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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Distinguishing Test for Organic Compounds

Given the following pairs of samples, how do I distinguish between them? benzamide vs ethanamide ethanoyl chloride vs ethanoic anhydride My Approach: We could easily convert the amides to amines by ...
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Nucleophilic attack at a carbonyl - angle of attack

What is the specific angle between the carbonyl carbon and the nucleophile during the nucleophilic addition reaction?
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259 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 ...
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338 views

Why are alpha-carbonyl relatively less stable?

So if we have an alpha halogen ketone, why is an Sn1 type mechanism so unfavorable for that species? I don't understand. It seems like the C+ would be resonance stabilized by the carbonyl's double ...
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257 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 ...
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760 views

Attack of amine on amide

I am confused with the last step of clozapine synthesis: How can the amine group attack the amide group to form the amidine in such acidic environment? Is the intermolecular reaction between an amine ...
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402 views

Why is bipolar resonating structure less stable than monopolar structure?

In my book, it is written: Resonance energy of a system involving monopolar resonance structures is greater than that involving bipolar resonance structures. The book cites example: ...
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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 ...
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802 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 ...
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Acid chlorides and reduction by hydrogenation

An acid chloride being reduced through catalytic hydrogenation is an "unobserved" event in the context of our class, according to my professor. Nonetheless, we are expected to predict that the ...
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194 views

IUPAC nomenclature [closed]

What is the IUPAC name of the following compound?
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135 views

Enolizablity of pyruvate and lactate

I understand that to create an enol, you simply eliminate a proton alpha to the relevant $\ce{C=O}$ and then tack the proton onto the $\ce{O}$ and there you have it — an alkene and an alcohol — or ...
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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?
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717 views

Enolate Ion formation

I was wondering why when acetaldehyde is treated with $\ce{OH-}$, the $\ce{OH-}$ will attack the methyl group instead of the carbonyl carbon, forming an enolate anion. I would have though that the $\...
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Dissociation constants of oxalic acid

For oxalic acid, $\mathrm{K}_{\rm a1}> \mathrm{K}_{\rm a2}$. My teacher told me that after first deprotonation, $\ce{COO-}$ acts as an electron donating group and hence reduces the acidic ...
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760 views

Rotational Barriers - Amide and Hydroxamic Acid

Why the barrier to rotation about the $\ce{C-N}$ bond higher in an amide than it is in a hydroxamic acid? (MO-based explanation preferred)
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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 $\ce{H-}$. ...
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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 ...
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254 views

Mechanism of Grignard addition to carbonyls

So from the general reaction we can see that the carbonyl is reduced while the Grignard is oxidized to an alkene. So for this hypothetical reaction (does this really occur?) we are asked to provide ...
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Protonation of ketone and ester

If there is a ketone and ester functional group in the same compound and I want to protonate with $\ce{HCl}$, which one will protonate first? Is it the carbonyl group in the ketone or the carbonyl ...
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269 views

How can rotamers of alpha-keto esters be named to distinguish between different geometries?

When talking about free rotation it is often helpful to determine about which geometric arrangement one is referring to. For example in the case of butane we talk about several eclipsed or staggered ...
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Most stable conformation of aldehydes and ketones

Why is the most favorable conformation of ketones and aldehydes the one where the alkyl group is anti to the other alkyl group (or hydrogen atom in an aldehyde) as attached? Why isn't more stable the ...
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1answer
98 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
576 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 $\ce{MeOH}$. After ...
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246 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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274 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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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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187 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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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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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 the ...
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925 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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202 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 this ...
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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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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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505 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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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 $\ce{...
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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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328 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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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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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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'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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411 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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492 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:
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1answer
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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
876 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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669 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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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 ...