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40700/A1200 Environmental Organic Chemistry Spring

2016
Problem Set #1 Out: Feb. 10, 2015 Due:
Feb. 22, 2016

1. (30 points) A covered pot contains 1.0 L of a very diluted, cold soup
(25 C), 1.0 L of air and a floating blob of fat of a volume of 2.0 mL.
The system also contains 2.0 mg of PCB52 (2,2,5,5-
tetrachlorobiphenyl). Estimate the amount of PCB52 in each of the
three phases. Assume that equilibrium is established.

In Appendix C of the textbook, you find the air-water portioning


constant (Kiaw) of PCB101 and its octanol-water partition coefficient
(Kiow) that you use as a surrogate for the fat-water portion
coefficient (Kifw). Note that these partition coefficients are given as
ratios of molar concentrations.
a) Estimate the amount of PCB52 in fat
b) Estimate the amount of PCB52 in the aqueous soup
c) Estimate the amount of PCB52 in the air

2. (30 points) Acetone is an important chemical solvent. When using


the pure liquid compound as a reference state, in which solvents
(give examples) would you expect that acetone has an activity
coefficient of (a) close to 1, (b) smaller than one, and (c) larger than
one? (Table 3.2 might be helpful)

3. (20 points) Here is a list of organic contaminants of the


environment that have been studied. Draw their structure and
classify the compounds (using the classification of nonpolar/polar
(Box 3.1, page 62).

- 2,3,7,8-tetrachloro-dibenzo-p-dioxin (highly toxic, can form


during combustion)
- p,p-DDT (legacy contaminant, insecticide)
- parathion (a typical organophosphorus insecticide)
- decabromodiphenyl ether (a PBDE, an important flame
retardant)
- atrazine (very important herbicide)
- your compound

4. (20 points) In table 3.4 you find the equilibrium constant of benzene
distributing between air and water (Ki12 = 0.21). This value is for 25
C. Table 3.4 also provides you with 12Hi for this phase transfer
process. This allows you to calculate Ki12 at a different
temperature. Calculate this Ki12 at 20 C (use equation 3-51,
remember: in thermodynamics temperature must be expressed in
K, also be careful with kJ vs J).

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