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A student tried to synthesis 4-nitro-N, ...


A student tried to synthesis 4-nitro-N, N-dimethylaniline from N, N-dimethylaniline via electrophilic aromati substitution using nitric acid `(HNO_3)` and sulphuric acid `(H_2SO_4)`. To his surprice, the major product he obtained was 3-nitro-N, N-dimethylaniline. Why the disigned reaction failed to provide the desired product, 4-nitro-N, N-dimethylaniline?

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.

Text Solution

Verified by Experts

The correct Answer is:
B
This is because of the protonation of amine group which makes it meta directing.
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  13. Which of the following is regenerated at the end of the reaction?

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  14. Which of the following compounds does not react with NaNO2 and HCl?

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