1. (6 pts) Dissolving compound 1 in basic solution (pH > 7) generates meso-ionic species 2, representing a class of
compounds which are potent against cell growth of Leishmania, a genus of trypanosome and a cause of the disease
leishmaniasis.
R
R
N-N
R PH > 7.0
N-N
R
N
R
S
R
S
1
2
a) Draw at least five alternate resonance structures of molecule 2. Use "curly-arrows" to show electron flow as
you go from one resonance structure to another. (I can see at least 8 structures total). At least two of your
structures should be "valid" octet rule violations. (you may want to review the situations where the octet rule
may be violated!)
b) Are there any valid resonance structures where all of the atoms are neutral? (yes or no?). If yes, please place a
square around the structure as drawn above