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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0answers
23 views

Direct addition (1,2) or conjugate addition (1,4)? [closed]

Problem: Reaction of alpha - beta unsaturated carboxylic acid derivatives with alcohol. I came to know that acid chloride gives direct addition Whereas amides,esters give conjugate addition However I ...
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1answer
391 views

Inductive vs conjugation effects in ester hydrolysis

I just came across the following problem about alkaline ester hydrolysis: Since all of the substituents are in the para position, I immediately thought about the ability of those substituents to ...
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Why doesn't HIO4 cleave acetals?

Recently, I started reading about the cleavage reactions done by $\ce{HIO4}$.I came across a statement which read $\ce{HIO4}$ can't cleave acetals but it can cleave hemiacetals. But when I tried to ...
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1answer
76 views

Does acetoacetic ester give haloform test?

According to my class notes, acetoacetic ester doesn't give haloform test, but I feel that it should. I know that the methyl group on acetoacetic ester is not responsible for the haloform test. First, ...
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Why do electronegative heteroatoms increase C=O stretching frequency (bond strength)

Why does a more electronegative heteroatom (i.e. $\ce{Cl}$ or $\ce{O}$) increase the stretching frequency of a carbonyl? I'd suspect it's that they donate their lone pairs and we end up with a ...
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2answers
5k views

Mechanism for acylation of benzene with succinic anhydride [duplicate]

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 ...
7
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1answer
39k 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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29 views

Enamine Formation in a Diketone

I am trying to form an enamine, and I was trying to figure out if the following reaction is possible: Would this reaction terminate after the formation of the shown product, or will the other ...
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1answer
32 views

Mesomeric effect in crotonaldehyde [closed]

I tried making structures using lone pair of oxygen but I am unable to achieve a structure which doesn't violate the octet rule.
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2answers
976 views

How do α,β-unsaturated acids undergo decarboxylation?

I know the concerted mechanism for β-keto acids, but neither could I figure out, nor was I able to find out the mechanism for α,β-unsaturated acids. Any help is appreciated.
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In which condition CO uses the oxygen end for bonding?

Generally Metal Carbonyl complex are formed from Carbon end. Is it possible under some specific condition that the Oxygen end is used? (PS -I know about the structures of M-CO bonding)
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1answer
597 views

Does acid anhydride give a positive iodoform test?

I thought that acetic anhydride $\ce{CH3COOCOCH3}$ would give a positive Iodoform test because it has a $\ce{CH3-(CO)}-$ group.But it is given that this does not happen. Is this true? If so, can ...
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Reduction of carbonyl compound by LAH (in anhydrous ether) followed by reaction by acidic water

What will be the final product upon reaction of $\ce{CH2=CH-CH2-C6H4-CH=CH-CHO}$ with $\ce{LiAlH4}$ (in dry ether) followed by acidic water? LAH will reduce the carbonyl group to alcoholic group and ...
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1answer
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How does sodium in ethanol reduce carbonyl compounds?

According to my teacher, Na in ethanol reduces carbonyl compounds (e.g. aldehydes and ketones) to alcohols. However, I can't see where the hydrogen needed for reduction comes from. How does the ...
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2answers
720 views

I am confused about the stability of carbanion III and IV in the image

I am confused about the stability of carbanion III and IV in the image, I think III is more unstable because of electron donating effect (+R) of $\ce{-OCH3}$ group but my book says III is more stable ...
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1answer
17 views

Selective carbonyl protection using ethylene glycol [closed]

Can anyone explain to me which position is more favourable to form ketal i.e aldehyde or ketone Also which reducing agent also reduce this ketal. And how thioketal formed from thioethyleneglycol ...
3
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1answer
3k views

Reaction of succinic acid with ammonia

When succinic acid is treated with excess $\ce{NH3}$, what will the mechanism be? I feel both $\ce{COOH}$ groups should be converted to $\ce{CONH2}$, but this is not the product.
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Reaction of multiple diols with sulphuric acid [closed]

Find the total number of possible products I can think of atleast three reactions that will take place in the acidic medium: Pinacol-Pinacolone rearrangement Intermolecular dehydration (leading to ...
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4answers
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Reasons for negative iodoform test

Why does 2',6'-dimethylacetophenone not give iodoform test?
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1answer
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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 ...
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0answers
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How does a cyclization occur with a carboxylic acid and (CF3CO)2O?

The product of the reaction below is unsaturated, bicyclic ketone, but I'm confused as to how (CF3CO)2O reacts with it to cause the cyclization. There is no base involved so I don't know how the ...
3
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1answer
402 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, $\...
9
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2answers
16k views

Does Br2/H2O oxidize all aldehydes including carbohydrates?

In many books, it is mentioned that aldehydes are easily oxidized even by mild oxidizing agents. However, I have never seen bromine water explicitly mentioned. But in the carbohydrates chapter, it is ...
3
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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
67 views

Decomposition of oxalic acid [closed]

Normally, carboxylic acids on heating form an anhydride. However, Oxalic acid on heating undergoes decomposition to yield $\ce{(CO + H2O)}$. Why does not Oxalic acid form an anhydride?
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1answer
40 views

Grignard reagent will act as a base or a nucleophile [duplicate]

R- from grignard reagent (RMgBr) and gilmann's reagent (R2CuLi) although being a strong base reduces the carbonyl group and does not act as a base. Why can't it abstract the alpha hydrogen forming an ...
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3answers
7k views

Which compound reacts faster in the Cannizzaro Reaction?

Which reacts faster in the Cannizzaro Reaction? a) $\ce{OHC-C6H4-NO2}$ b) $\ce{OHC-C6H4-OCH3}$ Obviously, a better hydride releasing group will react faster. Therefore my answer was b, as $\ce{-...
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1answer
119 views

What causes the blackening of light bulbs

in 1878, Thomas Edison (or rather William Joseph Hammer) added an anode in a light bulb in order to catch the flux of electrons coming out from the carbon filament and reduce the phenomenon of ...
4
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2answers
338 views

What are the organic reactions that are taking place in this reaction?

I know that A is the product of a Knoevenagel condensation between the aldehyde and the diethyl malonate, due to the acidic protons of the latter, but I don't know what the reaction between that ...
5
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1answer
69 views

Carboxylic acid bond lengths in 3-carboxycyclobutane-1-carboxylate

Select correct order of bond length of the above bond P, Q, R & S: (A) P > R > S > Q (B) Q > R = S > P (C) S > Q > R > P (D) None of these I think the answer should be (D) ...
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1answer
143 views

What is the difference in dehydration of cis- and trans-1,2-cyclohexanedicarboxylic acid in anhydride formation?

Is there some required stereochemistry for anhydride formation? Do both of them form the same product, or does one not even undergo dehydration? I looked up cyclohexane-1,2-dicarboxylic anhydride's ...
2
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1answer
87 views

How does methyl vinyl ketone dimerise with heating?

(A) to (B) is simply reduction, tosylation followed by intramolecular reaction and removal of tosylate. However, I am not able to guess how dimerization will take place, seems similar to Rauhut–...
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1answer
6k views

What is the product formed after nitrosation of ketones (HNO2 + ketone)?

On C-nitrosation of ketones we get oximes. After this, the oxime formed is hydrolyzed ($\ce{H3O+}$ is added). What will be formed in the end? Does it follow Beckmann rearrangement or what?
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1answer
241 views

Effect of phenyl and vinyl substituents on Acidity of carboxylic

Recently I came across this statement in my textbook: Direct attachment of groups such as phenyl or vinyl to the carboxylic acid, increases the acidity of corresponding carboxylic acid contrary ...
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2answers
248 views

Photochemical rearrangement of 4,4‐diphenylcyclohexa‐2,5‐dien‐1‐one

I can see how the option A and B are correct as it is just a standard dienone–phenol type reaction which involves a phenyl shift. However, the given answer is A, B, C and D. I do not see how C and D ...
4
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1answer
82 views

What is the product of reaction between 3,3-dimethyl butanal and SeO2 followed by conc. OH- ions?

So basically first step will be replacement of $\ce{-CH2 -}$ by a ($\ce{=O}$ bond) making a aldehyde and ketone side by side. Now what should I do after this? I tried attacking the aldehyde first as ...
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1answer
56 views

Which double bond is more electrophilic : carbon-carbon or carbon-oxygen?

Question Attempt It seems to me that the carbon-oxygen bond would be more electrophilic due to the higher electronegativity of oxygen. Hence I believe $\ce{CH3-}$ should attack the carbonyl site. ...
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1answer
242 views

How to compare the rate of decarboxylation?

For the following acids compare the rate of decarboxylation on heating I $\ce{Ph-CO-CH2COOH}$ II $\ce{Ph-CO-COOH}$ III $\ce{CH3-CH2-COOH}$ IV $\ce{HOOC-CH2-COOH}$ I tried this question by forming ...
2
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1answer
32 views

What would be the product of following elimination reaction?

Question Doubt The answer is given B. But why cant it be C after all formation of cyclopropane would increase angle strain?
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1answer
42 views

What would be the aldol condensation products in B

In this question (13) I figured out A,C were wrong and D would be correct choice but I am stuck at finding out products formed in B and also why it would be wrong? Please help.
3
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1answer
181 views

Specific reduction of certain functional groups

Consider the compound $\ce{Alkyl-(4 oxocyclopent-2-ene)carboxylate (A)}$. For example consider- Now consider the operations: $\ce{1. (A) + (i)BH3/THF (ii) H+}$ $\ce{2. (A) + H2/Pt}$ ...
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2answers
7k views
2
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1answer
73 views

IUPAC nomenclature for tricarboxylic acids

What is the rule for naming compounds with three carboxyl groups? I have the two following coumpunds 4-(Carboxymethyl)heptanedioic acid Pentane-1,3,5-tricarboxylic acid They both have 7 carbon ...
2
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0answers
62 views

What is the product of following iodoform reaction?

Question Attempt I think the product A would be as I have attempted below, but I am getting the answer as A but book says D. Where am I wrong? Please help.
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1answer
33 views

In the following reaction is E2 or Sn2 favorable?

Question Doubt It is quite obvious that carbonyl compound is going to convert into alkane, but what confuses me is whether Sn2 or E2 will occur at bromide position Although there is heating( which ...
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0answers
26 views

What is the product of reaction of carbonyl compound with HNO3 [duplicate]

Question Doubt I am unable to imagine what the first product would be? All I know is HNO3 is a strong oxidising agent. So would it convert the reactant into carboxylic acid? Please help
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0answers
37 views

What will be the product of following Wolf-kishner reduction?

Question Attempt 1.Wolf kishner would reduce double bond oxygen to alkane. 2.Also since water is present acetal should break. 3.SnAr doesn't seems possible due to adjacent bulky groups. So ...
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0answers
17 views

Does -M Effect increases rate of hydration of aldehyde and ketone?

I saw somewhere written, the rate of hydration of carbonyl compounds depends on: -I group Steric hindrance Intramolecular H bonding Can -M effect also increases rate of hydration?
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4answers
3k views

What's the mechanism of the reaction of (E)-methyl 3-(furan-2-yl)acrylate in acidic methanol?

In the organic chemistry textbook by Clayden et al. they mention that the reaction of (E)-methyl 3-(furan-2-yl)acrylate in acidic methanol yields dimethyl 4-oxoheptanedioate without providing the ...
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0answers
29 views

Complex Esterification reaction?

Question Attempt On seeing the question it seems like simple esterification reaction and the answer seems A. But the answer in book says C. How is it so I also tried to develop a mechanism as ...

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