We’re rewarding the question askers & reputations are being recalculated! Read more.

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.

Filter by
Sorted by
Tagged with
7
votes
0answers
151 views

How can I solve this synthesis?

I have this task to do: My solution: Is that possible? Can you please help me with the steps 2 and 3? This is what I did, but my teacher told me I should make the diketone (compound no. 5) from ...
3
votes
1answer
97 views

Origin of broad CO stretch in infrared spectrum of tricobalt cluster

I'm quite confident that the peaks around $\pu{2000 cm^{-1}}$ are $\ce{CO}$ stretches. But I cannot find any reference on that massive broad stretch following the $\ce{CO}$ stretches. Does it have ...
4
votes
2answers
713 views

If acyl chlorides are reacted with aqueous ammonia, will carboxylic acids also be formed?

As part of my A-level chemistry course, I have been taught that an acyl chloride will react violently with water to produce a carboxylic acid and hydrochloric acid. I have also been taught that an ...
4
votes
3answers
691 views

Reaction of NaOD/D2O with semicarbazone

I managed to solve the question till D but I'm stuck at the last reaction. I tried to find its solution and the source suggest it as
1
vote
1answer
119 views

What will be the product of this reaction?

We have an alpha beta unsaturated ether, along with a keto group in the same compound, which is being treated with a grignard reagent shown (assume the grignard reagent is in excess). Will it only ...
1
vote
0answers
142 views

What is first protonated aldehyde or lactone?

In a six membered lactone with carbaldehyde in beta position, which oxygen gets protonated first? the lactone or the aldehyde? (Using concentrated HCl)
1
vote
1answer
120 views

Methylnitrobenzene ring formation Synthetic Route

I know the malonic ester is probably used to make propanoic acid or some carboxylic acid, and then joined to the methylnitrobenzene. But I just can't figure out what glues to the methyl. I know the ...
0
votes
2answers
196 views

HCl/H2O with alkene: Which one reacts?

I think that the initial step forms a tertiary amine, which then in the presence of the ketone and trace acid undergoes nucleophilic addition. But then, for the $\ce{HCl/H2O}$ in the last step, which ...
0
votes
1answer
729 views

Why does Benzoin give positive Tollen's Test? [duplicate]

Certain alpha hydroxy ketones which can tautomerise to form an aldehyde will give a positive Tollen's Test. I was pretty clear with this idea until I came across this question and the answer given is ...
1
vote
0answers
322 views

Can 1,3,5-trihydroxybenzene perform haloform reaction?

As far as I know it's not possible for 1,3,5-trihydroxybenzene to give the haloform reaction. The prerequisites(that I know) for the haloform reaction are: Only those organic compounds which can be ...
10
votes
4answers
662 views

With which group does the middle oxygen atom of an anhydride remain, on hydrolysis?

With which group does the middle oxygen atom of an anhydride remain, on hydrolysis? As an example, let us say we have the following modification of ethanoic methanoic anhydride, with the middle oxygen ...
3
votes
2answers
2k views

Dehydration of carboxylic acids using P2O5

Why isn’t concentrated $\ce{H2SO4}$ used for the dehydration of carboxylic acids to anhydrides? What is special about $\ce{P2O5}$?
5
votes
1answer
179 views

Base-promoted rearrangement of β-ketoester

Propose a reasonable mechanism for the following transformation: I guess an enolate probably forms first, but then what does it attack to give something like the product in the question?
2
votes
0answers
78 views

Can an enol acetate be formed through Fischer esterification?

Since acetone is converted into its enol form under acidic conditions, could it participate in Fischer esterification to form an enol acetate? For example, would refluxing acetone, p-TSA, and acetic ...
0
votes
1answer
46 views

What kind of mechanism is adopted here? [duplicate]

The relative reactivities of acyl compounds towards nucleophilic substitution is acyl chloride> anhydride>ester>amide. I would like to know how this kinetic property is decided. Is it on the basis of ...
4
votes
0answers
29 views

Could creating ashpalt roads actually be net CO2 reducing? [closed]

I remember reading a popsci book, which at some point mentioned, that the problem with reducing $\ce{CO_2}$ emissions was to actually trap carbon in long-term permanent structures. It then half-...
9
votes
1answer
1k views

In what way could benzoin give Tollen's test?

In Q29 of Joint Entrance Exam (JEE) 2016 India, the official answer key mentions that benzoin gives Tollen's test. However, I saw this post which says that it doesn't: Why do α-hydroxy ketones give ...
7
votes
2answers
850 views

Why does formaldehyde exist primarily as the gem-diol in aqueous solution?

From Wikipedia, Methanediol is the product of the hydration of formaldehyde $\ce{H2C=O}$, and predominates in water solution: the equilibrium constant being about $10^3$ and in a 5% by weight ...
6
votes
1answer
1k views

Mechanism for conversion of ketone to dichloride with phosphorus pentachloride

I would like to know the mechanism of this reaction leading to the formation of a geminal dichloride. I am unable to predict how the $\ce{C=O}$ breaks and how the 2 $\ce{Cl}$ atoms replace the oxygen ...
10
votes
1answer
269 views

Protonating/basic site and Brønsted basicity orders of beta, gamma, and delta lactams

Consider the three cyclic amides: $\beta$-lactam $\gamma$-lactam $\delta$-lactam My question What is the basic site (site of protonation) for these three lactams? And what should be their Brønsted ...
3
votes
0answers
48 views

Transformation of an epoxido-carboxylic acid to an aldehyde [duplicate]

So I am battling with the last part of this transformation and was hoping someone could explain this mechanism to me so that I can confirm my answer. Treating an alcohol with a strong hydrohalic ...
-1
votes
2answers
61 views

Addition of a methyl group to a heterobicyclic ring [closed]

I am battling to understand how this reaction works. It should be a carbonyl addition reaction but I am not 100% sure how to reach each step. Could someone explain the mechanism to me?
1
vote
0answers
334 views

Acidity of aldehydes and ketones and enolate formation

In most academic courses you'd learn that aldehydes are more acidic (lower $\text{p}K_\text{a}$) than ketones due to the lower electron donating effect of the proton compared to the alkyl group of the ...
3
votes
1answer
201 views

Ring expansion of two fused rings to a larger ring

I saw the following reaction mechanism in paper Tetrahedron Lett. 1976, 17 (33), 2869–2872.: I'm not able to understand the following parts: How did the conversion of 27 to 29 take place? I've never ...
1
vote
1answer
223 views

Acid Catalysed Ring Expansion – Mechanism?

Ring expansion of vinyl cyclobutane - Could someone please help me with a detailed mechanism for the above conversion? It is the acid-catalyzed rearrangement of 4,7,7-trimethylbicyclo[3.2.0]hept-3-...
4
votes
1answer
363 views

Assignment of the 13C NMR of 2-heptanone

The 13C NMR of 2-heptanone is given below: I understand the assignments of the carbons labelled 7, 6, 4 and 1. My question is: Why is the shift of environment 5 higher than that of 3, despite being ...
5
votes
3answers
404 views

Decarboxylation of cyclohex-1-ene-1,2-dicarboxylic acid by electrolysis method

What is the major product when cyclohex-1-ene-1,2-dicarboxylic acid is electrolysed? My try: I got 2 cases but I am unable to decide which product is major, and need help here.
0
votes
1answer
85 views

Same set of carboxylate reagents yielding two different products with an alkylide

I recently came across two contrasting products for the same set of reagents - carboxylic acid and alkyllithium, and wish to understand why exactly any difference exists between the two. Reaction 1 ...
5
votes
0answers
182 views

pKa of different sites of butanone

From what I can tell, deprotonation of the central hydrogen leads to the more thermodynamically stable product (most substituted double bond. i.e. most stabilization by hyperconjugation). Therefore, ...
2
votes
1answer
113 views

One-pot synthesis of pyrazole [closed]

I am trying to follow a published paper. It is a one-pot synthesis of pyrazole from a ketone and and acid chloride via a diketone intermediate. Here is the produre from the paper: General Procedure:...
2
votes
3answers
385 views

Conversion from t-butanol to alkene

How can I accomplish the above conversion? My thoughts: One way of introducing the double bond, would be using the appropriate Grignard Reagent after oxidation of t-butanol (somehow) I think that ...
0
votes
1answer
2k views

Why is acetyl cyanide not obtained from acetyl chloride?

Why doesn't acetyl chloride or any other aliphatic acyl chloride react with cyanide ions and undergo nucleophilic addition elimination to form aliphatic acyl cyanide, even though this reaction occurs ...
4
votes
1answer
315 views

Deciding more electrophilic centre between ester and thioester for SN type reaction

My question: (though it won't alter the product) Which carbon is attacked first, the one adjacent to sulphur or the one adjacent to oxygen? The solution says that the carbon adjacent to sulphur is ...
-2
votes
1answer
536 views

Rate of formation of hydrate in a carbonyl compound [closed]

When water in presence of any acid is added to a carbonyl compound, it leads to the formation of its hydrate. But how do we determine the rate of reaction? Is it done by checking the amount of partial ...
5
votes
2answers
857 views

Does acrolein give Fehling's test?

Aromatic aldehydes do not give Fehling's test, which makes me believe that for the same reason acrolein should not. It has a double bond conjugated with the carbon oxygen double bond as in ...
1
vote
0answers
87 views

How to determine the pH range at which maximum hydrate is present?

Question: Find the $\mathrm{pH}$ range at which maximum hydrate is present in a solution of oxaloacetic acid (given $\mathrm{pK_a}$ of $\ce{-COOH}$ in the left is $=2.2$ and on the right is $=3.98$)...
8
votes
1answer
1k views

Racemization of ketones in presence of catalytic acid

Question: Which of the following ketones racemise in aqueous solution containing acidic or basic impurities? My answer: A and B should racemise in aqueous solution, for the carbonyl groups in A and B ...
1
vote
1answer
680 views

Base used in Claisen Condensation

Here's what I read about which base to use in Claisen Condensation reaction (two esters or ester + carbonyl compound forming a beta keto-ester or beta-diketone): The base used must not interfere ...
5
votes
1answer
2k views

Assignment of the IR spectrum of 2,4-pentanedione (acetylacetone)

The IR spectrum is shown here: My assignments so far: The 1728 and 1708 stretches correspond to $\ce{C=O}$ stretches in the keto form - the symmetric/asymmetric stretches respectively. The 3003 ...
7
votes
2answers
588 views

What is the driving force for imine formation?

I know this that when a primary amine is reacted with a carbonyl compound, an imine is formed: I'm wondering why the position of this equilibrium lies to the product side / right-hand side. Why is ...
3
votes
2answers
3k views

Mechanism for acylation of benzene with succinic anhydride

I've just started with EAS. I wanted to write down a mechanism for acylation of a cyclic anhydride (for some reason the formation of the carbocation is not given in my textbook). So I wish to know ...
4
votes
1answer
4k views

Why does adipic acid give a cyclic ketone on heating while glutaric acid and succinic acid give a cyclic anhydride?

Why does adipic acid give cyclic ketone on heating while glutaric and succinic acid give cyclic anhydride?
0
votes
1answer
713 views

How is using Jones reagent different than Potassium dichromate in Sulfuric acid for the oxidation of alcohols?

I was taught at an institution I study in that using $\ce{K2Cr2O7}$ in the presence of $\operatorname{dil}.\ce{H2SO4}$ will oxidise $1^{\circ}$ alcohols to aldehydes, and $2^{\circ}$ alcohols to ...
5
votes
1answer
517 views

Why are 3 equivalents of organolithium needed in synthesis of ketone from carboxylic acid?

For the reaction of a carboxylic acid and organolithium reagents to synthesise a ketone, Clayden's, on p 219, mentions: Notice that three equivalents of organolithium are needed in this reaction: ...
0
votes
1answer
439 views

Reaction of vicinal diol in presence of benzaldehyde

Could someone please help me figure out the products of the following reaction? Here are few possibilities I've come up with: The attacking reagent could the given vicinal diol, with its ...
5
votes
2answers
1k views

What is the mechanism for thermal decarboxylation of a generic carboxylic acid (not special cases like beta-ketocarboxylic acid or malonic acids)?

I am looking for the mechanism for thermal decarboxylation for any RCOOH, and I am guessing that its possible for the thermal energy to cleave the R-C bond homolytically leaving a R• and •COOH. Then I ...
1
vote
0answers
844 views

Why does benzaldehyde undergo Cannizzaro reaction?

Benzaldehyde has an aromatic ring in it which has a pi cloud of electrons surrounding it. Would they not repel the nucleophile when it attacks?
5
votes
1answer
4k views

Product of primary amine and acid anhydride

How does an acid anhydride react with a primary amine? I thought it'll be some sort of condensation reaction, so I made the product by removing a water molecule and got a cyclic product. However, the ...
4
votes
0answers
196 views

Stability of extended enolates

I'd expect an extended enolate to be more stable than a normal enolate, when both can form, but my textbook suggests otherwise. What is the stability of an extended enolate compared with a normal ...
2
votes
0answers
157 views

Condensation Reaction [closed]

In the aldol condensation reaction of a ketone with an aldehyde, both having acidic alpha hydrogens present; what is the major product? Is it formed from enol of the ketone, or of the aldehyde? Is ...