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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What is the mechanism of anthraquinone to anthrone using SnCl2 2H2O , acetic acid and HCl?

I have researched to find analagous reaction mechanisms but I cant seem to find anything. Im not the best at reaction mechanisms, however I do think the carbonyl bond transfers its electrons to the O ...
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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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65 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 ...
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1answer
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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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1answer
47 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 ...
2
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1answer
37 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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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 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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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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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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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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1answer
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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 ...
4
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1answer
244 views

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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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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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 $\ce{Mg/ether}$ ...
5
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1answer
262 views

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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1answer
304 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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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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1answer
138 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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1answer
50 views

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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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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1answer
144 views

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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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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2answers
68 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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3answers
252 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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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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1answer
96 views

Double bond or carbanion for nucleophillic attack [closed]

I came across this question: According to me the Hydride ion should take hydrogen from left (unsubstituted carbon) because carbanion will be more stable there and this carbanion will then act as a ...
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2answers
291 views

What is the major product in the reaction between 4-chloropentanal and lithium aluminium hydride?

What would be the major product between 4-chloropentanal and $\ce{LiAlH4}$? After the reduction of the aldehyde, would the hydroxyl group formed at $\ce{C-1}$ attack $\ce{C-4}$ causing cyclization to ...
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1answer
533 views

Does folic acid contain a benzyl or a phenyl group?

I'm studying for my MCAT currently and I stumbled upon this question. It gives the structure of a folic acid molecule and asks what functional groups can be found within the molecule. I understand ...
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1answer
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The dependency on electron density in the reactivity order of electrophilic and nucleophilic additions

It is well-known that for electrophilic addition across an alkene, the reactivity increases when intermediate carbocation is more stable (eg. addition of $\ce{HBr}$ or acid-catalyzed addition of $\ce{...
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158 views

Does formaldehyde and ethylene glycol give positive Fehling's test?

Fehling's test follows a single electron transfer mechanism, with electron transfer form the substrate to $\ce{Cu^2+}$, which forms $\ce{Cu^1+}$finally giving reddish brown precipitate of $\ce{Cu2O}$. ...
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1answer
81 views

D and L configuration of monosaccharides

I got this question in the last week's test from Organic Chemistry. I am a bit confused in assigning D and L configuration. Help me understand the topic of D and L configuration and help with this ...
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1answer
118 views

Why does a methyl shift occur during the pinacol-pinacolone rearrangement?

Why does a methyl shift occur during the pinacol-pinacolone rearrangement? I was told that methyl shift is done to stabilise the carbocation but here we are shifting the ...
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28 views

Trend in Boiling Points of Aldehydes vs Ketones

Up until 2-pentanone/3-pentanone and pentanal, the boiling points of unbranched ketones are higher than those of unbranched aldeyhdes that have equal number of carbons as explained by "matt_black&...
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1answer
118 views

What is the product when cyclohexanone reacts with morpholine?

The question asked to find the final product of the reaction between cylohexanone and morpholine. I attempted the reaction which is shown below: I have understood the heat symbol. It simply ...
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1answer
121 views

What is the LUMO of a molecule with an alkene and a carbonyl?

In a molecule that has both an alkene (C=C) and carbonyl (C=O) that are NOT conjugated, such as pent-4-en-2-one, how do you determine which π* anti-bonding orbital is the LUMO? Essentially, I'm trying ...
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1answer
172 views

What is the correct reaction mechanism?

I came across this question: I propose two things to happen: It can undergo Aldol condensation or it can undergo SN by replacing $\ce{-Cl}$ with $\ce{-OH}$. But apparently, both these mechanism ...
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1answer
73 views

Stereochemistry & mechanism of β-cyano enone methylation

I am helping a friend with some upper-level mechanism problems. We came across this one. This is my proposal. Do you agree/disagree? Thank you for any input. Source question:
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1answer
58 views

Why is the silver salt ammoniated to form the Tollen's reagent? [duplicate]

When doing a distinguishing test between aldehydes and ketones using Tollen's reagent, is it necessary to convert $\ce{Ag+}$ ions into $\ce{Ag(NH3)2+}$ in order to oxidize the aldehyde?
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1answer
176 views

Reaction of acyl chloride with excess Grignard reagent

I have a reaction to which I must find the majority organic product. I think I found the correct product but the fact that the reaction takes two moles of propylmagnesiumbromide confuses me a bit. I ...
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Why doesn't the acetic anhydride moeity react with the nucleophilic carbonyl oxygen of salicylic acid?

I know that salicylic acid with acetic anhydride under acidic conditions gives acetylsalicylic acid (aspirin). But my question is, why is it that post the protonation of carbonyl oxygen of acetic ...
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102 views

Mechanism for reaction between carboxylic acid and manganese(II) oxide [closed]

I am reading about redox reactions of carboxylic acids with $\ce{MnO}$ but I couldn't find any mechanism online,so can any one provide the mechanism.
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1answer
285 views

Synthesis of (1S,2S,4S)-4-ethenyl-5-methylcyclohexane-1,2-diol

I'm trying to devise a synthesis for the following question. I am aware it involves retrosynthetic, Wittig, Grignard and diels alder reactions, but unfortunately I can't really grasp all concepts ...
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Keto-Enol tautomerism acidity of α Hydrogen vs stability of double bond [duplicate]

If I consider a ketone that has an ethyl group and a methyl group attached to it. The α-Hydrogen of the methyl group would be more acidic than that of the ethyl group due to -I effect of the adjacent ...
6
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1answer
122 views

Will "soft nucleophiles" undergo 1,4-conjugate addition even if the β-carbon is sterically hindered?

In general soft nucleophiles do 1,4 conjugate addition to a carbonyl carbon under thermodynamic control. Will soft nucleophiles like organocuprates still preferentially undergo 1,4 addition if the β-...
3
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1answer
72 views

Synthesis of diethyloxalate from ethene

Outline the steps involved in the following transformation: $\ce{C2H4}$ to $\ce{(COOC2H5)2}$ (diethyl oxalate). I am familiar with the transformation of $\ce{C2H4}$ to ethyl acetate $\ce{CH3COOC2H5}$ ...
6
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2answers
186 views

Mechanisms for Reimer-Tiemann and Kolbe-Schmidt reaction on deuterium labelled phenol

I was solving a bunch of reactions when I encountered the following: So for the first question: This is a Reimer-Tiemann reaction. I felt that the tautomerism would result in the deuterium getting ...
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1answer
79 views

Determining the most stable enolic form of 1-phenylbutane-1,3-dione?

Question Which form of 1-phenylbutane-1,3-dione is more stable? Answer 3-hydroxy-1-phenylbut-2-en-1-one My question I've been told that between the above two, 3-hydroxy-1-phenylbut-2-en-1-one is ...

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