Questions tagged [esters]
For questions about the synthesis, properties, and reactions of ester compounds, both organic and inorganic.
137
questions
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1answer
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Does Fischer esterification occur when mixing alcoholic drinks with lemon juice?
I would assume it does happen because the ethanol in the drink would be in an acidic environment because of the lemon juice and would react with the citric acid in it. But the thing is, how come we ...
0
votes
1answer
48 views
What is the role of magnesium nitride in ammosamide B synthesis?
The following is a snapshot of the synthesis of ammosamide B from Synarchive:
In the final step $\ce{Mg3N2}$ is used to convert esters to amides or amides to amines. What is the mechanism of this ...
0
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0answers
42 views
Major product in the reaction of alcohol with unsymmetrical acid anhydride
When alcohol reacts with symmetrical acid anhydride to form ester. We have the following reaction,
But if the acid anhydride used is unsymmetrical how can we identify the major product? For example ...
0
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1answer
60 views
Why is ester more reactive to nucleophile than carboxylic acids?
I was given just this statement at face value, but I think it refers to nucleophilic reactions where the carbonyl is the electrophile.
From what I understand, the $\ce{-OR}$ in ester is more electron ...
1
vote
1answer
170 views
What is the product of the reaction between alcohol and acetyl chloride in presence of pyridine?
What happens when butan-2-ol reacts(under heat) with $\ce{CH3COCl}$ in the presence of pyridine? Does it form $\ce{CH3COOCH(CH3)CH2CH3}$? I got the ester mentioned but the solution says it gives an ...
0
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0answers
39 views
Reacting Grignard reagent with esters to excusively produce a ketone [duplicate]
Adding 2 moles of grignard reagent to an ester, gives out 2 alcohols. But, if 1 mole of grignard reagent is added, will the reaction exclusively produce a ketone? How to prepare a ketone in a reaction ...
1
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0answers
59 views
Why doesn't the acetic anhydride moeity react with the nucleophilic carbonyl oxygen of salicylic acid?
I know that salicylic acid with acetic anhydride under acidic conditions gives acetylsalicylic acid (aspirin). But my question is, why is it that post the protonation of carbonyl oxygen of acetic ...
3
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0answers
25 views
Preferred radical attack on a polyester
My question concerns the relative stability of a radical next to an ester oxygen compared to a radical next to an ester carbonyl carbon.
The stabilizing effect of the electron pairs of ether oxygen ...
3
votes
1answer
69 views
Synthesis of diethyloxalate from ethene
Outline the steps involved in the following transformation: $\ce{C2H4}$ to $\ce{(COOC2H5)2}$ (diethyl oxalate).
I am familiar with the transformation of $\ce{C2H4}$ to ethyl acetate $\ce{CH3COOC2H5}$ ...
3
votes
1answer
117 views
Can the RDS be different in different direction in a multi-step reversible reaction?
The following mechanism is given in Peter Sykes when they are "talking about de-esterification" of an ester where the alcohol part is bulky-
Here the second step is given as RDS. According ...
6
votes
1answer
265 views
On the use of hexane in the organic reduction by DIBAL-H
In some variations of the organic reduction by DIBAL-H, I've seen hexane used, as in this equation from this website;
I've looked it up, but I haven't seen any explanation for why hexane's used there....
2
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0answers
42 views
Comparison: Esterification with acyl chloride and alcohol vs Fischer esterification
I would like to know if there are more than mentioned pros and cons with the different methods in making an ester, and also ways to maximize product yield (comparing the two).
Fischer- Pros: cheap, ...
0
votes
1answer
179 views
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 ...
1
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0answers
366 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 ...
1
vote
0answers
39 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
votes
1answer
568 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
votes
1answer
148 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 ...
10
votes
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)?
...
3
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0answers
75 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
votes
1answer
461 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 ...
1
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1answer
1k 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 ...
5
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0answers
122 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-...
0
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0answers
226 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 ...
3
votes
1answer
65 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
votes
0answers
249 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 ...
-1
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1answer
60 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 ...
0
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0answers
57 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 ...
6
votes
1answer
285 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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0answers
26 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 ...
0
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0answers
229 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 ...
1
vote
1answer
612 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?
1
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0answers
82 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, ...
0
votes
0answers
403 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
votes
1answer
403 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
64 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 ...
0
votes
2answers
296 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 ...
1
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1answer
4k 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
5k 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 ...
1
vote
0answers
56 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
votes
0answers
67 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
vote
1answer
885 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 ...
-1
votes
1answer
108 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, ...
0
votes
0answers
50 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
votes
1answer
172 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
votes
1answer
169 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
votes
2answers
315 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 ...
0
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0answers
183 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?
1
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1answer
105 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-...
-3
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1answer
3k 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 ...