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MCAT Question of the Day
Q:
Acetone is shown below on the left. What will happen to the pK
a
after the addition of an azido group to one of its methyl groups (actually replacing one of the methyl hydrogens)? The site of deprotonation (and thus where the pK
a
directly refers to) is the hydrogens on the carbon where the azido group was substituted (the -CH
2
). The modified molecule (after azido addition) is shown in the middle, and the azido group itself is shown on the far right.
A
The pK
a
of the hydrogens of the azido-substituted molecule (the -CH
2
) will be lower than the hydrogens on the molecule without the azido (the -CH
3
) because the azido group stabilizes the conjugate base
B
The pK
a
of the hydrogens of the azido-substituted molecule (the -CH
2
) will be higher than the hydrogens on the molecule without the azido (the -CH
3
) because the azido group stabilizes the conjugate base
C
The pK
a
of the hydrogens of the azido-substituted molecule (the -CH
2
) will be lower than the hydrogens on the molecule without the azido (the -CH
3
) because the azido group destabilizes the conjugate base
D
The pK
a
of the hydrogens of the azido-substituted molecule (the -CH
2
) will be higher than the hydrogens on the molecule without the azido (the -CH
3
) because the azido group destabilizes the conjugate base
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