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.

Filter by
Sorted by
Tagged with
1
vote
1answer
62 views

Product of the reaction between chalcone and sodium methoxide in methanol

I'm a bit lost on how to do this, for Product C I can see two things happening: 1) The $\ce{-OCH3}$ attacks the alpha hydrogen, but that doesn't really make sense as then you would get two double ...
0
votes
0answers
23 views

does Hydrogen and nickel reduce c=c

In my course, I've come across H2 and Ni catalyst as a reducing agent for alkenes and LiAlH4/NaBH4 as a reducing agent for carbonyl groups. I know LiAlH4/NaBH4 can't reduce c=c as it is nucleophilic ...
0
votes
1answer
32 views

Why does Cinnamaldehyde pass the ferric chloride test?

I was given some data to determine what an unknown compound was and figured out that the data was Cinnamaldehyde. After reviewing the classification test given to me by my professor, I was a bit ...
3
votes
0answers
16 views

Will phosphorous Ylide participate in carbene generation and insertion?

The following question was sent to me . The answer for this question was given to me as option b I attempted it as following , recognizing the first step as a ylide reaction with a carbonyl compound....
-1
votes
1answer
37 views

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

Our teacher told us that amides can not be reduced by Wolff Kishner reaction. But he did not talked about esters, carboxylic acids, and other functional groups that contain the double bond between ...
0
votes
0answers
29 views

Does 1,3-diphenylprop-2-en-1-one give a positive Tollens test?

If we have 1,3-diphenylprop-2-en-1-one, will it give positive Tollens test? I think aldol reactions are reversible under basic conditions. Here there are mildly basic conditions, so will we get back ...
-1
votes
0answers
42 views

Extent of Clemmensen reduction

I came across Clemmensen reaction while studying and I learnt that it is used to reduce carbonyl groups or C=O groups. However, I have a doubt whether carboxylic acids can also be reduced or not. I ...
2
votes
0answers
44 views

Steric inhibition of resonance in substituted benzoic acid

Why does attaching an $\ce{-NO2}$ group at the ortho position of benzoic acid cause $\ce{-COOH}$ to become perpendicular to the plane of the benzene ring? Why doesn't the nitro group get pushed out ...
2
votes
0answers
112 views
+50

Specific reduction of certain functional groups

Consider the compound $\ce{Alkyl-(4 oxocyclopent-2-ene)carboxylate (A)}$. For example consider- Now consider the operations: $\ce{1. (A) + (i)BH3/THF (ii) H+}$ $\ce{2. (A) + H2/Pt}$ ...
2
votes
0answers
44 views

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 ...
1
vote
0answers
26 views

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 ...
12
votes
1answer
641 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 ...
1
vote
1answer
81 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 ...
1
vote
0answers
35 views

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?
0
votes
1answer
72 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 ...
1
vote
2answers
449 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{...
1
vote
0answers
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 ...
5
votes
0answers
50 views

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 ...
3
votes
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.
0
votes
0answers
91 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-...
1
vote
0answers
86 views

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 ...
6
votes
0answers
106 views

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 ...
1
vote
0answers
27 views

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 ...
1
vote
0answers
29 views

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 ...
1
vote
0answers
168 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 ...
0
votes
0answers
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 ...
1
vote
0answers
53 views

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 ...
1
vote
0answers
132 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 ...
1
vote
0answers
79 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. ~...
0
votes
0answers
113 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?
7
votes
0answers
85 views

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 ...
3
votes
1answer
122 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 ...
4
votes
1answer
67 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 ...
2
votes
2answers
655 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.
0
votes
0answers
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 ...
1
vote
1answer
209 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 ...
4
votes
0answers
102 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 ...
5
votes
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 ...
0
votes
1answer
504 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. ...
0
votes
1answer
95 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 ...
1
vote
1answer
1k 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 ...
4
votes
0answers
63 views

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 $\alpha$, $\beta$-...
-1
votes
1answer
930 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.
1
vote
0answers
190 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. ...
0
votes
0answers
92 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 ...
2
votes
2answers
1k 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 ...
2
votes
2answers
180 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 ...
-1
votes
1answer
82 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 ...
2
votes
1answer
146 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?
1
vote
0answers
74 views

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 ...

1
2 3 4 5
11