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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Specific reduction of certain functional groups

Consider the compound $\ce{Alkyl-(4 oxocyclopent-2-ene)carboxylate (A)}$. Now consider the operations: $\ce{1. (A) + (i)BH3/THF (ii) H+}$ $\ce{2. (A) + H2/Pt}$ $\ce{3. (A) + H2/Pd-C}$...
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Reaction of diamines with carboxylic acids to form imidazole

I've recently came across this reaction and my guess is that firstly an amide forms that later reacts with the second amine group. Is this a general reaction? Does it matter if the compounds used are ...
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Epoxide with solvent vs with water

The answer given is an epoxide. But is an epoxide stable at room temperature? And also epoxides tend to open in presence of water. Even if methyl alcohol is treated as a solvent, then too methyl ...
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1answer
637 views

What are the properties of COₓ where x ≥ 3?

$\ce{CO_x}$ are part of the oxocarbon molecule class. Commonly known are $\ce{CO}$ and $\ce{CO2}.$ However, there are molecules in which $x$ is equal to or larger than $3.$ Those molecules are barely ...
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1answer
79 views

Why doesn't H₄CO₄ exist as a stable compound? [closed]

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 ...
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Oxidation of ascorbic acid (Vitamin C) [closed]

What would you suggest me to use for oxidation of vitamin C to dehydroascorbic acid instead of bromine water?
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1answer
69 views

Which of the following isomers of 2,3‐dihydroxy‐4‐methoxy‐4‐oxobutanoic acid are identical?

Which of the following are identical? A and B are identical A and B are diastereomers A and C are enantiomers A and B are enantiomers What I know is that when we rotate a ...
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2answers
292 views

Why acidity of p-methoxybenzoic acid is more acidic than p-hydroxybenzoic acid?

I know +M effect of $\ce{OCH3}$ is more than $\ce{OH}$, but in my book (ALLEN General organic chemistry), it is given that $\mathrm{p}K_\mathrm{a}$ of para-substituted benzoic acid containing $\ce{...
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61 views

What should be IUPAC name of given compound (see image)? [closed]

I think the name should be 1-carbamoylpentane-3-sulphonic acid, but the answer sheet mentions it as 2-carbamoylpentane-3-sulphonic acid: Can anyone please explain why the chain starting with methyl ...
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Can a per-acetylated sugar anomerize?

So I have a question concerning a reaction mechanism for the reaction below. I know for certain that I get the alfa anomer, but I can't explain it. When I draw out the mechanism it doesn't make sense ...
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1answer
117 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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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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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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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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147 views

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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33 views

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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117 views

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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0answers
74 views

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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102 views

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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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
112 views

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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1answer
65 views

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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2answers
545 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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62 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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157 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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100 views

Reagents for synthesis of ethyl 2-(2,3-dihydrobenzofuran-2-yl)acetate from naphthalen-1(4H)-one

The following conversion can be performed in a few steps. Show key intermediates and reagents (detailed mechanisms are not required). So I've been looking at this for a while and I can't seem ...
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2answers
182 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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1answer
392 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. ...
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1answer
89 views

Why only ketone forms enolate in Claisen condensation between ester and ketone?

Claisen condensation involves nucleophilic substitution in esters by an enolate (formed by removing an alpha-H from an ester or a ketone) giving a beta-keto ester or a diketone. My textbook says ...
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1answer
831 views

Naming ester as a substituent to carboxylic acid

Can carboxylic acid functional group -COOH and ester's functional group R-COO-R' be in one structure? If yes, carboxylic acid will be the parent chain and ester will be the substituent as c.a. is ...
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An unconventional decarboxylation to form bullatenone

I recently had an assessment which required me to draw the mechanism of decarboxylation of a $\beta$-ketoacid. However, it is slightly peculiar because there is the presence of $\alpha$, $\beta$-...
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1answer
893 views

Predict the major product of the following reaction with mechanism [closed]

I started to do the problem by coordinating H+ with the lone pair of oxygen then after that I can't proceed .please send the solution by show the detailed mechanism.
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167 views

Reaction of Br2/KOH with succinic anhydride

What products will be formed when $\ce{Br2/KOH}$ reacts with the following compound in water at room temperature? Here is what I think is possible: $\ce{OH-}$ will take up the acidic hydrogen. ...
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0answers
86 views

Rate of nucleophilic addition reaction of carbonyl compounds

How should I compare the order of rate of 1.formaldehyde 2.ethanal 3.p-nitrobenzaldehyde 4.p-methoxybenzaldehyde For nucleophilic addition the rate depends on the intensity of electron deficiency of ...
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2answers
662 views

Synthetic steps for the interconversion between aldehydes and ketones

I am learning about carbonyl chemistry at the moment. So far, we have been able to make aldehydes and ketones from alcohols (via oxidizing agents). I can't help but wonder if there is possibly any way ...
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2answers
166 views

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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1answer
80 views

What happens in this reaction! Some hints needed

I understand step A involves reductive ozonolysis. and that step B is addition involves addition of ammonia to the carbonyl site to form imines. But what does the sodium salt of trichloroacetic acid ...
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1answer
131 views

Why does the carbonyl of carboxylic acids get protonated and not the hydroxyl group?

Is the O of the C=O group more electronegative or is it for the sake of getting from product A to B that the carbonyl is protonated rather than the hydroxyl?
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Ring contraction in benzilic rearrangement

Wikipedia says that, Benzilic acid rearrangement occurs with ring contraction when used on cyclic diketones. But gave no explanation, can you please elaborate on this with some mechanism. One ...
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0answers
83 views

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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0answers
135 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 ...
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223 views

Why don't acyl chlorides give positive test with 2,4-DNPH?

In this post, Ron discusses the reasons why carboxylic acid derivatives such as amides, acids and esters do not give a positive result with 2,4-dinitrophenylhydrazine. He mentions that it is largely ...
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1answer
169 views

What reaction takes place here? [duplicate]

Upon reading the given question, I realized that: The first reaction is an aldol condensation reaction between the given compound and formaldehyde. So the product after 1st step is: Now, the ...
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4answers
2k views

Reasons for negative iodoform test

Why does 2',6'-dimethylacetophenone not give iodoform test?
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1answer
134 views

Reaction of diacetyl with acid

What happens when diacetyl, that is, butan-2,3-dione is treated with acid? I guess there would be acid catalysed aldol formation. But what would the final product be? I can see too many ...
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1answer
146 views

Carbonation of Grignard reagent with a carbonyl group present in it

Here's the question in my book (see picture) Option A is a standard reaction which gives a carboxylic acid. Option B is definitely wrong because an acid base reaction will take place and CH4 will be ...
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How does chelation control result in rate acceleration?

In the chapter on diastereoselectivity in Clayden, Warren & Greeves (2012), the Cram-Chelate model is discussed. Most significantly, under chelation control, the diastereoselectivity of the ...

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