HN Uracil

Introduction to General, Organic and Biochemistry
11th Edition
ISBN:9781285869759
Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres
Publisher:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres
Chapter30: Nutrition
Section: Chapter Questions
Problem 30.12P
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(a) The two most acidic hydrogens of uracil have pKa’s of 9.5 and 14.2, respectively. Match these pKa’s with the hydrogens in the structural formula and provide structures for the most stable resonance contributors of the monoanion and the dianion.
(b) The pKa of the conjugate acid of triethylamine is 10.4. Is triethylamine a strong enough base to convert uracil to its monoanion? To its dianion?

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