Practice+Problems+for+Midterm+2+Answer+Key

Practice+Problems+for+Midterm+2+Answer+Key - 3) a) The...

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3) a) The second protonated acid has better resonance stabilization of the positive charge (tertiary carbocation resonance structures) than the first acid, stabilizing the second acid and resulting in a higher pKa. The third acid has increased steric hindrance surrounding the protonated site, which prevents solvent molecules from interacting with the positive charge and stabilizing it. The absence of the stabilizing solvent shell from the acid increases its energy and leads to a lower pKa. b) The conjugate base of the first acid places a lone pair of electrons in resonance with the aromatic ring, stabilizing the conjugate base and lowering the pKa of the first acid relative to the second acid. In the case of the third acid, there is poor salvation of the positive charge because of steric hinderance, resulting in a lower pKa compared to the second acid. c) The conjugate base of the first acid is stabilized by resonance, which accounts for the lower pKa compared to the second acid. d) The first two acids have conjugate bases that are stabilized by resonance, again accounting for
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Practice+Problems+for+Midterm+2+Answer+Key - 3) a) The...

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