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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4
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1answer
226 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 ...
4
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1answer
2k 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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1answer
235 views

Electrophilicities of carboxylic acid derivatives

I would like to ask about the rate of hydrolysis for 4-hydroxyphenyl acetate (A), N-(4-hydroxyphenyl)acetamide (B), 4-hydroxyphenyl chloroacetate (C), and methyl 4-hydroxybenzoate (D). I know that ...
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2answers
2k views

What are the products of the haloform reaction of acetylacetone?

I searched a lot to find the products of the haloform reaction of acetylacetone (pentane-2,4-dione), but I didn't find any results. What are the products of the haloform reaction of acetylacetone?
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1answer
433 views

Acidity order of acetone, methyl acetate and N,N-dimethylacetamide

Why is the acidity order true? $$\ce{CH3COCH3} > \ce{CH3CO2CH3} > \ce{CH3CON(CH3)2}$$ I deduced that in methyl acetate and N,N-dimethylacetamide there is a −I effect of the methoxy group, $\...
8
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2answers
45k 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 ...
6
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2answers
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Cannizarro reaction of chloral

When chloral undergoes reaction with a concentrated alkali, will it undergo Cannizarro reaction to form the corresponding alcohol and acidic salt, or should it form chloroform instead by departure of ...
9
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1answer
5k views

Does an acetal give a positive Tollens test?

In Organic Chemistry (Wade) there is a question: Which of the following compounds would give a positive Tollens' test? (Remember that the Tollens' test involves mild basic aqueous conditions.) The ...
4
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1answer
978 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 ...
7
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1answer
326 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 ...
12
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1answer
268 views

How do I synthesize 3-phenyloxirane-2-carbaldehyde from chloroacetonitrile?

How do I synthesize 3-phenyloxirane-2-carbaldehyde from chloroacetonitrile? My proposed route involves: hydrolysis of the nitrile to form a carboxylic acid, and subsequent esterification then, a ...
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3answers
506 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 ...
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1answer
2k views

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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1answer
2k views

Why is only bromine used in the degradation reaction?

Why specifically is bromine used in the degradation reaction (Hoffmann bromamide)? Why can't the same be performed using chlorine or iodine? In other words, what makes bromine a more convenient ...
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1answer
204 views

How do I know which atoms react during hydrolysis?

In the hydrolysis of propanamide ($\ce{CH3CH2CONH2}$) how do I know which molecules react with the water? $$ \ce{CH3CH2CONH2 + H2O -> ?} $$ I don't know how to split the molecule. In the videos ...
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1answer
321 views

Building an incomplete redox half reaction/reduction

I can't seem to figure out this redox reaction. $$ \ce{CH3COO- + CO2 -> CH3CH2COO-} $$ Is the charge on the carbon in the $\ce{CO2}$ supposed to match the charge on the carbon in the $\ce{CH3COO-}...
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2answers
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What are the products of the reaction of 1-methoxycyclohexene with dilute hydrochloric acid?

When 1-methoxycyclohexene is treated with dilute aqueous hydrochloric acid, methanol is produced along with another organic product. Identify this product. Explain why methoxycyclohexane is inert ...
3
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2answers
775 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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2answers
3k 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
552 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
1k views

Chromic acid oxidation of aldehydes and primary alcohols

The answer has to be both A and D. Chromic acid is a strong oxidizer and will take both aldehydes and primary alcohols to carboxylic acids. However the computer thinks otherwise. Am I just missing ...
5
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1answer
4k 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 $\ce{...
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1answer
27 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
679 views

Identify structure of compounds from their reactions and molecular formula

Compound P($\ce{C7H6O}$) on refluxing with aqueous ethanolic $\ce{KCN}$ solution for 1 hour, forms Q($\ce{C14H12O2}$). Q on oxidation gives R($\ce{C14H10O2}$). R on refluxing with aqueous $\ce{NaOH}$ ...
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1answer
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Why is benzoic acid a stronger acid than 3-aminobenzoic acid?

Why is benzoic acid a stronger acid than 3-aminobenzoic acid? Obviously at meta position, only negative inductive effect will operate. But, how does that make it a weaker acid than benzoic acid?
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1answer
4k views

How to Determine Acid Strength?

The correct answer is E But I do not understand why? Shouldn't (v) have the lowest $\mathrm{p}K_\mathrm{a}$ since it does not have a carboxyl group making it a strong acid? How do we determine the ...
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1answer
41k 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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1answer
457 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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3answers
2k views

Do the π-electrons from the C=O bond in tropone contribute to Hückel 's rule?

This is a continuation of Is tropone aromatic? I'm looking at the resonance form that does have the carbonyl double-bond, 1a. Can this resonance structure also be considered aromatic? Would the ...
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3answers
4k views

How to predict the outcome of a crossed Cannizzaro reaction?

My question is, how do we predict the products of a cross-Cannizzaro disproportionation in presence of a concentrated base? i.e, How to judge which of the aldehydes (both don't have any alpha hydrogen)...
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2answers
6k views

Reaction of Grignard reagents with esters

Suppose I have a phenyl Grignard and methyl benzoate. If I react the two, can I expect benzophenone and a triphenylmethoxide ion as my products? I ask because I know that Grignards react with ...
11
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1answer
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Is an ester or a ketone more acidic?

Two organic chemistry textbooks I've read (by Bruice and by Tandon) say: Esters are more acidic than ketones, because the resonance between the two oxygen atoms gives less opportunity for the ...
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1answer
176 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 ...
4
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1answer
10k views

Hydrolysis of cyclic acetal

What happens to 1,5-dimethyl-6,8-dioxabicyclo[3.2.1]octane when it is hydrolyzed under acidic conditions? I know that under acidic conditions the first thing to likely happen is protonation. Does it ...
10
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2answers
55k 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
3k 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
1k 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
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1answer
998 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
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2answers
3k 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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2answers
992 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?
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2answers
8k 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 ...
3
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1answer
2k views

Nomenclature of organic molecules with more than one functional group

I need some help naming compounds with more than one functional group based on their priority order. Here are some examples: A 4-membered carbon chain with an aldehyde at one end and a ketone right ...
26
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3answers
53k 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
17k 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 ...
10
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3answers
53k 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 ...
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1answer
465 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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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
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1answer
104 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
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1answer
248 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? ...
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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 ...

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