CLiC Problem Set #3

Autumn Quarter 2015

Problem 1
In last weeks problem set, we identified a hydrocarbon by combustion analysis. Similarly, begin this
question by writing out and balancing the equation for the combustion of the epilepsy drug
phenobarbital, C12H12N2O3. (Note: When combusted in hydrocarbons, nitrogen forms N2). Then,
answer the following questions:
a.) Draw the Lewis dot structures for all products in this reaction, indicating the formal charge for
each atom. For each molecule, state or indicate:
(1) Any dipole moments
(2) The steric number of the central atom (if applicable)
(3) The molecular geometry
(4) The overall molecular dipole moment (if applicable)

b.) One possible resonance structure of phenobarbital is given below. Would you expect this form
to be stable? Why or why not? If not, give a more stable resonance structure. (Hint: if you are
stuck, try reviewing how calculating formal charges might be of assistance)

Problem 2
Refer to your balanced reaction for the combustion of phenobarbital. If 151g of phenobarbital are
combusted, what volume of gases are produced? You may assume the temperature of all gaseous
products is 150 C, at a pressure of 1atm.
Problem 3
While volunteering at a hospital, you spill a tray of portioned-out pills on the counter. Oh no! You
quickly identify most pills by shape and color. However, phenobarbital and aspirin (C9H8O4) are both
white, round, 100mg1 tabletsone type unhelpfully labeled V, the other M. Recalling general
chemistry, you quickly devise a way to identify which tablet is which drug. You burn 3 M pills and
measure the temperature (150C) and volume (752mL) of gas produced from combustion. Just as you
are finishing up the experiment, your supervisor comes in and angrily asks you what you are doing.
Explain to her how your experiment works, and tell her which pills are which drug.

You may assume the tablets are pure and contain no filler agents.