0
Carbonyl compounds can be halogenated through either base or acid catalysis, although a difference in products can be expected; acid catalysis is more likely to produce alpha-monohalogenated carbonyl compounds (although polyhalogenation is also possible with acid), and base is more likely to produce a polyhalogenated alpha carbonyl compound.
Halogenation occurs through an enolate/enol intermediate (base or acid respectively).
In the case of basic halogenation an enolate is formed at the alpha position of the carbonyl carbon. The enolate (nucleohile) then attacks the halogen (Br2, Cl2, I2-typically not F2) since the halogen molecule acts as a polarized electrophile. The monohalogenated product is now more reactive than the unhalogenated reactant since the electron withdrawing halogen makes any alpha protons remaining even more acidic and susceptible to abstraction via base to create another enolate, and the process can be repeated.
Still curious? Ask our experts.
Chat with our AI personalities
Devin
Professor
SteveHalogenation of carbonyl compounds typically requires a halogenating agent like elemental bromine or chlorine in the presence of a Lewis acid catalyst, such as FeBr3 or AlCl3. The reaction proceeds through electrophilic halogenation, where the halogen is added to the carbonyl group. Product selectivity can be influenced by the reaction conditions and choice of solvent.
Add your answer:
Earn +20 pts
A family of organic compounds characterized by the presence of a carbonyl group bonbed to an oxygen atom or OH group?
This family of organic compounds is known as aldehydes and ketones. Aldehydes have a carbonyl group bonded to at least one hydrogen atom, while ketones have a carbonyl group bonded to two carbon atoms. They are important in various biological processes and serve as building blocks in organic synthesis.
Can you explain what halogenation is?
The process of halogenation is a chemical reaction between a compound, usually an organic compound and a halogen. An example of halogenation is fluorination or chlorination.
What is a short note of allylic halogenation?
Halogenation is the result that occurs when a chemical is mixed with a halogen.
How ethylene can be converted into ethane?
Halogenation
What is the group that distinguishes aldehydes from most other classes of compounds?
The functional group that distinguishes aldehydes from most other classes of compounds is the carbonyl group (-C=O) with a hydrogen atom bonded to the carbonyl carbon. This unique structure gives aldehydes distinct chemical properties, such as their characteristic reactivity towards oxidation and reduction reactions.
What is the mechanism of alpha halogenation in acidic conditions?
In acidic conditions, alpha halogenation involves the substitution of a hydrogen atom with a halogen atom at the alpha position of a carbonyl compound. This reaction is typically catalyzed by an acid, such as hydrochloric acid, and proceeds through the formation of an enol intermediate, which is then attacked by the halogen to form the halogenated product.
What is the role of NaBH4 in methanol in the reduction of carbonyl compounds?
NaBH4 in methanol serves as a reducing agent in the reduction of carbonyl compounds. It donates hydride ions to the carbonyl group, leading to the formation of alcohols. This reaction is commonly used in organic chemistry to convert carbonyl compounds into their corresponding alcohols.
Does ethanoic acid more closely resemble hydroxyl or carbonyl compounds in its reaction?
Ethanoic acid more closely resembles carbonyl compounds in its reactions because it has a carbonyl functional group, which is a key feature of carbonyl compounds. In reactions, ethanoic acid can participate in typical carbonyl reactions like nucleophilic addition to the carbonyl carbon.
Give the application of von Richter rearrangement?
The von Richter rearrangement is commonly used to synthesize a variety of carbonyl compounds from aryl nitro compounds. This rearrangement is important in organic chemistry for the conversion of nitroarenes to carbonyl compounds, such as ketones and aldehydes, under mild conditions.
What has the author Franco Agolini written?
Franco Agolini has written: 'Stereoelectronic effects in carbonyl compounds' -- subject(s): Stereochemistry, Spectra, Electrons, Molecular orbitals, Carbonyl compounds
How types of functional carbon group?
The term carbonyl can also refer to carbon monoxide as a ligand in an inorganic or organometallic complex (a metal carbonyl, e.g. nickel carbonyl). A carbonyl group characterizes the following types of compounds.
What is the reaction mechanism of carbonyl compounds with LiAlH4, where the effective reducing species is?
The reaction mechanism of carbonyl compounds with LiAlH4 involves the reduction of the carbonyl group to form an alcohol. LiAlH4 acts as the reducing agent in this reaction by donating a hydride ion to the carbonyl carbon, leading to the formation of an alkoxide intermediate which then undergoes protonation to yield the alcohol product.
Why carbonyl compounds undergo nucleophilic addition reactions?
Carbonyl compounds are electrophilic due to the partially positive carbon atom. Nucleophiles are attracted to this electrophilic carbon atom, leading to a nucleophilic addition reaction. The nucleophile attacks the carbonyl carbon, forming a tetrahedral intermediate, which then collapses to form the final product.
Thiol have a carbonyl group?
Thiols do not have a carbonyl group. Thiols, also known as mercaptans, are organic compounds that contain a sulfur atom with a hydrogen atom attached, characterized by the -SH functional group. Carboxylic acids, ketones, and aldehydes are examples of compounds that contain a carbonyl group.
What is a marine mollusk that produces ternary compounds both in pearls and shells?
carbonyl sulfide
What is the significance of the carbonyl bond length in determining the reactivity of organic compounds?
The carbonyl bond length in organic compounds is significant because it affects the stability and reactivity of the compound. A shorter carbonyl bond length indicates a stronger bond, making the compound more stable and less reactive. Conversely, a longer carbonyl bond length suggests a weaker bond, leading to increased reactivity. This bond length can influence how easily the compound undergoes chemical reactions, making it an important factor in understanding and predicting the behavior of organic compounds.
A family of organic compounds characterized by the presence of a carbonyl group bonbed to an oxygen atom or OH group?
This family of organic compounds is known as aldehydes and ketones. Aldehydes have a carbonyl group bonded to at least one hydrogen atom, while ketones have a carbonyl group bonded to two carbon atoms. They are important in various biological processes and serve as building blocks in organic synthesis.
