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Question

What is the reason for the formation of a meta product in the following reaction?

A
Aniline is ortho/para directing
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B
Aniline is meta directing
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C
In acidic medium, aniline is converted into anilinium ion, which is ortho/para directing
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D
In acidic medium, aniline is converted into anilinium ion which is meta directing
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Solution

The correct option is D In acidic medium, aniline is converted into anilinium ion which is meta directing
In an acidic medium, lone pair of electrons of nitrogen abstract a proton and gets converted into anilinium ion, which is a strong electron withdrawing group which deactivates the benzene ring and form a meta product.

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