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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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 ...
Jonathan's user avatar
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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 ...
mark's user avatar
  • 201
-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&...
Aurelius's user avatar
-3 votes
1 answer
85 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 ...
i dont know how to code's user avatar
0 votes
1 answer
128 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 ...
Vinay5101's user avatar
1 vote
0 answers
20 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 ...
AVS's user avatar
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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.
kzmom's user avatar
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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 ...
AVS's user avatar
  • 481
-3 votes
1 answer
140 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 ...
SAM4RTH's user avatar
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 ...
Akilan SS's user avatar
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 ...
Matt's user avatar
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-1 votes
0 answers
201 views

Temperature dependence of aldol condensations [duplicate]

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 ...
Harikrishnan M's user avatar
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 ...
AVS's user avatar
  • 481
-4 votes
2 answers
990 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
Patrick Schick's user avatar
4 votes
2 answers
289 views

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

In school, we had an experiment 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 ...
Harikrishnan M's user avatar
3 votes
1 answer
221 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 ...
AtoZ's user avatar
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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 ...
Fighter's user avatar
  • 21
4 votes
1 answer
280 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)...
Brenlla's user avatar
  • 191
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) ...
Muhammad Ihsan's user avatar
-5 votes
1 answer
200 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 ...
TheBorcanu's user avatar
1 vote
1 answer
255 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 ...
Chuck's user avatar
  • 23
2 votes
2 answers
311 views

Protonation in acid-catalyzed nucleophilic attack of alcohol on carbonyl

When studying acid-catalyzed nucleophilic attack of alcohol on carbonyl, I got puzzled by the first protonation step. In textbooks, they often show that the first step is to protonate the carbonyl ...
AlojzyBąbel's user avatar
3 votes
0 answers
133 views

Why is a protonated carboxylic acid less acidic than a protonated ester?

To my understanding, both have analogous resonance structures except that the ester has on -OR and the carboxylic acid has an -OH. Why is a positive charge on C-O-R more stable than on C-O-H?
gxyzv's user avatar
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1 vote
0 answers
89 views

Why are crystals of carboxylic acid fluffy

I'm an undergrad student and we recently performed saponification of esters which resulted in the formation of carboxylic acid which we had isolated out of the reaction mixture. After ...
Stu's user avatar
  • 29
-2 votes
2 answers
95 views

Racemization at stereogenic centre [closed]

I am getting a bit confused about why the configuration at the optical centre changes from d to l after enolization? Any stereogenic centre next to a carbonyl group will be destroyed by enolization. ...
Cara's user avatar
  • 15
-1 votes
1 answer
486 views

What kind of isomers are ethyl butanoate and propyl propanoate?

Are ethyl butanoate (1) and propyl propanoate (2) metamers or functional group isomers? My book claims they are metamers, but here one group is $\ce{-CO-OR}$ and another is $\ce{-CO-OR'}$ where $\ce{R}...
a_i_r's user avatar
  • 107
1 vote
1 answer
129 views

Does acrylic resin in acetone react with the same acrylic resin in ethyl acetate?

I am not at all familiar with organic chemistry. I am working in museum conservation where an acrylic resin (such as Paraloid B-72) is mixed acetone and sometimes ethyl acetate to produce a resin for ...
museumguy's user avatar
2 votes
1 answer
2k views

Oxidation of toluene, ethylbenzene and styrene with potassium permanganate in acidic medium

While I was studying my organic chemistry textbook, I came across the following reactions that need more clarifications: Oxidation of toluene (1) is the only reaction from the textbook, and I ...
donthababakka's user avatar
0 votes
1 answer
117 views

Is formation of cyclic carbonate from trimethyl orthoformate and vicinal aromatic 1,2-diol possible? [closed]

Hello, my question is, "is it possible cyclic carbonate formation between trimethyl orthoformate and vicinal aromatic 1,2-diol"
Sajad Khanlarkhani's user avatar
5 votes
1 answer
399 views

Why does the 1H NMR spectrum of methacryloyl chloride show two singlets instead of two doublets for vinyl protons?

Based on what I have understood, for methacryloyl chloride there is a geminal coupling of the vinyl protons since they are not chemically equivalent. Why are two singlets observed for vinyl protons ...
Elnani's user avatar
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3 votes
0 answers
283 views

What Is This Small Peak That Always Occurs Within Ketone Infra-Red Analysis?

After looking at a bunch of IR spectrums for ketones, I have noticed this tiny peak that I circled on the diagram below. Does anyone know what it actually is and if I can always use it to distinguish ...
Jamo's user avatar
  • 31
7 votes
1 answer
467 views

Retrosynthesis of (2E)-1-(2,4-dimethylphenyl)-3-(thiophen-2-yl)prop-2-en-1-one

I am struggling to find a way to disconnect this molecule and I am unsure of the order: First, I was thinking of disconnecting the C=C of the α,β-unsaturated carbonyl. Then for the thiophene group ...
Charlotte's user avatar
1 vote
0 answers
114 views

Wittig reaction without ketone or aldehyde?

In the reaction below the ethylene glycol would react with the ketone in the first step turning it into a protecting group. How would the ylide react, as I thought it only reacts with ketones and ...
crisps's user avatar
  • 107
4 votes
1 answer
790 views

Is 2-pyrone an aromatic compound?

I was told by my professor that α-pyrone is not an aromatic compound, but I count two π-electrons as well as one of the lone pairs on oxygen giving six total which would be one of Hückel's $4n + 2$ ...
crisps's user avatar
  • 107
3 votes
0 answers
253 views

Use of boron(III) oxide for drying acetone

Acetone undergoes aldol self-condensation in the presence of acids or bases: which makes drying agents such as 3A/4A molecular sieves, barium oxide, potassium hydroxide and carbonate (basic), copper(...
andselisk's user avatar
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0 votes
0 answers
43 views

Why isn't formyl chloride stable? [duplicate]

I am currently studying methods of synthesising ketones and aldehydes and one of the methods is Friedel-Crafts acylation. However, my teacher told our class that we can't use this to make benzaldehyde ...
math and physics forever's user avatar
6 votes
1 answer
213 views

Does methyl or aldehyde group have higher priority when choosing the main chain of carbonyl compound?

As far as I know, both following names seem to be correct for the compound below. Please explain which IUPAC name is correct by which IUPAC rules: 4-formylpentanoic acid (methyl group counted in the ...
Praveen's user avatar
  • 61
1 vote
0 answers
95 views

Rearrangement vs. Ring Strain in Cyclobutanecarboxaldehyde Nucleophilic Reaction

Predict the major product of the following reaction: Note: Product A is incorrectly marked as secondary halide, it should have been primary halide This question appeared in an national level ...
Prajval K's user avatar
-1 votes
1 answer
73 views

How to synthesize 1,1,1-trichloro-2,4-dimethylpentan-2-ol from methyl isobutyl ketone?

Chlorobutanol can be made with chloroform and acetone in the presence of potassium or sodium hydroxide. Would it work with other ketones such as methyl isobutyl ketone to yield 1,1,1-trichloro-2,4-...
That Guy's user avatar
3 votes
1 answer
455 views

Does carboxyl group interfere with reaction of 2-carboxybenzaldehyde with NaCN/HCl?

The aldehyde group of 2-carboxybenzaldehyde reacts with $\ce{NaCN/HCl}$ forming cyanohydrin. Does the carboxyl group remain intact? Does it react separately or with the cyanohydrin? I suspect possible ...
ultralegend5385's user avatar
0 votes
0 answers
369 views

Why isn't the Leuckart reaction used to make (meth)amphetamine?

For example, in Breaking Bad, they synthesize meth from phenylacetone. Why not just use methylammonium formate, if they already have methylamine?
kvanderfluegh's user avatar
1 vote
1 answer
278 views

Hydroboration then oxidation with carbon monoxide and hydrogen peroxide

Thus is the question given in my textbook This is my attempt at the question This is the solution given in the textbook. I don't understand how a ketone is formed instead of an acid. related ...
Manit Agarwal's user avatar
1 vote
1 answer
2k views

Effect of electron-donating and electron-withdrawing groups on the C=O bond

My notes states this: An electronegative element tends to draw in the electrons between the carbon and oxygen atoms through its electron-withdrawing effect. This strengthens the C=O bond. An electron-...
warren's user avatar
  • 67
2 votes
1 answer
157 views

Why is aminolysis of esters never drawn with an initial protonation step?

I had noticed that the aminolysis of esters is always shown without an initial protonation step: Mechanism for formation of amide by reaction of amine with ester https://www.chemistrysteps.com/esters-...
Heat's user avatar
  • 360
3 votes
1 answer
272 views

Systematic and preferred names of acetamide

My book says to use carboxamide when it is a carboxylic acid derivative (acyl). Ethanamide $\ce{CH3CONH2}$ is a carboxylic acid derivative, so shouldn’t it be named ethan-1-carboxamide rather than ...
Shashaank's user avatar
  • 352
1 vote
1 answer
101 views

How do I understand the IUPAC naming of 9-methyl-3-[(2-methylimidazol-1-yl)methyl]-2,3-dihydro-1H-carbazol-4-one? [closed]

I'm having trouble understanding the IUPAC naming convention of 9-methyl-3-[(2-methylimidazol-1-yl)methyl]-2,3-dihydro-1H-carbazol-4-one. It would be great if you can help to breakdown the naming ...
Lv.0 Shian's user avatar
1 vote
0 answers
35 views

What is the mechanism of the reaction between 1(3H)-Isobenzofuranone and benzaldehyde?

I have been trying to deduce a reaction mechanism for the reaction between the two compounds to give the compound labeled 2 in the diagram but I do not think I have a satisfactory answer. My thinking ...
Samuel Wango's user avatar
2 votes
0 answers
121 views

Various pathways of an alpha diketone reaction

This is a question from JEE Advanced 1997. I have found two possible products of the reaction: By intramolecular aldol condensation: By benzil-benzilic acid type rearrangement: Which reaction takes ...
Lost Anisole's user avatar
0 votes
0 answers
531 views

Resonance structure with allylic lone pair

Draw the appropriate resonance structure for 5-aminolevulinic acid: As there is an allylic lone pair, my first arrow goes from the lone pair to form a π-bond, and the second goes from the π-bond to ...
ninja_fun's user avatar
3 votes
1 answer
356 views

Can a carbon that has 5 bonds be explained by saying that one of its bonds is a coordination bond?

In my organometallic chemistry class at the university, the doctor told us that compound μ³-CO-[Fe₄(CO)₁₂]²⁻ had the structure that appears in the image. As you can see, there is a pentavalent carbon. ...
Fernando Gonzalez's user avatar

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