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Question
Which of the following is the most basic of the given compounds ?
Which of the following is the most basic of the given compounds ?
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Solution
The correct option is C
In (b) :
Due to steric inhibition of protonation,the conjugate acid of ortho substituted aniline becomes destabilised due to steric hindrance . So (b) is the least basic compound.
Between (a) and (c):
In (a) there are 2 methyl groups attached to nitrogen that show +I effect and hence increase the electron density, making the lone pair available for donation.
In (c) :
due to steric hindrance −N(CH3)2 group goes out of plane, so resonance with the ring is hampered. Lone pair becomes more available to accept H+ as comapred to (a) so basicity increases and due to steric inhibition of resonance (c) is the most basic compound.
Correct order is :
(c) > (a) > (b)
In (b) :
Due to steric inhibition of protonation,the conjugate acid of ortho substituted aniline becomes destabilised due to steric hindrance . So (b) is the least basic compound.
Between (a) and (c):
In (a) there are 2 methyl groups attached to nitrogen that show +I effect and hence increase the electron density, making the lone pair available for donation.
In (c) :
due to steric hindrance −N(CH3)2 group goes out of plane, so resonance with the ring is hampered. Lone pair becomes more available to accept H+ as comapred to (a) so basicity increases and due to steric inhibition of resonance (c) is the most basic compound.
Correct order is :
(c) > (a) > (b)
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