Compounds containing the carbonyl group, C=O. The tag is only used for the organic molecules containing this functional group. For questions about complexes involving carbon monoxide as a ligand use carbonyl-complexes instead.

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Reaction of PPh3 with a ketone

I understand that in the first step, mono-alpha halogenation occurs. Where I am slightly lost is in the second and third steps. Am I correct in thinking that because I have a substrate with a ...
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1answer
80 views

IUPAC name for citric acid

I was wondering what the name is of the following structure: I think it's something like ... 3-hyrodxypentanoic diacid However, I wasn't able to find how to name ...
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1answer
33 views

Competitive protonation between alkene and carbonyl

Given this compound in an acidic medium, what would get protonated first? Would the double bond not get protonated preferentially, since oxygen is more electronegative than carbon and less willing ...
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0answers
51 views

Why does two phenylhydrazine molecule react with glucose in osazone formation?

From Wikipedia: It involves two reactions. Firstly glucose with phenylhydrazine gives glucosephenylhydrazone by elimination of a water molecule from the functional group. The next step involves ...
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1answer
178 views

Mechanism of a dephenylation reaction

I recently came across this reaction in my undergraduate labs. The experiment is taken from this article: J. Chem. Educ., 2008, 85, 413. The condensation of 2-methoxynaphthalene with cinnamoyl ...
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2answers
90 views

Chemoselectivity in synthesis of paracetamol

In the reaction below, why does acetic anhydride not react with the -OH group to form an ester instead?
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1answer
142 views

How to dialkylate a cyclohexene, and convert a carbonyl to an alkene?

I'm trying to design a synthesis of D from C. All I can think of is using $\ce{Me2CuLi}$ to add the methyl group to the alkene. I thought maybe then if isobutyl bromide was in the reaction mixture ...
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1answer
170 views

Why does LiAlH4 reduce an amide to an amine but only reduce a ketone/aldehyde to an alcohol?

Here are two different reactions in which lithium aluminium hydride, $\ce{LiAlH4}$, reduces a carbonyl group: Why does $\ce{LiAlH4}$ completely remove the oxygen from the amide but only reduces the ...
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1answer
42 views

aldol or no aldol?

Will 2-methylbutanal undergo aldol condensation? We are taught that it will not because the +I effect makes the carbanion unstable but if we make an enolate ion, isn't it resonance stabilized by the ...
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1answer
87 views

Naming compounds with multiple -COX functional groups

I know that this compound is named propanoyl chloride. However I am not sure what to do when here are multiple -COX groups and they are of the highest seniority. There are two cases, when they are ...
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29 views

How can I create crotonaldehyde using only mineral reactants?

I tried using alkylation to get the correct chain lenght, but I can't find a way to create the double bond. I'm a total novice at chemistry, so please forgive my ignorance.
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1answer
81 views

How to explain two NMR spectra of the (allegedly) same compound with slightly different shifts?

For my synthetic lab work I synthesised a Horner-Wadsworth-Emmons phosphonate; for the sake of the question let’s assume it to be the one presented in the image below. When first synthesising it, I ...
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1answer
61 views

Naming compound with multiple carbonyl and/or hydroxyl groups

I think I understood the main idea behind naming compounds with carbonyl groups, however I am not sure about a few things. For the first compound, there is more than one carbonyl group and one of ...
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1answer
116 views

Decarboxylation / Elimination type reaction

I'm quite familiar with E1/E2 reactions and usually use those ideas to explain elimination reactions, however I came across a reaction which was a bit different (in the sense it isn't E1/E2) but still ...
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1answer
41 views

Why can't you use m-CPBA to synthesise isophorone oxide from isophorone?

Apparently you must use sodium hydroxide and hydrogen peroxide because using m-CPBA gives an undesired product Why doesn't m-CPBA work and what does it do instead? Why does sodium hydroxide and ...
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0answers
21 views

The density of ketene

On Wikipedia it says that the density of ketene is 1.93 grams per cubic cm, but that can't be true, can it?
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35 views

Whether amino acids exist as zwitterions in the liquid and gaseous phases

I am aware that in the solid state pure amino acids are crystalline structures composed of zwitterions, however I cannot find any information about whether somehow this changes as they move into ...
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1answer
43 views

Relative stability of carboxylic acid derivatives

This picture depicts the relative stability associated with resonance structure. My questions are: 1.1. Teacher says anhydride is less stable because of two reasons above. but it seems there's no ...
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0answers
31 views

How to explain the different regioselectivity of ketones/imines reacting with LDA?

When 1 equivalent of LDA is reacted with, for example, 2-pentanone, you get the thermodynamic (more substituted) product. But when you react butan-2-imine with 1.0 LDA, you receive the kinetic (less ...
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1answer
125 views

Single step transformation of a carboxylic acid into an aldehyde

What are the different ways of transforming a carboxylic acid into an aldehyde in a single step ? (as opposed as for instance first transforming it to an ester then to an aldehyde) The bottom of this ...
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2answers
82 views

Reactions of ketones and aldehydes

Our topic was about ketones and aldehydes (carbonyl group) including hemiketals and hemiacetals and he asked us to do a homework. I cannot find an answer to this one.Please explain me the reaction ...
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1answer
263 views

Doubt in Mechanism of Dieckmann Reaction

In the following mechanism of the Dieckmann Condensation, the product has been formed in the fourth step, but still the reaction proceeds and $ \ce{RO^{-}}$deprotonates the product. Then $\ce{H^{+}}$ ...
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43 views

Doubts with the reaction mechanism?

Here, this is the question and my approach. The product is coming out to be correct as mentioned in the answers, but I want to confirm the reaction mechanism. Also, what will happen if I add ...
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0answers
19 views

Number of stereo-isomeric products?

This is the question:- And this is my approach:- As you can see, according to my solution, the answer should be 2. But the answer is 4. Also, I have doubt in the first step that whether the anion ...
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1answer
44 views

Why only the unstable resonating structure proceeds in the reaction?

For example, in the given image, I have starred the step where the relatively unstable resonating structure proceeds forward in the reaction. Why?
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0answers
43 views

Does the synthesis of beta-keto phosphonates from esters have a name?

Consider the Horner-Wadsworth-Emmons reaction; one of its reactants is a phosphonate, usually stabilised by a β-carbonyl group which is then deprotonated in α position (figure 1). These ...
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58 views

Which will be the most acidic hydrogen in the following organic compounds?

Which will be the most acidic Hydrogen in both cases? Please explain. According to me, in the first compound 2 should be most acidic as in both 1 and 2, resonance occurs but 2 Carbon is closer to ...
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16 views

Resonance in carbonyl compounds [closed]

In the given compounds, the first compound exhibits resonance, but not the second one. Why? The electro-negativity difference, that's why? Answer in detail.
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0answers
34 views

Steric factor v's electronic factor?

When water approaches both of them, no reaction is seen in the first compound, but the second compound react readily with water. In my notes, it is written that CH3 causes steric effect and also ...
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2answers
333 views

Does acetic acid give a positive result with the iodoform test?

Acetic acid contains a $\ce{-COMe}$ group, so theoretically, it should give a positive result in the iodoform test (i.e. a yellow precipitate of $\ce{CHI3}$ being formed). But apparently the iodoform ...
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1answer
80 views

Is Carboxylic acid more soluble than ester? [closed]

Which is more soluble in water? I believe both of are sort of soluble in water as they have C=O and C-O, polar bonds which make them polar compound. But I'm not really sure how the structure can ...
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2answers
357 views

Nomenclature of a cyclic ketone

Why isn't this molecule named 2-fluorocyclopent-1-one?
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1answer
66 views

I am confused about the stability of carbanion III and IV in the image

I am confused about the stability of carbanion III and IV in the image, I think III is more unstable because of electron donating effect (+R) of -OCH3 group but my book says III is more stable than ...
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2answers
441 views

Why does benzaldehyde not respond to Fehling's test?

All aldehydes are supposed to respond to Fehling's test. So why doesn't benzaldehyde respond to it? Does it have something to do with the fact that benzaldehyde is an aromatic compound? If so, then ...
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3answers
194 views

Which tautomer of hexane-2,4-dione is more stable?

Which tautomer will be more stable? Both 1 and 2 show intramolecular hydrogen bonding and form 6 membered cyclic ring, thus increasing the stability. I think I need to compare the effect of the ...
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0answers
82 views

Does acid anhydride give a positive iodoform test?

I thought that acetic anhydride $\ce{CH3COOCOCH3}$ would give a positive Iodoform test because it has a $\ce{CH3-(CO)}-$ group.But it is given that this does not happen. Is this true? If so, can ...
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85 views

Masamune's rule of diastereoselectivity multiplicity

In a reaction between a chiral substrate and chiral reagent, their asymmetric inductions could cooperate (matched pairs) or compete (mismatched pair). According to Masamune, in a matched pair the ...
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2answers
56 views

Reduction of N,N-dimethylbenzamide with LiAlH4

Consider the reaction $$\ce{C6H5CON(CH3)2->[\ce{LiAlH4}]$\:\:$?}$$ What will the product be? According to me the product should be $\ce{C6H5CH2OH}$ but I am not sure. Also, I don't have any ...
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2answers
297 views

Why does the reduction of a Weinreb amide give an aldehyde instead of an amine?

The reduction of a regular amide with $\ce{LiAlH4}$ yields an amine. However, with a Weinreb amide, the product is an aldehyde. How can this be justified? I can't find the mechanism for the Weinreb ...
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1answer
207 views

Mechanism for oxidation of primary alcohol to carboxylic acid

My teacher told me that the following is the mechanism for oxidation of primary alcohols to carboxylic acids: $\ce{Primary~alcohol ...
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1answer
84 views

1-5 dicarboxylic acid to lactone with SOCl2?

I came across a reaction whereby a 1-5 dicarboxylic acid is converted to lactone with $\ce{SOCl2}$. I was wondering what the mechanism of this was. I know that $\ce{SOCl2}$ converts carboxylic acids ...
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2answers
262 views

Self aldol condensation of butanal under basic conditions

The reaction is such: I've counted the number of carbons on each side: LHS=4, RHS=8 My working is such:
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1answer
59 views

Enantiomerically pure ketone reaction under acidic conditions gives 1:1 mixture of diastereoisomers?

My problem is such: My thinking is that perhaps the explanation has something to do with the carbonyl group being prochiral and having two faces, each side generating one of two diastereoisomers? ...
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2answers
127 views

Bromination of Phenylacetone

Looking at the following reaction, I understand how the product forms, however, can somebody help me understand why two products are formed? Would the identical mechanism produce the two products? ...
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2answers
413 views

What does “less hindered hydrogen” mean?

In a book they have given a statement, In the process of pyrolysis of esters, esters having beta hydrogen are heated at high temperature and then alkenes are formed along with carboxylic acid. ...
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1answer
39 views

What is the problem with forming this product?

I have suggested a mechanism for the formation of A (see my working below), but the question says problems would be encountered if a similar route was used to make B … I think perhaps a ...
4
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1answer
125 views

How to distinguish diastereomers of unsaturated ketones by NMR?

I am synthesising a natural product that contains an α-methylated α,β-unsaturated ketone (see image below). The natural product’s stereochemistry is an (E) configured double bond. I ...
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1answer
324 views

Can an amide nitrogen be a hydrogen bond acceptor?

Can $\ce{N}$ (i.e. main chain $\ce{NH}$s of recognised residues in a peptide or protein) be a hydrogen bond acceptor? It is a well known fact that the main chain $\ce{NH}$s can be a hydrogen bond ...
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51 views

Finding unknown component in a reaction scheme

$$\ce{CH_3-CH_2-CO -CH_2COOC_2H_5 \xrightarrow{[x]}(a)\xrightarrow{LiAlH_4}(b)\xrightarrow{H_2O/H^+}}$$Gives final product $$\ce{CH_3-CH_2-CO-CH2-CH_2OH + C_2H_5OH}$$Find $\ce {[X]}.$ Now as ...
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1answer
192 views

Question on enol content

Arrange the following compounds in order of increasing enol content: I think it's $D>C>B>A$ considering conjugation, hyperconjugation and hydrogen bonding. The enol formed in case $D$ will ...