Questions tagged [carboxylic-acids]

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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 ...
2 votes
1 answer
45 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 ...
-3 votes
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Reduction of carboxylic acid with red phosporous/HI [closed]

According to the class 11 theory it is mentioned that red P/HI will reduce Carboxylic groups to alkanes at 200 degree.But I cannot find any article for it.Now I am doubted whether red P/HI reduce ...
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Into what are long-chain carboxylic acids in meat converted by fruit sauces?

I understand yesterday's meat tastes rancid and sweaty because the aliphatic ketones (which give meat its creamy, silky taste) are oxidised to their respective carboxylic acids. I understand that we ...
3 votes
0 answers
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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 ...
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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., ...
3 votes
0 answers
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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, ...
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-1 votes
1 answer
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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 ...
2 votes
1 answer
61 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 ...
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3 votes
1 answer
124 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 ...
8 votes
1 answer
244 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 ...
2 votes
1 answer
119 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 ...
3 votes
0 answers
79 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 ...
2 votes
0 answers
64 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 ...
0 votes
2 answers
214 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 ...
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1 vote
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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 ...
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5 votes
0 answers
186 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 ...
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-1 votes
1 answer
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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 ...
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-1 votes
1 answer
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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 ...
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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 ...
0 votes
0 answers
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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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5 votes
1 answer
633 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 ...
0 votes
1 answer
486 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 ...
7 votes
1 answer
247 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 ...
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