Questions tagged [esters]

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

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133 views

What will be produced when sucrose and potassium bitartrate react with each other?

What would happen if sugar and cream of tartar react with each other? Would it create an ester? $$\ce{KC4H5O6 + C12H22O11 -> KC16H21O14 + 3H2O}$$ Is this correct? If not, why?
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Reactions involving carboxylic acids

The following question was given in FIITJEE study material: I guess (i) step is de-esterification, which gives the compound of option (A). In next step, I wouldn't expect it to decarboxylate, ...
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Specific reduction of certain functional groups

Consider the compound $\ce{Alkyl-(4 oxocyclopent-2-ene)carboxylate (A)}$. Now consider the operations: $\ce{1. (A) + (i)BH3/THF (ii) H+}$ $\ce{2. (A) + H2/Pt}$ $\ce{3. (A) + H2/Pd-C}$...
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Pyridinium ion in inositol nicotinate

I have read about inositol nicotinate which is used as a medication for deficiency in vitamin B-3. I think that if acetic acid was applied to this medication it would form pyridinium ion and acetate ...
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42 views

Preparation of compounds using acetoacetic ester synthesis

I've been given the following exercise in organic chemistry, and I'm at a complete loss. The text book doesn't cover the subject at all. I have some knowledge of melonic ester synthesis. As an ...
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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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31 views

Reduction of ester / eneone in presence of epoxide

I want to reduce an ester and an eneone in the presence of a terminal epoxide. I read on here @jerepierre did an ester in the presence of an epoxide with DIBAL. I know the DIBAL works for my ester, ...
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112 views

Why can't carboxylic acid + NaH + tert-butyl bromide react to create an ester?

So, the picture I showed above asks for which reagents can form the ester product. I was wondering why D can't form it? I was thinking that first, the $\ce{NaH}$ would react with the carboxylic acid ...
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Does boric acid catalyze esterifications with isopropanol?

I am going to synthetise isopropyl salicylate. From what I have read on phillysim.org (pdf) the formation of ethyl salicylate can be catalyzed by boric acid. I could use sulfuric acid but it would be ...
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165 views

Mechanism of Acid Hydrolysis

I wanted to ask a question about acid catalysed hydrolysis. I learnt in an introductory course to Physical Organic Chemistry that there are different ways that an ester can be hydrolysed acidically: ...
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2answers
123 views

Does this reaction require catalyst/solvent?

Planning on synthesising 2-formylphenyl benzoate by reacting benzoyl chloride with salicylaldehyde. Since both Benzoyl chloride and salicylaldehyde is liquid, will it require a catalyst/ solvent? Or ...
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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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1answer
859 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 ...
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1answer
1k views

Rate of hydrolysis of ester in presence of an acidic medium

Does the rate of hydrolysis of an ester depend on the concentration of both the ester and the acid, or only the ester? I was told by my professor that hydrolysis of ester follows a pseudo-first order ...
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25 views

Using Wilkinson's Catalyst to reduce esters?

I was solving some questions on alcohols when I came upon a question in which it was asked that whether esters can be reduced using hydrogen in the prescence of wilkinson's catalyst. Now I know that ...
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Final product when sp2 oxygen of acid is O18 in fischer esterification

In the question above, i was curious about option 3. If the carbonyl oxygen is O18, shouldn't half of the product we obtain contain O18 on the carbonyl since we have two possible leaving groups with ...
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334 views

Thermal decomposition of ester [closed]

I have a clear liquid with a faint sweet smell. I know this compound contains an aromatic group and an ester. However, something strange happens when I try to distill it - it forms a white solid. I ...
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256 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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1answer
80 views

Ester of glycerol and glyceric acid

What is the ester of glycerol ($\ce{C3H8O3}$) and glyceric acid ($\ce{C3H6O4}$)? I couldn't find any information about it online, so is this reaction even possible? I'm not sure what would happen, ...
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42 views

Comparing acidity in 3,4-dihydroxyfuran-2(5H)-one and 2,3-dihydroxycyclopent-2-en-1-one

I have two compounds with two hydrogens namely (a),(b),(c) and (d). I have to compare the acidity of the following hydrogens. My approach: I removed the hydrogen atoms one by one and compared the ...
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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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1answer
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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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360 views

Hybridization of carbon atoms present in the smallest ester?

I found this question in the Resonance DLPD Organic Chemistry book on Page 55: What is the hybridization of carbon atoms present in the smallest ester? The smallest ester as far as I know is ...
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109 views

Why doesn't self condensation occur in acetoacetic ester synthesis

So, I came across a quite versatile method to synthesize aldehydes and ketones, its called the Acetoacetic ester synthesis. Suppose I need some 2-pentanone. So to synthesize it via this method I can ...
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1answer
182 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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Hydrolysis under basic medium

The first compound is said to be hydrolyzed more easily than the 2nd compound below under Alkaline medium . How is this possible ? I thought due to resonance, -NO2 acquires negative charge which ...
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246 views

Are there amide versions of lactides and lactones?

In my book, I read that Lactides and lactones are cyclic esters which contain two and one ester group in them, respectively. They are formed when $\alpha$-hydroxy; and $\gamma$- or $\delta$- hydroxy ...
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Differentiating esters from glycosidic linkages

What exactly is the difference between an ester linkage and a glycosidic linkage? I know both release a molecule of water, but what is the difference? Is it simply which types of monomers are involved ...
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103 views

Why mixture turns brown upon heating, during esterification with H2SO4?

In the lab I was synthesising an ester with sulphuric acid as a catalyst. However the mixture turned brown and my teacher said I had burnt the acid, but what does this actually mean?
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67 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-...
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Vinyl vs Acryl IUPAC Usage [closed]

I have read that the word Vinyl and Acryl, both refer to the same group. The difference is that Acryl is used for naming when the functional group attached itself contains a carbon atom while Vinyl ...
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56 views

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
126 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
276 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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2answers
223 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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1answer
363 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
124 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 ...
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835 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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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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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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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
397 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 ...
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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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528 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
750 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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61 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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322 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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142 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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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 ...
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1answer
836 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 ...