Questions tagged [esters]

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

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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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55 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 ...
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23 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 ...
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65 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 $\ce{CH3COOC2H5}$ ...
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109 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 ...
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219 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....
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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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130 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 ...
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330 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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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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454 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 ...
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134 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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124 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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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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61 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 ...
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457 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
887 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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120 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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200 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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62 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 ...
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210 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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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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55 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 ...
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275 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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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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219 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
585 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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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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385 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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357 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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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
290 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 ...
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4k 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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54 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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836 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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104 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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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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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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165 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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163 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 ...
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312 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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174 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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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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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 ...
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66 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
205 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
489 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 ...