Organic Chemistry III
	Professor Carl C. Wamser
Chem 336 - Spring Term	Quiz 26

1.  (2 points)  AZT is one of the first drugs used to treat HIV.  It is identical to one natural nucleoside with one major modification.  Name the natural nucleoside and describe the modification.

It is deoxythymidine with the 3' OH replaced by an azide group.

2.  (2 points)  Write the complete structure of adenosine diphosphate (ADP), in which the diphosphate is located on the 5’ position, as it would appear at pH 7.

3.  (3 points)  Write the complete structure of the two bases C and G so as to show their H-bonding with one another.

4.  (3 points)  Show an acid-catalyzed mechanism for the conversion shown below.  There is just one intermediate with multiple resonance forms - write them all.

(ignore the duplicate)