Can Gatterman-Koch reaction be considered similar to Friedel-Crafts acylation? Discuss.
(N/A) Yes,the Gatterman-Koch reaction is considered a special case of Friedel-Crafts acylation.
In standard Friedel-Crafts acylation,benzene (or an arene) reacts with an acid chloride (e.g.,$CH_3COCl$) in the presence of anhydrous $AlCl_3$ to form an aryl ketone.
In the Gatterman-Koch reaction,benzene is treated with $CO$ and $HCl$ in the presence of anhydrous $AlCl_3$. Since formyl chloride $(HCOCl)$ is unstable,it is generated in situ from $CO$ and $HCl$.
This in situ generated $HCOCl$ then acts as the acylating agent,similar to the acid chloride in Friedel-Crafts acylation,to produce benzaldehyde. Thus,the mechanism is analogous.
In standard Friedel-Crafts acylation,benzene (or an arene) reacts with an acid chloride (e.g.,$CH_3COCl$) in the presence of anhydrous $AlCl_3$ to form an aryl ketone.
In the Gatterman-Koch reaction,benzene is treated with $CO$ and $HCl$ in the presence of anhydrous $AlCl_3$. Since formyl chloride $(HCOCl)$ is unstable,it is generated in situ from $CO$ and $HCl$.
This in situ generated $HCOCl$ then acts as the acylating agent,similar to the acid chloride in Friedel-Crafts acylation,to produce benzaldehyde. Thus,the mechanism is analogous.
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