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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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
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2 answers
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Tollen's Test - Clean Up

In school, we had an experiment to find out the biomolecules contained by the different food-stuffs. After doing Tollen's test which turned out to be positive, our teacher instructed us to clean the ...
Harikrishnan M's user avatar
3 votes
1 answer
148 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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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
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4 votes
1 answer
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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
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1 answer
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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
120 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
169 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
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2 votes
2 answers
184 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
107 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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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
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2 answers
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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
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1 answer
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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
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1 answer
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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
1k 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
97 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
308 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
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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
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7 votes
1 answer
452 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
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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
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4 votes
1 answer
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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
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3 votes
0 answers
200 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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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
133 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
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0 answers
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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
70 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
265 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
316 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
161 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
1k 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
143 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
  • 362
3 votes
1 answer
252 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
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1 vote
1 answer
78 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
34 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
98 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
459 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
302 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
1 vote
1 answer
59 views

How to find out amount of carbon in metal

I am an student of archaeology and on my final work I am working with mining hammers, on which metallography was used. But my supervisor want to use some kind of acid on the surface of the metal so it ...
Filip Vološin's user avatar
5 votes
1 answer
963 views

Should the principal carbon chain contain maximum number of functional groups or just the principal functional group?

My answer was the 6 carbon chain, i.e. the name would be 2-(2-hydroxyethyl)-4-methylhexanoic acid. But the given answer is the 4 carbon chain, i.e. the name would be 4-hydroxy-2-(2-methylbutyl)...
Righter's user avatar
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1 vote
0 answers
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Comparing acidic strength of acetic and p-anisic acids

In p-anisic acid the phenyl ring with methoxy group acts as strong electron donating group by mesomeric effect (+M), whereas in acetic acid there is only an electron donating nature by inductive ...
TeslaBolt's user avatar
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4 votes
0 answers
92 views

A Multistep Reaction Provided with IR Spectra (Guessing Started with Esterification)

Below, IR spectra for this sequence are provided: For compound E, I suggest the formation of a conjugated ester with the elimination of $\ce{-OH}$ group. The IR peak at $\pu{1732 cm-1}$ is a ...
user4723's user avatar
  • 305
9 votes
2 answers
549 views

Comparing acidic strength of crotonic and isocrotonic acids

Compare acidic strength of crotonic acid (1) and isocrotonic acid (2): On comparing $\mathrm{p}K_\mathrm{a}$ values, cis-form $(4.44)$ turns out to be more acidic than the trans-form $(4.69)$. Most ...
Acc2's user avatar
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5 votes
0 answers
481 views

Comparing acidic strength of phthalic acid isomers

I'd like to compare the acidic strengths of phthalic, isophthalic and terephthalic acids. As I understand, phthalic acid is the most acidic due to steric inhibition of resonance (SIR), but as ...
TeslaBolt's user avatar
  • 156
3 votes
1 answer
326 views

Why does BH3/THF reduce the carbonyl group to a methylene rather than an alcohol?

This reaction is taken from: Pintér, Á.; Sud, A.; Sureshkumar, D.; Klussmann, M. Autoxidative Carbon-Carbon Bond Formation from Carbon-Hydrogen Bonds. Angew. Chem., Int. Ed. 2010, 49 (29), 5004–5007. ...
Eastman CAO's user avatar
6 votes
0 answers
131 views

Why are the unsaturated fatty acids usually unconjugated?

My textbook gives the structures of the unsaturated fatty acids in food including oleic acid, linoleic acid, linolenic acid and docosatetraenoic acid. I figure that when two or more $\ce{C=C}$ double ...
jiande's user avatar
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-1 votes
1 answer
105 views

What is the product when alcohol is added to carbonyl compounds? [closed]

How do we know if, on adding alcohol to carbonyl compound: nucleophilic addition reaction will take place or alcohol will take alpha hydrogen to form a carbanion and consequent aldol condensation ...
aaravm's user avatar
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4 votes
1 answer
119 views

What's the factor governing the order of wavenumbers of CO in metal carbonyls?

As a higher wavenumber means a lower wavelength, which in turn means higher energy, the complex with the most effective backbonding would have the least wavenumber. The backbonding, as I know, is ...
lazearoundallday's user avatar
2 votes
0 answers
141 views

IR Stretching in Hexacarbonyl Iron

With reference to this graph, my professor stated the following: "Since the IR band for the bridging carbonyls is single, it implies that the bridging carbonyls are oriented linearly. Since we ...
lazearoundallday's user avatar
0 votes
1 answer
295 views

Does changes in pH affects cyclic form of glucose in water solution?

Glucose in water solution is mainly in cyclic form. Both base and acid can catalize formation of hemiacetal, but in distinct mechanisms. I found information that monosacharides eg. glucose exist ...
Krzysztof Dryjka's user avatar
2 votes
1 answer
118 views

Why does the reaction of Brady's reagent and cyclohexanone not also form an enamine-type product?

In this reaction in a Khan academy video, cyclohexanone reacts with Brady's reagent to form hydrazone product. My question is why doea Brady's reagent + cyclohexanone not also form an enamine product ...
user119200's user avatar

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