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.

Filter by
Sorted by
Tagged with
2
votes
0answers
64 views

How would one disassociate the carboxylic acid on the end of a perfluorooctanoic acid molecule?

This is what a perfluorooctanoic acid molecule looks like. The carboxylate head on the end would normally disassociate in water because carboxylic acids are weak, but because of the fluorocarbon tail, ...
3
votes
1answer
392 views

Mechanism for conversion of imide to ester with NaH

What is the mechanism of this reaction? My proposed mechanism is shown below, would it work?
0
votes
1answer
16k views

What reaction happens when carboxylic acids are treated with calcium hydroxide and distilled? [closed]

What reaction takes place when $\ce{Ca(OH)2}$ reacts with $\ce{R-COOH}$? What is obtained after distillation?
4
votes
2answers
985 views

Does acrolein give Fehling's test?

Aromatic aldehydes do not give Fehling's test, which makes me believe that for the same reason acrolein should not. It has a double bond conjugated with the carbon oxygen double bond as in ...
4
votes
1answer
211 views

Can enamines be formed from α,β-unsaturated ketones?

This question was a result of discussion form here: α,β-unsaturated carbonyl compounds and alkyl addition The reaction below (condensation of cyclohexenone with a secondary amine) does not yield any ...
8
votes
2answers
2k views

How can an aromatic ketone be reduced in the presence of a nitro group?

Is it possible to reduce an acyl group to an alkane, but still keep a nitro group intact without its reduction to an amino group? A Clemmensen reduction would reduce the nitro group, and it seems like ...
1
vote
1answer
240 views

Haloform Reaction of Furfural

My instructor pointed out that furfural undergoes haloform reaction - I don't understand how. I couldn't figure out the mechanism on my own, and couldn't find much online either. (regarding the ...
4
votes
2answers
3k views

In Reimer-Tiemann reaction why does phenol attack the carbene from ortho position?

From the Wikipedia article on Reimer-Tiemann reation: In step 5, why doesn't the oxygen attack the carbene. The way I see it: upon attacking the carbene from ortho position, the mechanism ...
5
votes
1answer
2k views

Yellowish tinge during titration of oxalic acid with potassium permanganate

One of the our chemistry practicals involve finding the molarity of an oxalic acid solution by titrating it with standard $\ce{KMnO4}$ solution. The oxalic acid solution is heated and little sulfuric ...
7
votes
1answer
991 views

Selective alkylation of carboxylic acid versus phenol

Starting from the ketone shown, I plan to use a haloform reaction to transform the acetyl group into a carboxylic acid. Following that, there are two alkylations to be carried out: one esterification ...
1
vote
0answers
42 views

Why do amides react differently with PCl5? [duplicate]

In a reaction involving $\ce{PCl5}$ and any reactant containing oxygen atom, it generally takes out the oxygen and put chlorine their due to formation of strong bond between phosphorus and oxygen. ...
1
vote
1answer
379 views

Why do the amino groups in EDTA deprotonate first, in contrast to amino acids?

We know that in amino acids, carboxylic acid groups deprotonate first than the amine groups. For example, in alanine, $\mathrm{p}K_\mathrm{a,\ce{COOH}} = 2.34$, $\mathrm{p}K_\mathrm{a,\ce{NH3+}} = 9....
1
vote
1answer
615 views

What is the reaction of pentane-2,4-dione with chlorine in presence of NaOH? [duplicate]

We know that in haloform reaction alpha acidic hydrogen are substituted by halogen atom. But in the above case we find two acidic hydrogens in between the two keto groups (due to -R effect) which are ...
3
votes
2answers
2k views

Reduction of terephthalic acid to an alcohol (or phenol?)

I want to convert terephthalic acid (TPA) to an alcohol (however I think the correct term would be "a phenol"). I've read that lithium tetrahydridoaluminate ($\ce{LiAlH4}$) can produce an alcohol ...
3
votes
1answer
228 views

Ring expansion of two fused rings to a larger ring

I saw the following reaction mechanism in paper Tetrahedron Lett. 1976, 17 (33), 2869–2872.: I'm not able to understand the following parts: How did the conversion of 27 to 29 take place? I've never ...
7
votes
0answers
162 views

How can I solve this synthesis?

I have this task to do: My solution: Is that possible? Can you please help me with the steps 2 and 3? This is what I did, but my teacher told me I should make the diketone (compound no. 5) from ...
6
votes
1answer
4k views

Will the bond order of CO be greater in its existence as carbon monoxide or in metal carbonyl?

$$\text{Bond order} = \frac{N(b) - N(a)}{2}$$ Where $N(b)$ is the number of electrons in bonding orbitals and $N(a)$ is the number of electrons in antibonding orbitals. As in metal carbonyls, there ...
3
votes
1answer
392 views

Malic acid 3-step synthesis

I was quite puzzled by the answer for this question in my Carboxylic Acids and Derivatives tutorial question set. It is question 6 (a), on the synthesis of malic acid, as shown in the image below. ...
5
votes
2answers
4k views

Can substituted acetone undergo Cannizzaro reaction?

I know the Cannizzaro reaction takes place in carboxyl compounds without $\alpha$-H with the regular examples being formaldehyde and benzaldehyde. But can this reaction take place with say ...
0
votes
1answer
60 views

How far-reaching is the effect of conjugation?

Due to conjugation, it is possible for 1,4-addition, or conjugate addition, to occur. I was thinking, since conjugation and resonance effects do no diminish with distance, unlike inductive effects, ...
4
votes
0answers
231 views

Reaction of alpha hydroxyketone with KOH

What happens when 2-hydroxycyclohexan-1-one (an alpha hydroxyketone) reacts with aqueous $\ce{KOH}$? I tried something like Favorskii rearrangement, but it's wrong because OH isn't a good enough ...
4
votes
1answer
196 views

Cyclisation reaction through hydrazine

The following reaction confuses me - I don't understand how and why it happened (couldn't figure out the mechanism): I thought this is some Wolff Kishner sort of reduction, but the reagents don't ...
3
votes
1answer
98 views

Conjugate addition vs Electrophilic addition

I was just doing an organic chemistry problem from an online source recently, on the topic of conjugate additions (or 1,4-additions). Below is an image illustrating the problem. I chose the upper ...
1
vote
1answer
2k views

Why carbonyl groups are strong benzene deactivating group for electrophillic aromatic substitution?

In carbonyl group there is a resonance avaibility and also due to inductive effect it can also withdraw electron from benzene ring . As, resonance(e- donating chracter) dominates than Inductive effect ...
4
votes
1answer
350 views

Deciding more electrophilic centre between ester and thioester for SN type reaction

My question: (though it won't alter the product) Which carbon is attacked first, the one adjacent to sulphur or the one adjacent to oxygen? The solution says that the carbon adjacent to sulphur is ...
1
vote
1answer
988 views

Reaction of 2,4-DNPH with aromatic aldehydes

Does 2,4-dinitrophenylhydrazine react with aromatic aldehydes, e.g. benzaldehyde (phenylmethanal), in a condensation reaction similar to 2,4-DNPH's reaction with aldehydes and ketones ?
5
votes
1answer
513 views

Epoxide ring opening via decarboxylation

The answer for the above multiple choice problem is option (C), from which I can understand that at some point in the mechanism the molecule must've undergone decarboxylation. Also, I think the first ...
10
votes
1answer
303 views

Esterfication of 2,2,2-triphenylethanoic acid

Explain the formation of (1,1,1-triphenylmethyl)methyl ether when a solution of 2,2,2-triphenylethanoic acid in concentrated sulfuric acid is poured in methanol. I cannot figure out where is one ...
1
vote
1answer
60 views

Would this be a reasonable mechanism for the formation of a diazomethene?

I am mostly concerned about the first step. Are there any species in this mechanism that look too reactive for this mechanism to make sense? Any thoughts would be greatly appreciated.
4
votes
1answer
2k views

Why is only bromine used in the degradation reaction?

Why specifically is bromine used in the degradation reaction (Hoffmann bromamide)? Why can't the same be performed using chlorine or iodine? In other words, what makes bromine a more convenient ...
9
votes
2answers
51k views

Why doesn't the Brady's test (2,4-DNPH) work on carboxylic acids?

Why does the Brady's test, the reaction of 2,4-dinitrophenylhydrazine with aldehydes and ketones, fail with carboxylic acids?
11
votes
1answer
1k views

In what way could benzoin give Tollen's test?

In Q29 of Joint Entrance Exam (JEE) 2016 India, the official answer key mentions that benzoin gives Tollen's test. However, I saw this post which says that it doesn't: Why do α-hydroxy ketones give ...
3
votes
1answer
109 views

Origin of broad CO stretch in infrared spectrum of tricobalt cluster

I'm quite confident that the peaks around $\pu{2000 cm^{-1}}$ are $\ce{CO}$ stretches. But I cannot find any reference on that massive broad stretch following the $\ce{CO}$ stretches. Does it have ...
1
vote
1answer
137 views

What will be the product of this reaction?

We have an alpha beta unsaturated ether, along with a keto group in the same compound, which is being treated with a grignard reagent shown (assume the grignard reagent is in excess). Will it only ...
10
votes
4answers
733 views

With which group does the middle oxygen atom of an anhydride remain, on hydrolysis?

With which group does the middle oxygen atom of an anhydride remain, on hydrolysis? As an example, let us say we have the following modification of ethanoic methanoic anhydride, with the middle oxygen ...
1
vote
0answers
150 views

What is first protonated aldehyde or lactone?

In a six membered lactone with carbaldehyde in beta position, which oxygen gets protonated first? the lactone or the aldehyde? (Using concentrated HCl)
1
vote
1answer
121 views

Methylnitrobenzene ring formation Synthetic Route

I know the malonic ester is probably used to make propanoic acid or some carboxylic acid, and then joined to the methylnitrobenzene. But I just can't figure out what glues to the methyl. I know the ...
4
votes
2answers
513 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?
10
votes
2answers
6k views

What are the products of the reaction of 1-methoxycyclohexene with dilute hydrochloric acid?

When 1-methoxycyclohexene is treated with dilute aqueous hydrochloric acid, methanol is produced along with another organic product. Identify this product. Explain why methoxycyclohexane is inert ...
0
votes
2answers
245 views

HCl/H2O with alkene: Which one reacts?

I think that the initial step forms a tertiary amine, which then in the presence of the ketone and trace acid undergoes nucleophilic addition. But then, for the $\ce{HCl/H2O}$ in the last step, which ...
0
votes
1answer
838 views

Why does Benzoin give positive Tollen's Test? [duplicate]

Certain alpha hydroxy ketones which can tautomerise to form an aldehyde will give a positive Tollen's Test. I was pretty clear with this idea until I came across this question and the answer given is ...
3
votes
2answers
2k views

Dehydration of carboxylic acids using P2O5

Why isn’t concentrated $\ce{H2SO4}$ used for the dehydration of carboxylic acids to anhydrides? What is special about $\ce{P2O5}$?
6
votes
1answer
584 views

Is this really a comparison of the absolute energies in the reaction energy profile for ester formation?

In Clayden et al., Organic Chemistry, p. 332, the authors compare the reaction energy profile for ester formation from a) acyl chloride and b) anhydride: They then write: The energy levels of the ...
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 ...
9
votes
1answer
5k views

Why is benzoic acid a stronger acid than 3-aminobenzoic acid?

Why is benzoic acid a stronger acid than 3-aminobenzoic acid? Obviously at meta position, only negative inductive effect will operate. But, how does that make it a weaker acid than benzoic acid?
3
votes
2answers
571 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 ...
8
votes
1answer
1k views

Racemization of ketones in presence of catalytic acid

Question: Which of the following ketones racemise in aqueous solution containing acidic or basic impurities? My answer: A and B should racemise in aqueous solution, for the carbonyl groups in A and B ...
2
votes
0answers
80 views

Can an enol acetate be formed through Fischer esterification?

Since acetone is converted into its enol form under acidic conditions, could it participate in Fischer esterification to form an enol acetate? For example, would refluxing acetone, p-TSA, and acetic ...
1
vote
1answer
1k views

Chromic acid oxidation of aldehydes and primary alcohols

The answer has to be both A and D. Chromic acid is a strong oxidizer and will take both aldehydes and primary alcohols to carboxylic acids. However the computer thinks otherwise. Am I just missing ...
1
vote
1answer
665 views

Identify structure of compounds from their reactions and molecular formula

Compound P($\ce{C7H6O}$) on refluxing with aqueous ethanolic $\ce{KCN}$ solution for 1 hour, forms Q($\ce{C14H12O2}$). Q on oxidation gives R($\ce{C14H10O2}$). R on refluxing with aqueous $\ce{NaOH}$ ...