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Product of friedelscraft benzoylation ​with anhydrous AlCl3 or FeCl3

Product of friedelscraft benzoylation
​with anhydrous AlCl3 or FeCl3

Grade:12th pass

1 Answers

jyoti bhatia
202 Points
5 years ago
Friedel–Crafts reactions are of two main types: alkylation reactions and acylation reactions. Both proceed by electrophilic aromatic subtitutionFriedel–Crafts alkylation involves the alkylation of an aromatic ring with an alkyl halide using a strong Lewis acid catalyst. With anhydrous ferric chloride as a catalyst, the alkyl group attaches at the former site of the chloride ion.This reaction suffers from the disadvantage that the product is more nucleophilic than the reactant. Consequently, overalkylation occurs. Furthermore, the reaction is only very useful for tertiary alkylating agents, some secondary alkylating agents, or ones that yield stabilized carbocations (e.g., benzylic ones). In the case of primary alkyl halides, the incipient carbocation (R(+)---X---Al(-)Cl3) will undergo a carbocation rearrangement reactionAlkylations are not limited to alkyl halides: Friedel–Crafts reactions are possible with any carbo-cationic intermediate such as those derived from alkenes and a protic acid, Lewis acid, enones and epoxides. An example is the synthesis of neophyte chloride from benzene and methallyl chloride.
Friedel–Crafts acylation involves the acyltion of aromatic rings. Typical acylating agents are acyl chlorides. Typical Lewis acid catalysts are acids and aluminium trichloride. Friedel–Crafts acylation is also possible with acid anhydrides. Reaction conditions are similar to the Friedel–Crafts alkylation. This reaction has several advantages over the alkylation reaction. Due to the electron-withdrawing effect of the carbonyl group, the ketone product is always less reactive than the original molecule, so multiple acylations do not occur. Also, there are no carbocation rearrangements, as the acylium ion is stabilized by a resonance structure in which the positive charge is on the oxygenThe viability of the Friedel–Crafts acylation depends on the stability of the acyl chloride reagent. Formyl chloride, for example, is too unstable to be isolated. Thus, synthesis of benzaldehyde via the Friedel–Crafts pathway requires that formyl chloride be synthesized in situ. 

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