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Question

On Friedel-Crafts alkylation, anisole yields major product:

A
2-Methoxytoluene
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B
4-Methoxytoluene
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C
3-Methoxytoluene
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D
None of the above
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Solution

The correct option is B 4-Methoxytoluene
In Friedel craft alkylation, the alkyl chloride will react with anhydrous AlCl3 to form electrophilic carbocation.
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. Ether is ortho/para directing group. Thus, it gives both ortho and para products.
Hence, anisole on alkylation gives 4-Methoxytoluene as a major and 2-Methoxytoluene as a minor product.

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