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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 ...
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 ...
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. ...
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 ...
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 ...
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 ...
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)?
...
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 ...
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 ...
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 ...
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-...
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 ...
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 ...
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 ...
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 ...
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 ...
Consider the compound $\ce{Alkyl-(4 oxocyclopent-2-ene)carboxylate (A)}$. For example consider-
Now consider the operations:
$\ce{1. (A) + (i)BH3/THF (ii) H+}$
$\ce{2. (A) + H2/Pt}$
...
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 ...
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 ...
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?
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, ...
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 ...
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:
...
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 ...
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 ...
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 ...
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 ...
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 ...
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 ...
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 ...
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, ...
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 ...
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 ...
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 ...
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 ...
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 ...
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?
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-...
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 ...
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, ...
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 ...
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 ...
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 ...
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 ...
In a six membered lactone with carbaldehyde in beta position, which oxygen gets protonated first? the lactone or the aldehyde?
(Using concentrated HCl)
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.
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 ...
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 ...
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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