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4
votes
2answers
67 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?
1
vote
1answer
73 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.
2
votes
1answer
65 views

Aromaticity of cyclic ketone

By looking at the structure of the uploaded ketone, it doesn't seem that it is aromatic, but the resonance structure with C(+)-O(-) is aromatic. Is it correct to say that the ketone in the image is ...
6
votes
3answers
175 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 ...
2
votes
2answers
80 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 ...
1
vote
1answer
56 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?
0
votes
2answers
47 views

Oxidationsnumbers for ester?

How to find the oxidation numbers for ester. Sorry about my english I learn things in german. My main issue is about finding the numbers of Ester group. ...
0
votes
1answer
134 views

Predict the product (organic chemistry)

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: ...
2
votes
2answers
158 views

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

non-pure alkanes, .. have a taste .. (as far as I know, is it wrong or true?) but .. Are all pure alkanes, .. tasteless ..?
3
votes
1answer
675 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 ...
2
votes
2answers
203 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 ...
7
votes
1answer
563 views

Resonance stability: ester vs. thioester

My problem set solution cites: "Although sulfur is less electronegative than oxygen, overlap is a more important consideration. Sulfur is a member of the third period. As a consequence, a ...
6
votes
1answer
94 views

Which functional group is -CSSH?

If we replace two oxygen in $\ce{-COOH}$ what is the name of the compound we get?
2
votes
3answers
4k views

Why is the boiling point of aldehydes less than that of ketones?

Both have a carbonyl group. Since the carbonyl group of ketone is between alkyl groups it would be difficult for it to form hydrogen bonds compared to aldehydes.Then, aldehydes should have a higher ...
1
vote
1answer
128 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 ...
3
votes
1answer
65 views

Photochemical ligand substitution of metal carbonyls - role of water cooled lamp-jacket?

Why, in the photochemical substitution of a ligand in a carbonyl complex, is a water-cooled lamp jacket required to separate the solution and the mercury vapour lamp? It's shown in Figure 22.16 of ...
2
votes
3answers
121 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 ...
4
votes
1answer
829 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 ...
2
votes
1answer
250 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. ...
5
votes
1answer
4k views

Oxidation of ketones

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 says that during oxidation of ...
2
votes
0answers
705 views

Oxidation of cyclododecanol to cyclododecanone [closed]

In the oxidation of cyclododecanol to cyclododecanone. In the work up step, after I added diethyl ether and then separated the two layers, organic and aqueous. Then I added diethyl ether again, ...
8
votes
3answers
1k 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 ...
1
vote
1answer
292 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 ...
8
votes
3answers
1k 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 ...
5
votes
2answers
515 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. $$\cee{CH3COOCH2CH3 ...