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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48 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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1answer
154 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 $\ce{Mg/ether}$ ...
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1answer
259 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
163 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
88 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
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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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70 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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126 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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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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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
70 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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283 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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482 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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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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86 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
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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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69 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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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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65 views

ketone and amine condensation

My question is quite easy to solve. The question simply asked to find the final product of the reaction shown below, which I did. But the my question lies in the catalyst. What is the role of the ...
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1answer
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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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162 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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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
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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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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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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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276 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 ...
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1answer
101 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-...
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1answer
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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 $\ce{CH3COOC2H5}$ ...
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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
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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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Intramolecular Cannizzaro reaction product

I came across the following question : My reasoning was as follows : It can't be option (c) because there is no chance of losing a carbon during Cannizzaro's reaction It can't be option (b) because ...
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Reactivity order of DIBAL-H and diborane with esters and acids

I have been taught in class that DIBAL-H is more reactive towards esters than carboxylic acids while opposite is true for diborane. Also DIBAL-H mentioned is taken under low temperatures (−78 °C). I ...
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1answer
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Is the cannizaro reaction possible for a molecule having hydrogens attached to sp2 hybridised carbons?

As known benzaldehyde can undergo a cannizaro reaction in which a phenyl group is an electron donating group, so the reaction similar to below (of prop-2-enal) (cannizaro) should occur for similar ...
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A possible reaction of heating Terephthalic acid

There is no reaction of terephthalic acid heating effect on the internet (at least Wikipedia). I have written the most probable reaction possible as per my knowledge. Please tell if it is spontaneous ...
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1answer
148 views

Periodic acid oxidation of carbonyls?

The following reaction seem to be valid; $\ce{CH2OH-CHOH-CH2OH ->[HIO4]CH2O + HCOOH + CH2O + 2H2O}$ Apparently, there are similar reactions by 2,3-dihydroxypropanal, and also by the straight chain ...
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How can you qualitatively tell when the hydrolysis of aspirin is over?

I'm doing an experiment on the effect of temperature on the time taken to produce acetic acid and salicylic acid. Are there any qualitative observations I can make about when the reaction has finished?...
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On the use of hexane in the organic reduction by DIBAL-H

In some variations of the organic reduction by DIBAL-H, I've seen hexane used, as in this equation from this website; I've looked it up, but I haven't seen any explanation for why hexane's used there....
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Why is addition to acid chloride favoured over SN2 at the carbon even though it has a Beta-carbonyl?

I feel that the conditions highly favour $S_\mathrm{N}2$ reaction at the aliphatic center and so the aliphatic chlorine should be replaced before the carbonyl chlorine. But the solution suggests that ...
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1answer
193 views

Why is the formation of a peptide bond not spontaneous?

Why is the formation of a peptide bond from a carboxylic acid and amine not spontaneous? I'm not looking for the free energy calculation; I have it from several sources. I'm just asking for an ...
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Comparison of C=O bond strength in metal carbonyls

Find the weakest $\ce{C=O}$ bond among $\ce{[Mn(CO)6]+},$ $\ce{Fe[(CO)5]},$ $\ce{[Cr(CO)6]}$ and $\ce{[V(CO)6]-}.$ I thought the $\ce{C=O}$ bond strength would be lowest in $\ce{[V(CO)6]-}$ since the ...
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51 views

Possibility of removing two water molecules from glycerol

Not a chemist, but from a chemical formula perspective, how hard would it be to create acetone by acidifying glycerol? $$\ce{C3H8O3 + 2 H+ <=> C3H6O + 2 H2O}$$ Has anyone ever heard of this ...
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1answer
217 views

Why is 2-fluorobenzoic acid more acidic than 4-fluorobenzoic acid despite its intramolecular hydrogen bonding?

I was reading about $\mathrm{p}K_\mathrm{a}$ values of 2-fluorobenzoic acid and 4-fluorobenzoic acid and found that the latter had a higher value which was surprising to me. I think that ...
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1answer
34 views

How does NaOH modify pyranodioxins?

I am given the molecule in black which is treated with $\ce{NaOH}$. The product is in blue. Could someone explain the mechanism? All I have so far is that the $\ce{-OH}$ group on the bottom right ...

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