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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6
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0answers
134 views

Comparison of C=O bond strength in metal carbonyls

Find the weakest $\ce{C=O}$ bond among $\ce{[Mn(CO)6]+},$ $\ce{Fe[(CO)5]},$ $\ce{[Cr(CO)6]}$ and $\ce{[V(CO)6]-}.$ I thought the $\ce{C=O}$ bond strength would be lowest in $\ce{[V(CO)6]-}$ since the ...
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Possibility of removing two water molecules from glycerol

Not a chemist, but from a chemical formula perspective, how hard would it be to create acetone by acidifying glycerol? $$\ce{C3H8O3 + 2 H+ <=> C3H6O + 2 H2O}$$ Has anyone ever heard of this ...
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1answer
221 views

Why is 2-fluorobenzoic acid more acidic than 4-fluorobenzoic acid despite its intramolecular hydrogen bonding?

I was reading about $\mathrm{p}K_\mathrm{a}$ values of 2-fluorobenzoic acid and 4-fluorobenzoic acid and found that the latter had a higher value which was surprising to me. I think that ...
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1answer
35 views

How does NaOH modify pyranodioxins?

I am given the molecule in black which is treated with $\ce{NaOH}$. The product is in blue. Could someone explain the mechanism? All I have so far is that the $\ce{-OH}$ group on the bottom right ...
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Does KCN prefer SN2 or nucleophilic addition?

If we have a 1° halide that also contains a carbonyl group (like 5‐chloropentan‐2‐one), and we add 1 mole of KCN in DMSO to it, what will happen? Will the SN2 product by substitution of chlorine or ...
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1answer
110 views

Relative acidity of acetic acid derivatives with strongly withdrawing substituents

What would be the order of $\mathrm{p}K_\mathrm{a}$ values of the following: $\ce{O2N-CH2-CO2H},$ $\ce{Me3\overset{+}{N}-CH2-CO2H},$ $\ce{NC-CH2-CO2H},$ $\ce{HO-CH2-CO2H}?$ Since only the groups ...
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Number of π electrons in all trans-2,4,6-octatrienoic acid

Sketch the Lewis structure of all trans-2,4,6-octatrienoic acid. (a) Consider the delocalized π electrons. Employ the particle-in-a-box model. Drawing on your knowledge about the occupation of ...
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1answer
606 views

Why is para-aminobenzoic acid more acidic than ortho-aminobenzoic acid?

Compare the acidic strength of o-, m-, p-aminobenzoic acids. I got that meta will be the most acidic as it won't be able to show R+ effect of $\ce{NH2}.$ But among the other two, i.e. ortho and para, ...
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1answer
64 views

Why does the electron withdrawing group increase acidic nature of carboxylic acids?

The doubt in my mind is that the electron withdrawing group is attached to the carbon atom of the carbonyl group and that carbon doesn't have any negative charge..the negative charge lies on oxygen ...
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1answer
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iupac name please? [closed]

I am kind of confuse here whether to number $\ce{NO_2}$ or double bond in the ring.
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1answer
67 views

Acidity of Carbonyl group

I m a high school chemistry learner. I have learnt that acids are substance that can liberate H+ on hydrolysis. For that they must be connected to an electronegative atom. In carbonyl ( mainly ...
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Which one out of a keto group or a hydroxyl group would get protonated first if both are present in a compound (attachment)

In the solution provided by my teacher he protonated the ketone, moved the +ve above by resonance did methyl shift and then did dehydration to form a benzene type system. Is this only because for this ...
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1answer
191 views

Is cyclohexane‐1,3‐dicarboxylic acid a correct IUPAC name?

I did the numbering by taking all the functional groups in principal chain (scheme A), but my teacher did it differently and proposed the name cyclohexane‐1,3‐dicarboxylic acid (scheme B): The ...
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Assigning carbon-13 NMR for ethyl 2-oxo-2H-chromen3-carboxylate

I have a molecule and an NMR spectrum, and I need to assign the NMR peaks to each of the carbons to the molecule: I know that the 14.19 ppm and the 61.94 ppm correspond respectively to the carbon 12 ...
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71 views

What would be the product of this reaction?

A 3 membered carbon ring with a double bond to oxygen from one carbon and a double bond between the remaining carbon with a methyl group attached to one of the carbon is made to undergo acid catalyzed ...
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2answers
310 views

Why are halogens base sensitive groups (Wolff-Kishner Reduction)?

So while studying about Wolff-Kishner reduction reaction to form alkanes from carbonyl groups. I read that it is not suitable for base sensitive groups as the environment is highly basic and as an ...
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Why NaBH4 don't reduce this keto group?

I was solving problems related to Carbonyls. The question was: What would be the product formed after the reduction of this compound using $\ce{NaBH4}$? (This is an isomer of Glutaric Anhydride) I ...
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224 views

Optical activity of tartaric acid

The meso-form of tartaric acid is optically inactive due to the plane of symmetry. But how are these forms able to show optical activity when the σ-bonds can freely rotate, which can change the ...
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2answers
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How to synthesize 3‐cyclopentylpropanal from (chloromethyl)cyclopentane?

I am not sure on how to start, but I think of these two possible ways: Reacting the starting material with Grignard reagent and then oxidise the product with PCC to produce the aldehyde; Hydrolysis ...
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2answers
267 views

IUPAC name of aldehyde with two functional groups

I am confused as to what suffix to use for the following compound: Should it be carbaldehyde or just -al, like should it be propane-1,2-dicarbaldehyde or should it be propan-1,2-dial? Or maybe it's 1-...
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32 views

Name of proton directly bonded to a functional group e.g. carbonyl

For example, a carbon bonded to a carbonyl group is the alpha carbon, and has alpha protons. Following that there are beta and gamma carbons and protons. Is there a specific name for the proton in an ...
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1answer
67 views

Reaction of unsaturated lactone and alcohol

Image source I found this equation to turn this compound into an ketoester but I am unsure of the reaction mechanism. I postulate that the alcohol attacks the carboxyl carbon, the O becomes formally ...
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1answer
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Carboxyllic acid Test

I'm currently in high school doing a project in chemistry. So I had to make a project where concepts from physical chemistry will be used alongside organic chemistry. After going through my book I ...
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Reaction of mixed carbonyl compound with ethylene glycol in acidic medium

I Know that there is cyclic ketal or cyclic acetal is formed when carbonyl compound reacts with ethylene glycol. But I am confused here because I am unable to decide what will be the major product ...
2
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1answer
229 views

Mechanism of acid-catalyzed Robinson annulation?

My professor posed my organic chemistry class a challenge problem for bonus points and I've been racking my brain over the last three days trying to work it out and I want to know if my solution is ...
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What are the unique reactions of conjugated carbon containing carbonyl compounds?

Various sources give different ideas about the reduction reaction of α,β-unsaturated carbonyl compounds which have conjugated carbon. Just like cinnamaldehyde do aliphatic α,β-unsaturated carbonyl ...
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1answer
185 views

Formation of tetrazoles from ketones in Schmidt reaction

Normally in Schmidt reaction of ketones, amides are formed however for some reason here further reaction takes place and a tetrazole is formed. Here is my try for this reaction mechanism (if my ...
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135 views

Major product of Crossed-Cannizzaro Reaction between benzaldehyde and formaldehyde [duplicate]

I came across a question: Predict the major product when conc. $\ce{NaOH}$ is added to a mixture of $\ce{PhCHO}$ and $\ce{HCHO}$. According to me, as $\ce{HCHO}$ is less hindered and $\ce{>C=O}$ ...
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Does 2‐indanone form a stable hydrate?

Following up the question Formation of a stable hydrate. I understand that for cyclopropanone the change in hybridization is the reason for stabilization of hydrate since it relieves the angle strain. ...
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Comparing melting points of substituted benzaldehydes

The correct decreasing order of melting point for the given organic compounds is: 3 has maximum melting point because of intermolecular hydrogen bonding. I am unable to predict rest of the order ...
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2answers
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Étard Reaction of Ethylbenzene

What is the major product when the following compound undergoes Étard reaction? Is it acetophenone or a terminal aldehyde. The mechanism discussed in Mechanism for an Étard reaction (chromium complex)...
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2answers
422 views

Reaction of glucose acetal with acetic anhydride

The following problem was asked in JEE Mains 2020 (Sept 2, Shift 1), Consider the following reactions: $\ce{ (i) Glucose + ROH ->[dry HCl] Acetal ->[$x$ eq. of (CH3CO)2O] acetyl derivative }$ $\...
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1answer
45 views

How to activate polystyrene with carboxyl group?

Is there a simple (that is one that requires few and not very exotic reagents) chemical reaction to "activate" or "functionalize" the polystyrene of a simple microtitre plate? In ...
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110 views

Formation of methane using Kolbe's electrolysis reaction

I have read in my book that methane cannot be formed using Kolbe's reaction (mechanism — Organic Chemistry Portal). And honestly, I kinda think I get where they are coming from: that two radicals are ...
3
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1answer
10k views

Oxidation of Unsymmetrical Ketones using Selenium Dioxide

I have searched the whole internet but I could only see examples where the authors of the article took $\ce{R1}$ and $\ce{R2}$ as the alkyl groups around the carbon. This is regarding the oxidation of ...
4
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2answers
928 views

Oxidation of hydroxyl groups of glucose

In all oxidation reactions of glucose, it seems that the aldehyde group alone gets oxidised and none of the hydroxyl groups. In one reaction with nitric acid, the aldehyde group and the terminal ...
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1answer
84 views

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

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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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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1answer
160 views

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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1answer
3k views

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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44 views

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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1answer
118 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 ...
2
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126 views

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 ...
4
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1answer
1k views

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{...
2
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0answers
51 views

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 ...
12
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1answer
461 views

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 ...
4
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1answer
228 views

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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