both alcohol and carboxylic acid groups, so could it "esterify" with the other citric acid molecules in solution? I notice that it is a tertiary alcohol. I don't suppose that would ...
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1answer
267 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 ...
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1answer
206 views

Does the slippery feeling of bases always appear at certain pH?

My guess is that the saponification reaction is only dependent on the concentration of $OH^{-1}$ ions and of course the coposition and concentration of fats. I also guess that the fat part of the ...
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1answer
2k views

Ethyl Acetate: how to store

I'm a 3D printing hobbyist and a few months ago I bought some Ethyl Acetate after learning online that it might have a similar effect on PLA as acetone has on ABS. From the tests I made, I was either ...
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1answer
14k views

Sulphuric Acid in Esterification Reaction

Why is it that adding the sulphuric acid slowly to a solution of alcohol and carboxylic acid (making an ester) will increase the yield of the product? It seems that not only does the rate at which it ...
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1k views

Esterification Colour Change

I was in a chemistry lecture about the upcoming laboratory practical on esters that I would have to take. My lecturer had mentioned that we ought not worry about "the pink coloration that will occur" ...
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1answer
525 views

Hydrolysis of an ester

An organic compound X of formula $\ce{C5H10O2}$ forms two compounds when boiled in aqueous sodium hydroxide solution. One of these compounds forms a ketone when treated with acidified potassium ...
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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 ...
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822 views

Purification of polar NHS esters

What are the options that I might be missing for the purification of a molecule with the following characteristic: Contains an activated ester that reacts with water (NHS) Reacts readily with ...
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2k views

Esterification with tertiary alcohol

I saw a different mechanism for esterification of tertiary alcohol in a book. They say that first the $\ce{OH}$ is protonated and it leaves to form the tertiary carbocation. Then the oxygen's lone ...
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740 views

Saponification value of a fat/oil

The saponification value of a fat was determined by adding $\pu{9.0 g}$ of the fat to flask containing $\pu{50.0 cm3}$ of $\pu{1.00 M}$ ethanolic potassium hydroxide. The remaining solution was ...
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1answer
4k views

Protonation of Carbonyl oxygen in Fischer Esterification

In the Fischer Esterification, why is it the acid's carbonyl oxygen getting protonated and not the hydroxyl oxygen? This protonation occurs in Step 1 of the mechanism below. I read in some textbooks ...
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selective hydrolysis problem

I am aware that esters can be selectively hydrolysed depending on the type of alkyl group present e.g. Me ester vs t-butyl ester, the latter is reactive to acidic conditions and not basic because of ...
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634 views

Are esters and amides soluble in cold acids/bases? [closed]

The main problem I have is that we say amines are soluble in acids because they are bases, and they will thus react with acids. But if A reacts with B, how does that imply A is soluble in B? Yes, ...
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1answer
10k views

Is the reaction between a carboxylic acid and alcohol endothermic?

I would say that it is endothermic, and then by increasing the temperature, one could get more product, disturbing the equilibrium. Is this true, though? During an esterification, some bonds are ...
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305 views

Hoffmann's rule in ester pyrolysis

Why is the Hoffmann's product the major product in the pyrolysis of an ester to form a carboxylic acid and alkene?
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2answers
2k views

Which side of the C-O-C bond breaks in esters during hydrolysis in basic medium?

When an ester undergoes hydrolysis which side of the $\ce{C-O-C}$ breaks for instance in the following example: I believe the first is correct but is it a rule that the salt of a carboxylic acid is ...
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1answer
1k views

Why do esters have to be distilled during purification?

I am currently designing a lab experiment for a school project in which I am to determine the effect of catalyst concentration ($\ce{H2SO4}$) on the rate of reaction between methanoic (formic) acid ...
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1answer
2k views

Direct conversion of amides to esters

Rarely does the literature describe the synthesis of esters from amides. I understand that amides are a relatively unreactive functional group but they can easily be hydrolysed to give carboxylic ...
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760 views

Retrosynthesis of a lactone

We have been asked to do a retrosynthesis of (6⁠S)-6-[(2⁠S)-2-hydroxy-4-phenylbutyl]oxan-2-one J from 3-phenylpropan-1-ol K: My first instinct would be to do a functional group interconversion of the ...
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1answer
3k views

Finding the mystery ester strucuture using NMR

I have an unknown ester with the chemical formula $\ce{C9H10O2}$ that is used as a flavoring agent in candies. It exhibits the following H-NMR and C-NMR (Attached file: unknown ester NMR) Based on ...
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3k views

Will oxalic acid react with ethanol?

Will oxalic acid, in a saturated solution in ethanol, be able to undergo an esterification reaction with the ethanol? This is assuming no acidifying agents (or anything else, for that matter) are ...
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1answer
282 views

Why is the ester bond stable under Reformatsky reaction conditions?

The following reaction is a Reformatsky reaction. Why is the ester bond not attacked in the last step? Couldn’t $\ce{OR3}$ be replaced by $\ce{OH}$ or $\ce{O(molecule)}$?
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529 views

Naming of ester alkoxide

I'm trying to name the following compound: I believe the carboxyl group has priority and should make up the parent name. I'm not sure how to name the alcohol derivative portion. My first thought is: ...
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1answer
224 views

What is the major hydrolysis product of 2,2,2-trifluoroethyl 2-acetamido-3-phenylprop-2-enoate?

In the below reaction we have to find the major hydrolysis product of 2,2,2-trifluoroethyl 2-acetamido-3-phenylprop-2-enoate. My doubt is why the major hydrolysis is not when $\ce{OH-}$ at the $\ce{C}...
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1answer
6k views

Will glycerol and citric acid react? If yes, under what conditions?

I would like to know whether the reaction will take place if glycerol and citric acid are merged? In particular, what will happen if both substances are heated up to high temperature (+100°C)?
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1answer
421 views

Naming alkyl groups of an ester

$\hspace{6.4cm}$ I would like to know how to name the alkyl groups connected to the above molecule. For example, would the far left alkyl group be considered a methyl ester group? Would the alkyl ...
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1answer
284 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 ...
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1answer
1k views

What determines the boiling point of esters of the same number of carbon atoms but different structural formula?

The boiling point of esters increases with molecular weight (and therefore, number of carbon atoms) because of more dispersion forces. But if you had two different esters with the same number of ...
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962 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 ...
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1answer
707 views

Is Nitroglycerine a Nitro Compound or an Ester?

I looked up nitroglycerine in a science dictionary (Oxford Dictionary of Science, 2003), and it explicitly mentions that nitroglycerine is an ester and not a nitro compound. However my teacher told ...
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617 views

What is the name of this ester?

Can you tell me the name of this ester? It is two $\ce{C8}$ fatty acids ester-linked with a molecule of 1,3-butanediol in the middle. I would be tempted to say (R)-butanediol-1,3-diyl dihexanoate, but ...
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104 views

Organic polyether with carboxyl moiety reacting with aldehyde, following reaction with sulfuric acid

I want to react the following molecule with conc. sulfuric acid in the presence of methanol at room temperature: If I am right, this would make a methyl ester to be formed on the carboxyl. The aim ...
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275 views

Formation of Lactone from 5-amino-decanoic acid?

As expressed in the title, I am trying to figure out how to form a lactone from 5-amino-decanoic acid. The thing that comes to my mind as a start is the attachment of the amino group ($\ce{NH2}$) to ...
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1answer
2k views

In a condensation reaction, which of the reactants loses their OH group?

You have Propanoic Acid ($\ce{CH3CH2CO-O-H}$) so an $\ce{OH}$ on the end You have Ethanol ($\ce{CH3CH2-OH}$) so an $\ce{OH}$ on the end When you combine the two for a condensation reaction you have ...
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2answers
1k views

Will sulphuric acid react with water produced in an esterification process?

Sulphuric acid acts as a catalyst to catalyze the reactions of alcohol and carboxylic acid to form ester. Alcohol reacts with carboxylic acid to produce ester and water. However, as sulphuric acid ...