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 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 ...
1
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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 ...
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2
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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 ...
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0
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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?
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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 ...
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2
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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. ...
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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}...
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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 ...
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2
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1
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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 ...
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1
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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"
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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 ...
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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 ...
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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 ...
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1
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0
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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 ...
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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 $4n + 2$ ...
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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(...
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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 ...
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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 ...
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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 ...
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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-...
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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 ...
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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?
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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 ...
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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-...
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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-...
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Why is the cyclic form of glucose more stable than the linear form?
I am aware of this question
What makes the cyclic structure of glucose more stable than the open chain structure?
This is meant as a sort of follow-up question and if possible I would prefer if any ...
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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 ...
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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 ...
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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 ...
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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 ...
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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 ...
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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.
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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 ...
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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)...
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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 ...
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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 ...
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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 ...
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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 ...
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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. ...
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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 ...
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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 ...
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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 ...
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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 ...
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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 ...
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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 ...
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0
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Are Wacker oxidations tolerant of carbonyl groups?
I was wondering if there was anything in the mechanism of a Wacker oxidation that would interfere with ketones or aldehydes already present in the molecule. Ketones and aldehydes can't be oxidized any ...
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What is the condition to have a schiff base precipitate for sulfonamides?
In the sulfonamides group we observe that some category (like sulfanilamide, sulfamethizol) gives products of condensation with carbonyl so a precipitate, whereas other category (like sulfaguanine, ...
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Acidic strength comparison of squaric acid and rhodizonic acid
These two are dibasic acids with the following structures (squaric acid and rhodizonic acid in order).
Empirical evidence proves that squaric acid is more acidic than rhodizonic acid.
It is a ...
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0
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When do the Wolff-Kishner Reduction and Clemmensen Reduction not take place for carbonyl compounds?
I came across some examples of organic compounds with acidic groups that didn't undergo the Clemmensen reduction. So, I was wondering which types of compounds the two reagents cannot reduce. Also, why?...
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0
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IUPAC name for compound with various carbonyl groups
I found this question on a resource video for IUPAC Nomenclature for a competitive exam. It would be great if someone provided the approved IUPAC approved name for this compound. Source of the ...
