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 don't dicarboxylic acids show hydrogen bonding in spite of the fact that carboxylic acids exist usually as dimers in polar aprotic solvent?

I have seen several examples: The fact that maleic acid is more soluble in water than fumaric acid in spite of the fact that it must be able to show intramolecular hydrogen bonding. trans-...
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Help with mechanism similar to Robinson Annulation

I need to figure out a mechanism for this reaction. All I know is that it is supposed to have a similar mechanism to Robinson Annulation. This is the best I could come up with, but I've been told it ...
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What about the Methanal having Alkyl? [closed]

In my book, there is a question which mentions formula $$HCHO$$ of Methanal and asks to tell the functional group and alkyl radical. I am confused because its clear that functional group is aldehyde ...
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Reaction Of Grignard's Reagent with Acyl Chloride

My organic chemistry book says that Grignard reagents react with acyl chloride just as hydride reagents. Further in an in-text question now using above theory, my answer is But Answer in Solution ...
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Why doesn't propynal give cannizzaro reaction?

Cannizzaro reaction is a disproportionation reaction which is given by aldehydes and ketones having no α-H, forming alcohol (reduction) and carboxylic acid (oxidation) as its products. The compound, ...
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Reaction of carboxylic acid with phosphorus trichloride

The reaction of carboxylic acid $\ce{RCOOH}$ with $\ce{PCl5}$/ $\ce{SOCl2}$ / $\ce{PCl3}$ yields an acyl chloride $\ce{RCOCl}$. With $\ce{PCl5}$ and $\ce{SOCl2}$ the reaction is quite simple utilizing ...
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Why aren't the hydrogen bonds in carboxyllic acids like this?

Why don't carboxylic acids form H-bonds in this formation with the red dots (diagonal) instead of the black dots (horizontal)? I was always taught that H-bonds formed between partially negative and ...
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Fate of compounds after radioactive decay [duplicate]

Let us say there is a $\ce{CO2}$ molecule containing $\ce{^{14}C}$ isotope. $\ce{^{14}C}$ undergoes decay to form $\ce{^{14}N}$. What happens to the molecule?Does it form $\ce{NO2}$? How are the ...
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110 views

Reaction of 2,3-dichlorobutanoate with a decarboxylating agent followed by hydrochloric acid and then aq. potassium hydroxide

Question $$\ce{CH3-CH(Cl)-CH(Cl)-COO- ->[-CO2]A->[HCl]B->[aq KOH]C}$$ Product C is: a) $\ce{CH3-CH2-CHO}$ b) $\ce{CH3-CH(OH)-CH2-CH2-OH}$ c) $\ce{CH3-CHO}$ d)$\ce{CH3-C(=O)-CH3}$ Answer My ...
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Reagent to reduce aliphatic aldehyde to alcohol while protecting double bond

I have a straight chain, aliphatic aldehyde (liquid) with a double bond in it. I want to reduce the terminal carbonyl group to an alcohol but without touching the C=C double bond. The double bond is ...
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Product of the reaction of ethyl acetoacetate with alkaline benzoyl chloride followed by addition of ammonium chloride

What does this β-keto ester give when reacted with $\ce{PhCOCl/NaOH}$ followed by $\ce{NH4Cl(aq)}?$ According to me, the $\ce{PhCOCl}$ should react with $\ce{NaOH}$ forming benzoic acid which should ...
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Reaction of acyl chlorides with diazomethane and silver(I) oxide

$$\ce{R-COOH ->[SOCl2,CH2N2][Ag2O/CH3OH] X}$$ While solving Carboxylic derivatives recently, I came across this. so following the reagents one by one- $\ce{SOCl2}$ will form acid chloride. $\ce{...
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Equilibrium between hydroxides and ketones/aldehydes

In the reaction between hydroxides and ketones/aldehydes, an equilibrium will be established between the tetrahedral intermediate and the reactants. For aldehydes, significant amounts of the ...
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Reactivity comparison between benzaldehyde and acetaldehyde [duplicate]

One of my teacher says that $\ce{Ph-CHO}$ is more reactive than $\ce{CH3-CHO}$ in performing nucleophillic addition reaction because $\ce{—Ph}$ is planar and thus offers less steric hindrance as ...
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Unusual hydrolysis of methyl 2,4,6‐trimethylbenzoate

Problem 223 from Conceptual Problems in Organic Chemsitry by Singh [1, p. 367]: The given answer is b and I don't get why. Usual ester hydrolysis would've given a. I somehow managed to know that the ...
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1answer
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Tollen's Test with Salicylaldehyde

I have read that Tollens' test is given by aldehydes. The aldehyde is oxidised to a carboxylate ion and silver is deposited. My teacher had given me notes which pointed that salicylaldehyde does not ...
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Cleavage of C-C bond in 1,2-diketo compounds with periodic acid

Today we learned the Malaprade reaction in class. My teacher told me that a similar reaction can take place when the substrate is a 1,2-diketo or 1-keto-2-hydroxy or even 1-hydroxy-2-amino(in presence ...
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88 views

Beckmann rearrangement v/s dehydration of Oximes

In the above question, A is an oxime, which is then reacted with phosphorus pentoxide. Now, phosphorus pentoxide is both a dehydrating reagent and a reagent used for Beckmenn rearrangement, but which ...
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1answer
69 views

Stereoisomers of metaldehyde and paraldehyde

(1) In case of paraldehyde I see 3 similar chiral carbons. So I divided it into 2 subcases -two methyls above the plane and one below the plane -all three above the plane so, that makes it 2. When I ...
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111 views

Nitro-substitution [closed]

Here I expected (b) to happen via nucleophilic substitution, but contrary to that (a) is the one occuring. What exactly is happening here?
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Comparison between hot conc. KMnO4 and cold KMnO4

Recently while solving carbonyl compounds I came across this. What all can cold KMnO4 do? Can it oxidize aldehydes too, along with oxidizing alkene to vicinal diols? (I need a thorough comparison in ...
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1answer
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Priority order of attack of grignard reagents on functional groups

Recently I was solving carbonyl compounds and I came across this. Is there some priority order, or logic behind why alcohol reacts first with Grignard reagent and then ketone. Whereas ester could've ...
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Why aren't nitriles very good electrophiles?

I was wondering why nitriles do not react as electrophiles like carbonyl unless they have to, given that the C-N triple bond is still pretty polarized. The LUMO will be higher in energy than a ...
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Forming ester from amide using protonated alcohol as catalyst

In my level of understanding, if I want to make an amide from an ester, I should add: $\ce{H3O+}$ for hydrolysis to make carboxylic acid $\ce{SOCl2}$ to form acid chloride $\ce{ROH}$, pyridine 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
115 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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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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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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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
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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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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
68 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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76 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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176 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
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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103 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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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
61 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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339 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 ...
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93 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 ...
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1answer
92 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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