North Seattle Community College                                                           Spring 2007

Chemistry 239: Organic Chemistry Lab

Course meeting times:       MW, noon — 3 p.m.

Lectures and labs will be held in AS 1515

Text: Pavia, Lampman, Kriz, and Engel, Introduction to Organic Laboratory Techniques: A Microscale Approach, 4th ed. (abbreviated PLKE)

Other materials:

Lab coat or apron (optional)

Calculator (required, especially for exams)

Lab notebook (required; sewn binding, not glued or spiral-bound)

 

Course purpose: This course is the first quarter of the two-quarter organic chemistry lab series. It will introduce you to various organic chemistry laboratory procedures and techniques, including simple syntheses, separations, extractions and purifications. In addition, you will learn about infrared spectroscopy and its use in organic compound characterization. Finally, you will become familiar with organic chemistry lab safety procedures and working with extremely small quantities of chemicals. CHE 238 is a prerequisite for the course.

 

Instructor: Tracy Furutani              Office: IB 2328B

Phone: 528-4509                               Office hour: MW, 3:00 – 6:00 p.m.

e-mail: tfurutani@sccd.ctc.edu

website: http://faculty.northseattle.edu/tfurutani

 

Grading:        Lab reports               15 * # days on that lab         225

            OLED report and presentation                              40

                        Tests                          2 at 50 points each                100

                        Lab notebook                                                           20

Subjective grade                                                       15

 

Total                                                                           400 pts

 

The final grade will be based on the following point scale:

 

How to set up a lab notebook

Your total points:     380 - 400         Your grade:   4.0

                                    360 - 379                                 3.7

                                    340 - 359                                 3.3

                                    320 - 339                                 3.0

                                    300 - 319                                 2.7

                                    280 - 299                                 2.3

                                    260 - 279                                 2.0

                                    240 - 259                                 1.7

                                    220 - 239                                 1.3

                                    200 - 219                                 1.0

                                    < 200                                       0.0

This schedule is subject to a minimal amount of change.

 

Lab lecture: I will give a short lecture on each lab at the beginning of the meeting prior to when you will be performing the experiment. You are responsible to obtain notes from a fellow student if you miss a lecture. 

 

Attendance: In general, you will be performing the experiments individually, so you cannot rely on another person to get lab data. Show up to every class meeting. Due to space and time constraints, you cannot make up an exam or a lab. If you miss a lab, you cannot make it up and you will receive a 0. Unlike last quarter, the lowest grade will not be dropped for labs.

 

Lab reports will consist of (sometimes) a pre-laboratory exercise (“prelab”) and (always) a lab results report.  

 

The pre-lab should be written in your notebook and a photocopy should be given to your instructor at the beginning the experiment. You will not be allowed to start the experiment unless the prelab is complete. The prelab will generally consist of a purpose and a materials and methods section, unless that particular lab calls for something else (check the individual lab handout).

 

1)     The purpose section is a few sentences outlining the experiment’s objective(s).  Mention what techniques you will be using, what data you are collecting (and why you are collecting it) and, if appropriate, what compounds you are synthesizing.  It is also appropriate to include any synthesis schemes (i.e., chemical equations using organic molecule representations).

2)     The materials and methods section should contain the experimental procedure in your own words (including sketches of apparatus).  This section should also list the reagents (and quantities) used, and indicate possible side reactions and by-products. See pages 563-564 of PLKE for an example.

 

The lab result report is based on the handout that will be posted on the course web page prior to the lab date. The report handout will have some questions to be answered.

 

Lab reports will be due at the beginning of the lab period immediately after the period in which the experimental work is finished. The entire lab report must be turned in at the same time.  Reports turned in after the beginning of the lab period will be marked late.  Lab reports turned in up to one day late will be marked off 25%. Lab reports turned in between 1-7 days late will be marked off 50%. Lab reports turned in more than one week late will be given no credit.

 

Even though you will complete the experimental work in pairs, all lab report must be written up individually. Although you may discuss the lab report with other students, the report must be written in your own words. If there is evidence of copying for any part of the lab, all students involved will receive a grade of zero on the lab report. If this happens a second time during the quarter, you will receive a grade of zero on the lab report and your grade in the course will be dropped one full grade point. Plagiarism and cheating are quite serious offenses in academia.

 

Lab notebooks: Purchase a bound notebook at the bookstore or other supplier.  Spiral notebooks are not acceptable.  When performing an experiment, write down the procedure as you do it and note all observations.  During all times in the lab, you must have your lab notebook open and you must record data/observations in real time, i.e., as you see it. A good lab notebook is one that would allow another person to replicate the experiment using only your notebook.  Please read the section on “Lab Notebooks” on page 558ff. of PLKE. At the end of the quarter, I will collect your lab notebook to give an overall assessment of the completeness, neatness and professionalism your notebook displays – this will translated to a score out of 20 points.

 

Tests: Since this is to assess individual learning, all that follows will be done without collaboration with other students. There will be two written exams, each worth 50 points, covering the material in the course up to that point. Since it is to assess your understanding of the course material, and not so much your fact recall, the written exams are open lab notebook (but closed textbook and other resources).

 

Organic LED project: You (and your team) will fabricate an organic light-emitting diode, then write a follow-up report and present some aspect of OLEDs to the class. There will be a handout on this later.

 

Subjective grade: This is my assessment of your ability to perform organic chemistry techniques efficiently, intelligently and, above all, safely, which means there may or may not be a safety quiz as part of this grade. In addition, I will also be assessing your use of the lab notebook at appropriate times and your ability to follow instructions and work with your colleagues – all of this will be translated to a score out of 15 points.

 

Chemical sensitivities: Due to the increasing numbers of individuals developing chemical sensitivities and the increasing awareness of such conditions, everyone who attends this class is asked to refrain from wearing any fragrance or perfume. The greatest feasible efforts will also be taken to ensure a fresh air environment free of not only the above-mentioned fragrances but also potentially harmful substances such as carbon monoxide, formaldehyde, carpet odor, organic solvents, etc. Individuals who are unsure of the importance of this policy should see the Associate Dean for additional information. Also, if you are pregnant or nursing, you should discuss the situation with your doctor.

 

Cell phones and pagers: Please turn these devices off or switch them to “vibrate” mode during class.

 

Dates to remember:

            Last day to withdraw without a W                                   April 13

            Last day to drop course                                                      May 25

Lab schedule

All experiments are from the lab textbook (PLKE).

 

Monday                                          Wednesday

April 2

Check-in

4

Guest lecture: Jim Patterson on Experiment 38B and Ferrocene

9

Crystals and dyes (handout)

10

Experiment 38B: Benzoic acid synthesis (Grignard reaction)

16

Experiment 38B: Benzoic acid synthesis (Grignard reaction)

17

Ferrocene synthesis – column chromatography (handout)

23

Ferrocene synthesis – column chromatography

 

The monoacylated ferrocene NMR spectrum

 

25

Experiment 54: Identification of an unknown (creation of a derivative)

30

Experiment 54: Identification of an unknown (creation of a derivative)

May 2 (Exam #1 – take-home)

Experiment 54: Identification of an unknown

7

Experiment 64: Michael and aldol condensation reaction (Exp. 54 continues)

9

Experiment 64: Michael and aldol condensation reaction (Exp. 54 continues)

14

Experiment 64: Michael and aldol condensation reaction (Exp. 54 concludes)

16

Experiment 65: Esterification reaction of vanillin

21

Experiment 65: Esterification reaction of vanillin

23

Assemblon project (handout)

 

28

Memorial Day

 

30

Assemblon project (handout)

 

June 4

Organic LED (handout)

6

Organic LED

 

11

OLED presentations

Check-out

13

Exam #2 (special time — 1 p.m.)