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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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Knowledge Check

  • The major product formed on nitration of N, N - dimethylaniline with conc. H_2SO_4,NHO_3 mixture is

    A
    B
    C
    D

  • The indicator that is obtained by coupling the diazonium salt of sulphanilic acid with N, N-dimethylaniline is

    A
    phenanthroline
    B
    methyl orange
    C
    methyl red
    D
    phenolphthalein

  • The indicator that is obtained by coupling the diazonium salt of sulphanilic acid with N, N-dimethylaniline is

    A
    phenanthroline
    B
    methyl orange
    C
    methyl red
    D
    phenolphthalein.
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    7. An organic compound A has molecular formula C7H9N and it forms a clear...

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