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 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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Why do some nucleophiles attack at the carbonyl group while others at an alpha-carbon?

I was observing the following reaction: The only part I am confused on is the first step... why does the peroxide oxidize the reactant by attacking the alpha carbon of the carbonyl ester instead of ...
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1 vote
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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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-1 votes
1 answer
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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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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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1 vote
1 answer
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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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1 vote
1 answer
103 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-...
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1 answer
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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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1 answer
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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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1 answer
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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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2 votes
0 answers
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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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0 answers
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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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3 votes
1 answer
112 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. ...
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1 vote
1 answer
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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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5 votes
1 answer
310 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)...
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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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4 votes
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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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5 votes
1 answer
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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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3 votes
1 answer
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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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6 votes
0 answers
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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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1 answer
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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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4 votes
1 answer
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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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2 votes
0 answers
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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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0 votes
1 answer
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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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2 votes
1 answer
56 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 ...
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3 votes
0 answers
26 views

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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0 answers
17 views

What is the protocol for esterification reaction between nanocellulose and tartaric acid?

I am trying to prepare nanocellulose esters via esterification with Tartaric acid. I know that the traditional method employs a strong acid such as sulfuric acid. What would the process look like in ...
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1 vote
0 answers
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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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3 votes
2 answers
112 views

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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2 votes
0 answers
67 views

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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1 vote
0 answers
111 views

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 ...
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0 votes
1 answer
55 views

Mesylation of cyanohydrins [closed]

Is it possible to add methane sulfonyl chloride to benzaldehyde cyanohydrin, or add toluene sulfonyl chloride to form the tosylate group on the alcohol and then perfom a grignard reaction on the ...
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6 votes
1 answer
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Do all α-hydroxy ketones give Tollens’ test?

It is well known that terminal α-hydroxy ketones give Tollens’ test, via tautomerisation. Also, α-hydroxy ketones flanked by aromatic groups give Tollens’ test, such as benzoin. But do all α-hydroxy ...
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2 votes
0 answers
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Why aren't both alpha-carbons halogenated when acetone reacts with chlorine under UV?

My book shows the following reaction: Why is only one alpha carbon halogenated? I googled, but couldn’t find anything on it.
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2 votes
1 answer
193 views

Reactivity of Benzaldehyde vs Acetaldehyde and Benzoic acid vs Acetic acid

I was trying to compare the reactivity between acetaldehyde and benzaldehyde. After some googling, I found out that benzaldehyde is less reactive than acetaldehyde because the benzene ring can ...
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5 votes
2 answers
385 views

Can Mg/ether reduce carbonyl groups?

One of the ways of preparing Grignard reagent is: $\ce{R-X ->[Mg/ether] R-MgX}$ However let's assume that a carbonyl group is present along with a halide in the substrate. Will $\ce{Mg/ether}$ ...
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5 votes
1 answer
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Possible dehydration after nucleophilic addition

Here is the question: My reasoning was the following: The ethoxide ion first abstracts a proton from the $\mathrm{sp^3}$ carbon of the cycloalkene. This carbon then attacks the electrophilic carbonyl ...
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3 votes
1 answer
538 views

Mechanism of decarboxylation of alpha-keto carboxylic acid

What is the probable mechanism for the following reaction? $\alpha$-Keto acids on heating with conc.$\ce{H2SO4}$ undergo decarboxylation to give monocarboxylic acids: Also, which of the two carbons (...
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1 vote
0 answers
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A problem on Intramolecular Cannizzaro's Reaction

My textbook has the following reaction given as a special case of Intramolecular Cannizzaro reaction: As far as I understand, here one Phenyl group migrates (instead of hydride ion) from the carbonyl ...
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1 vote
1 answer
251 views

Can a Lindlar catalyst reduce aldehydes, nitriles, and carbonitriles?

The major product obtained in the following reaction is: Question source: JEE Main 2019 The molecule shown as product is the official answer given by JEE from the given options. I have written the ...
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-4 votes
1 answer
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Does rearrangement occur in schmidt reaction? [closed]

I recently read about schmidt reaction in which a carboxylic acid is converted to an amine. While forming this, acyl carbocation $(\ce{RCO+})$ is formed, so does rearrangement takes place or reaction ...
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1 vote
0 answers
192 views

Etard's reaction

My textbook says the following on Etard's reaction: Now, if the alkyl group attached to benzene is an unsymmetrical or branched alkyl group, such as this: What will be the reaction product(s)? Which ...
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8 votes
1 answer
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Why does LiAlH4 reduce the double bond of cinnamaldehyde, whereas it does not reduce the double bond in crotonaldehyde?

$\ce{LiAlH4}$ is a strong reducing agent capable of breaking the double bonds. It does break the double bonds in cinnamaldehyde. Shouldn't $\ce{LiAlH4}$ be able to break the double bond in ...
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4 votes
0 answers
80 views

2-Iodoxybenzoic acid oxidation reaction

I was thinking about using 2-Iodoxybenzoic acid to selectively oxidize primary alcohols to aldehydes. I've found papers using various solvents like acetone/water mixture1, 2-methyl-2-propanol2, DMSO ...
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  • 203
0 votes
2 answers
69 views

Major product formed when 4-Methoxybenzil is reacted with a base

What will be the major product formed in the given reaction: I am not able to apply any of the reactions or mechanisms I know of in this case. The only thing I am able to predict is that the $\ce{OH-}...
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3 votes
3 answers
468 views

Decarboxylation of primary amino acids

Since primary amino acids like glycine, alanine can't be decarboxylated under oxidative conditions, what would be the best catalyst for this reaction? I was thinking about copying decarboxylases with $...
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3 votes
0 answers
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Does the nucleophilic substitution in an acid chloride always proceed through a tetrahedral intermediate?

I am a beginner in organic chemistry and would like to ask for the mechanism for the nucleophilic substitution of carbonyl groups from acid chloride - especially regarding the tetrahedral intermediate?...
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