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Dear student,
The basic strength in aqueous solution depends not only upon electron releasing effect but also upon steric effect and hydration effect.
Steric effect refers to the crowding of alkyl groups around N atom which hinders the attack of proton on the amine molecule and this decreases its basic strength. Since crowding of alkyl groups around N atom increases from 1o to 3o amines, the basic strength of amine should decrease in the order 1o > 2o > 3o.
Hydration effect refers to the stabilization of the protonated amine by water molecules. The water molecules from H - bonds with the protonated amine and release energy called hydration energy.
Greater the extent of H - bonding in protonated amine more will be its stabilization and consequently greater will be the basic strength of the corresponding amine.
Hydration due to hydrogen-bonding is maximum in monoalkyl ammonium ion (protonated cation of 1o amine), it is less in dialkyl ammonia ion and still less in trialkyl ammonium ion. Thus basic strength should decrease from 1o > 2o > 3o.
In 3o amine, hydration is least, steric hinderance is maximum so least basic inspite of maximum inductive effect.
In 1o amine, steric hinderance is least, hydration is maximum and inductive effect is minimum. So its basic strength is more than 3o amine.
The resultant of all factors cause 2o amine to be still more basic than 1o amine.
So overall basic strength varies as 2o > 1o > 3o.
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Sagar Singh
B.Tech, IIT Delhi
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