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: (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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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:

(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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