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Questions tagged [carboxylic-acids]

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Delocalisation of electrons: Benzenecarboxylic acids

Naturally, the benzene ring will have a degree of delocalisation in the ring due to the pi cloud. Similarly, the carboxylic acid group will also have a degree of delocalisation. Correct me if Im wrong,...
Omar's user avatar
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-I effect vs +M effect of Chlorine on acidity of benzoic acid

The -I power of Halogens like Chlorine is stronger than their +M power. Therefore, we consider -I effect for comparing acidity of benzoic acid [Ka-> ortho > meta > para]. But shouldn't -I ...
EagerToLearn's user avatar
2 votes
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503 views

Why is the lysine side chain more basic?

As per PubChem: $pK_1 = 2.18$; $pK_2 = 8.95$; $pK_3 = 10.53$ at 38 °C, indicating that the side chain amino group is deprotonated at a higher pH, indicating it is more basic. I tried to justify this ...
Sid's user avatar
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1 answer
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Acidity of formic acid and 3-fluoropropanoic acid [duplicate]

I'm getting conflicting answers when I want to find out the acidity of 3-fluoropropanoic acid and formic acid. I argue that 3-fluoropropanoic acid is stronger acid than formic acid as it has a -I ...
Akilan SS's user avatar
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67 views

Acidic strength of alkanoic acids vs. benzoic acid vs. methanoic acid

I've heard some people say that benzoic acid has a $+\ce{M}$ effect due to the benzene ring which destabilizes the conjugate base. Also, this would be the dominating factor over the weak $-\ce{I}$ ...
AVS's user avatar
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5 votes
1 answer
191 views

Simplest existing tricarboxylic acid

I am wondering what is the simplest tricarboxylic acid that can be isolated in a pure form. Would it be methanetricarboxylic acid or ethane-1,1,2-tricarboxylic acid or maybe even longer chain is ...
pajacol's user avatar
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2 votes
1 answer
541 views

which is more acidic thiols or carboxylic acid?

According to me as the key atoms are different so when the h+ is released and each of them gets a negative charge as sulphur is a bigger atom compared to oxygen charge is more dispersed , hence the ...
zecrosis's user avatar
-5 votes
1 answer
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Can diols be oxidised to hydroxyacids? [closed]

Conversion of ethanol to ethanoic acid $ \ce{CH3CH2OH_{(aq)} \xrightarrow[KMnO^{-}_{4}]{NaOH} CH3CHO_{(aq)} + H2O_{(l)} }\\ $ $\ce{CH3CHO_{(aq)} + H+_{(aq)} \xrightarrow[KMnO^{-}_{4}]{HCl} ...
Nickotine's user avatar
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-4 votes
1 answer
294 views

Preparation of alkane through decarboxylation by soda lime

Can we still prepare alkane through decarboxylation (using soda lime) if instead of using sodium salt of carboxylic acid, we use the carboxylic acid directly. Because I have always seen the ...
Arnav Tyagi's user avatar
-3 votes
1 answer
104 views

Can acyl chloride give Wurtz reaction? [closed]

Since the mechanism involves formation of free radical so is it possible to yield a ketone from wurtz reaction of acyl chloride Such as CH3COCl reacts with Na in dry ether so can it yield CH3COCH3
Maanik Khurana's user avatar
1 vote
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What is the chemical mechanism at work during the carboxylation of graphene oxides?

The literature describes carboxylation as an efficient technique to increase the ability of graphene oxide to adsorb metals, as it increases the content of carboxylic acids in the material, while ...
Nathan Vinicius's user avatar
7 votes
1 answer
308 views

Why don’t Grignard reagants react with their alcohol products?

I’ve read that Grignard reagants react pretty quickly with alcohols and carboxylic acids to form their respective conjugate bases. I’ve also learned that Grignards can be used for the prepararion of ...
Allie's user avatar
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1 vote
1 answer
579 views

Why is the inductive effect possible?

Firstly, I must preface that I am a Biology student. To elaborate my question, I was looking for the reason why carboxylic acids are more acidic than alcohols, despite both compounds containing —OH ...
Growing6884's user avatar
-3 votes
1 answer
103 views

How does vinegar free deposits from a surface?

I use vinegar to clean/descale an electric kettle. How does this work? i.e. how does the vinegar free the deposits (calcium, manganese?) from the surface?
Al Lelopath's user avatar
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Why are crystals of carboxylic acid fluffy

I'm an undergrad student and we recently performed saponification of esters which resulted in the formation of carboxylic acid which we had isolated out of the reaction mixture. After ...
Stu's user avatar
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1 answer
140 views

Compare acidic strength of two different hydrogen in a Compound (2-hydroxycyclohex-1-encarboxylicacid)

I want to compare acidic strength between hydrogen-(a) and hydrogen-(b), I am getting answer as (a) but my classmate and my teacher said that (b) will have more acidic strength. I think (a) should ...
Bhavishya Singhal's user avatar
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Erythritol oxidation using acidified KMnO4

I have recently experimented with erythritol oxidation my primary aim was to make glyoxal. However regarding the nature and structure of erythritol several other side-products were also observed one ...
Copper Chopper's user avatar
4 votes
1 answer
1k views

Which is more acidic : 2,6- dihydroxy benzoic acid or 2-hydroxy benzoic acid?

This post address the acidity of ortho and para hydroxy benzoic acid. However, what effect is there if there are two hydroxy groups ortho to carboxylic group? I know hydrogen bonding is also at work ...
An_Elephant's user avatar
3 votes
0 answers
45 views

What are the other examples of compounds undergoing decarboxylation in the pericylic manner as shown by β-ketocarboxylic acids?

I know that β-ketocarboxylic acids undergo decarboxylation on light heating through an enol intermediate undergoing a pericyclic reaction. However, what other groups may be placed at the β position ...
Ansh's user avatar
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2 votes
1 answer
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Are carboxylic anhydrides in graphene oxides considered adsorption sites for metals? If so, are they more or less reactive than carboxylic acids?

The literature abundantly addresses the fact that carboxylic acids present in graphene oxides act as efficient adsorption sites for metals in aqueous solutions (e.g., HE et al., 2021; ZHAO et al., ...
Nathan Vinicius's user avatar
3 votes
0 answers
511 views

How to establish trend of carboxylic acid acidity in the presence of certain substituents?

I encountered a question in my textbook which asked the following: At first, i thought that i can approach it in the same way i sort the effect of EDG and EWG on the acidity of phenols, that is, ...
Doe Pual's user avatar
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-1 votes
1 answer
268 views

intramolecular h-bonding in maleic acid

While studying organic chemistry, I came across two practice questions given by my professor: Compare the acidic strength of:- Maleic acid and Fumaric acid o-nitrophenol and p-nitro phenol And the ...
Priyanshu Choubey's user avatar
2 votes
1 answer
146 views

Comparison of the acidic nature between substituted benzoic acids and acetic acid

p-Methoxybenzoic acid $(\mathrm{p}K_\mathrm{a} = 4.47)$ is a stronger acid than acetic acid $(\mathrm{p}K_\mathrm{a} = 4.76)$ despite the presence of an electron donating group. I understand this is ...
Skahoot's user avatar
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3 votes
1 answer
474 views

Does carboxyl group interfere with reaction of 2-carboxybenzaldehyde with NaCN/HCl?

The aldehyde group of 2-carboxybenzaldehyde reacts with $\ce{NaCN/HCl}$ forming cyanohydrin. Does the carboxyl group remain intact? Does it react separately or with the cyanohydrin? I suspect possible ...
ultralegend5385's user avatar
8 votes
1 answer
409 views

Is RCOOH + H2SO4 + heat a viable alternative to RCOCl + AlCl3 in Friedel-Crafts acylation?

Can concentrated strong acid like H₂SO₄ be used to protonate a carboxylic acid to RC(OH)₂⁺, forming RCO⁺ by removal of H₂O, analogous to the reaction with nitric acid to produce nitronium? Would this ...
kvanderfluegh's user avatar
2 votes
1 answer
145 views

Is hydrolysis of acid chlorides still favored when the resulting acids cannot donate their protons?

For example, take the reaction: MeCOCl + H₂O -> MeCOOH + HCl Bonds broken: C-Cl + H-O -> 330 + 460 = 790 kJ/mol Bonds formed: C-O + H-Cl -> 350 + 432 = 782 kJ/mol I realize that BDE is only ...
kvanderfluegh's user avatar
3 votes
0 answers
196 views

O-C-O bond angles in carboxylates vs carboxylic acids?

I am wondering how different the O-C-O angle is in a carboxylate vs its acid form. Does it (noticeably) increase because of the electron-electron repulsion caused by an additional lone pair? Bond ...
kvanderfluegh's user avatar
2 votes
0 answers
133 views

Various pathways of an alpha diketone reaction

This is a question from JEE Advanced 1997. I have found two possible products of the reaction: By intramolecular aldol condensation: By benzil-benzilic acid type rearrangement: Which reaction takes ...
Lost Anisole's user avatar
0 votes
2 answers
1k views

Hybridisation of the O atom in the hydroxyl group of ethanoic acid

Currently studying high school organic reaction mechanisms and encountered a question. It goes like this: The C=O bond and the C–O bond of an ethanoate ion is equal at 127 pm, while the C=O bond of ...
warren's user avatar
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1 vote
0 answers
103 views

Comparing acidic strength of acetic and p-anisic acids

In p-anisic acid the phenyl ring with methoxy group acts as strong electron donating group by mesomeric effect (+M), whereas in acetic acid there is only an electron donating nature by inductive ...
TeslaBolt's user avatar
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5 votes
0 answers
606 views

Comparing acidic strength of phthalic acid isomers

I'd like to compare the acidic strengths of phthalic, isophthalic and terephthalic acids. As I understand, phthalic acid is the most acidic due to steric inhibition of resonance (SIR), but as ...
TeslaBolt's user avatar
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-1 votes
1 answer
54 views

How to prevent Sodium Hydroxide (Catalyst) from reacting with the Formic Acid (product) after electrolysis is done [closed]

So, I am trying to create Formic Acid from PET and to break the ester bonds before electrolysis, I am planning on using water and sodium hydroxide. I was told that if I take this Plastic-Sodium ...
Tsar Asterov XVII's user avatar
-1 votes
1 answer
51 views

Why is acidic strength of A>B? [closed]

a) H-(C=O)-OH b) H-(C=O)-O-OH The acidic strength of the two structures given below was a>b . I think the explanation to that is in structure A, the O atom of carboxyllic acid is in resonance with ...
PRANAV's user avatar
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-1 votes
1 answer
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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 ...
zhoumingguang's user avatar
0 votes
0 answers
330 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 ...
Asher2211's user avatar
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6 votes
1 answer
2k views

Acetamide and Nitrous acid Reaction Mechanism

My book says that when acetamide is treated with nitrous acid, ethanoic acid, nitrogen and water are formed but it provides no mechanism. I googled but could not find any mechanism. My guess was that ...
Tahsin Choudhury's user avatar
0 votes
1 answer
2k 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 ...
CaptainTeemo OnDuty's user avatar
7 votes
1 answer
586 views

Why doesn't NGP happen in the bromination of fumaric acid?

In this question from JEE $2015$, a surprising neighbouring group participation occurs, and the product turns out to be $(3)$. A link for the mechanism can be found here. However, why doesn't the same ...
Aspirant's user avatar
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