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MCAT Question of the Day
Q:
The pKa of aniline, or C
6
H
5
NH
2
is 4.60 while the pKa of benzylamine, or C
6
H
5
CH
2
NH
2
is 9.34. Which of the following best explains the disparity in their pKa values?
A
The larger size of benzylamine increases its pKa.
B
The CH
2
group has electron-donating properties and separates the amine from the electron-withdrawing benzene ring.
C
The CH
2
group adds electron-withdrawing characteristics to raise the pKa.
D
The difference in steric hindrance between the two is sufficient to explain the difference in pKa.
Acid/Base Equilibria
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