Compounds containing the carbonyl group, C=O. The tag is only used for the organic molecules containing this functional group. For questions about complexes involving carbon monoxide as a ligand use carbonyl-complexes instead.

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25 views

How can a ketone selectively be reduced? (Frater Seebach Alkylation)

I'd like to reduce enantioselectively a ketone in presence of an ester (which should NOT be reduced to an aldehyde and further to an alcohol). Adding $\ce{LiAlH4}$ would also reduce the ester and ...
6
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0answers
67 views

Why does acetate aldol with Evans auxiliary give almost no diasteroselectivity?

Following acetate aldol gives no diasteroselectivity: Because I don't know what the basis of above statement is (I heard it in a lecture and read it on some internet web pages). I expect the two ...
3
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1answer
41 views

Does esterification require reactants to be present in the same plane?

In the image that follows (7) I believe that the first step is the Cannizzaro reaction which will give (c) as a product. But since we are also adding $\ce{H+}$ in the second step, shouldn't an ...
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1answer
56 views

Cannizzaro reaction and Aldol condenstion

Can all species that undergo aldol reactions also undergo Cannizzaro reactions? After all, the nucleophile can always attack the carbonyl group.
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2answers
240 views

Which compound reacts faster in the Cannizzaro Reaction?

Which reacts faster in the Cannizzaro Reaction? a) $\ce{OHC-Ph-NO2}$ b) $\ce{OHC-Ph-OCH3}$ A better hydride releasing group will be a better reactant, obviously. Therefore my answer was b, as ...
5
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1answer
143 views

Mechanism of enol ether formation

I assumed the the $\ce{TsOH}$ would dissociated to produce hydronium ions that would protonate the carbonyl. This would make the carbon more delta + and so susceptible to attack by $\ce{MeOH}$. ...
5
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1answer
49 views

Why is in the reaction of cyclic unsaturated aldehydes with hydrazine and hydrogen peroxide the aldehyde preserved?

What is the product of this reaction, which I found in our high school textbook? At first, I thought this was a typical Wolff-Kishner reduction, but then I saw the reagents didn't match up (no ...
2
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0answers
50 views

Carbonyl group Conjugation and IR spectroscopy

Here's the problem... Three isomeric structures with formula $\ce{C10H8O2}$ are shown: I understand that conjugation in the systems will affect the carbonyl stretching ...
11
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2answers
137 views

Does a Grignard reagent react with cyclohex-2-en-1-one to give the 1,2- or 1,4- product?

My attempt: The $\ce{PhMgBr}$ nucleophile attacks on the 1,2 position. But why, in this case, will it attack the 1,4 position?
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2answers
47 views

Keto Enol Equilibrium for Claisen Condensation Products

Do Claisen Condensation products prefer the di-keto form, or a keto/enol form due to increased conjugation and hydrogen bonding?
2
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1answer
34 views

Fehling's Test meaning for partial formation of a precipitate?

Whilst doing tests on two unknown solutions, I used Fehling's test. The solutions could be a mixture of compounds or just one compound dissolved in water/ another solvent - I don't know. Upon adding ...
4
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1answer
47 views

When will organometallics act as base or nucleophile?

I would like to ask if the hydrogen next to carbonyl group is acidic,and organometallics are strong base, when will it act as a base and extracts the acidic proton and when will it attack the carbonyl ...
6
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1answer
83 views

How to reduce an acyl group on a benzene without disturbing 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 ...
2
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0answers
46 views

Why do electronegative heteroatoms increase C=O stretching frequency (bond strength)

Why does a more electronegative heteroatom (i.e. $\ce{Cl}$ or $\ce{O}$) increase the stretching frequency of a carbonyl? I'd suspect it's that they donate their lone pairs and we end up with a ...
2
votes
1answer
98 views

Can carboxylic acids be used in the aldol reaction?

A question in a practice paper I did recently showed the aldol condensation of benzaldehyde with ethanoic acid. I think I am right in saying that carboxylic acids do not form enolates because the ...
3
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1answer
62 views

Mechanism of enolether formation with ethyl orthoformate in estr-4-ene-3,17-dione (Djerassi's norethisterone synthesis)

The second step of Djerassi's synthesis of 19-nor-17α-ethynyltestosterone (norethindrone), involves the protection of the ketone in position 3 via enolether formation, as in the picture: What is ...
6
votes
1answer
138 views

Synthesis of ethyl methyl ketone from 2-(4-hydroxyphenyl)ethyl methyl ketone

Is it possible to reduce raspberry ketone (4-(4-Hydroxyphenyl)butan-2-one) to ethyl methyl ketone? How would I do this in practice?
4
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1answer
103 views

Why should alkylation of enols/carbonyl compounds be done at low temperature with a strong base?

Alkylation of acetone: This reaction is done with a strong base (LDA in this case). Is this because the protons aren't particularly acidic? Secondly it should be done at low temperatures; why is ...
5
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1answer
467 views

Can carbon monoxide contaminate water?

Just wondering if you fitted a cold water tank overflow pipe into a car park at the height of a car exhaust , if the carbon monoxide fumes went back up the oveflow pipe into the tank would this ...
6
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1answer
82 views

Carbonyl electrophilic reactivity

Hi there, I would like to ask about the rate of hydrolysis for these compounds A to D. I know that hydrolysis depends on the positive charge of the carbonyl carbon and also the substituent around it ...
3
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1answer
234 views

How do you identify reducing / non-reducing sugar by looking at structure?

Identifying reducing / non-reducing sugar been confusing me for a while now , I know that reducing sugar contain aldehyde or ketone group . It's easy to identify them in monosaccharides but this ...
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2answers
51 views

Alkali metal enolates

Why do lithium enolates add to an electrophile in direct addition manner, while the sodium and potassium enolates tend to add in conjugated additions? The sodium and potassium enolates are well ...
3
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2answers
116 views

Halogenation of an alpha-halogen ketone in acidic conditions

When a methyl ketone is submitted to halogenation in acidic conditions with two equivalents of a halogen, the first halogenation happens at the secondary alpha carbon atom , while the second ...
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1answer
323 views

Regioselectivity of alpha halogenation of ketones

Why does alpha halogenation of a ketone in acidic conditions happen at the more substituted alpha carbon atom, and in basic conditions at the less substituted alpha carbon atom?
2
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1answer
63 views

Do molecules with carboxyl groups have properties of carboxyl's sub-functional-groups?

We're learning about functional groups of different organic molecules, and there are some I'm confused about: carboxyl, carbonyl, and hydroxyl. I was looking online but I couldn't find a direct answer ...
3
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1answer
115 views

Why can alkali metal hydrides usually not act as nucleophiles towards carbonyl groups?

Think for example of $\ce{KH}$ or $\ce{NaH}$ in enolization reactions. This remark was made in one of my textbook, but I could not remember why this was actually the case. Why can't $\ce{NaH}$ or ...
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1answer
21 views

How does higher carbonyl compounds disolve in water?

We know that higher the carbon, the more is hydrophobic the compound nature is, Still when we take a compound like sugar , a hand of sugar, it readily dissolves in water? can someone explain me reg ...
5
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1answer
830 views

What is the effect of conjugation of a carbonyl group in IR spectroscopy?

Doing an exchange term so I've missed some classes that the others have attended, and unfortunately we're getting contradictionary explanations, so I thought I'd try and ask you. Would be extremely ...
4
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2answers
4k 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?
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2answers
211 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 ...
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1answer
178 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.
4
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1answer
364 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 ...
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3answers
4k 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 ...
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2answers
866 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 ...
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1answer
78 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?
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2answers
80 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
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1answer
204 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
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2answers
338 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 ..?
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1answer
2k 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
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2answers
943 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 ...
8
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1answer
2k 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
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1answer
124 views

Which functional group is -CSSH?

If we replace two oxygen in $\ce{-COOH}$ what is the name of the compound we get?
6
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3answers
8k 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? Whey then, ...
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1answer
207 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
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3answers
198 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
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1answer
1k 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
360 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. ...
6
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1answer
8k 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
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0answers
1k 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, ...
10
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3answers
2k 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 ...