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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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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33 views

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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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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50 views

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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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
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 ...
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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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55 views

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 ...
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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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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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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 ...
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1answer
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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?
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 ...
9
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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 ...
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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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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 ...
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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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
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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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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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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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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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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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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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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Reaction of ketones with cyclic diols

Question In this reaction I am able to figure all reaction except first. What confuses me is the fact than in solution, the cyclic diol reacts only with the aldehydic group. But It can also react ...
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Reactivity Order of Nucleophilic addition

My teacher asked me this question. "Compare the reactivities of acetaldehyde and trimethylacetaldehyde towards nucleophilic addition". I explained how trimethylacetaldehyde was sterically hindered and ...
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Effect of EWG on groups undergoing decarboxylation

I have been reading Peter's Sykes and there I came across certain compounds which show decarboxylation. My doubt is that how the acidity of the groups attached to the carboxyl groups will help in ...
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Bond strength of carbon compounds

I read online that C=O is more stronger than C=N and the reason behind this was, 'Since bond between C and O is more polar hence it will have a slightly higher ionic nature than C and N. As we know ...
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2answers
48 views

How to determine which compound will get oxidised and which will be reduced in a cross cannizzaro reaction?

How to determine which compound will get oxidised and which will be reduced in a cross cannizzaro reaction? As a general rule of thumb, I have always been told that Formaldehyde is always oxidised, ...
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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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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.
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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 ...
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1answer
95 views

Addition of Methyl Grignard and use of HClO4 in this question

Okay so the first step is the use of Grignard. I know that Grignard does a 1,2 addition(generally) and the attack happens directly on the carbonyl,and I think HClO4 basically does protonation.Not sure ...
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1answer
106 views

Unable to form the product formed via rearrangement

Ok so I first reacted one of the carbonyl groups with NH2OH to form an oxime. And then a Beckmann rearrangement takes place followed by tautomerism. Then the lone pair on nitrogen did an ...
5
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2answers
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Counting number of acidic-H in a molecule

In a recent exam, following question was asked: Number of acidic hydrogen present in X are: I've found 8 of them as shown: 7 of them (marked with numerals) were correct according to solution, but ...
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1answer
143 views

Product of the reaction between chalcone and sodium methoxide in methanol

I'm a bit lost on how to do this, for Product C I can see two things happening: 1) The $\ce{-OCH3}$ attacks the alpha hydrogen, but that doesn't really make sense as then you would get two double ...
3
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1answer
117 views

How can a β,γ-unsaturated ketone be converted to 1-pyrroline?

I am working towards a natural product. Presented are three intermediate compounds. After oxidation of the hydroxyl to a carbonyl, I want to introduce an imino-nitrogen atom into the structure. This ...
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does Hydrogen and nickel reduce c=c

In my course, I've come across H2 and Ni catalyst as a reducing agent for alkenes and LiAlH4/NaBH4 as a reducing agent for carbonyl groups. I know LiAlH4/NaBH4 can't reduce c=c as it is nucleophilic ...
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1answer
91 views

Why does cinnamaldehyde pass the ferric chloride test?

I was given some data to determine what the unknown compound was and figured out that it was cinnamaldehyde. After reviewing the classification test given to me by my professor, I was a bit confused ...
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Will phosphorous Ylide participate in carbene generation and insertion?

The following question was sent to me . The answer for this question was given to me as option b I attempted it as following , recognizing the first step as a ylide reaction with a carbonyl compound....
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1answer
95 views

Do esters/carboxylic acids/acid anhydride, etc. show Wolff Kishner reaction or not? [closed]

Our teacher told us that amides can not be reduced by Wolff Kishner reaction. But he did not talked about esters, carboxylic acids, and other functional groups that contain the double bond between ...
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Does 1,3-diphenylprop-2-en-1-one give a positive Tollens test?

If we have 1,3-diphenylprop-2-en-1-one, will it give positive Tollens test? I think aldol reactions are reversible under basic conditions. Here there are mildly basic conditions, so will we get back ...
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44 views

Steric inhibition of resonance in substituted benzoic acid

Why does attaching an $\ce{-NO2}$ group at the ortho position of benzoic acid cause $\ce{-COOH}$ to become perpendicular to the plane of the benzene ring? Why doesn't the nitro group get pushed out ...
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: $\ce{1. (A) + (i)BH3/THF (ii) H+}$ $\ce{2. (A) + H2/Pt}$ ...
2
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0answers
59 views

Reaction of diamines with carboxylic acids to form imidazole

I've recently came across this reaction and my guess is that firstly an amide forms that later reacts with the second amine group. Is this a general reaction? Does it matter if the compounds used are ...
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0answers
26 views

Epoxide with solvent vs with water

The answer given is an epoxide. But is an epoxide stable at room temperature? And also epoxides tend to open in presence of water. Even if methyl alcohol is treated as a solvent, then too methyl ...

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