Most common amines (RNH 2 ) exhibit pK a 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 pK a is found to be drastically lower (a) Explain why the presence of the cyano group so drastically impacts the pK a (b) Can you suggest a different replacement for R that would lead to an even stronger acid (pK a lower than 17) R N' NEC N , 35 45 , 17

Question: Most common amines (RNH 2 ) exhibit pK a values between 35 and 45. R represents the rest of the compound (generally carbon and hydrogen

Most common amines (RNH₂) exhibit pK_avalues between 35 and 45. R represents the rest of the compound (generally carbon and hydrogen atoms). However, when R is a cyano group, the pK_ais found to be drastically lower:

Н R-N' н NEC-N Н Н рк, - 35-45 рк, - 17

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

(b) Can you suggest a different replacement for R that would lead to an even stronger acid (pK_a lower than 17)?

R-N' NEC-N , - 35-45 , - 17

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