AGRY/NRES 385 Worksheet (100 points) Due: Tuesday 11/22/22

Cl
1. What is the molecular formula for each of the following compounds?
Cl

Cl Cl

Cl Cl

Benzene Chlorobenzene 1,2-Dichlorobenzene 1,2, 4 - trichlorobenzene

Dichlorobenzene
log Sw = -1.64 (mol/L) log Sw = -2.36 (mol/L) log Sw = -2.98 (mol/L) log Sw = -3.57 (mol/L)
log Kow = 2.17 log Kow = 2.84 log Kow = 3.38 log Kow = 4.02

2. Table 1 is a summary of soil % organic carbon (OC) and the soil-water distribution
coefficients (Kd, L/kg) measured for each of the compounds listed in 1 above.

Table 1. % OC and Soil-water distribution coefficients (Kd, L/kg) for benzene and
chlorinated benzenes.
Soil Kd Kd Kd Kd
% OC Benzene Chlorobenzene 1,2- 1,2,3-
dichlorobenzene trichlorobenzne
Drummer 2.95 7.2 34 124 527
LFA 0.79 2.2 10 35 155
Toronto-20 1.3 3.3 14.5 53 230
BLF 0.36 1.0 4.5 16 70

(a) Using the data provided, calculate a Koc and log Koc for each compound on each soil.
(b) For each compound, calculate an average log Koc value and associated standard deviation
for each compound.
(c) Plot log Koc versus log Kow and quantify the trend (regression).
(d) Plot log Koc versus log Sw and quantify the trend (regression).
(e) Plot log Kow versus log Sw (aqueous solubility) and quantify the trend (regression).

3. Using the information and correlations you quantified in #2, estimate the sorption coefficient
(Kd value) for p-chlorotoluene (1,4-chloromethylbenzene) for the Drummer soil in Table 1.
 AGRY/NRES 385 HW, p 2 of 2

4. Rank the compounds 1 (highest) to 3 (lowest) within each group as requested (solubility for
group A and B; vapor pressure for group C and D) assuming no degradation. Briefly
comment on the basis for your ranking.
Group A - Solubility Group C – Vapor Pressure
Mobility Volatility Ranking
Ranking
Naphthalene naphthalene
tetrachlorobiphenyl tetrachlorobiphenyl
decachlorobiphenyl decachlorobiphenyl

Group B - Solubility Group D – Vapor Pressure

Mobility Ranking Volatility Ranking
tetrachlorobiphenyl pentane
phenol Octanol
benzene Octane

5. The table below contains data for the total concentrations of the insecticide chlorpyrifos
(apparent solubility, Sw*) with increasing dissolved organic carbon concentrations
([DOC]) present in animal-wastse derived lagoon effluent.
6.

Bottle [DOC] Sw* Sw* / Sw

# (mg OC/L) (mg/L)
1 0 0.4 1
2 38 0.52 1.3
3 62 0.61 1.525
4 75 0.66 1.65
5 95 0.71 1.775
6 125 0.83 2.075
NOTE: Sw = solubility of chemical in pure water; Sw*
solubility in the presence of DOC

Recall from lecture the graph showing solubility enhancements by DOC with the y-axis
( )
S
*
being relative solubility (solubility in the presence of DOC relative to pure water: w )
Sw
versus (DOC) on the x-axis,. The slope on the graph is the association constant between
compound I and DOC (Ki,doc). The mathematical relationship shown in the graph is simlpy:
*
Sw
= [ DOC ] ⋅ K doc + 1
Sw