CHMY 222 – Organic Chemistry Laboratory
Autumn 2011
Professor: Gerald Olbu
Office: CP117
Office Hours: Tue. and Thur. 12-1, or by arrangement.
Phone: 243-4774
email: gerald.olbu@umontana.edu
Prerequisite: CHMY 221 or the equivalent is a co- or prerequisite. Also, one semester of 100level chemistry lab is a prerequisite. For safety and other important reasons, lab prerequisites are
very important and will be enforced. You may be required to provide proof (transcript or name,
number and term of the UM course).
Course Objective: To illustrate organic chemical reactions and the analysis techniques for organic
compounds and to successfully manipulate small amounts of organic compounds.
Text: Pavia, Lampman, Kriz and Engel, Organic Laboratory Techniques, 4th edition.
Required Materials: Splash-protection safety goggles and a bound laboratory notebook must be
purchased.
Grading: There are eight labs, each worth 100 points for 800 points total. The following are the
guaranteed grades for course numerical scores.
A
AB+
B
BC+
90.0% and above
86.7
83.3
80.0
76.7
73.3
C
CD+
D
DF
70.0
66.7
63.3
60.0
56.7
56.6 and below
Disabilities: Any student in this course who has a disability that may prevent him or her from fully
demonstrating his or her abilities should contact me personally as soon as possible so we can
discuss accommodations necessary to ensure full participation and facilitate your educational
opportunities.
Legal Notices: This course syllabus is not a contract; it is a tentative outline of course policies.
Changes may be made before, during, or after the semester at my discretion.
All students must practice academic honesty. Academic misconduct is subject to an academic
penalty by the course instructor and/or a disciplinary sanction by the university. All students need
to be familiar with the Student Conduct Code. The Code is available for review online at:
http://ordway.umt.edu/SA/VPSA/index.cfm/name/StudentConductCode.
Tentative Schedule – Fall 2011
Note: If it says “Discussion,” meet in the lecture room at the beginning of the 2-hour period.
If it does not say “Discussion,” meet in the lab at the beginning of the 2-hour period.
MW Date TTh Date Lab
Aug 29, M Aug 30, T
31, W Sept 1, Th
Sept 5, M Sept 6, T
7, W
8, Th L1
12, M
13, T L1
14, W
15, Th L2
19, M
20, T L2
21, W
22, Th
26, M
27, T L3
28, W
29, Th L3
Oct 3, M
Oct 4, T L4
5, W
6, Th
10 M
11, T L4
12, W
13, Th L4
17, M
18, T
19, W
20, Th L5
24, M
25, T L5
26, W
27, Th L5
31, M Nov 1, T L5
Nov 2, W
3, Th L6
7, M
8, T L6
9, W
10, Th L6
14, M
15, T
16, W
17, Th L7
21, M
22, T L7
23, W
24, Th
28, M
29, T L8
30, W Dec 1, Th L8
Dec 5, M
6, T L8
7, W
8, Th
Activity
Sign-In, Introduction Discussion
Safety Discussion and Check-in Lab 2nd hour
Holiday
Discussion, (µScale Lab Exercises in 2nd hour)
Discussion, (µScale Lab Exercises in 2nd hour)
L2 Distillation/GC
L3 Distillation/GC
Discussion, (Finish GC in 2nd hour)
Acetaminophen Prep
Acetaminophen Prep
Acetaminophen Prep
Discussion, (Finish Exp. in 2nd hour)
Steam Distillation
Steam Distillation
Discussions (L5-L8), (Finish IR’s in 2nd hour)
n-Butyl Bromide Prep
n-Butyl Bromide Prep
n-Butyl Bromide Prep
n-Butyl Bromide Prep and IR spectrum
t-Pentyl Chloride Prep
t-Pentyl Chloride Prep
t-Pentyl Chloride Prep and IR spectrum
Methylcyclohexene Prep
Methylcyclohexene Prep
Methylcyclohexene Prep and IR spectrum
Holiday
Nitration of Methyl Benzoate
Nitration of Methyl Benzoate
Nitration of Methyl Benzoate
Check out of lab. You must check out during this period.
Experiments and Reading assignments
Pavia, Lampman, Kriz and Engel, 4th edition
Pages 542-573 are to be read before the first experiment is started. All sections which precede an
experimental procedure, such as Required Reading (Techniques), Special Instructions, Waste
Disposal, must be read before each experiment is started. Assigned problems must be included
with the lab report.
L1 – Introduction to Microscale
Essay: p. 2-10
Procedure: Lab Exercises 1A, 1C and 2, p. 10-11
New Techniques: none
Problems: none from text
L2 – Distillation/GC
Procedure: Handout
New Techniques: 14.1-14.4, 15.1-15.2, 15.4-15.7 and 22.1-22.12
Problems: p. 714, #1-4; p. 731-732, #2, 6-8; and p.817-818, #1, 2, 4
L3 – Recrystallization (Acetaminophen Prep)
Essay: p. 61-62 and p.67-70
Procedure: Exp 10A, p. 76
New Techniques: 9.1-9.5, 9.7-9.9 and 11.1-11.10
Problems: p.80, #1-4
L4 – Steam Distillation
Essay: p.108-111
Procedure: Exp 14B, p. 115
New Techniques: 18.1-18.3
Problems: p.116, #1, 2, 4; p. 755, #1, #2 (estimate, don’t calculate), 3
L5 – n-Butyl Bromide Prep
Procedure: Exp 23A, p. 197
Problems: p. 203, #1-6
L6 – t-Pentyl Chloride Prep
Procedure: Exp 23C, p. 200
Problems: p. 203, #2, 3, 5
L7 – Methylcyclohexene Prep
Procedure: Exp 25A, p.213
Problems: p.216-217, #1, 2a-d, 3, 5
L8 – Nitration of Methyl Benzoate
Procedure: Exp 28, p. 228
Problems: none from text
Prelab (10 points)
Prior to coming to lab, you are required to prepare a typed, one-sheet, pre-lab exercise that will
detail the following:
Title of the experiment.
Introduction. Briefly describe the purpose of the lab, usually to synthesize a product. Write the
overall reaction.
Table of chemicals used. Include name, structure, molecular weight, physical properties, amount
used (g, mL) and any relevant safety information (toxic, flammable, corrosive, etc.).
Flow diagram or briefly summarize procedure. Be brief.
This information should also be recorded neatly in your laboratory notebook. This pre-lab exercise
will make up the first portion of your final, written lab report. Ten points will be deducted from the
final lab report grade if the pre-lab component is not completed prior to class. The TAs will be
checking prior to the start of the experiments to see that this has been completed.
Laboratory Notebook and Technique (20 points)
Students must use a laboratory notebook which has a permanent stitched binding. All details of the
experiments, must be recorded accurately and neatly in the notebook. Record what was done, how
it was done and what happened. A reference to the text by page number is allowed, but any
changes in the procedure must be recorded. The final written reports will be a reflection of what
was recorded during the experiment.
All observations, weights, m.p.’s, etc must be entered directly into the notebook (not a slip of
paper). Points may be deducted for failure to record data directly into the notebook. The notebook
is to be kept up-to-date. Write the information as you do it, not afterwards. Notebooks can be
graded in lab for completeness at any time.
If a mistake is made, draw one or two lines through it and write the correct entry. Never obliterate
an incorrect entry or remove pages. Numbers must have units and tabulate data whenever possible.
Begin a new experiment on a new page.
Students will also be graded on laboratory technique, safety, cleanliness, etc.
Laboratory Reports (70 points)
Lab reports must be typed. It’s ok to handwrite chemical structures and calculations. Below is the
format for most lab reports. Not all lab reports will have the same format or points breakdown; for
example Lab 1 will not include a product synthesis. More information will be given for each lab.
Title of the experiment (approx. 5 points).
Introduction. (approx. 5 points). See Prelab.
Table of chemicals used (approx. 5 points). See Prelab.
Flow diagram or briefly summarize procedure (approx. 5 points). See Prelab.
Procedure and observations (approx. 15 points). Review your laboratory notebook and report
what was done, how it was done and what happened. Write in the past tense.
Mechanism of product synthesis (approx. 10 points). Write the reaction mechanism, including
the electron pushing.
Results (approx. 10 points). Qualitatively describe your results (color and appearance of product).
Report your melting point, percent yield and any other results.
Conclusions (approx. 15 points). Discuss the experimental procedure, your observations and
sources of error. Try to relate your discussion to the reaction mechanism where possible. Also,
answer questions assigned from the text. There may be other assignments announced during the
lecture or lab.
Total for the Lab Report (70 points).
Typed lab reports are due to your TA one week following the completion of the lab. Late lab
reports will penalized 5 points for each lab period it is late.
Safety Rules
Read pages 542-558 of your lab text.
1. GENERAL SAFETY RULES
a. Safety goggles must always be worn in the laboratory. Contact lens are not allowed.
b. You are not allowed in the lab unless an instructor (TA or professor) is present.
c. Learn the location of the lab’s safety equipment – fire extinguisher, safety shower, eyewash facilities, hoods and bench vent.
d. Adequate clothing must be worn. Clothing which exposes a lot of skin (tank tops, shorts,
sandals, etc.) is not allowed.
e. No food or drinks in the lab.
f. Turn off cell phones.
g. Use only the explosions-proof freezer in room 217 for storing flammable solvents.
h. Unauthorized experiments are not allowed.
i. Flames are never to be used in the organic lab.
j. Read “Lab Safety” in your lab textbook (pages 542-558).
k. Material Safety Data Sheets (MSDS) are on file at Chemistry Stores. Read page 548-554 in
your lab text. The web page: www.chem.utah.edu/MSDS/msds.html provides links to other
web pages which have MSDSs.
l. Chemical products are never taken out of the lab.
m. Don’t lick anything.
2. GENERAL ADVICE
a. Keep your work area and glassware clean.
b. Use caution when mixing chemicals. Sometimes heat is evolved.
c. Always add concentrated acids and bases to the water when diluting them. Never mix
concentrated acids and bases.
d. Never heat a closed system. Always provide a vent.
e. When boiling any liquid, always use adequate stirring.
f. When inserting thermometers into adapters, always use an o-ring and only gentle force.
3. ACCIDENTS
a. If a chemical is spilled on the skin, wash it off immediately with cold water and notify the
instructor.
b. Use the pull-down eye-wash fountains if chemicals get in your eyes.
c. If large amounts of chemicals are spilled on you, use the safety shower.
d. If you are burned from a heat source, soak the area in very cold water and notify the
instructor.
e. Report any cut to your instructor. We have been advised to give first aid wearing plastic or
rubber gloves. Please do not be offended.