Professor Donald Pavia
ORGANIC CHEMISTRY LABORATORY I
Chem 354 Winter 2007
(revised version)


Class Times
Email
Office
Office Hours
Telephone

MW 3-6 pm CB310, F 2 pm SL120
pavia@chem.wwu.edu
CB 345 (Chemistry Bldg
MTWF 1:00-2:30, or by appt.
650-3155 or campus x3155


Textbook:

D.L.Pavia, G.M.Lampman, G.S.Kriz, and R.G.Engel, Organic Laboratory Techniques - A Microscale Approach, 4th edition, Saunders College Publishing (2007).

Course
Web Site:

http://atom.chem.wwu.edu/dept/facstaff//pavia/354pavia.html

Safety:

1 Pair Approved Safety Goggles

Records:

Bound Laboratory Notebook (sewn)


LABORATORY SAFETY QUIZ

EACH STUDENT MUST PASS THE ONLINE SAFETY QUIZ OR
THEY WILL NOT BE ALLOWED TO WORK IN THE LABORATORY
YOU MUST PASS BY THURSDAY, JANUARY 18 at 1 PM

In order to be sucessfully enrolled in lab, each student must pass the organic safety quiz. The quiz is on-line, and consists of 25 multiple-choice questions. The safety quiz will cover material provided in the textbook:

Laboratory Safety, Technique 1: 1.1-1.4, pp 542-558
Heating and Cooling Methods, Technique 6: 6.1-6.7, pp 589-597
Reaction Methods, Technique 7: 7.1-7.4, pp 598-604

and the material provided in the organic safety review provided in the departmental web page links at the address:

http://www.chem.wwu.edu/dept/dept/safety.shtml

A link to the complete instruction page for taking the organic safety quiz may be found at the same location or at:

http://argon.chem.wwu.edu/SafetyQ/OCQLink.htm

You will be provided with three openings in which to pass the safety quiz. You may only take the quiz once during each opening. In order to pass the safety quiz during the first administration period, you must obtain a minimum passing score of 20 questions (80%) correct out of a total of 25 questions. In order to pass the safety quiz during the second administration period, you must answer 21 questions correctly (84%). To pass during the third administration period, you must answer 22 questions correctly (88%). Failure to pass the quiz before the end of the third opeing means that you will not be able to continue in the class.

The schedule of each safety quiz administration period is:

It is your responsibility to take and pass the quiz. No make-up quizzes will be given.


ORGANIC CHEMISTRY LABORATORY
WINTER 2007 SCHEDULE



All assigned readings should be completed before the date where they are listed.
It is necessary to do the reading before attempting the experiment.
You must wear approved safety goggles at all times !!!!

-----------------------------------WEEK ONE
 Wed Jan 10

PERFORM : 
Orientation, Lab Safety, Check-in
Exp 1 Intro to the Microscale Laboratory
   (Exercises 1A, 1B and 2) pp 2-13
READ : Experiment 1, Introduction to Microscale Laboratory pp 2-13 -----------------------------------WEEK TWO Mon Jan 15 PERFORM : No Class Today, Martin Luther King Day Wed Jan 17 READ : Introductory Techniques on Safety, Records, Glassware and Measurement T1-T5: pp 542-589 (general useful information - read these ASAP) Especially Read (necessary for the experiment): "Measurement of Volume and Weight", Technique 5 pp 581-589 "Solubility" Technique 10 pp 637-646 and Experiment 2, Solubility pp 13-20 PERFORM : Experiment 2, Solubility (Parts A, B,C,D) -----------------------------------WEEK THREE Mon Jan 22 READ : "Filtration", Technique 8 pp 616-627 "Physical Constants of Solids: Melting Point", Tech 9, pp 627-637 "Crystallization: Purification of Solids", Technique 11, pp 647-668 Experiment 3, Crystallization pp 21-32 PERFORM : Experiment 3, Crystallization Wed Jan 24 PERFORM : Experiment 3, Crystallization (continued) -----------------------------------WEEK FOUR Mon Jan 29 READ : "Column Chromatography", Technique 19 pp 756-777 "Thin-Layer Chromatography", Technique 20, pp 777-792 Experiment 5, Chromatography, pp 42-50 PERFORM : Experiment 5, Chromatography Wed Jan 31 PERFORM : Experiment 5, Chromatography (continued) -----------------------------------WEEK FIVE Mon Feb 05 READ : "Physical Constants of Liquids: Boiling Points", Tech 13, pp 694-703 "Simple Distillation", Technique 14 pp 703-715 "Fractional Distillation", Technique 15, pp 715-732 "Gas Chromatography", Technique 22, pp 797-818 Experiment 6, Simple anad Fractional Distillation pp 51-57 PERFORM : Experiment 6, Simple and Fractional Distillation Wed Feb 07 PERFORM : Experiment 6 (continued) -----------------------------------WEEK SIX Mon Feb 12 READ : "Reaction Methods", Technique 7, Section 7.10 p 611 "Extraction" Technique 12, pp 669-693 "Sublimation", Technique 17, pp 745-749 Essay "Caffeine" pp 87-90 Experiment 12, Isolation of Caffeine from Tea, pp 90-99 PERFORM : Experiment 12, Isolation of Caffeine from Tea Wed Feb 14 PERFORM: Experiment 12 (continued) Friday Feb 16 *** MID-TERM EXAMINATION *** The mid-term examination will cover : Techniques 1-6, 8-10, 13-15, 19, 20, 22; Experiments 1, 2, 3, 5, 6; Essays will not be tested. -----------------------------------WEEK SEVEN Mon Feb 19 President's Day PERFORM : No Class Today, President's Day Wed Feb 21 READ : "Extractions" Technique 12, Sections 12.5, 12.9 "Physical Constants of Liquids" Technique 13 pp 694-702 "Infrared Spectroscopy", Technique 25 pp 833-867 Review elimination reactions in your lecture text (Chap 9) PERFORM Experiment 25, 4-Methylcyclohexene -----------------------------------WEEK EIGHT Mon Feb 26 READ : "Reaction Methods", Technique 7, Sections 7.2-7.4 and 7.6 pp 600-606 "Gas Chromatography", Technique 22 pp 797-818 Essay "Esters - Flavors and Fragrances" pp 99-102 Experiments 13 and 56, pp 103-108 and 498-501 PERFORM : Experiment 56, Preparation of a C-4 or C-5 Ester Wed Feb 28 PERFORM : Experiment 56 (continued) -----------------------------------WEEK NINE Mon Mar 05 READ : "Reaction Methods", Technique 7, Sections 7.2, 7.4, 7.5 and 7.8 "Extractions" Technique 12, Sections 12.5, 12.9, 12.11 "Refractometry" Technique 24 pp 827-832 "NMR Spectroscopy" Technique 26, pp 868-8905 Experiments 21/58, Nucleophilic Substitution - Competing Nucleophiles pp 180-190 and 510-514 Review Nucleophilic Substituion in your lecture text (Chap 10) PERFORM : Experiment 21A, 21B and 58 (Note: we will use the pentanols described in Experiment 58) Wed March 07 READ : Experiment 28, Nitration of Methyl Benzoate pp 228-233 REVIEW : Techniques 11 and 25 PERFORM : Experiment 28, Nitration of Methyl Benzoate -----------------------------------WEEK TEN Mon March 12 PERFORM : Experiment 28 (continued) Wed March 14 PERFORM : Laboratory Clean Up and Check Out -----------------------------------FINALS WEEK FINAL EXAM: Tuesday March 20, 3:30-5:30 PM SL120 The final examination will be comprehensive.


PRE-LAB QUIZZES AND POST-LAB REPORT SHEETS

Take-home pre-lab exams are required for each experiment. These are due at the beginning of any period where a new experiment starts.

Laboratory report sheets will be required following each experiment. They are due two laboratory periods following the last day spent on the experiment (see dates below).

YOU MUST DOWNLOAD PRELAB AND POSTLAB
REPORT SHEETS FROM THE COURSE WEB SITE

All laboratory report sheets must be downloaded prior to lab from the course web site by the student. The reports are in Adobe Acrobat (.pdf) file format. Your computer must have Adobe Acrobat Reader in order to read and print these files. Acrobat Reader is free from http://www.adobe.com. If you do not wish to install Acrobat Reader on your own computer, you may print these forms on the printers in the Chemistry Computer Lab (CB280) or most other University Computer Labs where Acrobat is a common feature.

Due Dates for Laboratory Report Sheets


POINTS AND GRADING PROCEDURE

The Mid-Term and Final Exams are each worth 100 points.
Each Pre-Lab Report is worth 5 points.
Each final Lab Report is worth 20 points.
An Overall-Performance/Technique grade, assigned by the instructor, is worth 25 points.

Points Summary

You are required to keep your data in a bound laboratory notebook. While the notebook will not be graded directly, the instructor may ask at any time to inspect it. An inadequate notebook could affect your technique score.

The class will be curved but expect the normal cutoff scale of 90%=A, 75%=B, 60%=C
Plus/minus (+/-) grades are at my discretion.


ORGANIC CHEMISTRY LABORATORY REGULATIONS

  1. Safety goggles of an approved type must be worn at all times in the laboratory.
    Ordinary eyeglasses are not adequate.
  2. Closed-toe shoes are required when working in the laboratory.
  3. You should wear long pants; shorts or short skirts are not recommended unless covered by a laboratory coat.
  4. Long hair should be tied back if you are working with flames.
  5. Smoking is not permitted in the laboratory. No Bunsen burners may be used unless their use is specifically authorized by the instructor.
  6. Eating or drinking of food or beverages will not be permitted in the laboratory.
  7. Work in the laboratory will be permitted only during your regularly scheduled laboratory hours. Exceptions must be approved in writing by the instructor.
  8. All equipment must be put away not later than the end of the laboratory class. Bench tops, side shelves, balances and hoods must be left clean and in order.
  9. Attendance at laboratory sessions is required unless officially excused.
  10. Make-up laboratory sessions will be provided only in cases of excused absence or unavoidable class conflict. It is expected that students have sufficient time to complete the scheduled experiment, without the need for additional laboratory time.
  11. If experiments are not completed to the instructor's satisfaction, you may be required to repeat them until the results are satisfactory.
  12. All students must be present at the scheduled check-out time. Failure to check out of the laboratory (including mid-quarter withdrawals) will result in an automatic fee of at least $10.
  13. The laboratory fee is intended to offset the costs of normal breakage that you may incur during the quarter, as well as supplies, consumable items and chemicals. However, if your breakage is excessive, and involves multiple expensive items, you may be held responsible. You are also responsible for lost items, and these are not covered by the fee.
  14. According to University policy students are responsible for their own medical coverage. Be sure you are covered by your family policy. If not, you should consider the University-sponsored Student Health Plan (contact Health Services).