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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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-1
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1answer
704 views

Reagents to synthesise butanedioic acid from 1,2-dibromoethane

Why can't we use $\ce{HCN (g)}$ and $\ce{HCl (aq)}$ to convert 1,2-dibromoethane into butanedioic acid? I found out that the answer is $\ce{KCN (aq/alcoholic)}$ and $\ce{H2SO4 (aq)}$, I don't ...
3
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1answer
13k 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 ...
6
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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 ...
15
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1answer
588 views

ICHO Synthesis Problem 2018

I've several doubts about this ICHO synthesis problem, which was a part of the preparatory problem package of 2018 (so yes, it's not a part of an ongoing contest) Before sharing the answer given, I'...
8
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1answer
243 views

Alcohol or Carbonyl - Which is more reactive towards PCl5?

We're aware that ketones and alcohols both react with phosphorus pentachloride, to produce geminal dichlorides and alkyl chlorides respectively. What happens in the compound shown below, when ...
-1
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1answer
140 views

What is the final product of a carbohydrate treated successively with hydrogen cyanide, water, and hydrogen iodide/ phosphorus?

An unknown carbohydrate is successively treated with (1) hydrogen cyanide, (2) water, and (3) hydrogen iodide and phosphorus: $$\ce{C6H12O6 ->[HCN] X ->[H2O] Y ->[HI,P]Z}$$ What is the ...
7
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2answers
9k views

How can an α,β-unsaturated ketone tautomerise?

I was taught that for aldehydes and ketone to exhibit keto-enol tautomerism, it is essential that there must be at least one α-hydrogen. For example, acetophenone and butan-2-one show keto-enol ...
2
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3answers
410 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 ...
-1
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1answer
83 views

Why can't you form an anhydride from an ester via nucleophilic attack?

The reaction referred to is the nucleophilic acyl substitution reaction, where the nucleophile is a carboxylate ion and the electrophile is the ester. I am having a difficult time visualizing why this ...
2
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0answers
90 views

Why does gilman reagent react with acyl chlorides but not with other carbonyls?

According to HSAB (hard-soft acid-base) concept, a soft nucleophile preferentially reacts with soft electrophile and a hard nucleophile with a hard electrophile. Since $\ce {R2CuLi}$ is a soft ...
4
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1answer
1k views

How can this ketone show Cannizzaro reaction?

According to answer key, Cannizzaro reaction of 3-hydroxy-2,2-dimethyl-1-phenylpropan-1-one (a ketone) takes place but how is that possible when we know only aldehydes show Cannizzaro reaction?
1
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1answer
328 views

Ketone prefix organic chemistry nomenclature

Is there a difference between the prefixes keto- and oxo-?
4
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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 ...
2
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1answer
250 views

Molecular orbital explanation of why the protonation of the oxygen atom makes a carbonyl group more electrophilic

I was working on nucleophilic addition reactions to the carbonyl group (namely, hemiacetal formation) when I came across the following explanation for the use of acid catalyst and how it increases ...
1
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0answers
130 views

What is a probable mechanism for acid catalysed decarboxylation of alpha-hydroxy acid?

The following question was on one of the tests we had recently Now i worked out the intermediates and the product as follows: The first step is an intramolecular Cannizzaro reaction in which the ...
25
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1answer
919 views

How can I determine if there are π-π interactions between an amide and an aromatic ring in a protein?

In a crystal structure I've determined, a triazole ring on my ligand appears to be stacking with a tyrosine (top in picture): However, there is also an amide, courtesy a glutamine, near it (bottom). ...
3
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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 ...
1
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0answers
41 views

Are alkaline conditions required for Maillard reaction?

The Maillard reaction, a form of non-enzymatic browning, refers to a cascade of chemical reactions that frequently occurs in the cooking of foods (e.g. baking of pastries, roasting of meats). It ...
6
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1answer
105 views

How does this ring expansion on a steroid system occur?

The correct answer is supposedly B, as shown by Gravestock et al.[1] In this reaction after ozonolysis of the C=C double bond, two ketones are formed. How is a rearrangement or expansion of the ring ...
3
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1answer
581 views

Conditions for imine formation

Firstly, note that this is not a duplicate of Acid in Imine Formation. Clayden, Warren, & Greeves (2012) states explicitly on p. 231 that imine formation requires acid catalysis, and that the ...
5
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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?
0
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1answer
10k views

Mechanism for decarboxylation

Propose a mechanism for the following transformation. I gather that this mechanism might be similar to decarboxylation of keto acids: However, I am unsure of how to begin.
15
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2answers
31k views

Why does benzaldehyde not respond to Fehling's test?

All aldehydes are supposed to respond to Fehling's test. So why doesn't benzaldehyde respond to it? Does it have something to do with the fact that benzaldehyde is an aromatic compound? If so, then ...
0
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0answers
77 views

Why don't zwitter ions show ortho effect?

I recently came across a statement which said that zwitter ions are an exception to the ortho effect. Is it because the ions attract each other and the -COOH group is brought back into the plane ...
3
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0answers
59 views

Claisen-like condensation with acid chloride

In the Claisen condensation, an ester enolate attacks an ester, with an alkoxide anion leaving subsequently to give a $\beta$-keto ester. Is it possible for a typical enolate of an aldehyde or ketone ...
3
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1answer
400 views

Why cyclohexane-1,4-dicarbaldehyde does not give aldol condensation?

I was recently came to know as a fact that cyclohexane-1,4-dicarbaldehyde does not give the aldol condensation reaction in spite of possessing α-hydrogens. I was told that this is due to steric ...
1
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3answers
14k views

What is reaction between isopropyl alcohol and acetone?

What would be the probable reaction between acetone, $\ce{(CH3)2CO}$, and isopropyl alcohol, $\ce{CH3CHOHCH3}$, at room temperature without any catalyst in different concentrations?
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1answer
212 views

Converting a thioester to an amide

What reagents can I use for the following transformation? I think this has something to do with formation of an iminium salt and reductive amination, but I'm not so sure.
4
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1answer
4k views

Why does the Rosenmund reduction stop at the aldehyde stage?

In the Rosenmund reduction, an acyl chloride can be reduced to an aldehyde by hydrogenation over a palladium catalyst poisoned with barium sulfate. Why isn't the aldehyde product further reduced to ...
5
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1answer
5k views

Chemoselectivity in reduction of 3′-nitroacetophenone

When 3′-nitroacetophenone is treated with sodium borohydride, only the carbonyl group is reduced (top); however, when reacted with tin and hydrochloric acid only the nitro group is reduced (bottom). ...
4
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0answers
282 views

Regioselectivity of the Beckmann rearrangement

It seems to be that the Beckmann rearrangement is a nice way to prepare secondary amines. This can be achieved by removal of oxygen via the use of $\ce{HI}$/$\ce{P}$. However, if ketones are used, ...
4
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1answer
3k views

Is propane-1,2,3-tricarbaldehyde the correct IUPAC name of CHO-CH2-CH(CHO)-CH2-CHO?

We were asked this question in class: What is the IUPAC name of the compound $\ce{CHO-CH2-CH(CHO)-CH2-CHO}?$ I don't know for sure, but I think the answer should either be 3-formylpentan-1,5-dial ...
4
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1answer
2k views

Cram's rule for nucleophilic addition to carbonyl groups

I recently heard about Cram's rule for predicting the stereoselectivity in nucleophilic additions to carbonyl groups. Can anybody explain what this is and whether it is an accurate rule?
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1answer
36 views

Will a reverse osmosis membrane exclude perfluorobutanoic acid?

I recently did a water quality test and it showed a detectable level of perfluorobutanoic acid, a potentially dangerous carboxylate PFC. Will a reverse osmosis water purification system exclude this ...
0
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0answers
205 views

Why is ninhydrin stable as a geminal diol? [duplicate]

The following image depicts the structure of ninhydrin - $\ce{C9H6O4}$ Ninhydrin, as you see has two hydroxyl group attached to same carbon. In general, geminal diol (or gem-diol, for short) are ...
11
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1answer
204 views

Mechanism of radical cyclisation to form hydroazulene core

Recent studies on radical-induced cyclisation reactions have led to a simple, one-step method for the preparation of hydroazulenes from appropriately substituted cyclopentanone precursors. Treatment ...
2
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1answer
262 views

What side reactions are suppressed by the use of TMSCl in the acyloin condensation?

I was reading about the acyloin condensation and came across a statemant according to which, the use of TMSCl obviates competing reactions. My question is what kind of competing reaction would happen ...
18
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4answers
23k views

Why is acetic acid more acidic than phenol?

Acetic acid (ethanoic acid, $\mathrm pK_\mathrm a \approx 5$) is more acidic than phenol ($\mathrm pK_\mathrm a \approx 10$), which is reflected in their reactivity with a weak base such as sodium ...
8
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0answers
269 views

Sulfonyl azides: diazo or azide transfer?

Sulfonyl azides, $\ce{RSO2N3}$, are capable of acting as sources of electrophilic azide ("$\ce{N+3}$"), but are also capable of effecting diazo transfer, as shown in the scheme below, taken from ref 1:...
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1answer
231 views

Give the order of nucleophilic addition reaction in the following -

I am confused that whether we should take only inductive or hyperconjugation effect also into consideration while finding the order. As the answer in the book is only according to inductive effect . ...
1
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1answer
155 views

Do carboxylic acids form hydrates like aldehydes and ketones?

Having learned that aldehydes exist in equilibrium with their hydrate form - Do carboxylic acids do the same in a water solvent and form a hydrate with 3 $\ce{OH}$ groups and one alkyl group?
10
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1answer
733 views

Enolate formation and tosylate displacement in cis/trans decalin

What will happen in the following reactions? This is Problem 3d from Chapter 6 of Zweifel and Nantz's Modern Organic Synthesis. I thought that after the hydroxyl group is converted into a good ...
2
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0answers
64 views

How would one disassociate the carboxylic acid on the end of a perfluorooctanoic acid molecule?

This is what a perfluorooctanoic acid molecule looks like. The carboxylate head on the end would normally disassociate in water because carboxylic acids are weak, but because of the fluorocarbon tail, ...
3
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1answer
344 views

Mechanism for conversion of imide to ester with NaH

What is the mechanism of this reaction? My proposed mechanism is shown below, would it work?
0
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1answer
15k views

What reaction happens when carboxylic acids are treated with calcium hydroxide and distilled? [closed]

What reaction takes place when $\ce{Ca(OH)2}$ reacts with $\ce{R-COOH}$? What is obtained after distillation?
5
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2answers
856 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 ...
4
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1answer
191 views

Can enamines be formed from α,β-unsaturated ketones?

This question was a result of discussion form here: α,β-unsaturated carbonyl compounds and alkyl addition The reaction below (condensation of cyclohexenone with a secondary amine) does not yield any ...
8
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2answers
1k views

How can an aromatic ketone be reduced in the presence of a 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 ...
1
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1answer
221 views

Haloform Reaction of Furfural

My instructor pointed out that furfural undergoes haloform reaction - I don't understand how. I couldn't figure out the mechanism on my own, and couldn't find much online either. (regarding the ...
4
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2answers
2k views

In Reimer-Tiemann reaction why does phenol attack the carbene from ortho position?

From the Wikipedia article on Reimer-Tiemann reation: In step 5, why doesn't the oxygen attack the carbene. The way I see it: upon attacking the carbene from ortho position, the mechanism ...