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Question

On Friedel-Crafts acetylation, anisole yields:

A
2-Methoxyacetophenone
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B
4-Methoxyacetophenone
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C
Both (a) and (b)
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D
None of the above
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Solution

The correct option is C Both (a) and (b)
In Friedel craft acetylation, the acetyl chloride will react with anhydrous AlCl3 to form acylium ion. The acylium ion will act as an electrophile.
Alkoxy benzene will undergo electrophilic aromatic substitution. The ether group will undergo resonating with benzene ring and form resonating structure. In the resonating structures, the electron density at ortho and para position are increased which will attack the electrophile (in this case, it is acylium ion). Ether is ortho/para directing group. Thus, it gives both ortho and para products.
Hence, anisole on acetylation gives 2-Methoxyacetophenone and 4-Methoxyacetophenone.

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