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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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Aldol Reaction in Water Not Working

I am conducting an Aldol formation reaction in water, and below is the experimental protocol I am following (from J. Org. Chem. 1994, 59, 3590—3596): Formation of Aldol in Water using Yb(OTf)3 ...
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62 views

1,4-addition vs 1,2-addition aldol/aldol type reactions

In the aldol/cross aldol reaction, of $α,β$-unsaturated carbonyl compound, under what circumstances does a 1,2-addition i.e. aldol condensation (carbanion formed directly attacking carbon of carbonyl ...
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Reagents for synthesis of ethyl 2-(2,3-dihydrobenzofuran-2-yl)acetate from naphthalen-1(4H)-one

The following conversion can be performed in a few steps. Show key intermediates and reagents (detailed mechanisms are not required). So I've been looking at this for a while and I can't seem ...
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2answers
123 views

LiOH hydrolysis of methyl 2,2-dimethoxyacetate not giving product?

I am forming 2,2-dimethoxyacetic acid from its methyl ester, and below is the experimental protocol I am following (from Tetrahedron 2016, 72 (3), 420–430): 2,2-Dimethoxy Acetic Acid Formation ...
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1answer
77 views

Dehydration of carboxylic acids with phosphoric acid

To find Z one must find X. Finding Y is of no use to find Z. I get X as: After addition of $\ce{H2/Pd-C}$, the unsaturated portion becomes saturated and the carboxylic acid remains unchanged. ...
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1answer
52 views

Why only ketone forms enolate in Claisen condensation between ester and ketone?

Claisen condensation involves nucleophilic substitution in esters by an enolate (formed by removing an alpha-H from an ester or a ketone) giving a beta-keto ester or a diketone. My textbook says ...
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1answer
44 views

Naming ester as a substituent to carboxylic acid

Can carboxylic acid functional group -COOH and ester's functional group R-COO-R' be in one structure? If yes, carboxylic acid will be the parent chain and ester will be the substituent as c.a. is ...
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An unconventional decarboxylation to form bullatenone

I recently had an assessment which required me to draw the mechanism of decarboxylation of a $\beta$-ketoacid. However, it is slightly peculiar because there is the presence of $\alpha$, $\beta$-...
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1answer
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Predict the major product of the following reaction with mechanism [closed]

I started to do the problem by coordinating H+ with the lone pair of oxygen then after that I can't proceed .please send the solution by show the detailed mechanism.
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Reaction of Br2/KOH with succinic anhydride

What products will be formed when $\ce{Br2/KOH}$ reacts with the following compound in water at room temperature? Here is what I think is possible: $\ce{OH-}$ will take up the acidic hydrogen. ...
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Rate of nucleophilic addition reaction of carbonyl compounds

How should I compare the order of rate of 1.formaldehyde 2.ethanal 3.p-nitrobenzaldehyde 4.p-methoxybenzaldehyde For nucleophilic addition the rate depends on the intensity of electron deficiency of ...
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2answers
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Synthetic steps for the interconversion between aldehydes and ketones

I am learning about carbonyl chemistry at the moment. So far, we have been able to make aldehydes and ketones from alcohols (via oxidizing agents). I can't help but wonder if there is possibly any way ...
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1answer
38 views

Orbital size of Carbon and Oxygen in Methanal

I was given an introductory question into Carbonyl chemistry today and I wanted to ask a question about Methanal. The following picture was shown below of Methanal: and I noted that the orbital ...
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1answer
59 views

What happens in this reaction! Some hints needed

I understand step A involves reductive ozonolysis. and that step B is addition involves addition of ammonia to the carbonyl site to form imines. But what does the sodium salt of trichloroacetic acid ...
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1answer
36 views

Why does the carbonyl of carboxylic acids get protonated and not the hydroxyl group?

Is the O of the C=O group more electronegative or is it for the sake of getting from product A to B that the carbonyl is protonated rather than the hydroxyl?
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Ring contraction in benzilic rearrangement

Wikipedia says that, Benzilic acid rearrangement occurs with ring contraction when used on cyclic diketones. But gave no explanation, can you please elaborate on this with some mechanism. One ...
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1answer
36 views

Acidity order of carboxylic compounds

Arrange the following acids in decreasing order of acidity: (a) X > Z > Y (b) X > Y > Z (c) Z > X > Y (d) Z > Y > X I arrived at option (c) according to -I effect, but the answer ...
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Mechanism for formation of amides from ammonium carboxylate salts

One of the reactions that you can do with a carboxylic acid is to react it with ammonia or an amine, which produces the corresponding ammonium carboxylate salt. When this salt is heated, amide is ...
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Why don't acyl chlorides give positive test with 2,4-DNPH?

In this post, Ron discusses the reasons why carboxylic acid derivatives such as amides, acids and esters do not give a positive result with 2,4-dinitrophenylhydrazine. He mentions that it is largely ...
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1answer
60 views

What reaction takes place here? [duplicate]

Upon reading the given question, I realized that: The first reaction is an aldol condensation reaction between the given compound and formaldehyde. So the product after 1st step is: Now, the ...
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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
60 views

Reaction of diacetyl with acid

What happens when diacetyl, that is, butan-2,3-dione is treated with acid? I guess there would be acid catalysed aldol formation. But what would the final product be? I can see too many ...
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1answer
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Carbonation of Grignard reagent with a carbonyl group present in it

Here's the question in my book (see picture) Option A is a standard reaction which gives a carboxylic acid. Option B is definitely wrong because an acid base reaction will take place and CH4 will be ...
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How does chelation control result in rate acceleration?

In the chapter on diastereoselectivity in Clayden, Warren & Greeves (2012), the Cram-Chelate model is discussed. Most significantly, under chelation control, the diastereoselectivity of the ...
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Reactivity of formaldehyde and 2-chloroethanal towards nucleophillic addition

Formaldehyde is sterically less hindered than 2-chloroethanal and inductiv effects also support a greater reactivity of formaldehyde over the later. However my textbook states that the reactivity ...
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1answer
55 views

Reduction with NH2-NH2 , OH-, and glycol

this question was asked in my exam and I have done it properly until the very third step but unfortunately, although the last step looked like wolfkishner reduction to me I could not do it. My ...
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1answer
109 views

Mechanism with hypohalite in haloform reaction

The haloform reaction is usually done in a solution of NaOH and $\ce{I2}$ (or indeed, any halogen). Now the first part of the reaction mechanism in the wikipedia page and in the most organic books ...
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0answers
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The use of silyl enol ethers over aza-enolates

I do not quite understand how alkylations using tertiary halides would work better with silyl enol ethers, compared with using the aza-enolate nucleophile. The following was mentioned in Clayden, ...
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1answer
56 views

Preference for basic conditions in ester hydrolysis

It has occurred to me that it is very common see the use of basic conditions for ester hydrolysis in various syntheses. One such sequence commonly seen in the case of the malonic ester synthesis is: $...
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0answers
36 views

What takes place in this transformation of the 1,3-dicarbonyl?

I was just looking at a particular synthesis method on the Organic Chemistry Portal when I saw a particularly puzzling step, involving a 1,3-dicarbonyl compound. The step which I am puzzled by is ...
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1answer
35 views

Reagents in Krapcho's decarboxylation

Krapcho's decarboxylation is a reaction involving esters with a electron-withdrawing group $\beta$ to the carbonyl group and halide ions. It is typically conducted with $\ce {LiCl}$ and $\ce {DMSO}$ ...
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26 views

Cross Cannizzarro reaction for ketones

I want to ask that cross cannizzarro could be possible between any aldehyde + ketone mixture(without alpha H) and we get products as aldehyde get oxidised and ketone get reduced(along with self ...
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1answer
90 views

Oxalate Anion MO Diagram

I figured I’d study $\ce{C2O4^2-}$ as an organometallic ligand, and found that it is weak field (pi donor). I hence decided to construct a MO diagram. The oxalate anion is of D2h symmetry, so one ...
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1answer
102 views

Nucleophillic addition vs SN2

The following question came in Paper 2 of JEE Advanced 2014- Here we have $\ce{CH3-}$ as the nucleophile. There are 2 possible attacks: SN2 type attack on the chlorine group. Nucleophilic addition ...
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2answers
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Less substituted vs more substituted alkene [closed]

In general, more substituted alkenes are more thermodynamically stable. However, in certain cases such as enamine alkylation, the less substituted double bond is favored. How do we know that which is ...
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1answer
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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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1answer
315 views

Reaction between carboxylic acids and amines

Would some be able to explain why when I mix a carboxylic acid, like ethanoic acid, and an amine, say ethylamine, I get ethylammonium ethanoate. But when I mix a bi-functional group carboxylic acid (...
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1answer
164 views

Why are pi antibonding orbitals lower in energy than sigma antibonding orbitals?

I know when a carbonyl group is attacked by a nucleophile, the electrons of the nucleophile enter the antibonding π orbital of the $\ce{C=O}$ bond, which breaks the π bond. My textbook says that ...
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Kolbe's electrolysis of acetylenedicarboxylic acid

I have been wondering what this reaction would lead to? The ethyne diradical can't dimerize because triple bonded cyclic structures don't form until 8 carbons. And even if it polymerizes I find no way ...
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Regarding Clemensen Reduction of the following compound [duplicate]

While I was doing problems on reduction of aldehydes and ketones, I encountered this particular question Here, I know that Clemensen reduction reduces the ketone group to $-CH_2-$ group. But, the ...
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1answer
428 views

ICHO Synthesis Problem 2018

I've several doubts about this ICHO synthesis problem, which was a part of the preparatory problem package of 2018 (so yes, it's not a part of an ongoing contest) Before sharing the answer given, I'...
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1answer
134 views

Alcohol or Carbonyl - Which is more reactive towards PCl5?

We're aware that ketones and alcohols both react with phosphorus pentachloride, to produce geminal dichlorides and alkyl chlorides respectively. What happens in the compound shown below, when ...
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2answers
461 views

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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Why does gilman reagent react with acyl chlorides but not with other carbonyls?

According to HSAB (hard-soft acid-base) concept, a soft nucleophile preferentially reacts with soft electrophile and a hard nucleophile with a hard electrophile. Since $\ce {R2CuLi}$ is a soft ...
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1answer
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Why can't you form an anhydride from an ester via nucleophilic attack?

The reaction referred to is the nucleophilic acyl substitution reaction, where the nucleophile is a carboxylate ion and the electrophile is the ester. I am having a difficult time visualizing why this ...
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1answer
99 views

Ketone prefix organic chemistry nomenclature

Is there a difference between the prefixes keto- and oxo-?
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1answer
120 views

Molecular orbital explanation of why the protonation of the oxygen atom makes a carbonyl group more electrophilic

I was working on nucleophilic addition reactions to the carbonyl group (namely, hemiacetal formation) when I came across the following explanation for the use of acid catalyst and how it increases ...
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What is a probable mechanism for acid catalysed decarboxylation of alpha-hydroxy acid?

The following question was on one of the tests we had recently Now i worked out the intermediates and the product as follows: The first step is an intramolecular Cannizzaro reaction in which the ...
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Are alkaline conditions required for Maillard reaction?

The Maillard reaction, a form of non-enzymatic browning, refers to a cascade of chemical reactions that frequently occurs in the cooking of foods (e.g. baking of pastries, roasting of meats). It ...
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293 views

Conditions for imine formation

Firstly, note that this is not a duplicate of Acid in Imine Formation. Clayden, Warren, & Greeves (2012) states explicitly on p. 231 that imine formation requires acid catalysis, and that the ...