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
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I want MO diagram of triiorn dodecacarbonyl Fe3(CO)12 [closed]

help me to draw MOT diagram of Fe3(CO)12 Complex
4
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2answers
268 views

What is the major product in the reaction between 4-chloropentanal and lithium aluminium hydride?

What would be the major product between 4-chloropentanal and $\ce{LiAlH4}$? After the reduction of the aldehyde, would the hydroxyl group formed at $\ce{C-1}$ attack $\ce{C-4}$ causing cyclization to ...
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1answer
450 views

Does folic acid contain a benzyl or a phenyl group?

I'm studying for my MCAT currently and I stumbled upon this question. It gives the structure of a folic acid molecule and asks what functional groups can be found within the molecule. I understand ...
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40 views

Does formaldehyde and ethylene glycol give positive Fehling's test?

Fehling's test follows a single electron transfer mechanism, with electron transfer form the substrate to $\ce{Cu^2+}$, which forms $\ce{Cu^1+}$finally giving reddish brown precipitate of $\ce{Cu2O}$. ...
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1answer
56 views

D and L configuration of monosaccharides

I got this question in the last week's test from Organic Chemistry. I am a bit confused in assigning D and L configuration. Help me understand the topic of D and L configuration and help with this ...
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1answer
46 views

Why does a methyl shift occur during the pinacol-pinacolone rearrangement?

Why does a methyl shift occur during the pinacol-pinacolone rearrangement? I was told that methyl shift is done to stabilise the carbocation but here we are shifting the ...
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0answers
20 views

Trend in Boiling Points of Aldehydes vs Ketones

Up until 2-pentanone/3-pentanone and pentanal, the boiling points of unbranched ketones are higher than those of unbranched aldeyhdes that have equal number of carbons as explained by "matt_black&...
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1answer
48 views

ketone and amine condensation

My question is quite easy to solve. The question simply asked to find the final product of the reaction shown below, which I did. But the my question lies in the catalyst. What is the role of the ...
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0answers
40 views

What is the mechanism followed in the hydrolysis of geminal dihalides using sodium hydroxide?

When a geminal dihalide is treated by alkaline $\ce{NaOH}$ we get a geminal diol which subsequently gets dehydrated to give carbonyl compounds. What type of mechanism is followed in this reaction? I ...
2
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1answer
31 views

What is the LUMO of a molecule with an alkene and a carbonyl?

In a molecule that has both an alkene (C=C) and carbonyl (C=O) that are NOT conjugated, such as pent-4-en-2-one, how do you determine which π* anti-bonding orbital is the LUMO? Essentially, I'm trying ...
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1answer
156 views

What is the correct reaction mechanism?

I came across this question: I propose two things to happen: It can undergo Aldol condensation or it can undergo SN by replacing $\ce{-Cl}$ with $\ce{-OH}$. But apparently, both these mechanism ...
7
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1answer
66 views

Stereochemistry & mechanism of β-cyano enone methylation

I am helping a friend with some upper-level mechanism problems. We came across this one. This is my proposal. Do you agree/disagree? Thank you for any input. Source question:
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1answer
50 views

Why is the silver salt ammoniated to form the Tollen's reagent? [duplicate]

When doing a distinguishing test between aldehydes and ketones using Tollen's reagent, is it necessary to convert $\ce{Ag+}$ ions into $\ce{Ag(NH3)2+}$ in order to oxidize the aldehyde?
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1answer
69 views

Reaction of acyl chloride with excess Grignard reagent

I have a reaction to which I must find the majority organic product. I think I found the correct product but the fact that the reaction takes two moles of propylmagnesiumbromide confuses me a bit. I ...
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0answers
53 views

Why doesn't the acetic anhydride moeity react with the nucleophilic carbonyl oxygen of salicylic acid?

I know that salicylic acid with acetic anhydride under acidic conditions gives acetylsalicylic acid (aspirin). But my question is, why is it that post the protonation of carbonyl oxygen of acetic ...
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69 views

Mechanism for reaction between carboxylic acid and manganese(II) oxide [closed]

I am reading about redox reactions of carboxylic acids with $\ce{MnO}$ but I couldn't find any mechanism online,so can any one provide the mechanism.
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Why does glucose test positive for aldehydes having lost aldehydic nature to gain aromaticity?

It has been proved that glucose 99% of the times is in its cyclic structure (source - khan academy) and that the oxygen atom is busy bridging the 1st and 5th carbon. Then why does it even show ...
7
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1answer
273 views

Synthesis of (1S,2S,4S)-4-ethenyl-5-methylcyclohexane-1,2-diol

I'm trying to devise a synthesis for the following question. I am aware it involves retrosynthetic, Wittig, Grignard and diels alder reactions, but unfortunately I can't really grasp all concepts ...
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0answers
21 views

Keto-Enol tautomerism acidity of α Hydrogen vs stability of double bond [duplicate]

If I consider a ketone that has an ethyl group and a methyl group attached to it. The α-Hydrogen of the methyl group would be more acidic than that of the ethyl group due to -I effect of the adjacent ...
6
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1answer
89 views

Will “soft nucleophiles” undergo 1,4-conjugate addition even if the β-carbon is sterically hindered?

In general soft nucleophiles do 1,4 conjugate addition to a carbonyl carbon under thermodynamic control. Will soft nucleophiles like organocuprates still preferentially undergo 1,4 addition if the β-...
3
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1answer
65 views

Synthesis of diethyloxalate from ethene

Outline the steps involved in the following transformation: $\ce{C2H4}$ to $\ce{(COOC2H5)2}$ (diethyl oxalate). I am familiar with the transformation of $\ce{C2H4}$ to ethyl acetate $\ce{CH3COOC2H5}$ ...
5
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2answers
116 views

Mechanisms for Reimer-Tiemann and Kolbe-Schmidt reaction on deuterium labelled phenol

I was solving a bunch of reactions when I encountered the following: So for the first question: This is a Reimer-Tiemann reaction. I felt that the tautomerism would result in the deuterium getting ...
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1answer
68 views

Determining the most stable enolic form of 1-phenylbutane-1,3-dione?

Question Which form of 1-phenylbutane-1,3-dione is more stable? Answer 3-hydroxy-1-phenylbut-2-en-1-one My question I've been told that between the above two, 3-hydroxy-1-phenylbut-2-en-1-one is ...
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2answers
52 views

Intramolecular Cannizzaro reaction product

I came across the following question : My reasoning was as follows : It can't be option (c) because there is no chance of losing a carbon during Cannizzaro's reaction It can't be option (b) because ...
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37 views

Reactivity order of DIBAL-H and diborane with esters and acids

I have been taught in class that DIBAL-H is more reactive towards esters than carboxylic acids while opposite is true for diborane. Also DIBAL-H mentioned is taken under low temperatures (−78 °C). I ...
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1answer
80 views

Is the cannizaro reaction possible for a molecule having hydrogens attached to sp2 hybridised carbons?

As known benzaldehyde can undergo a cannizaro reaction in which a phenyl group is an electron donating group, so the reaction similar to below (of prop-2-enal) (cannizaro) should occur for similar ...
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2answers
339 views

A possible reaction of heating Terephthalic acid

There is no reaction of terephthalic acid heating effect on internet (atleast Wikipedia). I have written the most probable reaction possible as per my knowledge. Please tell if it is spontaneous and ...
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1answer
66 views

In naming salicylic acid the rule is not followed. Why? [closed]

We have two compounds: 3-(Bromo)-cyclo-but-1-ene and {2-Hydroxybenzoic acid (Salicylic acid). While naming the compounds we number the rings as follows: Now the problem is that in the first compound ...
2
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1answer
75 views

Periodic acid oxidation of carbonyls?

The following reaction seem to be valid; $\ce{CH2OH-CHOH-CH2OH ->[HIO4]CH2O + HCOOH + CH2O + 2H2O}$ Apparently, there are similar reactions by 2,3-dihydroxypropanal, and also by the straight chain ...
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2answers
57 views

How can you qualitatively tell when the hydrolysis of aspirin is over?

I'm doing an experiment on the effect of temperature on the time taken to produce acetic acid and salicylic acid. Are there any qualitative observations I can make about when the reaction has finished?...
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1answer
199 views

On the use of hexane in the organic reduction by DIBAL-H

In some variations of the organic reduction by DIBAL-H, I've seen hexane used, as in this equation from this website; I've looked it up, but I haven't seen any explanation for why hexane's used there....
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36 views

Why is addition to acid chloride favoured over SN2 at the carbon even though it has a Beta-carbonyl?

I feel that the conditions highly favour $S_\mathrm{N}2$ reaction at the aliphatic center and so the aliphatic chlorine should be replaced before the carbonyl chlorine. But the solution suggests that ...
3
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1answer
132 views

Why is the formation of a peptide bond not spontaneous?

Why is the formation of a peptide bond from a carboxylic acid and amine not spontaneous? I'm not looking for the free energy calculation; I have it from several sources. I'm just asking for an ...
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0answers
86 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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0answers
51 views

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 ...
2
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1answer
171 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
34 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 ...
2
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0answers
47 views

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 ...
3
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1answer
101 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 ...
2
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0answers
33 views

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 ...
5
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1answer
261 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
33 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
54 views

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
63 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 ...
2
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0answers
22 views

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 ...
4
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1answer
177 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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0answers
29 views

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 ...
1
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0answers
56 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
155 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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0answers
96 views

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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