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Q.

Which one of the following amine has the highest pkb value

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a

meta-methyl aniline

b

para-methyl aniline

c

para-methoxy aniline

d

para -nitro  aniline

answer is A.

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Detailed Solution

-NO2 group at para position shows - I , -M effect .  thus it is a strong electron withdrawing group.  it decreases the basic strength of aniline . -CH3 group is always an ERG or EDG....it increases the basic strength -OCH3 group is EDG or ERG at ortho and para positions.....increases the basic strength; -OCH3 gp is a stronger EDG as compared to -CH3 gp; Thus basic strength of 4 > 2 > 3 >1..... pKb will be highest for option 1 ;

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Which one of the following amine has the highest pkb value