MCAT Question of the Day
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    Q:

    		 Acetone is shown below on the left. What will happen to the pKa 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 pKa directly refers to) is the hydrogens on the carbon where the azido group was substituted (the -CH2). The modified molecule (after azido addition) is shown in the middle, and the azido group itself is shown on the far right.



    		 

    A

    		 The pKa of the hydrogens of the azido-substituted molecule (the -CH2) will be lower than the hydrogens on the molecule without the azido (the -CH3) because the azido group stabilizes the conjugate base

    B

    		 The pKa of the hydrogens of the azido-substituted molecule (the -CH2) will be higher than the hydrogens on the molecule without the azido (the -CH3) because the azido group stabilizes the conjugate base

    C

    		 The pKa of the hydrogens of the azido-substituted molecule (the -CH2) will be lower than the hydrogens on the molecule without the azido (the -CH3) because the azido group destabilizes the conjugate base

    D

    		 The pKa of the hydrogens of the azido-substituted molecule (the -CH2) will be higher than the hydrogens on the molecule without the azido (the -CH3) because the azido group destabilizes the conjugate base



    Acid/Base Equilibria | Aldehydes and Ketones |
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