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Questions tagged [carbonyl-compounds]

For questions about compounds containing the carbonyl group, C=O, the carboxylic acid group (-COOH), or its derivatives (anhydrides/esters/amides/acid halides). For questions about complexes involving carbon monoxide as a ligand use [carbonyl-complexes] instead.

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4 votes
2 answers
314 views

Using potassium dichromate and sulfuric acid to clean test tubes after Tollens’ test

We had an experiment at school to find out the biomolecules contained in the different foodstuffs. After doing Tollens’ test which turned out to be positive, our teacher instructed us to clean the ...
-1 votes
0 answers
223 views

Temperature dependence of aldol condensations

Aldol condensation of acetophenone and benzaldehyde, typically goes like this: Still, acetophenone molecules can also condense with with each other. The result depends on concentration, but is there ...
8 votes
1 answer
2k views

Do all α-hydroxy ketones give Tollens’ test?

It is well known that terminal α-hydroxy ketones give Tollens’ test, via tautomerisation. Also, α-hydroxy ketones flanked by aromatic groups give Tollens’ test, such as benzoin. But do all α-hydroxy ...
8 votes
2 answers
621 views

FTIR Spectra: Did I synthesize ethyl gallate from gallic acid?

I successfully synthesized ethyl gallate from gallic acid and ethanol (of course there are other reagents too, like DCC and Pyridine). Before conducting FTIR analysis, I performed column ...
2 votes
0 answers
33 views

Oxidation of 1,2 dicarbonyls by tollens reagent

According to the wiki page on Tollen's reagent https://en.wikipedia.org/wiki/Tollens%27_reagent#Qualitative_organic_analysis It also gives a positive test with hydrazines, hydrazones, α-hydroxy ...
9 votes
2 answers
20k views

Does DIBAL-H reduce carboxylic acids?

Diisobutylaluminium hydride(DIBAL-H) reduces only carboxylic acid, ester or both? The answer given was that it only reduces ester. Is it correct that under any condition carboxylic acids are not ...
13 votes
1 answer
657 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 ...
-2 votes
1 answer
70 views

Why is Chromium hexacarbonyl diamagnetic?

So there was a question in coordination chemistry regarding the nature of $\ce{[Cr(CO)_6]}$ The book had the question under VBT and solved it using "strong ligands cause all electrons to pair up&...
-4 votes
2 answers
1k views

Does H2, Pd/C reduce a conjugated ketone?

Would H2, Pd/C be a sufficient reagent for this reaction to proceed? The question is from a test which asked what would be the most suitable reagent for the above reaction
2 votes
1 answer
797 views

Identify structure of compounds from their reactions and molecular formula

Compound P ($\ce{C7H6O}$) on refluxing with aqueous ethanolic $\ce{KCN}$ solution for 1 hour, forms Q ($\ce{C14H12O2}$). Q on oxidation gives R ($\ce{C14H10O2}$). R on refluxing with aqueous $\ce{NaOH}...
13 votes
3 answers
513 views

Comparison of C=O bond strength in metal carbonyls

Find the weakest $\ce{C=O}$ bond among $\ce{[Mn(CO)6]+},$ $\ce{Fe[(CO)5]},$ $\ce{[Cr(CO)6]}$ and $\ce{[V(CO)6]-}.$ I thought the $\ce{C=O}$ bond strength would be lowest in $\ce{[V(CO)6]-}$ since the ...
-3 votes
1 answer
86 views

Can someone help me name this molecule? [closed]

I'm having a hard time deciphering it's IUPAC name like I have 4-butanoxy and 3-propanoxy so far, but how do you put it all together with the double-bonded oxygen? Thank you and really sorry for the ...
19 votes
1 answer
25k views

Does Br2/H2O oxidize all aldehydes including carbohydrates?

In many books, it is mentioned that aldehydes are easily oxidized even by mild oxidizing agents. However, I have never seen bromine water explicitly mentioned. But in the carbohydrates chapter, it is ...
7 votes
1 answer
15k views

Preparation of oxalic acid from acetylene

I think that using ozonolysis would be a good idea to prepare oxalic acid from acetylene. Upon ozonolysis of acetylene we would get glyoxal: $$\ce{O=CH-HC=O}$$ Would I obtain the oxalic acid upon ...
0 votes
1 answer
129 views

Is acetophenone a saturated compound?

In many of the sites in online, acetophenone is mentioned as an unsaturated compound because of the presence of C=C bond in the phenyl group. But, many of my teachers say that it is a saturated ...
19 votes
1 answer
4k views

How can benzaldehyde have a pKa of 14.9?

There are numerous websites out there which claim that the pKa of benzaldehyde – C6H5CHO – is 14.90. (Just do a Google search for benzaldehyde pka to see what I ...
1 vote
0 answers
21 views

Does nitroprusside test only work for ketones and not aldehydes?

Since the Brady test will be positive for both aldehydes and ketones, we need a way to distinguish between the two. The Tollen's test is only positive for aldehydes (and $\alpha$-hydroxyketones). I ...
0 votes
0 answers
184 views

How phenyl shift is possible in Benzil-benzilic rearrangement?

We know $\ce{C-C}$ bond is much stronger than $\ce{C-OH}$ bond (because similar sized atoms have maximum overlap) as in case of phenyl-carbonyl carbon bond. Also due to resonance there is double bond ...
13 votes
2 answers
6k views

Why is benzoic acid a stronger acid than 3-aminobenzoic acid?

Why is benzoic acid a stronger acid than 3-aminobenzoic acid? Obviously at meta position, only negative inductive effect will operate. But, how does that make it a weaker acid than benzoic acid?
14 votes
1 answer
1k views

Ambiguous nature of aldehydic group in glucose

In aqueous solution, α-anomer and β-anomer of glucose remain in equilibrium with each other along with a small amount of glucose in open chain form ($0.02~\%$). The open chain form in ...
4 votes
1 answer
299 views

Nomenclature of C6H5CO-O-NH2

How to name the following compound using IUPAC nomenclature? I found benzyl carbamate to be very close to my structure, but couldn't find an exact compound online which matches mine.
0 votes
0 answers
119 views

Oxidation of substituted cyclic ketone using permanganate

From what I had learnt, reaction of this with $\ce{KMnO4}$ should give a dicarboxylic acid after cleavage of the carbon-carbon bond. But apparently this is the reaction that happens: Why is there a ...
-3 votes
1 answer
142 views

Why is Benzaldehyde more reactive than propanone in nucleophilic addition, even though it has resonance? [closed]

I am not 100% sure that this is true but this was given in the JEE Main 2020 (03 Sep Shift 2). Benzaldehyde has resonance and propanone has just +I effect why is then benzaldehyde more reactive in ...
21 votes
1 answer
2k views

Can we use phosphorus triiodide in Hell-Volhard-Zelinsky reaction?

Using the Hell–Volhard—Zelinksy (HVZ) reaction, we can get alpha-chloro or alpha-bromo carboxylic acids: Is it possible to similarly make alpha-iodo carboxylic acids with the help of HVZ reaction? I ...
2 votes
0 answers
2k views

Effect of H-bonding on o-nitrobenzoic acid

My argument here is regarding the acidity of o-nitrobenzoic acid being greater than p,m-nitrobenzoic acid. In o-nitrobenzoic acid, there is an intramolecular hydrogen bond which makes the bond ...
1 vote
0 answers
1k views

Can 1,3,5-trihydroxybenzene perform haloform reaction?

As far as I know it's not possible for 1,3,5-trihydroxybenzene to give the haloform reaction. The prerequisites(that I know) for the haloform reaction are: Only those organic compounds which can be ...
0 votes
1 answer
65 views

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 ...
2 votes
2 answers
209 views

Should I remove inhibitor from methyl acrylate?

I need to run multiple aza-Michael additions of methyl acrylate with various amines (dimethylamine, benzylamine, phenylethylamine, aniline, etc.) in order to get the bis-ester. I was wondering if the ...
3 votes
2 answers
2k views

Do the amino groups in EDTA deprotonate first, in contrast to amino acids?

We know that in amino acids, carboxylic acid groups deprotonate first than the amine groups. For example, in alanine, $\mathrm{p}K_\mathrm{a,\ce{COOH}} = 2.34$, $\mathrm{p}K_\mathrm{a,\ce{NH3+}} = 9....
3 votes
2 answers
991 views

How to determine which compound will get oxidised and which will be reduced in a cross cannizzaro reaction?

How to determine which compound will get oxidised and which will be reduced in a cross cannizzaro reaction? As a general rule of thumb, I have always been told that Formaldehyde is always oxidised, ...
11 votes
1 answer
6k views

Mechanism for conversion of ketone to dichloride with phosphorus pentachloride

I would like to know the mechanism of this reaction leading to the formation of a geminal dichloride. I am unable to predict how the $\ce{C=O}$ breaks and how the 2 $\ce{Cl}$ atoms replace the oxygen ...
0 votes
2 answers
459 views

Mechanism for formation of amides from ammonium carboxylate salts

One of the reactions that you can do with a carboxylic acid is to react it with ammonia or an amine, which produces the corresponding ammonium carboxylate salt. When this salt is heated, amide is ...
2 votes
0 answers
38 views

Comparing reactivity of benzaldehyde and 2-butanone for nucleophilic addition

I was taught that, in general, aldehydes are more reactive than ketones because of two reasons: 1) less steric hindrance, and 2) alkyl groups on both sides of carbonyl group in ketones have a stronger ...
4 votes
1 answer
6k views

Dehydration of carboxylic acids with phosphoric acid

To find Z one must find X. Finding Y is of no use to find Z. I get X as: After addition of $\ce{H2/Pd-C}$, the unsaturated portion becomes saturated and the carboxylic acid remains unchanged. ...
9 votes
0 answers
310 views

The Action of Nitrogen Iodide on Methyl Ketones

I recently encountered two old publications on action of nitrogen iodide on various compounds (Ref.1 and Ref.2). Between them, Ref.1 described the iodoform formation by methyl ketones upon treatment ...
11 votes
1 answer
28k views

Is an ester or a ketone more acidic?

Two organic chemistry textbooks I've read (by Bruice and by Tandon) say: Esters are more acidic than ketones, because the resonance between the two oxygen atoms gives less opportunity for the ...
8 votes
3 answers
407 views

Is 2-oxobicyclo[2.2.1]heptan-1-ide resonance stabilized?

Is the following compound resonance stabilized? I think its not resonance stabilized because the p-orbital of carbanion and pure p-orbital of carbonyl carbon are not in same plane. So they can't ...
2 votes
1 answer
419 views

Why doesn't H₄CO₄ exist as a stable compound?

Why doesn't $\ce{H4CO4}$ exist as a relatively stable compound? Its heavier homologue $\ce{H4SiO4}$ seems to exist although it is unstable to some extent but new methods have been able to stabilise ...
3 votes
1 answer
22k views

What reaction happens when carboxylic acids are treated with calcium hydroxide and distilled? [closed]

What reaction takes place when $\ce{Ca(OH)2}$ reacts with $\ce{R-COOH}$? What is obtained after distillation?
4 votes
1 answer
281 views

What are the best conditions for EDC coupling of 2 small molecules?

I want to couple 2 small molecules, one is a DNA oligo with an amine group and the other one a small molecule with with a carboxyl group. I found protocols for EDC (1-Ethyl-3-(3-dimethylaminopropyl)...
13 votes
1 answer
7k views

Why do alpha-hydroxy ketones respond positively to Tollens', Fehling's, Benedict's, Schiff's and HgCl2 tests?

I learnt from a certain textbook that aldehydes and formic acid respond positively to Tollens', Fehling's, Benedict's, Schiff's and HgCl2 tests. However, in another textbook I read that even alpha-...
3 votes
1 answer
223 views

Oxidation Number of the middle carbon in $\ce{C3O2}$ (Carbon Suboxide)

By taking the oxidation state of the terminal oxygen atoms as -2, and oxidation state of the carbon atoms adjacent to these oxygen atoms as +2, we are left with the oxidation state of the middle ...
1 vote
0 answers
90 views

Does heating 3-phenylpropionic acid decarboxylate it?

Here, when P is reacted with $\ce{SOCl2}$ and then NaCN to give 3-phenylpropionitrile and then hydrolysed to give 3-phenylpropionic acid. Why shouldn't it further decarboxylate and dehydrogenate to ...
3 votes
1 answer
113 views

Glutaraldehyde or Glutardialdehyde

Recently I was searching for a chemical compound to meet my research needs, i.e. glutaraldehyde, and later I found that Merck has been released different name of compound: (1) glutaraldehyde and (2) ...
3 votes
2 answers
392 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 ...
-5 votes
1 answer
201 views

Does KMnO4 Oxidize Alpha-Beta Unsaturated Aldehydes? [closed]

I suspect that since $\ce{KMnO4}$ is a strong oxidizing agent it will react with the $\alpha,\beta$-unsaturated part of the carbonyl forming an epoxide. Are there any secondary reactions that one ...
0 votes
1 answer
3k views

Do esters/carboxylic acids/acid anhydride, etc. show Wolff Kishner reaction or not?

Do carboxylic acid and it's derivatives such as esters, amides, acid halides and anhydrides show Wolff-Kishner reductions and why?
5 votes
1 answer
2k views

Do formaldehyde and ethylene glycol give positive Fehling's test?

Fehling's test follows a single electron transfer mechanism, with electron transfer form the substrate to $\ce{Cu^2+}$, which forms $\ce{Cu^+},$ finally giving reddish brown precipitate of $\ce{Cu2O}$....
1 vote
1 answer
256 views

How to name ether with ketone and carboxyl groups?

Carboxylic acid is the main functional group due to higher priority, but since it's an ether, what's the proper way to name the following compound? My attempt: 2-(1-methyl oxo propyl ether) ethanoic ...
6 votes
2 answers
302 views

How to name aliphatic chain with carboxyl and amide terminal groups?

I know the name 5-carboxyl-2-methylethanoic acid is wrong for the compound $\ce{HOOC-CH(CH3)-CH2-CH2-CH(CH3)-C(=O)-NH2}$ drawn below. Can we just use 5-amido?

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