Questions tagged [carboxylic-acids]
The carboxylic-acids tag has no usage guidance.
35
questions
-2
votes
0
answers
52
views
Synthesis Route Inquiry: Converting Aniline to 1,3,5-Tribromobenzene [duplicate]
Hello Chemistry Stack Exchange community,
I am currently working on a homework assignment that involves the synthesis of 1,3,5-tribromobenzene from aniline, and I am seeking guidance on the ...
5
votes
1
answer
163
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 ...
- 83
3
votes
1
answer
332
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 ...
- 43
-5
votes
1
answer
74
views
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}
...
- 131
-4
votes
1
answer
149
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 ...
-3
votes
1
answer
72
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
1
vote
0
answers
22
views
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 ...
0
votes
0
answers
307
views
Order of acidity of chloroacetic, acetic, formic and propanoic acid in terms of their electronegativity and inductive effect
What is the order of acidity of chloroacetic, acetic, formic and propanoic acid in terms of their electronegativity and inductive effect?
This is my explanation:
Propanoic acid is the weakest acid ...
- 527
7
votes
1
answer
217
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 ...
- 79
1
vote
1
answer
442
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 ...
- 67
-3
votes
1
answer
72
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?
- 435
1
vote
0
answers
73
views
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 ...
- 29
1
vote
1
answer
71
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 ...
1
vote
0
answers
66
views
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 ...
4
votes
1
answer
566
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 ...
- 219
3
votes
0
answers
43
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 ...
- 99
2
votes
1
answer
95
views
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
343
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, ...
- 107
-1
votes
1
answer
149
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 ...
2
votes
1
answer
115
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 ...
- 43
3
votes
1
answer
275
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 ...
- 299
8
votes
1
answer
363
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 ...
- 111
2
votes
1
answer
143
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 ...
- 111
3
votes
0
answers
174
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 ...
- 111
2
votes
0
answers
100
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 ...
- 101
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 ...
- 67
1
vote
0
answers
92
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 ...
- 156
5
votes
0
answers
488
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 ...
- 156
-1
votes
1
answer
51
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 ...
-1
votes
1
answer
45
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 ...
- 9
-1
votes
1
answer
202
views
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
261
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 ...
- 159
6
votes
1
answer
1k
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 ...
- 153
0
votes
1
answer
1k
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
485
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 ...
- 237