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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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9
votes
2answers
49k 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?
12
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2answers
2k views

Regioselective enolate formation

Our professor only told us that A is favored, and B is not getting formed. I thought about the resonance structures and saw a contradiction to that what the prof told us. To be honest I think my ...
1
vote
1answer
867 views

Does the iodoform reaction form hydrogen iodide or water?

I am currently learning about the iodoform reaction, i.e. when CH3COR compounds react with iodine and sodium hydroxide to form iodoform. My course book and Chemguide both says that the reaction is as ...
3
votes
1answer
828 views

Triple Bond Character in Acyl Chlorides

I am told that because of the poor overlap between a chlorine atom and a carbon atom and chlorine's relatively high electronegativity, there is a strong partial positive character on the central ...
6
votes
2answers
2k views

Why are imines more susceptible to reduction than carbonyl compounds?

Why are imines more susceptible to reduction than carbonyl compounds? Imines react with $\ce{NaCNBH3}$ while the carbonyls don't.
3
votes
2answers
703 views

Which is the correct way to name pentan-3-one?

I have seen this organic compound named in two different ways. According to some sources it is written pentan-3-one.. Other sources call it 3-pentanone. Which one is correct?
15
votes
2answers
6k views

Is tropone aromatic?

Looking at resonance structure 1a, it doesn't seem that tropone is aromatic. However, the resonance structure 1b with $\ce{C+-O-}$ satisfies Hückel's rule for aromaticity. Is it correct to say that ...
2
votes
1answer
2k views

Molecules with more than 1 functional group

I need some help naming compounds with more than 1 functional group. Here are some examples: A 4-carbon alkane with an aldehyde and a ketone for both the ketone being right next to the aldehyde and ...
24
votes
3answers
47k views

Rationalising the order of reactivity of carbonyl compounds towards nucleophiles

This is immediately following ron's answer from Why is a ketone more nucleophilic than an ester? One of the most simplest questions you can ask, how can you rationalise the order of reactivity ...
12
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2answers
14k views

Why is a ketone more nucleophilic than an ester?

I guess the ester is a weaker nucleophile because it does have an additional oxygen atom, unlike the ketone, that is pulling electrons from the C-O double bond towards the carbon atom (this happens ...
9
votes
3answers
44k views

Mechanism for reaction of Tollens' reagent with aldehydes

Upon treatment with Tollens' reagent (ammoniacal silver(I) nitrate), aldehydes are oxidised to carboxylic acid, and silver(I) is reduced to silver metal. I am trying to find a mechanism for the this ...
1
vote
1answer
419 views

Does the carboxyl group count as a branched chain

Do carboxylic acids (or any compound with a carbonyl group) count as a branch chained organic compound due to the C=O? Or does it need a carbon - carbon branch?
5
votes
1answer
2k views

Reaction mechanism of a terminal alkene with an anhydride

In a reaction (as given in my textbook), $$\ce{R-CH=CH2 + (CH3-CO)2O -> R-CH2=CH-COCH3}$$ an alkene reacts with acetic anhydride to give methyl alkenyl ketone. I am not sure of how this ...
2
votes
1answer
101 views

Would a carbamate be attacked twice by an alkyl lithium cuprate reagent?

For example, say you react ethyl carbamate with methyl-$\ce{LiCu}$; would two methyl groups displace both the amide and the ester, creating an isopropyl alcohol?
2
votes
1answer
230 views

Nitrogen lone pair electrons on 2-acetyl-1-pyrroline

Please consider 2-acetyl-1-pyrroline: http://en.wikipedia.org/wiki/2-Acetyl-1-pyrroline What is the molecular geometry of the nitrogen lone pair? Is the lone pair oriented in-plane with the ring? ...
7
votes
2answers
2k views

Why does no Robinson Annulation occur after the Michael addition?

Under basic conditions a Michael addition reaction can be used to convert compound A into product C. Explain why no Robinson annulation cyclic product is observed? Compound A Product C ...
1
vote
1answer
496 views

Predict the product (organic chemistry) [closed]

I think that the first reaction would add into the ketone carbon, but I don't know where to go after that. A step-by-step explanation of the answer would be greatly appreciated! Answer choices:
3
votes
2answers
2k views

Are all (pure) alkanes, alkenes and alkynes - tasteless, odourless and colourless? [closed]

non-pure alkanes have a taste, but Are all pure hydrocarbons, tasteless, colourless and odorless? Are there hydrocarbons that do have a taste, colour, odor? If so, what makes these pure hydrocarbons ...
3
votes
1answer
16k views

'Hard' soap vs. 'Soft' soap: Why do they work this way?

In school, we did an experiment using fat and $\ce{KOH}$ to create 'soft' soap. Afterwards, we added $\ce{NaOH}$ to change it into 'hard' soap. I read on multiple places on the internet that the ...
1
vote
1answer
1k views

Reaction of a vicinal diol with acetone

I have the first part correct; however, I can't seem to understand what the 2nd part's answer is. I realize the water leaves, but then what?
12
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4answers
2k views

What's the mechanism of the reaction of (E)-methyl 3-(furan-2-yl)acrylate in acidic methanol?

In the organic chemistry textbook by Clayden et al. they mention that the reaction of (E)-methyl 3-(furan-2-yl)acrylate in acidic methanol yields dimethyl 4-oxoheptanedioate without providing the ...
3
votes
1answer
13k views

aldehydes are easily oxidised but ketones are not

Aldehydes are easily oxidized to carboxylic acid but ketones are difficult to oxidise. Most books say that the hydrogen directly bonded to the $\ce{C=O}$ in the aldehyde is what aids the oxidation ...
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 ...
18
votes
2answers
9k views

Comparing acidities of substituted and aromatic carboxylic acids

When comparing the acidities of carboxylic acids, we primarily see the electropositivity of the carboxylic acid carbons, i.e. we see how effectively the negative charge on the carboxylate ion is ...
10
votes
2answers
1k views

Prediction of products in reaction of dicarbonyl with alpha-haloketone

Following is the question that was asked in my exam. a,b,c,d are the various options, one of which is the answer. I am familiar with the Reformatsky reaction, Aldol condensation, Knoevenagel's ...
7
votes
1answer
2k views

Does aldol condensation give different products in different conditions?

I know the mechanism of aldol condensation and general method to determine products in crossed aldol reactions, or reactions between dissimilar molecules. But the following statement in my class notes ...
6
votes
1answer
581 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 ...
6
votes
1answer
340 views

Which functional group is -CSSH?

If we replace two oxygen in $\ce{-COOH}$ what is the name of the compound we get?
12
votes
3answers
52k views

Why are the boiling points of aldehydes less than those of ketones?

Both aldehydes and ketones have a carbonyl group, but since the carbonyl group of ketone is between alkyl groups, wouldn't it be more difficult for it to form hydrogen bonds than aldehydes? Why then, ...
1
vote
1answer
410 views

Equations for UV degradation of condensation polymers

I'm an A-level student studying the F324 unit of OCR GCE Chemistry 'A'. The exact question is Explain how condensation polymers may be photodegradable. Equations needed! I understand: What a ...
2
votes
1answer
19k views

How does sodium in ethanol reduce carbonyl compounds?

According to my teacher, Na in ethanol reduces carbonyl compounds (e.g. aldehydes and ketones) to alcohols. However, I can't see where the hydrogen needed for reduction comes from. How does the ...
4
votes
1answer
3k views

Best reagent for reducing a ketone in the presence of an alkene

The following reduction is best accomplished with: (a) Zn/Hg, conc. HCl (b) N2H4, C2H5ONa (c) H2, Pd (d) All of the above My thoughts: By looking at the question it is evident that ...
18
votes
1answer
12k views

Migratory aptitude in Baeyer-Villiger reaction

In short, I do not understand how or why the migratory aptitude is as listed in every textbook I've read. Firstly, they talk about a positive charge being built up that is stabilised by the movement ...
18
votes
4answers
23k views

Why is acetic acid more acidic than phenol?

Acetic acid (ethanoic acid, $\mathrm pK_\mathrm a \approx 5$) is more acidic than phenol ($\mathrm pK_\mathrm a \approx 10$), which is reflected in their reactivity with a weak base such as sodium ...
1
vote
3answers
904 views

Are dicarbonyl amides stable in water?

Dicarbonyl amides, that is carboxylic acid anhydrides with their single-bonded oxygen between their carbonyl groups replaced with an amide group, I'm curious as to whether they're stable in water or ...
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 ...
4
votes
0answers
260 views

What is the average chain length of a glutaraldehyde crosslink between primary amines?

Imagine I'm performing a primary amine to primary amine (i.e. PA to PA) crosslinking reaction at $37~^{\circ}\mathrm{C}$ in phosphate-buffered saline (pH $\approx 7.4$) with glutaraldehyde drawn from ...
7
votes
3answers
9k views

Esterification of a carboxylic acid and the production of water

In an esterification reaction between a carboxylic acid and an alcohol, a carboxylate ester and water is produced. I found the following diagram online, and my textbook has a similar one as well ...
3
votes
1answer
282 views

Degradation mechanism of hydroxymethylfurfural to 2,5-dioxo-3-hexenal and 4-oxopentanoic acid

I want to understand the degradation mechanism of hydroxymethylfurfural (HMF). According to the Wikipedia article, HMF is degraded in honey. Someone said that the degradation proceeds via 2 possible ...
15
votes
1answer
16k views

Reduction of carboxylic acids by LiAlH4

I've read that when a carboxylic acid reacts with $\ce{LiAlH4}$ the corresponding alcohol is formed: But when I try to think of the mechanism, I get stuck here: $\ce{LiAlH4}$ produces $\ce{H-}$. ...
2
votes
1answer
679 views

Bonding in a bridged metal carbonyl

Can someone please explain the bonding in a bridged metal carbonyl (like diiron nonacarbonyl)? I cannot understand what kind of bonds (sigma/pi) exist between the bridging carbonyls and the metals. ...
11
votes
1answer
46k views

What is the mechanism for oxidation of ketones by the Popoff's rule?

Ketones are relatively much harder to oxidise, but they do undergo oxidation reactions at extreme temperatures. Our teacher also told us about Popoff's rule which states that, on oxidation of ...
2
votes
0answers
258 views

Primary amine versus phosphoramidate reactivity with succinate esters

I have posted two reactions below. The top reaction is well known and occurs readily and near quantitatively (e.g. in protein modification), while the bottom reaction to my knowledge does not exist in ...
21
votes
4answers
6k views

Why do Organolithium or Grignard reagents act as nucleophiles and not as bases with aldehydes and ketones

I've read entire Chapter 14: Organometallic Compounds of Francis Carey's "Organic Chemistry" but I still didn't get an answer to my question. Quote from the book: Because of their basicity ...
2
votes
1answer
2k views

Can bromide ion ever act like a base?

I was reading MECHANISM OF α-HALOGENATION OF ALDEHYDES AND KETONES: As you can see in the third step. Bromide ion is picking up a base from protonated acetone. Doesn't that step mean that protonated ...
12
votes
4answers
7k views

Is it possible to synthesise ethers from carboxylic acids?

Is it possible to synthesise ethers from carboxylic acids, and if so, how? By ether I mean an ether in general ($\ce{R-O-R'}$), not just specific examples. I theorised one could perform Fischer ...
7
votes
1answer
3k views

What is the product formed in the reaction of dimedone and benzaldehyde?

I'm having a hard time deducing the structure of the product formed when dimedone and benzaldehyde react in the presence of catalytic piperidine. I think that a Knoevenagel reaction will get me to ...
8
votes
2answers
2k views

Why do lipids in a cell hydrolyze into glycerol and fatty acids?

Most Lipids in a cell have ester bonds (made up of glycerol and fatty acids). I have learned in my chemistry class that we can hydrolyze an ester by simply adding water to it. $$\ce{CH3COOCH2CH3 + ...
14
votes
1answer
3k views

Synthesis of mandelic acid from benzaldehyde

For an upcoming exam, I have to describe the synthesis of 2-hydroxy-2-phenylacetic acid (mandelic acid) from benzaldehyde. The provided answers describe quite a long process, consisting of 8 stages. ...
25
votes
1answer
922 views

How can I determine if there are π-π interactions between an amide and an aromatic ring in a protein?

In a crystal structure I've determined, a triazole ring on my ligand appears to be stacking with a tyrosine (top in picture): However, there is also an amide, courtesy a glutamine, near it (bottom). ...