Questions tagged [esters]

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

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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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1answer
50 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 ...
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49 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 ...
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140 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 ...
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213 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 ...
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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 ...
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65 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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26 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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1answer
72 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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291 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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1answer
127 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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320 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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222 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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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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439 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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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. ...
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674 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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1answer
73 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 ...
3
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1answer
154 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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1answer
681 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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426 views

Naming alkyl groups of an ester

$\hspace{6.4cm}$ I would like to know how to name the alkyl groups connected to the above molecule. For example, would the far left alkyl group be considered a methyl ester group? Would the alkyl ...
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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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Which side of the C-O-C bond breaks in esters during hydrolysis in basic medium?

When an ester undergoes hydrolysis which side of the $\ce{C-O-C}$ breaks for instance in the following example: I believe the first is correct but is it a rule that the salt of a carboxylic acid is ...
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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 ...
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1answer
2k views

Direct conversion of amides to esters

Rarely does the literature describe the synthesis of esters from amides. I understand that amides are a relatively unreactive functional group but they can easily be hydrolysed to give carboxylic ...
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473 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
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 ...
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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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246 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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Will oxalic acid react with ethanol?

Will oxalic acid, in a saturated solution in ethanol, be able to undergo an esterification reaction with the ethanol? This is assuming no acidifying agents (or anything else, for that matter) are ...
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2answers
170 views

How does this brominated intermediate lose its methyl group?

The problem is such: So far my working has been: I'm concerned about the last step where the ester forms a ring. The methyl group doesn't look like a plausible leaving group, but it does not ...
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298 views

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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741 views

Saponification value of a fat/oil

The saponification value of a fat was determined by adding $\pu{9.0 g}$ of the fat to flask containing $\pu{50.0 cm3}$ of $\pu{1.00 M}$ ethanolic potassium hydroxide. The remaining solution was ...
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71 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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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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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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247 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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During the development of aspartame, why was the methyl ester chosen?

One frequent argument against the safety of the synthetic sweetener aspartame is that it can be hydrolyzed, with one of the hydrolysis products being methanol, which is known to be toxic. Of course, ...
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87 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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431 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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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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1answer
435 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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2answers
300 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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2k views

How many grams of each substance will be present at equilibrium in the reaction of ethanol and ethanoic acid?

In the following reaction, $K_c=4.0$: $$\ce{C2H5OH + CH3COOH <=> CH3COOC2H5 + H2O}$$ A reaction is allowed to occur in a mixture of $\pu{17.2 g}$ $\ce{C2H5OH}$, $\pu{23.8 g}$ $\ce{CH3COOH}...
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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 ...
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57 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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1answer
938 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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306 views

Hoffmann's rule in ester pyrolysis

Why is the Hoffmann's product the major product in the pyrolysis of an ester to form a carboxylic acid and alkene?