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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: H H Incorrect. 人 R N H PK = 35-45 N N H PK = = 17 (a) Explain why the presence of the cyano group so drastically impacts the pKa. ○ When R is a cyano group, the acidic proton is on an sp-hybridized atom. ○ When R is a cyano group, the conjugate base is destabilized by resonance. ○ When R is a cyano group, the conjugate base is destabilized by inductive effects. ● When R is a cyano group, the conjugate base is stabilized by resonance.

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: H H Incorrect. 人 R N H PK = 35-45 N N H PK = = 17 (a) Explain why the presence of the cyano group so drastically impacts the pKa. ○ When R is a cyano group, the acidic proton is on an sp-hybridized atom. ○ When R is a cyano group, the conjugate base is destabilized by resonance. ○ When R is a cyano group, the conjugate base is destabilized by inductive effects. ● When R is a cyano group, the conjugate base is stabilized by resonance.

Organic Chemistry
Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter26: Biomolecules: Amino Acids, Peptides, And Proteins
Section26.SE: Something Extra
Problem 53AP
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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: H H Incorrect. 人 R N H PK = 35-45 N N H PK = = 17 (a) Explain why the presence of the cyano group so drastically impacts the pKa. ○ When R is a cyano group, the acidic proton is on an sp-hybridized atom. ○ When R is a cyano group, the conjugate base is destabilized by resonance. ○ When R is a cyano group, the conjugate base is destabilized by inductive effects. ● When R is a cyano group, the conjugate base is stabilized by resonance.
Transcribed Image Text: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: H H Incorrect. 人 R N H PK = 35-45 N N H PK = = 17 (a) Explain why the presence of the cyano group so drastically impacts the pKa. ○ When R is a cyano group, the acidic proton is on an sp-hybridized atom. ○ When R is a cyano group, the conjugate base is destabilized by resonance. ○ When R is a cyano group, the conjugate base is destabilized by inductive effects. ● When R is a cyano group, the conjugate base is stabilized by resonance.
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