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why effect of resonance isn't considered in comparing basicity of amines

why effect of resonance isn't considered in comparing basicity of amines

Grade:12

2 Answers

Ashwin Sinha
520 Points
9 years ago

Dear Hemant,

 It is so, bcoz of +I effects of alkyl groups attached to Nitrogen!!!!! It is much dominant here!!!!

 

         Good Luck!!!!!

 

 Plz. approve my answer by clicking 'Yes' given below!!!!  Plz. Plz. Plz.!!!!!!!! Don't forget!!!!!!Smile

SAGAR SINGH - IIT DELHI
879 Points
9 years ago

Although resonance delocalization generally reduces the basicity of amines, a dramatic example of the reverse effect is found in the compound guanidine (pKa = 13.6). Here, as shown below, resonance stabilization of the base is small, due to charge separation, while the conjugate acid is stabilized strongly by charge delocalization. Consequently, aqueous solutions of guanidine are nearly as basic as are solutions of sodium hydroxide.

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