Questions tagged [esters]
For questions about the synthesis, properties, and reactions of ester compounds, both organic and inorganic.
126
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Succinic anhydride esterification won't go forward
I'm trying to react succinic anhydride with a decyl alcohol to produce mono-decyl succinate. Literature and Google searches suggest that the monoesterification should proceed without catalyst. However ...
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173 views
While treating 4-aminophenol with acetic anhydride why does the reaction stop at Paracetamol and does not undergo esterification with acetic acid?
This needs a little background so I will be showing you a question from one of my Organic Chemistry problem books:-
Now, the book shows the answer as Option (c) which is Paracetamol.
I tried to work ...
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0answers
34 views
Red Compound from Glycine and Glycerol?
I got an unexpected reaction which I'm trying to explain to myself:
I mixed 10 parts glycerol with 1 part glycine at ~90C and to my great surprise the mixture turned from transparent to a tint of red. ...
3
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1answer
266 views
Why do amides require much harsher conditions for hydrolysis than esters?
Amides require much harsher conditions to hydrolyse than its ester homologue. An explanation given is that the orbitals holding the lone pair on the nitrogen overlaps with the C=O π-bond to give ...
3
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1answer
117 views
Nitration vs Nitrolysis
I am interested in nitrating an aromatic ester in a solution of dichloromethane. I found the following paper that describes creating a nitric acid solution in dichloromethane using KNO3 and sulfuric ...
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83 views
How come the reaction with glycerol and formic acid to form glycerol formates is not as probable as with acetic acid to yield glycerol acetates
I come across various literature when searching for the esterification reaction between glycerol and acetic acid to yield three glycerol acetates as in the image below. Essentially, each OH- group of ...
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2answers
1k views
What is the name origin of ester?
Ester is quite a random nomenclature for a compound derived from a parent acid and parent alcohol.
Is there any reasoning behind using the word 'ester' to name such compound (for memorising purpose)?
...
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39 views
How can I solubilize fragrance oil into polyvinyl acetate/clear glue?
I'm a high school student who makes slime for fun, using polyvinyl acetate (PVA) glue and borax as my main ingredients.
Earlier, I had the idea of adding fragrance oils to clear glue. However, because ...
12
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1answer
434 views
Unusual hydrolysis of methyl 2,4,6‐trimethylbenzoate
Problem 223 from Conceptual Problems in Organic Chemsitry by Singh [1, p. 367]:
The given answer is b and I don't get why.
Usual ester hydrolysis would've given a.
I somehow managed to know that the ...
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1answer
562 views
What happens on heating an ester?
While solving a few questions a came across a problem which asked me what would happen when sec-butyl ethanoate was heated.
I had never read about this reaction before and took to researching through ...
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114 views
Interaction of trifluoroacetates with acetylcholinesterase
There exists a substance called TMTFA, or 3-(N,N,N-Trimethylammonio)-2,2,2-trifluoroacetophenone. It is known for being able to inhibit acetylcholinesterase at femtomolar concentrations. The TMTFA-...
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150 views
Why ester reaction with one equivalent of Grignard reagent produces ketone?
While reviewing my old materials before an external exam which also covers these topic I stopped by one of the reactions - Grignard w/esters:
From what I remember, and what my notes are also telling ...
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1answer
55 views
Grignard alkoxide intermediate as starting material for ether or ester synthesis
I'm having a Grignard reaction between a ketone or aldehyde with RMgX in mind.
The average workup uses water to hydrolize the intermediate alkoxide. But could this intermediate be used without ...
5
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0answers
158 views
The IUPAC name of a multifunctional carboxylic acid compound
What is more preferred name when ester is present as junior functional group bis-carboxylic acid? (refer the image attached):
to count carbon of ester and consider two branches on it (one oxo and ...
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1answer
44 views
Is it necessary that hydrolysis of ester will only take place in excess of water?
I was given a question on chemical kinetics in which the statement was given-
"The Concentration of water in hydrolysis of ester does not change to much extent"
I marked the statement to be false ...
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53 views
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, instead ...
5
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1answer
230 views
Specific reduction of certain functional groups
Consider the compound $\ce{Alkyl-(4 oxocyclopent-2-ene)carboxylate (A)}$. For example consider-
Now consider the operations:
$\ce{1. (A) + (i)BH3/THF (ii) H+}$
$\ce{2. (A) + H2/Pt}$
...
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24 views
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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174 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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1answer
518 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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0answers
59 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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0answers
319 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 ...
4
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1answer
296 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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0answers
54 views
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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2answers
227 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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1answer
3k 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 ...
2
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1answer
3k 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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0answers
44 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 ...
2
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0answers
56 views
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 ...
1
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1answer
737 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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1answer
98 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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0answers
46 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 ...
0
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1answer
1k 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 ...
0
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1answer
144 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 ...
2
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1answer
139 views
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 ...
4
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2answers
299 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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0answers
149 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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1answer
92 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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1answer
2k views
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 ...
0
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1answer
60 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, ...
0
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1answer
194 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
448 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 ...
3
votes
1answer
202 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 ...
4
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2answers
299 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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0answers
162 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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0answers
44 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.
2
votes
0answers
106 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 ...
0
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1answer
530 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 ...
2
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0answers
57 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?
4
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1answer
530 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 ...
