CHML211
Exp. 1 Structure, Intermolecular Forces, and Solubility
IN-LAB ASSIGNMENT: (EACH STUDENT will record the following data in his/her laboratory notebook in a well organized
manner during lab period. Yellow carbon copies will be submitted for grading along with Post-Lab assignment.) …..max
score = 20 pts.
1. Data/Calculations (The following information should be recorded directly into laboratory notebook.)
NONE. All data will be entered directly into tables located in POST-LAB RESULTS section.
2. In-lab Questions (The following questions should be answered in laboratory notebook.)
a.
List the four factors that determine the relative polarity of a substance.
b.
Classify the following structures as hydrogen bond donors and acceptors (HDA), hydrogen bond acceptors only
(HA), or neither. For the structures classified as HDA and HA, use an arrow to indicate where the hydrogen
bonding can occur with another molecule.
H
H
N
O
N
OH
O
O
isopropyl alcohol
O
propyl acetate
O
diethyl ether
o-nitroaniline
benzene
CHML211
Exp. 1 Structure, Intermolecular Forces, and Solubility
POST-LAB ASSIGNMENT: (EACH LAB GROUP will submit one copy of a typewritten, paragraph style report addressing
all of the points listed below. Must be written using PAST TENSE, PASSIVE VOICE. ) …..max score = 50 pts.
3. Experimental (Write 1-2 paragraphs including all of the following. Do NOT present a bulleted outline.)

Briefly describe the process used to determine the miscibility of organic liquids in water. Be sure to include names
and volumes of any compounds used in this process.
Briefly describe the process used to determine the miscibility of alcohols in hexane vs. water. Be sure to include
names and volumes of any compounds used in this process.
Briefly describe the process used to determine the solubility of organic solids. Be sure to include names and
volume/mass of any compounds used in this process.


4. Results (Copy and paste the completed tables into your document.)
Table 1.1 Miscibility of organic liquids and water
Solvent
IMF
H2O Miscibility
Structure
(circle all
(M or IM)
that apply)
Solvent
Identity
A
methanol
LDF
HBA
D-D
HBD
B
ethyl acetate
LDF
HBA
D-D
HBD
C
dichloromethane
LDF
HBA
D-D
HBD
D
toluene
LDF
HBA
D-D
HBD
E
hexane
LDF
HBA
D-D
HBD
Alcohol
methanol
F
ethanol
G
1-propanol
H
1-butanol
I
Organic
Layer
(Top or Bottom)
Table 1.2 Structure and miscibility of alcohols in hexane and water
IMF
Hexane
Boiling
Structure
(circle all
Miscibility
Point (Co)
that apply)
(M or IM)
LDF
D-D
HBA
HBD
LDF
D-D
HBA
HBD
LDF
D-D
HBA
HBD
LDF
D-D
HBA
HBD
H2O
Miscibility
(M or IM)
Table 1.3 Structure and solubility of organic solids
Organic
Solid
Structure
IMF
(circle all
that apply)
hexane
J
K
L
benzoic
acid
sodium
benzoate
naphthalene
LDF
HBA
Solubility
(Sol or Insol)
water
10%
NaHCO3
1M
HCl
D-D
HBD
I-D
LDF
HBA
D-D
HBD
I-D
LDF
HBA
D-D
HBD
I-D
M
p-nitroaniline
LDF
HBA
D-D
HBD
I-D
5. Discussion (Write 1-2 paragraphs including the following.)







Which solvents formed the top layer when mixed with water? Which solvents formed the bottom layer when
mixed with water? Does this make sense based on the density of these solvents compared to that of water? Give
actual numerical values to support your conclusion.
Which alcohols were miscible with water, but not hexane? Which alcohols were miscible with hexane, but not
water? How does the length of the carbon chain affect the molecular weight? Which intermolecular force
increases with increasing molecular weight? How does the length of the carbon chain affect the boiling point of
the alcohol? Does increasing the carbon chain length result in the alcohol becoming more polar or more
nonpolar?
Which organic solids were soluble in hexane? What intermolecular forces do the solid and hexane have in
common?
Which organic solids were soluble in water? What intermolecular forces do the solid and water have in common?
Which organic solids were soluble in 10% NaHCO3? Some solids which were insoluble in water appear to be
soluble in 10% NaHCO3. What effect does adding this aqueous basic solution have on this solid that accounts for
this difference in solubility?
Which organic solids were soluble in 1M HCl? Some solids which were soluble in water appear to be insoluble in
1M HCl. What effect does adding this aqueous acidic solution have on this solid that accounts for this difference in
solubility?
Include a short comment addressing what could be done differently to improve the experimental results, if
repeated.