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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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10
votes
1answer
602 views

What is the significance of the 2 and 4 positions in 2,4-DNP?

2,4-dinitrophenylhydrazine, a popular laboratory reagent is used to identify carbonyl compounds by forming 2,4-dinitrophenylhydrazones, which are often red or yellow colored precipitates. Why is the ...
0
votes
1answer
63 views

Will an acyl chloride be attacked by water molecule to form carboxylic acid?

$\ce{H2O}$ molecules can act as a nucleophile. So it should attack the carbonyl carbon. However, I think that that when the $\ce{O-}$ "kicks back" it will once again remove the water molecule keeping ...
1
vote
3answers
341 views

Can any other common reagent other than than H3PO4 cause this conversion?

Can any other common reagent other than than $\ce{H3PO4}$ cause this conversion? What about (conc) $\ce{H2SO4}$ or (conc) $\ce{HNO3}$ or (conc) $\ce{HCl}$?
8
votes
0answers
128 views

In the mechanism of Cannizzaro reaction why does the hydride migrate rather than the benzene ring? [duplicate]

The hydride ion is not very stable. On the contrary a negative charge on a $\ce{sp^2}$ on the benzene ring would be much more stable. So why doesn't the benzene ring migrate instead of the hydride, as ...
0
votes
2answers
251 views

Explain the selectivity in bromination of this compound with two substituted benzene rings

As I know, when $\ce{Br2/FeBr3}$ is added to acetophenone ($\ce{C6H5-CO-CH3}$), Br will substitute a H from the meta position which leads to 3-bromoacetophenone. So why doesn't a Br substitute a H ...
3
votes
2answers
2k views

Does acetamide respond positively to iodoform test?

This answer explains why acetic acid does not give a positive iodoform test. Does acetamide respond positively to the test?
2
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3answers
3k views

Why do carbonyl compounds undergo nucleophilic and not electrophilic addition?

Why aldehydes and ketones undergo nucleophilic addition reactions and not electrophilic addition? Alkenes show electrophilic addition because of pi bond, which is also present in aldehydes and ...
5
votes
2answers
664 views

Reaction of coumarin with phenylmagnesium bromide

I came across this problem.. I thought that the Grignard reagent, PhMgBr, would cleave the lactone and then subsequently add to the ketone formed, giving an allylic tertiary alcohol after aqueous ...
6
votes
1answer
432 views

Can you produce activated carbon from toast?

On the Skeptics stack exchange we have a question about burned toast being used as a treatment for poison, the idea being that burned toast acts as activated carbon. We are skeptical due to the fact ...
11
votes
1answer
205 views

Mechanism of radical cyclisation to form hydroazulene core

Recent studies on radical-induced cyclisation reactions have led to a simple, one-step method for the preparation of hydroazulenes from appropriately substituted cyclopentanone precursors. Treatment ...
8
votes
1answer
2k views

Why doesn't this β-hydroxycarboxylic acid undergo dehydration upon heating?

This is a β-hydroxyacid, but why doesn't it get dehydrated to give an α,β-unsaturated acid on heating? The mechanism which I think should occur is:
-3
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1answer
856 views

Why does aceto acetic ester not respond to haloform test even though it has a keto methyl group? [closed]

Why does aceto acetic ester not respond to haloform test even though it has a keto methyl group?
2
votes
0answers
511 views

What should be the correct sequence of reagents to be used in this reaction?

The correct sequence of reagents for the following conversion will be (1) $\ce{CH3MgBr, H+/CH3OH, [Ag(NH3)2]+OH-}$ (2) $\ce{CH3MgBr, [Ag(NH3)2]+OH-, H+/CH3OH}$ (3) $\ce{[Ag(NH3)2]+...
-1
votes
1answer
356 views

How would you carry out complete reduction of enone to form saturated alcohol?

I have been reading some literature on enone reduction. Some conditions favour enol formation, others favour ketone formation. For example, using $\ce{NaBH4}$ with $\ce{CeCl3}$ selects the unsaturated ...
1
vote
0answers
133 views

synthesis of bicyclic diol from cyclohexanone

I am trying to come up with a synthetic route for the following reaction, my ideas below it. I think it is a bit of a long shot making this alkene as it would probably be quite strained-any other ...
4
votes
2answers
294 views

How to synthesize 1,3-pentadiene from butanal?

How do you synthesize 1,3-pentadiene from butanal? I have the (possible) last steps of bromination of 1-pentene at the allylic position and then an E1 reaction to give the final product. I don't ...
1
vote
0answers
508 views

Why is the hydrogen adjacent to carbonyl carbon of aldehyde not acidic?

In $\ce{H^a-CH_2-CO-H^b}$, why is $\ce{H^a}$ more acidic than $\ce{H^b}$ ? From what I know, $\alpha$ hydrogen ($\ce{H^a}$) is highly acidic and is easily abstracted in presence of base $\ce{OH^-}$. ...
8
votes
2answers
5k views

Dess–Martin oxidation work up

I'm doing an oxidation of an alcohol with Dess–Martin periodinane which works really well but having trouble with the work up. Doing this reaction with about 5 g of alcohol so the reaction ends up ...
4
votes
1answer
1k views

Can decarboxylation of carboxylic acids be effected by bases other than soda lime?

What about other bases such as Group 1 or Group 2 hydroxides? Does it have to do something with the mechanism? I don't understand the mechanism either: What is NaOH supposed to with the acetate ion? ...
7
votes
2answers
13k views

Does Br2/H2O oxidize all aldehydes?

In many books, it is mentioned that aldehydes are easily oxidized even by mild oxidizing agents. However, I have never seen bromine water explicitly mentioned. But in the carbohydrates chapter, it is ...
7
votes
1answer
685 views

Ambigious nature of aldehydic group in glucose

In aqueous solution, α-anomer and β-anomer of glucose remain in equilibrium with each other along with a small amount of glucose in open chain form ($0.02~\%$). The open chain form in ...
9
votes
1answer
2k views

Mechanism of homologation of aldehyde to alkyne: Ohira–Bestmann reaction

This reaction was part of an organic scheme I was doing, and I was wondering what the mechanism of the reaction would be. I tried first forming a carbene by letting $\ce{N2}$ leave from the ...
5
votes
2answers
2k views

Factors affecting strengths of carboxylic acids [closed]

For carboxylic acids, I read that electron-withdrawing groups like CF3 allow the anion resulting from dissociation to be more stabilized. However if CF3 is replaced with an electron-donating group ...
14
votes
1answer
2k views

Mechanism for basic hydrolysis of α-chloronitrile to ketone?

In Corey's 1969 prostaglandin synthesis,1 compound 2 is formed from compound 1 by: [...] treatment with 2.5 equiv of potassium hydroxide (added as a hot saturated aqueous solution) in dimethyl ...
5
votes
1answer
1k views

How is phosphoryl chloride attaching an aldehyde to benzene?

This reaction was part of an organic scheme I was doing: I thought that $\ce{POCl3}$ just converts the OH group into Cl, but looking at the chemical formula for A, I noticed that A has an extra ...
4
votes
1answer
7k views

Mechanism for hydrolysis of enol ether to aldehyde

I'm fairly confident in my answers for steps 1-3, but I am not certain how to have the methyl group bonded that is bonded to the alkene carbon leave in step 5 without forming methanol. Here is what I ...
4
votes
1answer
86 views

How does O-benzoyl-N-methylhydroxylamine hydrochloride oxidise this ketone?

How does the mechanism of this reaction with BzONHMe work? Can part of it act as a base and abstract the alpha proton? Would be great if someone could help me!
3
votes
2answers
517 views

Wavenumbers of cyclic ketones

Rank the compounds below in order of increasing C=O absorption frequency in IR spectrum (top - lowest wavenumber, bottom - highest wavenumber): Question: Would I count compound #1's cyclopentane or ...
7
votes
2answers
1k views

Mechanism of a cyclization reaction - why does an enol ether form?

I was asked to predict compound A from the follwing organic scheme: Looking at the formation of A, my prediction was that since TsOH is a strong acid, it would dehydrate the alcohols (like sulfuric ...
1
vote
0answers
47 views

Reaction of phosphonates with conjugated carbonyl compounds

I was wondering whether the phosphonate ion would do a Michael addition on to the double bond rather than attacking the $\ce{C=O}$ bond to form the alkene product as it usually does (e.g. in a Horner–...
3
votes
0answers
839 views

Which enolate of butanone is more stable?

Consider butanone (A) and its two possible enolates B & C. Which of the two enolates will be more stable? B because of the more stable primary carbanion, or C because of more stable enolate (...
7
votes
2answers
2k views

Will cinnamaldehyde undergo self-aldol condensation?

Will cinnamaldehyde undergo self-aldol condensation? My book says it won't, but since it has an α-hydrogen, I'm confused.
0
votes
2answers
116 views

Question on organic chemistry where we are required to find enol content

Which of the following compounds is expected to have maximum enol content in ethanol? (A) $\ce{CH3COCH2CO2CH3}$ (B) $\ce{CH3COCH2CO2C2H5}$ ✔(I think this is the correct answer) (C) $\...
-2
votes
1answer
80 views

Is this an aldehyde?

$\ce{CH3CH2CH2CHO}$ I think it is an aldehyde but I saw somewhere that it might be an alcohol... I believe that it looks like this. Is that correct?
5
votes
3answers
326 views

What is the keto form of a hexahydroxybenzene?

159. The keto isomer of the following compound is: The answer has been given as (c). I cannot seem to understand why is it not possible for the keto form to only have one OH convert into keto ...
7
votes
2answers
760 views

Ring chain tautomerization of hydroxyacetone

My chemistry textbook says that hydroxypropane-2-one and 1,2-epoxy-2-hydroxypropane are ring chain tautomers, but it did not mention the steps for conversion of one into the other. I tried to figure ...
6
votes
1answer
1k views

Evaluation of a synthesis from aspirin to paracetamol from YouTube

Recently the YouTube chemist Nile Red performed an interesting conversion from aspirin to paracetamol (Link: https://www.youtube.com/watch?v=YPIr26-Tg5c), using the following steps: He performed the ...
1
vote
1answer
3k views

How or why can carboxylic acids be protonated?

In the wikipedia article "Step-growth Polymerization/Kinetics", it is stated that: The simple esterification is an acid-catalyzed process in which the protonation of the acid is followed by ...
-3
votes
1answer
2k views

Effect of Clemmensen reduction on carboxylic acids

Does the Clemmensen reduction have any effect on the carboxyl group $\ce{-COOH}$ if it is attached to some organic compound? If yes, what does it get reduced to?
-1
votes
1answer
704 views

Reagents to synthesise butanedioic acid from 1,2-dibromoethane

Why can't we use $\ce{HCN (g)}$ and $\ce{HCl (aq)}$ to convert 1,2-dibromoethane into butanedioic acid? I found out that the answer is $\ce{KCN (aq/alcoholic)}$ and $\ce{H2SO4 (aq)}$, I don't ...
4
votes
3answers
588 views

What is the mechanism of addition of glycine into 5-chloro-N-methylisatoic anhydride?

The following transformation is involved in a step in the synthesis of diazepam: (†) What is the mechanism of the transformation from the second to the third intermediate (N-methylisatoic anhydride ...
0
votes
1answer
62 views

how do i synthesize (E) 2-methyl-1-phenylpent-1-en-3-one? [closed]

i need a way to synthesize the (E) 2-methyl-1-phenylpent-1-en-3-one it's 2 days and still i can't find a solution.
4
votes
2answers
472 views

What is the mechanism for the oxidation of a lactol to a lactone?

Recently, I came to know that lactols can be converted to lactones but I wasn't able to find the suitable reagent and the reaction mechanism. Can someone elaborate the same?
0
votes
1answer
765 views

Why does a hydride shift take place in the cannizzaro reaction?

Hydride is a poor leaving group so a hydride shift should not take place and instead the attacking hydroxyl should leave the carbonyl group. I don’t understand why this doesn’t happen?
1
vote
1answer
227 views

Why is the ester bond stable under Reformatsky reaction conditions?

The following reaction is a Reformatsky reaction. Why is the ester bond not attacked in the last step? Couldn’t $\ce{OR3}$ be replaced by $\ce{OH}$ or $\ce{O(molecule)}$?
2
votes
2answers
3k views

Dehydration of amide with PCl5

Can $\ce{PCl5}$, phosphorus pentachloride, react with an amide? I saw a reaction where the corresponding cyanide was formed in this process. What other reagents could do the same?
-2
votes
1answer
2k views

Naming a keto ester

Find the IUPAC name of the above structure. This question was asked in my Chemistry exam. I could not figure out whether it is a ketone or an ester. My attempts: 1.If i consider the whole compound ...
0
votes
1answer
306 views

Why is the melting point of lactic acid higher than pyruvic acid

I have a quick question about pyruvic acid and lactic acid, which I think I know the answer too but I'm unsure. The melting point of lactic acid is said to be higher than that of pyruvic acid ...
5
votes
1answer
701 views

Why does N-phenylhydroxylamine give Fehling's test?

I have studied that Fehling's test is given by aldehydes and alpha hydroxy ketones. I read in a book that it is also given by phenylhydroxylamine converting it to nitrosobenzene. Does it gives the ...
0
votes
1answer
828 views

Negative charged intermediate in acidic conditions - what's the problem?

Why positively charged intermediates are preferred over negative charged intermediates, when formed during a reaction taking place in acidic conditions? For example: Image source: Organic Chemistry ...