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Question
Choose the correct order of basic strength of given anilines.
Choose the correct order of basic strength of given anilines.
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Solution
The correct option is B m-nitroaniline > p-nitroaniline > o-nitroaniline
−NO2 is an electron withdrawing group so it has -R and -I effect. This will decrease the electron density on N and makes it less basic. -R effect is absent at meta position, so m-nitroaniline has more basic strength than p-nitroaniline.
The conjugate acid of o-nitroaniline formed after abstraction of H+ will experience steric hindrance due to presence of −NO2 at ortho position. This is called Steric inhibition of protonation. This will make the conjugate acid less stable so it is less basic than others.
Therefore, order of basic strength is
m-nitroaniline > p-nitroaniline > o-nitroaniline
−NO2 is an electron withdrawing group so it has -R and -I effect. This will decrease the electron density on N and makes it less basic. -R effect is absent at meta position, so m-nitroaniline has more basic strength than p-nitroaniline.
The conjugate acid of o-nitroaniline formed after abstraction of H+ will experience steric hindrance due to presence of −NO2 at ortho position. This is called Steric inhibition of protonation. This will make the conjugate acid less stable so it is less basic than others.
Therefore, order of basic strength is
m-nitroaniline > p-nitroaniline > o-nitroaniline
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