Compounds containing the carbonyl group, C=O. The tag is only used for the organic molecules containing this functional group. For questions about complexes involving carbon monoxide as a ligand use carbonyl-complexes instead.

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2
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2answers
45 views

Suggestion for a Synthesis of Paracetamol — plausible?

I have seen a number of different plausible syntheses for paracetamol but they suffer from problems such poor regioselectivity of aromatic substitution (usually when nitrating phenol getting a mixture ...
0
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0answers
12 views

Easieast method of air oxidation of octan-2-one to two carboxylic acid? [closed]

im trying to find simplest method to convert methyl hexyl ketone to two carboxylic acid with out using catalyst as i need to apply in industry scale. can anybody help me in this regard
6
votes
1answer
98 views

Predict the product of reaction of quinone and hydrochloric acid

This is the question: And this is my solution: In the last step, I have tautomerised, and in the second last step, there is no double bond between carbon attached with Cl and OH (just some ...
3
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2answers
147 views

Is acetone saturated or not?

This was a question in a chemistry exam: How many moles of hydrogen is required to convert 1 mole of this compound into a saturated compound? $\ce{CH3COCH3}$ (acetone) Some teachers said ...
6
votes
3answers
346 views

Is sodium borohydride really a better base than an alcohol?

I have learnt that sodium borohydride can reduce aldehydes, ketones and acyl chlorides into alcohols. However, it fails to react with esters or acid anhydrides. On the other hand, alcohols — ...
6
votes
1answer
143 views

Why are beta-ketoacids better at decarboxylation than gamma or delta?

My book claims that beta-ketoacids and beta-dicarboxylic acids are better at decarboxylating than their gamma and delta counterparts. Why is that? I would assume that since gamma and delta keto-acids ...
0
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0answers
26 views

How phenyl shift is possible in Benzil-benzilic rearrangement?

We know C-C bond is much stronger than C-OH bond (because similar sized atoms have maximum overlap)as in case of phenyl-cabonyl carbon bond. Also due to resonance there is double bond character in ...
2
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0answers
27 views

Amide from acyl azide

There are several reports of synthesis of amines from acyl azides via Staudinger reaction with triphenylphosphine. Are there any reports of Staudinger reactions of acyl azides to amides? If not, are ...
1
vote
2answers
60 views

Can nitrogens in urea be protonated?

Is it possible in very acidic solutions for the nitrogens ($\ce{N}$) to get another $\ce{H+}$, making it $\ce{R-NH2+-R}$? Since it has a free electron pair, it might be possible right? If so, at which ...
0
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2answers
52 views

Formation of Lactone from 5-amino-decanoic acid?

As expressed in the title, I am trying to figure out how to form a lactone from 5-amino-decanoic acid. The thing that comes to my mind as a start is the attachment of the amino group ($\ce{NH2}$) to ...
5
votes
1answer
159 views

How is NaOH able to clear a solution of Paraformaldehyde?

While making a solution of $4~\%$ para-formaldehyde for immunohistochemistry (to fix the tissue), we add para-formaldehyde into water and stir. It looks like a chalky supersaturated solution even ...
9
votes
0answers
70 views

Why are protic acids not used for the formation of thioacetals?

The standard procedure for protecting a carbonyl group as an acetal uses dry acid, such as $\ce{TsOH}$, but when forming a thioacetal, the Lewis acid $\ce{BF3}$ seems to be the catalyst of choice. For ...
1
vote
0answers
21 views

Reaction of PPh3 with a ketone

I understand that in the first step, mono-alpha halogenation occurs. Where I am slightly lost is in the second and third steps. Am I correct in thinking that because I have a substrate with a halogen, ...
1
vote
1answer
106 views

IUPAC name for citric acid

I was wondering what the name is of the following structure: I think it's something like ... 3-hyrodxypentanoic diacid However, I wasn't able to find how to name ...
3
votes
2answers
52 views

Competitive protonation between alkene and carbonyl

Given this compound in an acidic medium, what would get protonated first? Would the double bond not get protonated preferentially, since oxygen is more electronegative than carbon and less willing to ...
1
vote
0answers
74 views

Why does two phenylhydrazine molecule react with glucose in osazone formation?

From Wikipedia: It involves two reactions. Firstly glucose with phenylhydrazine gives glucosephenylhydrazone by elimination of a water molecule from the functional group. The next step involves ...
10
votes
1answer
191 views

Mechanism of a dephenylation reaction

I recently came across this reaction in my undergraduate labs. The experiment is taken from this article: J. Chem. Educ., 2008, 85, 413. The condensation of 2-methoxynaphthalene with cinnamoyl ...
4
votes
2answers
111 views

Chemoselectivity in synthesis of paracetamol

In the reaction below, why does acetic anhydride not react with the -OH group to form an ester instead?
5
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1answer
145 views

How to dialkylate a cyclohexene, and convert a carbonyl to an alkene?

I'm trying to design a synthesis of D from C. All I can think of is using $\ce{Me2CuLi}$ to add the methyl group to the alkene. I thought maybe then if isobutyl bromide was in the reaction mixture ...
4
votes
1answer
190 views

Why does LiAlH4 reduce an amide to an amine but only reduce a ketone/aldehyde to an alcohol?

Here are two different reactions in which lithium aluminium hydride, $\ce{LiAlH4}$, reduces a carbonyl group: Why does $\ce{LiAlH4}$ completely remove the oxygen from the amide but only reduces the ...
3
votes
1answer
44 views

aldol or no aldol?

Will 2-methylbutanal undergo aldol condensation? We are taught that it will not because the +I effect makes the carbanion unstable but if we make an enolate ion, isn't it resonance stabilized by the ...
4
votes
1answer
91 views

Naming compounds with multiple -COX functional groups

I know that this compound is named propanoyl chloride. However I am not sure what to do when here are multiple -COX groups and they are of the highest seniority. There are two cases, when they are ...
0
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0answers
31 views

How can I create crotonaldehyde using only mineral reactants?

I tried using alkylation to get the correct chain lenght, but I can't find a way to create the double bond. I'm a total novice at chemistry, so please forgive my ignorance.
4
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1answer
83 views

How to explain two NMR spectra of the (allegedly) same compound with slightly different shifts?

For my synthetic lab work I synthesised a Horner-Wadsworth-Emmons phosphonate; for the sake of the question let’s assume it to be the one presented in the image below. When first synthesising it, I ...
-1
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1answer
65 views

Naming compound with multiple carbonyl and/or hydroxyl groups

I think I understood the main idea behind naming compounds with carbonyl groups, however I am not sure about a few things. For the first compound, there is more than one carbonyl group and one of ...
5
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1answer
128 views

Decarboxylation / Elimination type reaction

I'm quite familiar with E1/E2 reactions and usually use those ideas to explain elimination reactions, however I came across a reaction which was a bit different (in the sense it isn't E1/E2) but still ...
3
votes
1answer
41 views

Why can't you use m-CPBA to synthesise isophorone oxide from isophorone?

Apparently you must use sodium hydroxide and hydrogen peroxide because using m-CPBA gives an undesired product Why doesn't m-CPBA work and what does it do instead? Why does sodium hydroxide and ...
0
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0answers
24 views

The density of ketene

On Wikipedia it says that the density of ketene is 1.93 grams per cubic cm, but that can't be true, can it?
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0answers
36 views

Whether amino acids exist as zwitterions in the liquid and gaseous phases

I am aware that in the solid state pure amino acids are crystalline structures composed of zwitterions, however I cannot find any information about whether somehow this changes as they move into ...
0
votes
1answer
48 views

Relative stability of carboxylic acid derivatives

This picture depicts the relative stability associated with resonance structure. My questions are: 1.1. Teacher says anhydride is less stable because of two reasons above. but it seems there's no ...
2
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0answers
32 views

How to explain the different regioselectivity of ketones/imines reacting with LDA?

When 1 equivalent of LDA is reacted with, for example, 2-pentanone, you get the thermodynamic (more substituted) product. But when you react butan-2-imine with 1.0 LDA, you receive the kinetic (less ...
7
votes
1answer
135 views

Single step transformation of a carboxylic acid into an aldehyde

What are the different ways of transforming a carboxylic acid into an aldehyde in a single step ? (as opposed as for instance first transforming it to an ester then to an aldehyde) The bottom of this ...
0
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2answers
86 views

Reactions of ketones and aldehydes

Our topic was about ketones and aldehydes (carbonyl group) including hemiketals and hemiacetals and he asked us to do a homework. I cannot find an answer to this one.Please explain me the reaction and ...
5
votes
1answer
312 views

Doubt in Mechanism of Dieckmann Reaction

In the following mechanism of the Dieckmann Condensation, the product has been formed in the fourth step, but still the reaction proceeds and $ \ce{RO^{-}}$deprotonates the product. Then $\ce{H^{+}}$ ...
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0answers
47 views

Doubts with the reaction mechanism?

Here, this is the question and my approach. The product is coming out to be correct as mentioned in the answers, but I want to confirm the reaction mechanism. Also, what will happen if I add $\ce{...
1
vote
0answers
21 views

Number of stereo-isomeric products?

This is the question:- And this is my approach:- As you can see, according to my solution, the answer should be 2. But the answer is 4. Also, I have doubt in the first step that whether the anion ...
0
votes
1answer
46 views

Why only the unstable resonating structure proceeds in the reaction?

For example, in the given image, I have starred the step where the relatively unstable resonating structure proceeds forward in the reaction. Why?
4
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0answers
44 views

Does the synthesis of beta-keto phosphonates from esters have a name?

Consider the Horner-Wadsworth-Emmons reaction; one of its reactants is a phosphonate, usually stabilised by a β-carbonyl group which is then deprotonated in α position (figure 1). These ...
5
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0answers
71 views

Which will be the most acidic hydrogen in the following organic compounds?

Which will be the most acidic Hydrogen in both cases? Please explain. According to me, in the first compound 2 should be most acidic as in both 1 and 2, resonance occurs but 2 Carbon is closer to O, ...
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0answers
17 views

Resonance in carbonyl compounds [closed]

In the given compounds, the first compound exhibits resonance, but not the second one. Why? The electro-negativity difference, that's why? Answer in detail.
1
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0answers
37 views

Steric factor v's electronic factor?

When water approaches both of them, no reaction is seen in the first compound, but the second compound react readily with water. In my notes, it is written that CH3 causes steric effect and also +I ...
7
votes
2answers
447 views

Does acetic acid give a positive result with the iodoform test?

Acetic acid contains a $\ce{-COMe}$ group, so theoretically, it should give a positive result in the iodoform test (i.e. a yellow precipitate of $\ce{CHI3}$ being formed). But apparently the iodoform ...
0
votes
1answer
90 views

Is Carboxylic acid more soluble than ester? [closed]

Which is more soluble in water? I believe both of are sort of soluble in water as they have C=O and C-O, polar bonds which make them polar compound. But I'm not really sure how the structure can ...
10
votes
2answers
361 views

Nomenclature of a cyclic ketone

Why isn't this molecule named 2-fluorocyclopent-1-one?
2
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1answer
67 views

I am confused about the stability of carbanion III and IV in the image

I am confused about the stability of carbanion III and IV in the image, I think III is more unstable because of electron donating effect (+R) of -OCH3 group but my book says III is more stable than ...
3
votes
2answers
603 views

Why does benzaldehyde not respond to Fehling's test?

All aldehydes are supposed to respond to Fehling's test. So why doesn't benzaldehyde respond to it? Does it have something to do with the fact that benzaldehyde is an aromatic compound? If so, then ...
4
votes
3answers
198 views

Which tautomer of hexane-2,4-dione is more stable?

Which tautomer will be more stable? Both 1 and 2 show intramolecular hydrogen bonding and form 6 membered cyclic ring, thus increasing the stability. I think I need to compare the effect of the two ...
2
votes
0answers
90 views

Does acid anhydride give a positive iodoform test?

I thought that acetic anhydride $\ce{CH3COOCOCH3}$ would give a positive Iodoform test because it has a $\ce{CH3-(CO)}-$ group.But it is given that this does not happen. Is this true? If so, can ...
6
votes
0answers
88 views

Masamune's rule of diastereoselectivity multiplicity

In a reaction between a chiral substrate and chiral reagent, their asymmetric inductions could cooperate (matched pairs) or compete (mismatched pair). According to Masamune, in a matched pair the ...
1
vote
2answers
57 views

Reduction of N,N-dimethylbenzamide with LiAlH4

Consider the reaction $$\ce{C6H5CON(CH3)2->[\ce{LiAlH4}]$\:\:$?}$$ What will the product be? According to me the product should be $\ce{C6H5CH2OH}$ but I am not sure. Also, I don't have any ...