Questions tagged [esters]
For questions about the synthesis, properties, and reactions of ester compounds, both organic and inorganic.
157 questions
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Retrosynthesis of saffron pyranone from acetone and acetic acid
I have an assignment on the retrosynthesis of a lactone (4,4,6‐trimethyloxan‐2‐one) from acetone and acetic acid as precursors:
And I came up with the following scheme:
I initially went for a 1,4-...
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Why does LiBH4 reduce esters while NaBH4 does not?
Clayden (pg 531) mentions that LiBH4 reduces esters, while NaBH4 does so, but at a very slow rate. Why?
Ref.: "Organic Chemistry" Second edition Jonathan Clayden Nick Greeves Stuart Warren ...
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Can complex polyols like cellulose be acetylated with manganese acetate?
The paper by Gowda and Lokanatha Rai [1] describes the usage of manganese(III) acetate for the acetylation of primary, secondary and tertiary alcohols.
As far as I know, cellulose acetate uses acetic ...
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In the Fischer Esterification mechanism, what happens to the second alcohol group used catalytically for proton removal?
In the Fischer Esterification Mechanism, the alcohol group is used twice catalytically as I have shown with $A_1$ in the picture. While the first $A_1$ gets converted back to $A_1$, I'm not sure how ...
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Why does the H-NMR of propyl butanoate show up as 4 signals when there are 6 distinct hydrogens in the structure?
I am trying to learn NMR, but I cannot properly explain this. I understand that I can draw a resulting resonance structure, however, I do not see a plane of symmetry that would make the hydrogens on ...
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Effect of heating alkyd enamel paint during drying/curing & maximum acceptable temperature
I will be painting some boat paddles with Solignum Marine Paint (Alkyd enamel) (compliant with new VOC regulations) for a relative. The label lists that it contains mineral spirits and Stoddard ...
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Will electrolysis hydrolyze esters?
I'm doing some electroplating. Now, I want to know which components of my electroplating solution are being expended as I go about electroplating. I needed a wetting agent/surfactant & decided to ...
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TsOH and 5% NaHCO3 Interaction: Unexpected Dark Green Color
Here's the brief:
I synthesized alkyl gallates (ethyl gallate, butyl gallate, and amyl gallate) using Fischer esterification.
I used TsOH instead of concentrated H2SO4 as the catalyst.
After ...
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FTIR Spectra: Did I synthesize ethyl gallate from gallic acid?
I successfully synthesized ethyl gallate from gallic acid and ethanol (of course there are other reagents too, like DCC and Pyridine). Before conducting FTIR analysis, I performed column ...
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Removing DCC and its by-product from Steglich Esterfication
In my small research, I want to synthesize 3 alkyl gallates (ethyl gallate, butyl gallate, and hexyl gallate), and here's my overall reaction using Steglich esterification):
However, from reading ...
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How to name an ester with an alkene or alkyne as the R group? [closed]
More specifically, see the image down below:
Would it be pentan-2-ene-3-yl propanoate? Do you just add the 2-ene to specify the position of the double bond?
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Steglich Esterification in Alkyl Gallates
Based on my research (reading some articles), some alkyl gallate syntheses used Steglich esterification instead of the usual esterification (Fischer esterification). The reason why Steglich ...
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Why doesn't the reaction between molecule "B" and diethyl oxalate yield a diester?
Problem
Answer
Question
Why isn't this structure the answer for the second reaction?
From my understanding, the resonant structure (B) with the full negative charge on the oxygen is the most stable ...
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Why sulfuric acid is used in esterification of alcohol and carboxylic acid anhydride?
I have a question regarding why sulfuric acid is used in esterification of alcohol and carboxylic acid anhydride.
I know that in case of esterification of alcohol and carboxylic acid, sulfuric acid ...
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Esterification of Serine
I came across this question above, and I'm unsure about the reaction with H+(aq). The answer is that the amine group is protonated as usual, but I am not sure why H+(aq) doesn't catalyse ...
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Reaction of methyl triphenylbenzoate with concentrated sulphuric acid
In the following reaction, compound Q is obtained from compound P via an ionic intermediate.
What is the degree of unsaturation of Q?
This question was asked in JEE ADV 2020
I thought that the ester ...
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Process of Arecoline Extraction
What would be the proper procedure to extract and isolate arecoline, an alkaloid ester, from the seed of the Areca nut, and is it possible to mass produce arecoline using that method?
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Will ethyl 2-amino-1H-imidazole-5-carboxylate undergo ester aminlysos with the primary amines of bPEI efficiently in methanol?
I was about to set up the following reaction, but before I do, I wanted to see if anyone has some suggestions or thinks this will not work:
24mmol Nboc protected ethyl 2-amino-1H-imidazole-5-...
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What kind of isomers are ethyl butanoate and propyl propanoate?
Are ethyl butanoate (1) and propyl propanoate (2) metamers or functional group isomers? My book claims they are metamers, but here one group is $\ce{-CO-OR}$ and another is $\ce{-CO-OR'}$ where $\ce{R}...
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Formation of ester during preparation of Fluorescein
I was going through PYQ of JEE where, I encountered the following question:
Q) Phthalic acid reacts with resorcinol in the presence of concentrated $H_2SO_4 $ to give :
In the solution provided I ...
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Can two 1st order reactants in an overall 2nd order reaction have different rates?
I've recently done a saponification reaction of ethyl acetate with sodium hydroxide and used the initial rates method to find the order of reaction. (I change the concentration of one reactant and ...
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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 ...
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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 ...
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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 ...
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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 ...
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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 ...
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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 ...
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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 ...
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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 ...
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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 $\ce{CH3COOC2H5}$ ...
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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 ...
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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....
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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, ...
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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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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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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. ...
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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 ...
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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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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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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 ...
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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 ...
user96046
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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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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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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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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 ...
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The IUPAC name of a multifunctional carboxylic acid compound [duplicate]
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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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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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 ...
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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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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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