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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How to convert ethanal to 2-hydroxy-3 butenoic acid?

How to convert ethanal to 2-hydroxy-3 butenoic acid? I tried crossed aldol condensation with formaldehyde followed by acid addition.After that how should I proceed ?
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Why do BH3 and NaBH4 have different selectivities?

I've always known borane ($\ce{BH3}$), as a reagent for alkene hydroboration. Recently in class we talked about its use in the reduction of carboxylic acids to alcohols as well. Now obviously $\ce{...
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How can rotamers of alpha-keto esters be named to distinguish between different geometries?

When talking about free rotation it is often helpful to determine about which geometric arrangement one is referring to. For example in the case of butane we talk about several eclipsed or staggered ...
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Does esterification require reactants to be present in the same plane?

I believe that the first step is the Cannizzaro reaction which will give (c) as a product. But since we are also adding $\ce{H+}$ in the second step, shouldn't an esterification reaction take place? ...
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Can all species that undergo aldol reactions also undergo Cannizzaro reactions?

Can all species that undergo aldol reactions also undergo Cannizzaro reactions? Ater all, the nucleophile can always attack the carbonyl group.
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Which compound reacts faster in the Cannizzaro Reaction?

Which reacts faster in the Cannizzaro Reaction? a) $\ce{OHC-C6H4-NO2}$ b) $\ce{OHC-C6H4-OCH3}$ Obviously, a better hydride releasing group will react faster. Therefore my answer was b, as $\ce{-...
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Why amino acids (Zwitterion) become either negative or positive at low and high pH solutions?

The amino acids are Zwitterions. In neutral pH, an Amino acid's amino group has a postive charge and Carboxyl group has negative charge. They cancel each others charge thanks to the $Hydrogen$ that's ...
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641 views

Mechanism of enol ether formation

I assumed the the $\ce{TsOH}$ would dissociated to produce hydronium ions that would protonate the carbonyl. This would make the carbon more delta + and so susceptible to attack by $\ce{MeOH}$. After ...
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Why is in the reaction of cyclic unsaturated aldehydes with hydrazine and hydrogen peroxide the aldehyde preserved?

Question What is the product of this reaction? The answer given: At first, I thought this was a typical Wolff-Kishner reduction, but then I saw the reagents didn't match up (no $\ce{OH-}$...
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Selective alkylation of carboxylic acid versus phenol

Starting from the ketone shown, I plan to use a haloform reaction to transform the acetyl group into a carboxylic acid. Following that, there are two alkylations to be carried out: one esterification ...
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Clarifications about the mechanism of the Wittig reaction [closed]

Ok so this is the proposed mechanism for the Wittig Reaction as stated by my textbook, LG Wade. I have some doubts regarding this mechanism: 1) Why is only triphenyl phosphine used here? Why not ...
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Does a Grignard reagent react with enones to give the 1,2- or 1,4- product?

Cyclohexenone, an α,β-unsaturated ketone, is electrophilic at both the carbonyl carbon, as well as the β-carbon. So, it can either undergo 1,2-addition to give the allylic alcohol 1, or 1,4-addition ...
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Keto Enol Equilibrium for Claisen Condensation Products

Do Claisen Condensation products prefer the di-keto form, or a keto/enol form due to increased conjugation and hydrogen bonding?
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Fehling's Test meaning for partial formation of a precipitate?

Whilst doing tests on two unknown solutions, I used Fehling's test. The solutions could be a mixture of compounds or just one compound dissolved in water/ another solvent - I don't know. Upon adding ...
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Protonation of ketone and ester

If there is a ketone and ester functional group in the same compound and I want to protonate with $\ce{HCl}$, which one will protonate first? Is it the carbonyl group in the ketone or the carbonyl ...
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When will organometallics act as base or nucleophile?

I would like to ask if the hydrogen next to carbonyl group is acidic,and organometallics are strong base, when will it act as a base and extracts the acidic proton and when will it attack the carbonyl ...
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Enolate Ion formation

I was wondering why when acetaldehyde is treated with $\ce{OH-}$, the $\ce{OH-}$ will attack the methyl group instead of the carbonyl carbon, forming an enolate anion. I would have though that the $\...
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How can an aromatic ketone be reduced in the presence of a nitro group?

Is it possible to reduce an acyl group to an alkane, but still keep a nitro group intact without its reduction to an amino group? A Clemmensen reduction would reduce the nitro group, and it seems like ...
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Why do electronegative heteroatoms increase C=O stretching frequency (bond strength)

Why does a more electronegative heteroatom (i.e. $\ce{Cl}$ or $\ce{O}$) increase the stretching frequency of a carbonyl? I'd suspect it's that they donate their lone pairs and we end up with a ...
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Clemmensen reduction of 1,3 diketones

As part of a synthesis I was considering the following reaction: How selective is the Clemmensen reduction? I know that this reduction favours ketones adjacent to benzene rings but will it also ...
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1answer
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Can carboxylic acids be used in the aldol reaction?

A question in a practice paper I did recently showed the aldol condensation of benzaldehyde with ethanoic acid. I think I am right in saying that carboxylic acids do not form enolates because the ...
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Mechanism of enolether formation with ethyl orthoformate in estr-4-ene-3,17-dione (Djerassi's norethisterone synthesis)

The second step of Djerassi's synthesis of 19-nor-17α-ethynyltestosterone (norethindrone), involves the protection of the ketone in position 3 via enolether formation, as in the picture: What is the ...
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Synthesis of ethyl methyl ketone from 2-(4-hydroxyphenyl)ethyl methyl ketone

Is it possible to reduce raspberry ketone (4-(4-Hydroxyphenyl)butan-2-one) to ethyl methyl ketone? How would I do this in practice?
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Why are alpha-carbonyl relatively less stable?

So if we have an alpha halogen ketone, why is an Sn1 type mechanism so unfavorable for that species? I don't understand. It seems like the C+ would be resonance stabilized by the carbonyl's double ...
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Why should alkylation of enols/carbonyl compounds be done at low temperature with a strong base?

Alkylation of acetone: This reaction is done with a strong base (LDA in this case). Is this because the protons aren't particularly acidic? Secondly it should be done at low temperatures; why is this ...
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Can carbon monoxide contaminate water?

Just wondering if you fitted a cold water tank overflow pipe into a car park at the height of a car exhaust , if the carbon monoxide fumes went back up the oveflow pipe into the tank would this ...
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Electrophilicities of carboxylic acid derivatives

I would like to ask about the rate of hydrolysis for 4-hydroxyphenyl acetate (A), N-(4-hydroxyphenyl)acetamide (B), 4-hydroxyphenyl chloroacetate (C), and methyl 4-hydroxybenzoate (D). I know that ...
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What are the products of the haloform reaction of acetylacetone?

I searched a lot to find the products of the haloform reaction of acetylacetone (pentane-2,4-dione), but I didn't find any results. What are the products of the haloform reaction of acetylacetone?
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Acidity order of acetone, methyl acetate and N,N-dimethylacetamide

Why is the acidity order true? $$\ce{CH3COCH3} > \ce{CH3CO2CH3} > \ce{CH3CON(CH3)2}$$ I deduced that in methyl acetate and N,N-dimethylacetamide there is a −I effect of the methoxy group, $\...
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How do you identify reducing / non-reducing sugar by looking at structure?

Identifying reducing / non-reducing sugar been confusing me for a while now , I know that reducing sugar contain aldehyde or ketone group . It's easy to identify them in monosaccharides but this ...
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Cannizarro reaction of chloral

When chloral undergoes reaction with a concentrated alkali, will it undergo Cannizarro reaction to form the corresponding alcohol and acidic salt, or should it form chloroform instead by departure of ...
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Does an acetal give a positive Tollens test?

In Organic Chemistry (Wade) there is a question: Which of the following compounds would give a positive Tollens' test? (Remember that the Tollens' test involves mild basic aqueous conditions.) The ...
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Attack of amine on amide

I am confused with the last step of clozapine synthesis: How can the amine group attack the amide group to form the amidine in such acidic environment? Is the intermolecular reaction between an amine ...
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Mechanism of Grignard addition to carbonyls

So from the general reaction we can see that the carbonyl is reduced while the Grignard is oxidized to an alkene. So for this hypothetical reaction (does this really occur?) we are asked to provide ...
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How do I synthesize 3-phenyloxirane-2-carbaldehyde from chloroacetonitrile?

How do I synthesize 3-phenyloxirane-2-carbaldehyde from chloroacetonitrile? My proposed route involves: hydrolysis of the nitrile to form a carboxylic acid, and subsequent esterification then, a ...
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Alkali metal enolates

Why do lithium enolates add to an electrophile in direct addition manner, while the sodium and potassium enolates tend to add in conjugated additions? The sodium and potassium enolates are well ...
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Acid chlorides and reduction by hydrogenation

An acid chloride being reduced through catalytic hydrogenation is an "unobserved" event in the context of our class, according to my professor. Nonetheless, we are expected to predict that the ...
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Why is only bromine used in the degradation reaction?

Why specifically is bromine used in the degradation reaction (Hoffmann bromamide)? Why can't the same be performed using chlorine or iodine? In other words, what makes bromine a more convenient ...
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1answer
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How do I know which atoms react during hydrolysis?

In the hydrolysis of propanamide ($\ce{CH3CH2CONH2}$) how do I know which molecules react with the water? $$ \ce{CH3CH2CONH2 + H2O -> ?} $$ I don't know how to split the molecule. In the videos ...
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Building an incomplete redox half reaction/reduction

I can't seem to figure out this redox reaction. $$ \ce{CH3COO- + CO2 -> CH3CH2COO-} $$ Is the charge on the carbon in the $\ce{CO2}$ supposed to match the charge on the carbon in the $\ce{CH3COO-}...
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What are the products of the reaction of 1-methoxycyclohexene with dilute hydrochloric acid?

When 1-methoxycyclohexene is treated with dilute aqueous hydrochloric acid, methanol is produced along with another organic product. Identify this product. Explain why methoxycyclohexane is inert ...
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Halogenation of an alpha-halogen ketone in acidic conditions

When a methyl ketone is submitted to halogenation in acidic conditions with two equivalents of a halogen, the first halogenation happens at the secondary alpha carbon atom , while the second ...
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Regioselectivity of alpha halogenation of ketones

Why does alpha halogenation of a ketone in acidic conditions happen at the more substituted alpha carbon atom, and in basic conditions at the less substituted alpha carbon atom?
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Do molecules with carboxyl groups have properties of carboxyl's sub-functional-groups?

We're learning about functional groups of different organic molecules, and there are some I'm confused about: carboxyl, carbonyl, and hydroxyl. I was looking online but I couldn't find a direct answer ...
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Chromic acid oxidation of aldehydes and primary alcohols

The answer has to be both A and D. Chromic acid is a strong oxidizer and will take both aldehydes and primary alcohols to carboxylic acids. However the computer thinks otherwise. Am I just missing ...
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Why can alkali metal hydrides usually not act as nucleophiles towards carbonyl groups?

Think for example of $\ce{KH}$ or $\ce{NaH}$ in enolization reactions. This remark was made in one of my textbook, but I could not remember why this was actually the case. Why can't $\ce{NaH}$ or $\ce{...
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How does higher carbonyl compounds disolve in water?

We know that higher the carbon, the more is hydrophobic the compound nature is, Still when we take a compound like sugar , a hand of sugar, it readily dissolves in water? can someone explain me reg ...
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Identify structure of compounds from their reactions and molecular formula

Compound P($\ce{C7H6O}$) on refluxing with aqueous ethanolic $\ce{KCN}$ solution for 1 hour, forms Q($\ce{C14H12O2}$). Q on oxidation gives R($\ce{C14H10O2}$). R on refluxing with aqueous $\ce{NaOH}$ ...
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Why is benzoic acid a stronger acid than 3-aminobenzoic acid?

Why is benzoic acid a stronger acid than 3-aminobenzoic acid? Obviously at meta position, only negative inductive effect will operate. But, how does that make it a weaker acid than benzoic acid?
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How to Determine Acid Strength?

The correct answer is E But I do not understand why? Shouldn't (v) have the lowest $\mathrm{p}K_\mathrm{a}$ since it does not have a carboxyl group making it a strong acid? How do we determine the ...

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