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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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 ...
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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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40 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?
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23 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 ...
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1answer
34 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 ...
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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 ...
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1answer
73 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 ...
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1answer
37 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 ...
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1answer
107 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?
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1answer
94 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 ...
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1answer
433 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 ...
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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 ...
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1answer
107 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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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 ...
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2answers
81 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
247 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?
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1answer
51 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 ...
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1answer
92 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
20 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 ...
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1answer
572 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 ...
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2answers
3k 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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1answer
145 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.
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1answer
285 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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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
650 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
75 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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71 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. ...
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1answer
190 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: ...
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292 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 ...
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2answers
803 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 ...
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1answer
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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 ...
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113 views

Which functional group is -CSSH?

If we replace two oxygen in $\ce{-COOH}$ what is the name of the compound we get?
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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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185 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 ...
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3answers
179 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 ...
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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 ...
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1answer
340 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. ...
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1answer
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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 ...
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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, ...
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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 ...
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1answer
470 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 ...
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3answers
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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 ...
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2answers
705 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 ...