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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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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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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 ...
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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 ...
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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 ...
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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 ...
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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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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 ...
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Oxidation of hexan-3-one (unsymmetrical ketone) [on hold]

Hexan-3-one is an unsymmetrical ketone; therefore, it's oxidation is carried out by Popoff's rule, which is based on concept of alpha hydrogens. But there are equal numbers of alpha hydrogens on both ...
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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 ...
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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 ...
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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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Does alkali metal salts of poly carboxylic polymer have less reactivity than hydrogen forms?

Does the metal-cation bond in sodium hyaluronan make the carboxyl group less reactive than the hydrogen form in hyaluronic acid? I am researching HA coatings for microfluidic surfaces and in ...
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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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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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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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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 ...
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1answer
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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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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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71 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?
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108 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?
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166 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 ...
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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, ...
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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 ...
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1answer
125 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 ...
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1answer
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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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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. ...
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1answer
138 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 ...
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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, ...
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1answer
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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 ...
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1answer
39 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 ...
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101 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 ...
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1answer
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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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232 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 ...
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316 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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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.
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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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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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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 ...
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1answer
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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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Would the reaction to produce amides from acyl chlorides also produce carboxylic acids?

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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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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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
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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 ...
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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)
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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 ...
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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 ...
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243 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 ...
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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 ...
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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 ...
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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 $\ce{P2O5}$?