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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31 views

What is the mechanism of hydrolysis of caprolactam? [on hold]

It says in the book: The water initiates the reaction by attacking the carbonyl group in the ring to form the open-chain species, ε-aminocaproic acid. but I couldn't figure it out.
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295 views

What's the reason for the instability of ethylene dione?

Ethylene dione, with a chemical formula $\ce{C2O2}$ and an IUPAC name of ethene-1,2-dione, is an oxocarbon. The Wikipedia page says: The existence of $\ce{OCCO}$ was first suggested in 1913. ...
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180 views

Inductive vs conjugation effects in ester hydrolysis

I just came across the following problem about alkaline ester hydrolysis: Since all of the substituents are in the para position, I immediately thought about the ability of those substituents to ...
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6k views

In the condensation reaction of an aldehyde with a hydroxyl amine, why is an oxime formed and not an amide?

Condensation reactions are those that involve removal of a water molecule. When you analyze the reaction between an aldehyde and hydroxyl amine, I don't understand why it's not possible for the acidic ...
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1answer
114 views

Energy cost of C−N rotation in hydroxamate group

I am looking for a literature reference on the energetic cost of C−N rotation in hydroxamate group such in LC5 in water. I have been googling for a while.
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175 views

LiOH hydrolysis of methyl 2,2-dimethoxyacetate not giving product?

I am forming 2,2-dimethoxyacetic acid from its methyl ester, and below is the experimental protocol I am following (from Tetrahedron 2016, 72 (3), 420–430): 2,2-Dimethoxy Acetic Acid Formation ...
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632 views

Why does formic acid give positive Fehling's test?

$$\ce{HCOOH ->[\text{Fehling's solution}] CO2 + H2O}$$ The points discussed in a previous question do not account for the fact that formic acid also gives positive Fehling's test since it is not ...
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501 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 ...
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3k views

Dehydration of amide with PCl5

Can $\ce{PCl5}$, phosphorus pentachloride, react with an amide? I saw a reaction where the corresponding cyanide was formed in this process. What other reagents could do the same?
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Esterification of a carboxylic acid and the production of water

In an esterification reaction between a carboxylic acid and an alcohol, a carboxylate ester and water is produced. I found the following diagram online, and my textbook has a similar one as well ...
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Why amino acids (Zwitterion) become either negative or positive at low and high pH solutions?

The amino acids are Zwitterions. In neutral pH, an Amino acid's amino group has a postive charge and Carboxyl group has negative charge. They cancel each others charge thanks to the $Hydrogen$ that's ...
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Orbital size of Carbon and Oxygen in Methanal

I was given an introductory question into Carbonyl chemistry today and I wanted to ask a question about Methanal. The following picture was shown below of Methanal: and I noted that the orbital ...
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Will cinnamaldehyde undergo self-aldol condensation?

Will cinnamaldehyde undergo self-aldol condensation? My book says it won't, but since it has an α-hydrogen, I'm confused.
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On the mechanism of the nitrogen-removal step of the Wharton olefin synthesis

In today’s reaction seminar, the Wharton transposition made an appearance. In our practice case it started from the epoxide as in scheme 1 below as on Wikipedia; Kürti/Czakó (page 482) begin from the ...
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Reaction of glucose with 2,4-dinitrophenylhydrazine (DNPH)

In its open-chain form, glucose possesses an aldehyde group; however, glucose does not test positive with 2,4-dinitrophenylhydrazine (which typically forms a yellow/orange/red precipitate with ...
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55 views

Confusion with IUPAC naming of Morphine

I'm having trouble understand what sections of the molecule morphine relate to what sections of its corresponding IUPAC name of (4R,4aR,7S,7aR,12bS)-3-methyl-2,4,4a,7,7a,13-hexahydro-1H-4,12-...
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Do alpha hydroxy ketones give iodoform test

So, we know that alpha hydroxy ketones give tollens test as the tautomerise into their enol form and the then have an equilibrium between the 2 keto forms. So going ahead with the same logic. Do ...
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What can we say about the dipole moment of terephthalic acid?

The dipole moment of quinol is not zero because it can exist in two different energetically favourable conformations. The weighted average is calculated to arrive a dipole moment of 1.6 D. According ...
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1answer
57 views

Fluorination of Carbonyl Compounds using Molybdenum Hexafluoride

What is the mechanism of halogenation of carbonyl compounds using molybdenum hexafluoride? How does it work? Here's a reaction I came across: Can we use it for all carbonyl compounds? Are there ...
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Protonating/basic site and Brønsted basicity orders of beta, gamma, and delta lactams

Consider the three cyclic amides: $\beta$-lactam $\gamma$-lactam $\delta$-lactam My question What is the basic site (site of protonation) for these three lactams? And what should be their Brønsted ...
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Which compound reacts faster in the Cannizzaro Reaction?

Which reacts faster in the Cannizzaro Reaction? a) $\ce{OHC-C6H4-NO2}$ b) $\ce{OHC-C6H4-OCH3}$ Obviously, a better hydride releasing group will react faster. Therefore my answer was b, as $\ce{-...
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Can an amide nitrogen be a hydrogen bond acceptor?

Can $\ce{N}$ (i.e. main chain $\ce{NH}$s of recognised residues in a peptide or protein) be a hydrogen bond acceptor? It is a well known fact that the main chain $\ce{NH}$s can be a hydrogen bond ...
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Mechanism of decarboxylation of cyclohexane-1,2-dicarboxylic acid

According to FIITJEE's Sankalp Test-II answer key, it was given that the following compound decarboxylates on heating: Then, I read Why are beta-ketoacids better at decarboxylation than gamma or ...
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Diketone intramolecular reaction question

I realize that one of the methyl groups on either carbonyl compound will become deprotonated and then it will attack the other carbonyl to form a pentane ring. However, with the methyl group in the ...
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1answer
136 views

Equation for the equilibrium constant for the hydration of carbonyls using UV spectroscopy

I was looking through the literature when I found this source: https://pubs.rsc.org/En/content/articlepdf/1967/tf/tf9676302131 Which states that the equilibrium constant Khyd is: Khyd = $\frac{[...
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Is the 1,4-adduct of carbonyl compounds ever a major product over the 1,2-adduct?

If, say, propenal undergoes nucleophilic addition of hydrazine, will the 1,2- adduct or the 1,4-adduct be preferred? Why? There is an obvious reasonace structure with an electrophilic beta carbon so ...
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Is there a systematic naming system to name carbonyl derivatives?

I had asked a question earlier about how the “$\ce{-COOCl}$” functional group would be named. I had received a satisfactory answer that helped me completely understand how that compound was named. ...
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Sources of carbon monoxide in dwellings

I am doing some research on indoor environmental quality and come across a number of spikes in CO in a dwelling. This is a dwelling in central London with no gas-fired equipment: electric cooker and ...
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Why do carbonyl groups lower antibonding orbital energies of conjugated systems?

In the chapter on conjugation in Organic Chemistry by Clayden, Greeves, Warren and Wothers, there's a brief discussion of pigments with conjugated systems that includes the following paragraph (first ...
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255 views

Does alcohol hydrogen in the enol tautomer of a β-dicarbonyl have sp² character?

My reasoning for the somewhat implausible "$\mathrm{sp^2}$" character of the hydrogen between these two oxygens on the enol structure of the right comes from recognizing that if it were, then we would ...
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Rearrangements of α-aminoketones in Clemmensen reduction

What is the possible mechanism for this reaction? Activated zinc in presence of concentrated hydrochloric acid is used for Clemmensen reduction, that is conversion of ketone group to methylene group. ...
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Heating of cyclic dicarboxylic acid [closed]

How do we predict the products formed when we heat cyclic dicarboxylic acids? I know that in case of aliphatic dicarboxylic acids we apply Blanc's rule and predict the product formed based on the ...
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1answer
170 views

Intramolecular lactonisation in an unsaturated carboxylic acid

I am having some trouble figuring out how this reaction proceeds: Attempt 1: The most obvious thing to do is deprotonate the acid group. I tried using the carboxylate group to attack the alkene, ...
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1answer
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Are all fatty acids monocarboxylic acids?

The answer to this question might solve a multiple choice in my previous chemistry exam, which caused an argument with my teacher. We know that fatty acids form fats and oil due to their carboxylic ...
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311 views

How do α,β-unsaturated acids undergo decarboxylation?

I know the concerted mechanism for β-keto acids, but neither could I figure out, nor was I able to find out the mechanism for α,β-unsaturated acids. Any help is appreciated.
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Why are carbonyl groups so important [closed]

The most important are π orbitals as they are lower in energy than σ orbitals and the carbonyl group (C=O) is the most important of these—indeed it is the most important functional group of all. ~...
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Difference between base-promoted and base-catalysed

Why is halogenation of ketones in base described as being "base-promoted" and not "base-catalysed"? If the reaction is not "catalyzed" then how is the base used up?
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Why do carbonyl compounds undergo nucleophilic and not electrophilic addition?

Why aldehydes and ketones undergo nucleophilic addition reactions and not electrophilic addition? Alkenes show electrophilic addition because of pi bond, which is also present in aldehydes and ...
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What causes the blackening of light bulbs

in 1878, Thomas Edison (or rather William Joseph Hammer) added an anode in a light bulb in order to catch the flux of electrons coming out from the carbon filament and reduce the phenomenon of ...
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1answer
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Grignard alkene on a carbonyl

I was given the following mechanism to prove today post-lecture: and my attempt is given below. Now, when the negative charge on the alkene attacks the carbonyl, the electrons are pushed onto the ...
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658 views

Reaction of coumarin with phenylmagnesium bromide

I came across this problem.. I thought that the Grignard reagent, PhMgBr, would cleave the lactone and then subsequently add to the ketone formed, giving an allylic tertiary alcohol after aqueous ...
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Acidity order of carboxylic compounds [duplicate]

Arrange the following acids in decreasing order of acidity: (a) X > Z > Y (b) X > Y > Z (c) Z > X > Y (d) Z > Y > X I arrived at option (c) according to -I effect, but the answer ...
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323 views

What is the keto form of a hexahydroxybenzene?

159. The keto isomer of the following compound is: The answer has been given as (c). I cannot seem to understand why is it not possible for the keto form to only have one OH convert into keto ...
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742 views

Decarboxylation mechanism and stability of α,β-unsaturated and α-hydroxy acids

I was wondering why α,β-unsaturated and α-hydroxy acids undergo decarboxylation. Also, I'm aware of neither the products nor mechanism. All I know is that β-keto acids and α-nitro compounds have ...
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853 views

Why does aceto acetic ester not respond to haloform test even though it has a keto methyl group? [closed]

Why does aceto acetic ester not respond to haloform test even though it has a keto methyl group?
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59 views

Aldol Reaction in Water Not Working

I am conducting an Aldol formation reaction in water, and below is the experimental protocol I am following (from J. Org. Chem. 1994, 59, 3590—3596): Formation of Aldol in Water using Yb(OTf)3 ...
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Haloform reaction with limited bromine

We were asked the reaction between 1 mole acetone and 1 mole $\ce{Br2}$ in basic medium. Since only a limited amount of bromine was given I got the final answer as 1-bromopropan-2-one (mono bromo ...
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120 views

1,4-addition vs 1,2-addition aldol/aldol type reactions

In the aldol/cross aldol reaction, of $α,β$-unsaturated carbonyl compound, under what circumstances does a 1,2-addition i.e. aldol condensation (carbanion formed directly attacking carbon of carbonyl ...
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Mechanism of a cyclization reaction - why does an enol ether form?

I was asked to predict compound A from the follwing organic scheme: Looking at the formation of A, my prediction was that since TsOH is a strong acid, it would dehydrate the alcohols (like sulfuric ...