Organic Chemistry Practice Problems Ranking Acidity Practice Problems Solution: Most common amines (RNH 2) exhibit pKa values betw...

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Solution: Most common amines (RNH 2) 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: (a) Explain why the presence of the cyano group so drastically impacts the pKa.

Problem

Most common amines (RNH 2) 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:

(a) Explain why the presence of the cyano group so drastically impacts the pKa.