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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.

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6mo ago

Halogenation 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.

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Q: What are the conditions for the halogenation of carbonyl compounds?
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