1

CHEM 2430: Organic Chemistry Laboratory I

Tulane University - Department of Chemistry, Fall 2010
Lab Coordinator: Dr. Carol Zhang, Room 5035C Stern Hall
E-mail: czhang1@tulane.edu; Phone: 862-3586

Office Hour: Wednesday 1:30-3:00pm

Textbook (Your Lab manual): Lehman, J. W. Multiscale Operational Organic Chemistry; A Problem-Solving
Approach to the Laboratory Course, 2nd Edition, Prentice-Hall: Upper Saddle River, NJ, 2008. ISBN-10: 0-13-241375-2

Notebook: For writing lab reports, you can purchase a "Laboratory Research Notebook (with carbon)" from the
Tulane Bookstore.

Outline of Course Contents and Exam schedule: There will be 9 regular experiments worth a
total of 900 points; the schedule of experiments is on page 5 of this syllabus. The last lab will be worth 200 point,
which includes a lab final (150 points) and proper check-out (50 points). The total point possible is thus 1100
points. The lab final will present you an opportunity for pre-lab investigation/research of a set of given compounds
and in-lab identification of an unknown using either Infrared Spectroscopy or chemical analysis or both; the unknown
will be selected from the type of compounds you have done your research upon.

Attendance and Lab Make-up:

Students must come to their registered section on time. The prelaboratory quiz is scheduled to start at 1:00pm for each and all lab period and typically is limited for 20
minutes. Once the quiz time is over, all students must turn it in and the instruction for the designated
experiment is scheduled to follow. If a student is late for 10 minutes, then the student will have 10 minutes less
to do his/her quiz; if a student misses the quiz period entirely, then a zero will be assigned to the students prelaboratory quiz and there will be NO make-up option. If a student misses his lab period for legitimate
excuse, such as serious sickness and family emergence (supporting documents will be needed), you
should notify your TA by writing as soon as possible and no later than the end of the day. In such
cases, you may make up a missed lab in a different section in the same week; you can make the
arrangement with your TA as which day and time (within the same week) for you to do the make-up.
After the week scheduled for a specific experiment is over, no make-up option will be available,
because the materials for the designated experiment of the week will be put away as we prepare for
the new lab scheduled for next week.

Your Locker and Equipments

At check-in, you will be assigned a locker with a set of glassware/equipment, and a
combination code for your locker according to the Yellow Lab Inventory Card. Please note
that you may not have EVERYTHING listed on the inventory card, make sure to check what
you have and dont have. You should write the missing item in your locker/drawer on a
separate sheet and put your name and lock number on top of it; turn in the sheet to your
TA. Well try to fill in the missing items according to your list. To identify the glassware in
your locker, refer to Appendix I on page 908-911 of your Lemhan book. We emphasize the following:
Once checked in. you are responsible for the inventory in your locker.
Always thoroughly clean the glassware after en experiment; lock your locker at the end of each lab period.

Labtory Safety
Safety comes first in organic chemistry lab. The first lab quiz will be safety quiz. You must
prepare for this safety quiz BEFORE you come for your first lab period, by reading the
designated sections of the Lehman lab book and by downloading and reading the note, Safety in
the Organic Laboratory, that I will have put on Blackboard by Sept 10, 2010. A safety video
may be also played to you as needed. Students may not be allowed to conduct an experiment
if fails to achieve a satisfactory grade on the safety quiz (85%).
1. Eye protection (Safety Goggles and/or safety glasses will be provided): EVERYONE must wear safety goggles
at all times in the laboratory. Contact lenses may be worn in the lab if needed for therapeutic reasons, provided
that safety goggles are worn over the contact lenses, the same goes with prescription glasses. Contact
lenses without goggles are dangerous because splashed chemicals make them difficult to remove. If
chemicals accumulate under a lens, permanent eye damage can result. If a chemical should splash into your
eyes, flush the eyes with water at the eyewash fountain. Continue to rinse with water for at least 10 minutes.
Goggle lenses in need of cleaning should be wiped with a moist paper towel but NOT with acetone or other
organic solvents, which will partially dissolve and irreversibly cloud the lenses.
2. Dress code: Wear sensible clothing in the laboratory. Loose sleeves, shorts, or open-toed shoes can be
dangerous. Wear shoes that cover your feet to prevent glass cuts and wear long pants. Long hair should be
tied back so it does not fall into chemicals or onto a heating device. You will be sent back home to
change clothes or have a 20-point deduction taken by your TA if you are: (a) not wearing long pants, or
(b) wearing sandals or other footwear that does not completely cover your feet. Repeated violations of the safety
rules will have the consequence of receiving a ZERO for the related lab to a F for this course.
3. Gloves: (a) should always be worn when handling corrosive or highly toxic chemicals; (b) should usually be worn for
washing glassware.
No food, drink, excessive and loud talking, running in the lab, answering cell phone, etc are allowed at any
time in the laboratory. No unauthorized experiment or procedure can be conducted at any time; no
unauthorized personnel can be brought in the labs. If you have visitors during your lab periods, have them wait
outside.
Remember: Read the detailed safety note Safety in the Organic Laboratory that I have put on

Blackboard before your first lab period. You will be required to take a safety quiz, sign the
Safety Commitment Sheet , and turn them in before end of your first lab period.

Safety Equipments
During your first laboratory period, you need to locate the following safety equipments, and be certain you know
how to use them before you proceed to check in:
(1) Fire extinguishers: one each near the doors to Labs 520, 530, and 540 (three total);
(2) Showers: one each near the doors to Labs 520,530, and 540 (three total);
(3) Eye-wash fountains: one each near the doors to Labs 520, 530, and 540 and one each at the sinks at the back of Labs
520,530, and 540 (six total);
(4) Fire blankets: one each near the doors to Labs 520,530, and 540 (three total).
(5) A First-Aid Kit is in Lab 530.

Conducting an Experiment, Lab Report, Grading

General comments: The laboratory notebook that you will be using, which is available in Tulane Bookstore, contains
two sets of pre-numbered pages with a carbon-copy sheet placed in-between. Thus, for each lab report, you hand in the
original writing and retain the copy for your records. Notebook entries should be made on consecutive pages in permanent
ink; skipping pages is not acceptable. If one wishes to delete a page, simply place an X across that page; original pages
must NOT be torn out or added to the notebook for any reason. Each page of your lab reports should have a completed
heading (your name, lab section, date, experiment title and number, etc.).
Grade distribution: The total point for one lab period will be typically composed of the following 5 components (A to E):
A. Pre-laboratory quiz (20 %) The purpose of this pre-lab quiz is to encourage/require students getting well prepared for the lab
scheduled. Before you come to the laboratory, read the experiment you will be doing and make your lab plan.
Make sure you understand the chemistry involved and the experimental procedures. You should check the
MSDS (Material Safety Data Sheet) for all chemicals you will be handling. The quiz questions will largely be
related to the aforementioned aspects of the scheduled experiment. If you have a question, whether it's
regarding a chemical or a procedure, ask the question first. Only the designated experiment will be allowed
B. Pre-lab write up (20%): This is your experiment plan and it is due at the beginning of the lab period (before you take the
pre-lab quiz). The pre-lab typically includes: (1) Experiment number and title, (2) objective and reaction(s) involved, (3) a
table or list that contains the identity/structure, quantity, and other property, such as, boiling point, density, solubility, molecular
weight, melting point, etc of starting materials, product, and other key reagents, (4) and your experiment plan. An example of
experiment plan can be found on page 66-67; detailed discussion of writing lab report can be found on page 912-923 of your
lab manual.
Property Information for specific chemicals can be found in either (i)The Aldrich Catalog Handbook of Fine
Chemicals or The Merck Index, which should be accessible at the reference desk of the Howard-Tilton Memorial
Library, or (2) online at http://hazard.com/msds/, a searchable database of Material Safety Data Sheets
(MSDS) from a large number of manufacturers. When plan your lab, please note that All
experiments of CHEM2430 will be conducted in HALF of the Standard Scale unless otherwise
indicated in specific case.
C. Procedure and Observations (20%): This part is a description of the lab procedure, including relevant observations that are
made in the course of the experiment; it is a record of what has happened, and/or what is happening in the lab, not just restate what is described on the book. More details can be found on page 913 of your book.
Your procedure should begin on the notebook page following the end of the Pre-lab section, and the rest of your
report should begin on the notebook page following the end of the Procedure and Observations section.
D. Your experiment results (20%): This part includes: (a) calculations (of theoretical and actual yield of your product, and
other calculations pertinent to a given experiment), 10%; (b) quality of your product and its analytical/spectroscopy/other
physical data, 10%. Please note that certain calculations can be done ahead of time, together with your pre-lab write-up.
E. Discussion (20%): Your report should conclude with a section that includes:
(1) a brief summary of the outcome of the experiment;
(2) your interpretation of your results and raw data, the factors that affect the outcome, either negatively or positively; whether
you have achieved your objective, or whether the results support the original hypothesis, and any possible side reactions you
surmise. If you failed in obtaining the product or had poor yield or quality of product, analyze the possible cause, it still makes a
good lab practice and report if you can identify where, why, and how it went wrong for an unexpected, undesired result.
(3) a reaction mechanism, if relevant.

Sequence of things-to-do for a lab period in a nutshell:

(1) At the beginning of each lab, show your pre-lab write-up to your TA and have him/her to sign it.
(2) Take the Quiz
(3) Proceed to conduct your experiment. You should pay full attention to what is happening and record it in the The
Procedure and Observations section while the experiment/reaction is ongoing.
(4) After finish the experiment, complete the entire write-up, including any calculations, analysis, and discussion and turn it
to your TA before you leave for the day.
Further information about writing lab report can be found on page 913 of the Lehman book.

The completed lab report is due by end of the same lab period for all experiments, except the first lab, as noted
in the e-mail sent on August 20, 2010.

Academic Honor Codes

All Students are expected to critically monitor their experimental progress and record what have been done by them and/or
what change has occurred/been observed during the lab period, from which they then base upon their subsequent analysis
and discussion. Copying experiment data or report from others is a violation of academic honor codes, which, and the likes,
bear serious consequences, from an automatic zero for the specific lab, to failing the course, to subjecting to Tulane Honor
Board hearing.

Tentative Schedule of Experiments*

Fall 2010, Tulane University
Lab 1: Week of Sept 13
Check-in, safety quiz, and Experiment 1 on your book: Learning Basic Operations. The Effect of pH on a Food
Preservative. No reports due until next week (for this lab only). For check-in assistance, you can refer to Lehman book,
page 908-911 for glassware/equipment names.
Lab 2: Week of Sept 20
Lehman, Experiment 2: Extraction and Evaporation. Separating the Components of "Panacetin"
Lab 3: Week of Sept 27
Lehman, Experiment 3: Recrystallization and Melting-Point Measurement. Identifying a Constituent of Panacetin
Lab 4: Week of Oct 4
Lehman, Experiment 4: Heating Under Reflux. Synthesis of Salicylic Acid from Wintergreen Oil
Lab 5: Week of October18
Lehman, Experiment 5: Simple Distillation, Gas Chromatography. Preparation of Synthetic Banana Oil
Lab 6: Week of October 25
Lehman, Experiment 7: Addition. Mixing. Sublimation. Preparation of Camphor
Lab 7: Week of Nov 1
Lehman, Experiment 23: Stereochemistry of Bromine Addition to trans-Cinnamic Acid
Lab 8: Week of November 8
Lehman, Experiment 21: Dehydration of methylcyclohexanols and the Evelyn Effect
Lab 9: Week of November 15
Lehman, Experiment 20: Reaction of Iodoethane with Sodium Saccharin, an Ambident Nucleophile
Lab 10: Week of November 29
Lab Final Exam, check out. You must thoroughly clean your glassware and working area, failure to do so will result in 50 point
deduction

Reading Assignments for August 30-Sept 10, 2010---You will be quizzed.

A. General Reading
(1) Introduction: Lehman, page 1-32
(2) Planning an Experiment: Lehman, Appendix V (page 922-923)
(3) Keeping a Laboratory Notebook: Lehman, Appendix II (page 912-913)
(4) Writing a Laboratory Report Lehman, Appendix III (page 913-917)
(5) Calculations for Organic Synthesis: Lehman, Appendix IV (page 918-922)
B. Lab Preparation Reading: read Lab 1 in Lehman (page 40-47) and the associated sections under "Before You Begin" heading
(page 40). Additionally, review organic acid-base concepts and reactions in your McMurry book.
REMEMBER: Pre-lab for the first experiment (Lehman, Lab 1) is due at the beginning of the first lab period in the
week of Sept 13.
The experiment schedule and/or experiment may be adjusted based on material availability