Tonya

5+ Year Member
May 16, 2011
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Pre-Dental
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Most Acidic Proton
Which labeled proton in the following molecule is most acidic?


Correct Answer: B

why B is true?
 

Drenalin

5+ Year Member
Oct 31, 2013
65
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Status
Dental Student
The stability of each resulting conjugate base should be considered; the more stable this is, the stronger the parent acid. For enolates, the greater the degree of charge delocalization (i.e. the more resonance
structures that can be drawn) the stronger the acid. Proton Hb is most acidic due to the charge (and lone pair of electrons) on the conjugate base being delocalized over both carbonyl groups and the benzene ring.

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