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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.

13
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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
56 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 ...
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19 views

Nucleophilic attack on carbonyl vs. SN2 - who wins?

If a nucleophile is to attack the above compound, how do I determine wheather it kick the chlorine atom out via an SN2, or will it attack the electron deficient carbonyl? Does it depend on the ...
11
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2answers
141 views

How can benzaldehyde have a pKa of 14.9?

There are numerous websites out there which claim that the pKa of benzaldehyde – C6H5CHO – is 14.90. (Just do a Google search for benzaldehyde pka to see what I ...
2
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0answers
29 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 ...
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1answer
48 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 ...
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1answer
33 views

Ketone prefix organic chemistry nomenclature

Is there a difference between the prefixes keto- and oxo-?
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0answers
43 views

Why does fructose forms its osazone faster than glucose in the reaction of monosaccharides with phenylhydrazin?

In the reaction of monosaccharides with phenylhydrazine, fructose reacts and forms an osazone within 2 minutes while glucose takes longer time about 5-6 minutes(although both sugars form the same ...
2
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1answer
45 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 ...
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0answers
40 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 ...
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0answers
13 views

Why is a thioester more reactive than an ester? [duplicate]

I'm curious as to why a thioester is more reactive than an ester when it comes to reactivity towards nucleophilic attack. I know that the two factors affecting the reactivity towards nucleophilic ...
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0answers
19 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 ...
3
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1answer
111 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 ...
0
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1answer
75 views

Which one is the stronger base?

I'm studying Wolff-Kishner reduction and I don't understand why after this step the leaving group is $\ce{OH-}$ instead of $\ce{^-HN-NH2}$. I guess it's because hydroxide ion is less strong than the ...
6
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1answer
46 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 ...
0
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1answer
46 views

Equation for the equilibrium constant for the hydration of carbonyls using UV spectroscopy

I was looking through the literature when I found this source: https://pubs.rsc.org/En/content/articlepdf/1967/tf/tf9676302131 Which states that the equilibrium constant Khyd is: Khyd = $\frac{[...
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0answers
31 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 ...
0
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0answers
45 views

Effect of H-bonding on o-nitrobenzoic acid

My argument here is regarding the acidity of o-nitrobenzoic acid being greater than p,m-nitrobenzoic acid. In o-nitrobenzoic acid, there is an intramolecular hydrogen bond which makes the bond ...
3
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0answers
33 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
104 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 ...
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1answer
64 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.
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0answers
229 views

How many enolisable hydrogens are there in 2-methylcyclohex-2-en-1-one?

For me there are 4 enolisable hydrogens, 2 alpha to the keto group on left and two allyl hydrogens in the ring. But the book says there are 7. Which 3 am I missing?
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0answers
66 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 ...
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1answer
20 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 ...
2
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1answer
104 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 ...
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1answer
48 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 . ...
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1answer
73 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?
3
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1answer
116 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?
3
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0answers
221 views

Why does formic acid give positive Fehling's test?

$$\ce{HCOOH ->[\text{Fehling's solution}] CO2 + H2O}$$ The points discussed in a previous question do not account for the fact that formic acid also gives positive Fehling's test since it is not ...
2
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0answers
53 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, ...
2
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0answers
17 views

Fluorination of Carbonyl Compounds using Molybdenum Hexafluoride

What is the mechanism of halogenation of carbonyl compounds using molybdenum hexafluoride? How does it work? Here's a reaction I came across - Can we use it for all carbonyl compounds, or, are there ...
1
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1answer
130 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 ...
3
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1answer
114 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 ...
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0answers
35 views

Why do amides react differently with PCl5? [duplicate]

In a reaction involving $\ce{PCl5}$ and any reactant containing oxygen atom, it generally takes out the oxygen and put chlorine their due to formation of strong bond between phosphorus and oxygen. ...
1
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1answer
164 views

What is the reaction of pentane-2,4-dione with chlorine in presence of NaOH? [duplicate]

We know that in haloform reaction alpha acidic hydrogen are substituted by halogen atom. But in the above case we find two acidic hydrogens in between the two keto groups (due to -R effect) which are ...
0
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1answer
35 views

How far-reaching is the effect of conjugation?

Due to conjugation, it is possible for 1,4-addition, or conjugate addition, to occur. I was thinking, since conjugation and resonance effects do no diminish with distance, unlike inductive effects, ...
4
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1answer
83 views

Cyclisation reaction through hydrazine

The following reaction confuses me - I don't understand how and why it happened (couldn't figure out the mechanism): I thought this is some Wolff Kishner sort of reduction, but the reagents don't ...
3
votes
1answer
41 views

Conjugate addition vs Electrophilic addition

I was just doing an organic chemistry problem from an online source recently, on the topic of conjugate additions (or 1,4-additions). Below is an image illustrating the problem. I chose the upper ...
4
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0answers
118 views

Reaction of alpha hydroxyketone with KOH

What happens when 2-hydroxycyclohexan-1-one (an alpha hydroxyketone) reacts with aqueous $\ce{KOH}$? I tried something like Favorskii rearrangement, but it's wrong because OH isn't a good enough ...
3
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1answer
131 views

Malic acid 3-step synthesis

I was quite puzzled by the answer for this question in my Carboxylic Acids and Derivatives tutorial question set. It is question 6 (a), on the synthesis of malic acid, as shown in the image below. ...
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1answer
285 views

Why carbonyl groups are strong benzene deactivating group for electrophillic aromatic substitution?

In carbonyl group there is a resonance avaibility and also due to inductive effect it can also withdraw electron from benzene ring . As, resonance(e- donating chracter) dominates than Inductive effect ...
1
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1answer
337 views

Reaction of 2,4-DNPH with aromatic aldehydes

Does 2,4-dinitrophenylhydrazine react with aromatic aldehydes, e.g. benzaldehyde (phenylmethanal), in a condensation reaction similar to 2,4-DNPH's reaction with aldehydes and ketones ?
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1answer
44 views

Would this be a reasonable mechanism for the formation of a diazomethene?

I am mostly concerned about the first step. Are there any species in this mechanism that look too reactive for this mechanism to make sense? Any thoughts would be greatly appreciated.
3
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2answers
891 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 ...
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0answers
45 views

Equivalent for the N prefix of amides and amines in common naming

Are there common names for amines and amides that have more than one carbon group attached to the nitrogen atom? IUPAC names are written using N,N- but I don't know if there's any equivalent for ...
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0answers
126 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 ...
2
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1answer
50 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 ...
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2answers
359 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 ...
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0answers
27 views

Diamond surface graphitization

Wikipedia says that diamond converts to graphite at ~700 °C. But then, in the same article we can find an information: "But diamonds (sp3C) are unstable against high temperature (above about 400 °C (...
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2answers
210 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