Organic Chemistry  Laboratory II – Spring 2008

Chemistry 343

Instructor

Office

Phone

Email

Office Hours

Daniel Dyer

Neckers 325

453-2897

ddyer@chem.siu.edu

MWF 12-1 pm

Required Text: Experimental Organic Chemistry - Gilbert & Martin (4th  Ed.)

Supplemental Text: Organic Chemistry McMurry (7th Ed.)

Lectures are Mondays at 3 pm in Neckers 240 and Laboratories are in Neckers 203/205

Textbook website: http://www.brookscole.com/chemistry/gilbert4

Course website: http://www.chem.siu.edu/chem343/index.html

Laboratory Schedule:

Week 1 (Jan. 14 - 18) – Check-In & Review of Spectroscopy

Reading: Gilbert & Martin - p. 1 - 25, p. 257 - 299; McMurry - p. 418 - 430, p. 500 - 507

Week 2 (Jan. 21 - 25) Spectroscopy (No Lecture Monday)

Reading: Gilbert & Martin - p. 834 - 840; McMurry - p. 440 - 470

Week 3 (Jan. 28 - Feb. 1) The Grignard Reaction - Synthesis of Triphenylmethanol 

Reading: Gilbert & Martin - p. 623 - 639; p. 643 - 650; McMurry - p. 345 - 346, p. 613 - 617; Quiz 1

Week 4 (Feb. 4 - 8) – The Grignard Reaction - (cont.)

Quiz 2

Week 5 (Feb. 11 - 15) – The Wittig & Wadsworth-Emmons Rx - Synthesis of Stilbene

Reading: Gilbert & Martin - p. 585 - 600; McMurry - p. 720 - 723; Quiz 3

Week 6 (Feb. 18 - 22) – The Wittig & Wadsworth-Emmons Rx - (cont.)

Quiz 4

Week 7 (Feb. 25 – Feb. 29) – Electrophilic Aromatic Substitution - Nitration of Bromobenzene

Reading: Gilbert & Martin - p. 481 - 482, p. 502 - 513; McMurry - p. 547 - 571; Quiz 5

Week 8 (Mar. 3 - 7) – Electrophilic Aromatic Substitution (cont.) – Unknowns/Mass Spectrometry

Reading: Gilbert & Martin - p. 300 - 306; McMurry - p. 409 - 418; Quiz 6

Week 9 (Mar. 10 - 14) - Spring Break

Week 10 (Mar. 17 - 21) – Synthesis of Lidocaine

Reading: Gilbert & Martin - p. 685 – 686, p. 729 - 747; Quiz 7

Week 11 (Mar. 24 - 28) – Synthesis of Lidocaine  – Cont.

Reading: (http://en.wikipedia.org/wiki/Lidocaine); Quiz 8

Week 12 (Mar. 31 – Apr. 4) – Enzymatic Reduction  

Reading: Gilbert & Martin - p. 551 – 553, p. 575 - 584; McMurry - p. 289 – 311, p. 315 - 322; Quiz 9

Week 13 (Apr. 7 - 11) – Enzymatic Reduction (cont.)

Quiz 10

 

Week 14 (Apr. 14 - 18) – Synthesis and Characterization of Polymers

Reading: Gilbert & Martin - p. 700 - 720; McMurry - p. 1206 - 1220; Quiz 11

 

Week 15 (Apr. 21 - 24) – Polymers – Cont.

Reading: Gilbert & Martin – p. 706 - 708; Quiz 12

Week 16 (Apr. 28 – May 2) – Check-Out & Final Exam

Grading

PreLabs                                         8 x 10          80 Pts. 

Formal Laboratory Reports           8 x 75        600 Pts.

Laboratory Notebook                                        20 Pts.

TA Evaluations                                                  50 Pts.

Product Evaluations                       6 x 10          50 Pts.  (Lowest score is dropped)

Quizzes                                         12 x 10      100 Pts.  (Lowest two scores are dropped)

Final Exam                                                     100 Pts.

Total                                                             1000 Pts.

 

The following grades are guaranteed with these point totals: 900 - A; 800 - B; 700 - C; 600 - D.

 

PreLabs consist of assigned questions that are found in the textbook and on the website for the textbook.  The prelab will be due at the beginning of the laboratory period and is worth (10 Pts). 

Formal laboratory reports will consist of the following sections:

1. Introduction (15 Pts.):

a) Goal

b) Significance

c) Reaction Scheme

d) Reaction Mechanism

e) Theory    - New Techniques 

- Characterization Methods

(Do not discuss techniques or characterization methods that were covered in previous reports)

2. Procedure (10 Pts.): The procedure should be of sufficient detail that someone skilled in the art of chemistry could successfully repeat the experiment.

3. Relevant Data (5 Pts.)

4. Results & Discussions (30 Pts.):  Describe important results and observations and draw inferences from this data.

5. Conclusions (5 Pts.): Summarize and indicate the significance of the laboratory.

 

6. Questions (10 Pts.): Answer the assigned questions from the text.

 (Sections 1-5 should be typed with double spacing. Hand drawings are acceptable)

 

Cheating will result in a zero for the assignment.  Any instance of cheating will be reported to the Department Chair and the Dean.  To prevent plagiarism you must submit an electronic copy of your introduction/reports to http://www.turnitin.com as an MS Word or pdf file prior to turning the paper copy in to your TA.  Scanned documents will not be accepted by Turnitin.com. Your written introductions or reports will be compared to an extensive database of reports from previous semesters, as well as the web and scientific journals. You can add figures and schemes to the paper copy after the electronic search.  If you are a new turnitin user, then you will need to setup a student profile prior to joining the class. The class ID and password will depend on your section, which are listed in the table below:

 

Chem 343

Class ID

Password

Section 1

2135484

chem343-1

Section 2

2135488

chem343-2

Section 3

2135494

chem343-3

 

Product Evaluations will be based on the quantity and quality of the recovered product.  It is more important to have a pure product than a high yield.  Products should be placed in clearly labeled screwcap vials with the following information:  1) Date; 2) Your Name; 3) TA's Name; 4) Product Name; and 5) Yield in grams.  Any omitted information will result in a zero.

 

Quizzes will be given during most laboratory periods after a brief lecture by the TA, and before the experiment begins.  Questions will be based on the prelab readings, weekly lectures, and practical knowledge gained from previous laboratory experience.  Each quiz will contain questions from the previous, as well as the current laboratory.

 

Absentee Policy:  A maximum of two laboratories may be missed over the course of the semester.  The first missed lab will receive a grade based on the average of the remaining reports, provided the absence is excused.  The second missed lab will be given a zero and students that miss more than two labs will be given a failure for the course.  You will not be allowed to repeat a laboratory.  There are no make-up quizzes since the lowest two scores are dropped.  We will not accept partially completed reports. 

 

Excused Absence: Students must provide a reasonable excuse or they will receive a zero. In rare circumstances, a student may be allowed to make-up an excused absence in another laboratory session; make-upÕs are generally not allowed when the laboratory section is doing a different lab due to safety and hazardous waste considerations.  All make-upÕs will be at the discretion of the instructor and in consultation with the TA.  If at all possible, please inform your TA in advance when you will miss a laboratory, this will greatly enhance your chances of being excused.  After you return from an absence, you must fill out an Òexcused absence requestÓ form and have it signed by your TA and myself; you may get this form from the course website.

 

Handing in Late Work:  Each week your TA will assign a due date for the reports, typically the beginning of the next laboratory session.  Reports that are handed in to the instructor or the TA by Monday at 5pm after the due date will receive a 20% deduction from the total score.  Reports that are one week late will receive a 25% deduction.  Any work handed in more than one week after the due date will be reduced from 30% to 100% at the discretion of the TA, and in consultation with the instructor.  Each TA has a mailbox in Neckers 224, please note that this office typically closes at 4pm.  Written work will not be accepted after Friday, May 2.

 

Laboratory Safety:  Organic chemistry is inherently dangerous since we work with flammable solvents and glassware.  Explosions and spills do happen and people do get hurt, however, these incidents are very rare when proper precautions are taken.  Therefore, it is extremely important that all students and TA's follow well-defined safety protocols.  Such protocols are outlined in the textbook (p. 15 - 23). Goggles or safety glasses must be worn at all times when experiments are in progress.  Furthermore, the instructors and TA's will remind students of important safety precautions before each laboratory.  However, there is no substitute for preparation and common sense!

 

Emergency Procedures: Southern Illinois University Carbondale is committed to providing a safe and healthy environment for study and work.  Because some health and safety circumstances are beyond our control, we ask that you become familiar with the SIUC Emergency Response Plan and building Emergency Response Team (BERT) program.  Emergency response information is available on posters in buildings on campus, available BERTÕs website at www.bert.siu.edu, Department of SafetyÕs website www.dps.siu.edu (disaster drop down) and in Emergency Response Guideline pamphlet.  Know how to respond to each type of emergency.

 

Instructors will provide guidance and direction to students in the classroom in the event of an emergency affecting your location.  It is important that you follow these instructions and stay with your instructor during an evacuation or sheltering emergency.  The Building Emergency Response Team will provide assistance to your instructor in evacuating the building or sheltering within the facility.

 

Hazardous Chemical Disposal:  Most of the chemicals that we work with in the laboratory must be disposed of in properly labeled waste containers.  We are legally required to make an accurate account of the contents of these waste containers, which are found in the laboratory hoods.  Thus, it is very important that you place your waste in the appropriate container; always double-check the waste container before you add waste.

 

Health Problems: It is important that you notify the instructor and TA of any health related issues at the beginning of the semester.  Particularly if you are prone to serious allergies or Asthmatic attacks; you should withdraw from this course if you are pregnant.

 

Laboratory Cleanliness:  Each laboratory period the TA will assign two people as "clean-up supervisors".  It is the responsibility of these supervisors to ensure that the entire laboratory is cleaned and prepared for the next laboratory section.  Thus, the supervisors must wait until the other students have completed their work and the TA inspects the laboratory before they may be excused.  If the laboratory is closed and does not pass inspection by the instructor or the laboratory coordinator, the supervisors will have ten points deducted from their TA evaluation grade and the TA will be reprimanded.  All students will be supervisors at least once per semester.  The TA should provide a checklist with specific cleaning duties for each lab. 

 

Laboratory Notebook:  All students are required to have a laboratory notebook where they will record experimental data and procedures.  This notebook should be bound, not spiral, so that the pages are not easily removed. Notebooks play an important role in science by archiving valuable data and procedures.  A good notebook includes detailed procedures and observations that allows someone skilled in the art of organic chemistry to reproduce those results. TAÕs will periodically check the notebook and give you a grade (4 x 5 pts.).

 

Late Entry :  Requests for late entry or for changing your lab section must be processed in the Chemistry Department office, Neckers 224.  Typically these are only approved when space is available in the requested section (20 students maximum).   

 

Drop Dates:  Jan. 25  - last day to withdraw without affecting your transcript.

                       Mar. 17 - last day to withdraw.