Most common amines (RNH2) exhibit pKa values between 35 and 45. R represents the rest of
Chapter 3, Problem 3.62(choose chapter or problem)
Most common amines (RNH2) exhibit pKa values between 35 and 45. R represents the rest of the compound (generally carbon and hydrogen atoms). However, when R is a cyano group, the pKa is found to be drastically lower: R N H H H pKa = 3545 N C N H pKa = 17 (a) Explain why the presence of the cyano group so drastically impacts the pKa. (b) Can you suggest a different replacement for R that would lead to an even stronger acid (pKa lower than 17)?
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