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What is the mechanism of the Friedel-Crafts acylation reaction, and how does it differ from the Friedel-Crafts alkylation reaction, in the context of synthesizing monoacylated benzene derivatives? Explain with an example of the reaction.

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The Friedel-Crafts acylation reaction is an electrophilic aromatic substitution reaction in which an acyl group is introduced into an aromatic ring, typically using an acyl halide and a Lewis acid catalyst. The Friedel-Crafts alkylation reaction, on the other hand, involves the introduction of an alkyl group into the aromatic ring using an alkyl halide and a Lewis acid catalyst. Both reactions are used to functionalize aromatic compounds, but the acylation reaction is more useful for synthesizing monoacylated benzene derivatives due to the absence of carbocation rearrangement and over-alkylation issues.Mechanism of Friedel-Crafts Acylation:1. Formation of the acylium ion: The Lewis acid catalyst  e.g., AlCl3  reacts with the acyl halide  e.g., RCOCl  to form a complex. This complex undergoes a heterolytic cleavage of the carbon-halogen bond, generating an electrophilic acylium ion  RCO+  and a halide ion.RCOCl + AlCl3  RCO+ + AlCl4-2. Electrophilic attack on the aromatic ring: The acylium ion  RCO+  acts as an electrophile and attacks the aromatic ring, forming a resonance-stabilized carbocation  sigma complex .3. Deprotonation and regeneration of the aromatic system: A base  e.g., AlCl4-  abstracts a proton from the sigma complex, regenerating the aromatic system and releasing the Lewis acid catalyst.Example of Friedel-Crafts Acylation:Acetyl chloride  CH3COCl  reacts with benzene in the presence of aluminum chloride  AlCl3  as a catalyst to form acetophenone  C6H5COCH3 .CH3COCl + C6H6 + AlCl3  C6H5COCH3 + HCl + AlCl3In summary, the Friedel-Crafts acylation reaction is a useful method for synthesizing monoacylated benzene derivatives, as it avoids the issues of carbocation rearrangement and over-alkylation that can occur in the Friedel-Crafts alkylation reaction. The mechanism involves the formation of an electrophilic acylium ion, which attacks the aromatic ring, followed by deprotonation to regenerate the aromatic system.
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