Chemistry 201 Laboratory
Fall, 2013
Instructors:
Thomas S. Straub, Holroyd 337, Phone: 215-951-1263, email: straub@lasalle.edu
William A. Price,
Holroyd 345, Phone: 215-951-1261, email: price@lasalle.edu
James Murray, Holroyd
343, email: jmurray@immaculata.edu
Required
Materials:
(1) Laboratory Text: Package containing Techniques in Organic Chemistry, third edition (2010), together
with custom laboratory manual from Modern
Projects and Experiments in Organic Chemistry, second edition, J. R. Mohrig, C. N. Hammond, P.F Schatz, and T. C. Morrill W. H.
Freeman, 2003.
(2) Approved safety goggles with
side protection. Prescription or reading
glasses alone are not suitable substitutes.
Safety goggles are normally designed to fit over such glasses. Also, because of the hazard associated with
vapor irritation, the use of contact lenses in the lab is discouraged. Approved goggles can be purchased at the
chemistry department stockroom.
(3) A laboratory apron will be
required at all times in the lab. Black
rubberized aprons can be purchased at the chemistry department stockroom.
(4) Rubber gloves that are rated
solvent resistant.
(5) A bound laboratory notebook
with numbered pages will be required.
This can also be purchased at the stockroom.
(6) A pocket calculator with
basic functions is recommended.
(7) A breakage card is required
and should be brought to each laboratory meeting. This should be purchased at the stockroom
before the first meeting.
Laboratory Objectives:
The primary objective of the laboratory program for the Chemistry
201-202 sequence is to exemplify, through experimentation, the basic principles
of Organic Chemistry. In actuality, the
Chemistry 201 lab will emphasize traditional laboratory techniques suitable for
a first course in Organic Chemistry.
These techniques will include recrystallization,
extraction, reflux, distillation and the determination of melting and boiling
points. Each of the above may be done as
a discrete operation, or in combination with other techniques. These basic techniques will form the
foundation for performing later experiments primarily involving synthesis and
structural analysis of organic compounds.
In addition, instrumental techniques including Gas Chromatography (GC),
Infrared Spectroscopy (IR) and Nuclear Magnetic Resonance Spectroscopy (NMR)
will be introduced in the 201 course and expanded to include additional
experiments in Chemistry 202. Since a
major objective of the Organic Chemistry laboratory is to learn a large number
of totally new laboratory techniques, you will be carefully observed on the
safe and proper methods for implementing these techniques. You will also be evaluated as to the respect
that you show delicate instruments, the safe handling and disposal of
chemicals, the neatness of your work area and adherence to all safety regulations.
Safety:
Please adhere strictly to all safety precautions as outlined by me
and/or your lab text. Make yourself
aware of the location of emergency equipment located in the lab, and know how
to use each item. Consider every
chemical that you handle to be, at the very least, toxic! Read each
label carefully. Nitrile
gloves should be wore when dispensing chemicals. Be assured that violation of any safety
regulation, especially the consistent failure to wear safety goggles AT ALL TIMES in the lab, may result in
your immediate expulsion from the lab, and an assigned grade of zero for that
experiment. Any chemistry faculty
member may expel you from lab for not strictly following safety regulations.
You should wear
practical clothing with little to no loose jewelry, tie your hair back and closed toe shoes – no sandals allowed!
Recitation:
The first 20-30 minutes of each session will be devoted to a “recitation
period”. Class will meet in its assigned
recitation room to review any previous experiment, and to discuss the scheduled
experiment for that day. Students are
expected to be prepared for lab. If
there are no student questions, the class will proceed immediately to lab.
Laboratory Notebook and Reports:
Each student is required to have a sturdy, bound laboratory notebook
with duplicate numbered pages. Upon
obtaining your notebook, print your name, starting date, course and laboratory
section on the front cover. Reserve the
first page for a Table of Contents, and start each new experiment on a new
page. The notebook will serve as an
original record of everything that you observe during the experiment. The
white pages will serve as the laboratory report and the duplicate pages as your
copy. Write in ink. The notebook should be organized in such a
manner that another person reading it would be able to easily reproduce all of
the steps that you performed in the experiment.
The following items should be recorded in your notebook before coming to lab in approximately
the order indicated below:
(1) Experiment number and Title
(2) Your Name, lab partner’s name, lab section
(3) Date experiment is performed
(4) Introduction
including:
- Brief
statement of the purpose and learning objective(s) of the experiment. What are the new techniques introduced by the experiment. If there is a hypothesis to prove, it should be included here. For example, “Does the dehydration of 3- methylcyclohexanol follow Zaitzev’s
Rule?”
-
Theoretical background. Here you include
a brief discussion of the theory behind the experiment. If the experiment involves a chemical reaction, a balanced chemical
equation with structures should be
shown. When applicable, a reaction mechanism
should be included.
(5)
An organized table listing
the identity and physical properties of reagents to be used (main reactants and
solvents) including structure (for organic compounds), molecular weight,
melting point (for solids) or boiling point (for liquids), density or specific
gravity (for liquids) and concentration (where applicable).
The following items should be recorded in your notebook during lab:
(6) An organized data table listing the identities and actual amounts of reagents used in grams or milliliters, and a
listing of the number of moles used
for all reactants.
(7) A flow
chart outlining the experimental procedure.
(8)
All observations, as they are
made. This should consist of a complete,
coherent record of every step that you perform in the experiment, followed by
anything that you may have observed.
This may include such things as the initiation of reflux, the
observation of distillation temperature(s), the formation of two or more liquid
layers, any signs of reaction such as temperature change, gas evolution, color
changes, precipitation, violent reactions or anything unexpected. Any variations from the directions in the
manual should also be noted. In short,
write in complete sentences, everything that you do and everything that you
observe.
(9)
Data and Results, including
observed melting or boiling points (distillation temperature), actual yield,
theoretical yield and percent yield should be tabulated. All calculations should be shown. Note:
Product yield and purity will be included, where appropriate, as part of
the lab report grade. Your signature at the bottom of each page,
along with my initials as witness,
should be completed before you leave lab.
At this
point, you will have about 80% of your report completed. The following items should be added to your
report before submitting it for grading:
(10) A Discussion
(one-half to three-fourths page) of the experiment paying particular
attention to an explanation of why each procedure or technique was used, e.g.
“the organic layer was washed with 5% sodium bicarbonate in order to remove any
acidic contaminants”, or “the organic layer was treated with saturated NaCl in order to salt-out (remove) any water”. It is not necessary to repeat items covered
in the supplemental questions.
A brief discussion of
your observed results and any non-human sources of error should also be
included, e.g. “the observed melting point of my product was 140-146 compared to
the literature value of 152-154. This
difference may be due to the presence of byproduct (speculate on what it may
be) and/or incomplete drying.” "The
observed 30% yield reflects a significant amount of unreacted
starting material (name) and the formation of significant byproduct (name if
possible). The yield may be increased by
…" Try to
avoid colloquial comments like “Overall, the experiment went really well.” Let your results speak for themselves. Include references
for all literature properties (Aldrich
catalogue, Chemfinder®,
Merck Index, etc.)
(11) Supplementary
questions for each experiment will be assigned at the end of each
recitation period. These should be
answered, and included as the very last part of the laboratory report. These can constitute up to 30% of the report
grade.
Please see attached document on Organic Chemistry
Laboratory Reports.
All work must be done neatly, and in
ink, with no scribbles, erasures or white-out (draw a single line through
mistakes). Gross errors in spelling or
grammar will be penalized on the report.
Illegible or sloppily submitted reports will be returned to you for
resubmission with a 10% penalty. IMPORTANT: Make sure that you write legibly and that you
press hard when writing so the duplicate copy will be legible.
All work in the lab is to be performed in pairs, unless otherwise
instructed. The report is considered
officially due during the next scheduled laboratory period following completion
of the experiment. 10% of the maximum
attainable grade will be deducted from the report for each week late. No reports will be accepted after the last
scheduled lab period.
Grade breakdown:
(1) Lab Reports 90%
(2) Lab Technique 10%
Any missed lab may not be made-up as a matter of course. Only reasonable excuses for absence will be
accepted. If permission is given to make
up work, that work should be made-up within one week of the time the work was
scheduled to be done.
A passing laboratory grade is necessary to pass Chemistry 201 and/or
202!
Check-in:
At the beginning of each semester, you and your lab partner will be
assigned a locker. This locker will be
used by only yourself and your partner.
The locker will contain the common laboratory equipment necessary to
perform most experiments, including an expensive
ground glass kit. On the first day of
lab, you will be asked to check the contents of your locker and kit against a
master list. Any missing or broken items
may be replaced at no charge on the day of check-in only. After this day, missing or broken equipment
can only be replaced by using your breakage card(s) at the stockroom. At the end of the semester (check-out), any
unused portion of your breakage card will be refunded to you. At the end of each lab, please make certain
that you clean up all of the equipment that you used and return them to your
locker. Lock the drawers and return the
locker key to the board assigned to your section.
CHL 201- Laboratory for
Organic Chemistry I
Fall Semester, 2013
Sections 41, 42: William A.
Price, Ph.D.
Section 43, 44: Thomas S.
Straub, Ph.D.
Section 45: James Murray, Ph.D.
La Salle
University CHL 201-202 Custom Laboratory Manual from Mohrig,
Hammond, Schatz and Morrill, Modern
Projects in Organic Chemistry , 3rd edition, W.H. Freeman Custom
Publishing, New York, 2010.
Date Experiment
Aug.
26-29 Safety, Check-in
Sept.
2-5 EXP 4,
Synthesis of Aspirin, pp 20-25
Sept.
9-12 Handout,
Extraction and Evaporation: Separating the Components of “Panacetin”
Sept. 16-19 Handout, “Panacetin”
continued, and
Technique 13.2 – Fractional
Distillation, pp 145-149, 157-161 (techniques book)
Sept.
23-26 EXP 5,
Hydrolysis of an Unknown Ester: part 1: Hydrolysis and Azeotropic Distillation, pp 29-34
Sept.
30, Oct. 1-3 EXP 5, part 2: Recrystallization and Extraction, pp 34-36
Oct.
7-10 EXP 5, part 3: Distillation,
Boiling Points, Melting Points, and Identification, pp 36-40
Oct.
16-17, 21-22 EXP 7,
Isolation of (R)-(+)-Limonene from Orange Peels, pp 51-53, 58-60
Oct.
23-24, 28-29 EXP 7,
continued
Oct. 30-31,
Nov. 4-5 EXP 8,
Radical Chlorination Reactions, pp 61-67
Nov.
6-7, 11-12 EXP 10, SN1/SN2
Reactivity of Alkyl Halides, pp 79-83
Nov. 13-14,
18-19 EXP 9,
Acid-Catalyzed Dehydration of 3-Methylcyclohexanol, pp 70-73, 76-78
Nov. 20-21,
25-26 EXP 6, Free-Radical versus Ionic Addition of HBr to Alkenes, pp 41-47
Dec. 2-5 Check-out. Last laboratory report due.