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If the pKb value of N,N-diethylethanamine is 3.25, predict the pKb value of ethanamine.

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in Chemistry – Class 12 by (188k points)
If the pKb value of N,N-diethylethanamine is 3.25, predict the pKb value of ethanamine.

(a) 3.00

(b) 3.29

(c) 4.75

(d) 9.38

This question was posed to me during an online exam.

This intriguing question originated from Amines Chemical Reactions in chapter Amines of Chemistry – Class 12

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The correct choice is (b) 3.29

To elaborate: In ethyl substituted amines (aqueous), the inductive effect has a bigger role than the solvation effect (because the size of ethyl is larger than methyl group), and as a result the basic strength of N,N-diethylethanamine will be higher than that of ethanamine. Thus, the pKb value of the latter will be very slightly higher than the former.

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