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Q.

A student tried to synthesis 4-nitro-N, N-dimethylaniline from N, N-dimethylaniline via electrophilic aromatic substitution using nitric acid (HNO3) and sulphuric acid (H2SO4). To his surprise, the major product he obtained was 3-nitro-N, N-dimethylaniline. why the designed reaction failed to provide the desired product, 4-nitro-N, N-dimethylaniline?

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a

The amine group is meta directing.

b

Protonation at amine group makes it meta directing.

c

The amine group is strong electron withdrawing group by – I effect.

d

Steric inhibition to resonance is responsible for the above result.

answer is B.

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Detailed Solution

This is because of the protonation of amine group which makes it meta directing.
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