Organic Chemistry Lab II (Chemistry 322L) Syllabus

Organic Lab Coordinator and Instructor: Dr. Andrea Drew Gounev (drewa@umkc.edu)

Office: Flarsheim Hall 510D,

Office Hours MW 9:00-11:00am, and by appointment

Course Website: http://cas.umkc.edu/chem/chm_courses.htm.

Meets	Day	Time	Teaching Assistants (Office Hours on Blackboard))	Instructors in charge
SCB 212	M	2:00 - 4:50 PM (V02 20910)	George Gao (GeGao@umkc.edu) Julie Mumm (jnmnpc@umkc.edu) Colin Warnock (cgwrh6@umkc.edu)	Dr. Drew Gounev
SCB 214	T	8:00 - 10:50 AM (V03 20911)	George Gao (GeGao@umkc.edu) Nalin Chandrasoma (dncx3b@umkc.edu)	Dr. Drew Gounev
SCB 212	T	2:00 - 4:50 PM (V07 20915)	George Gao (GeGao@umkc.edu) Lincoln Maina (lwmfh3@umkc.edu)	Dr. Drew Gounev
SCB 212	W	2:00 - 4:50 PM (V05 20913)	Sanjiban Chakraborty (sc8n8@umkc.edu) Hunter Hsu (hhd2c@umkc.edu) Richard Van Trump (rmv337@umkc.edu)	Dr. Drew Gounev
SCB 214	R	8:00 - 10:50 AM (V06 20914)	Sanjiban Chakraborty (sc8n8@umkc.edu) Joe Frye (jsfkt7@umkc.edu) Christopher Slifer (css352@umkc.edu)	Dr. Drew Gounev
SCB 212	R	2:00 - 4:50 PM (V04 20912)	Sanjiban Chakraborty (sc8n8@umkc.edu) Lincoln Maina (lwmfh3@umkc.edu)	Dr. Drew Gounev
SCB 212	F	2:00 - 4:50 PM (V08 22583)	Lincoln Maina (lwmfh3@umkc.edu) Cecilia Bichara (fcb4z3@umkc.edu) Abdul Tufail (amtry3@umkc.edu)	Dr. Drew Gounev

GENERAL

Pre-requisites and Co-requisite

A grade of “C-” or better in General Chemistry I and II with lab (CHEM 211/211L and 212R /212LR) and Organic Chemistry I with lab (CHEM 321/321L), or the equivalent courses, is required for enrollment in this course. There is also a co-requisite of CHEM 322 Lecture.

Course objectives

The objective of this course is to provide students with advanced organic laboratory experiences, i.e., performing multi-step organic syntheses and writing scientific reports.

Pre-lab lectures and announcements

All classes will convene in room C212 or C214 in the Spencer Chemistry Building before entering the lab for class announcements, pre-lab lectures, and submission of lab reports. Attendance will be taken in pre-lab.

Required materials

· Mohring et al. Techniques in Organic Chemistry, 2^nd ed.; 2006, W.H. Freeman (ISBN 0-7167-6935-2).

· A lab notebook capable of making carbon copies (100 pages is a good size). The copies are submitted to your GTA as you leave the lab each session and become part of your report; you retain the originals.

· Padlock, safety glasses, black felt-tip pen with permanent ink (Sharpie).

· Non-graphing calculator (as the one you used in General Chemistry I and II).

· Appropriate clothing (i.e., no shorts, open-toed shoes, etc.).

GRADING During the pre-lab lecture, the GTAs will tell you what you need to hand in for your report on that lab. You will turn in eight regular lab reports, each worth 20 points. Your lowest lab report score will be dropped (if you have an “excused” lab, it will your dropped lab), for a total of 140 points for your reports. The ninth and tenth labs, Diels-Alder Reaction: Hexaphenylbenzene, Dimethyl tetraphenyl phthalate, 1,2,3,4-Tetraphenylnaphthalene and Diels-Alder Reaction: Triptycene (lab numbers 3 and 4 on the syllabus) have an extended lab write-up and cannot be dropped.

Laboratory Performance and Technique: Part of the grade for each lab report will include a score for laboratory performance and technique. You are expected to be prepared for lab, maintain your drawer, space and wastes appropriately, wear safety goggles/glasses at all times while in the lab, and follow all check-in and check-out procedures. You will have points deducted for tardiness, lack of preparation, non-completion of lab or other infractions of safety and good lab practice.

Extended Laboratory Write-Ups:

The first extended laboratory write-up will be over the Experimental Part of the Diels-Alder experiments and is worth 20 points.

The second extended laboratory write-up will also be over the same Diels-Alder experiments, but will be a full write-up including an Introduction, revised Experimental Part, Results and Discussion, Conclusion and Bibliography. The second laboratory write-up is worth 50 points. The GTAs will tell you what kind of information you need to include in both of these labs; it can also be found on the course website. You will be submitting a hard copy of the extended lab report to your lab TA, as well as submitting it to TurnItIn through Blackboard.

Saturday Laboratory Exams:

There are two laboratory exams, each worth 50 points, which will be held on Saturdays. Please mark them in your calendar and bring a calculator.

LAB EXAM 1: MARCH 14 (Saturday) from 12:00pm-2:00pm in Royall Hall 111.

LAB EXAM 2: APRIL 25 (Saturday) from 12:00pm-2:00pm in Royall Hall 111.

Grading Detail:

Assignment Total

Lab Experiments (20 points each) 140

First Extended Lab Report 20

Second Extended Lab Report 50

Lab Exam I 50

Lab Exam II 50

TOTAL POINTS POSSIBLE 310

The total amount of points for this class will be 310 points. Grades will be assigned as follows: 90% and above = A; 89% = A-; 88% = B+; 80 – 87% = B; 79% = B-; 78% = C+; 70 – 77% = C; 69% = C-; 68% = D+; 60 – 67% = D; below 60% = F.

Note: You will lose 1 point on anything that you hand in as a lab report for the first occurrence of the following: a spelling error, grammatical error, and partial sentence. Spell-check and proof-read your typed work.

Your lab grades may be checked via Blackboard at Blackboard.umkc.edu. Your Blackboard User ID and Password are the same as your UMKC Exchange/SSO user ID (the alias from your Alias@umkc.edu e-mail address). If you don’t know your Exchange/SSO User ID, you can obtain it at www.umkc.edu/exchange-faq. Lab handouts may also be found on the Blackboard site or at the Chemistry 322L course website http://cas.umkc.edu/chem/chm_courses.htm.

POLICIES Enrollment and Attendance

You must be enrolled in the section you are attending. If you are not enrolled by the end of the second week of classes (January 26^th), you will be asked to leave the lab.

Attendance is required and will be taken by GTAs at all laboratory classes. The class starts on time and finishes on time. Please observe the following:

· Students must attend their assigned laboratory section.

· Only substantial and unavoidable reasons (e.g., serious illness, unavoidable out-of-town professional travel, death in the family, or religious observance) should cause students to miss a regularly scheduled lab. You should not miss a lab simply because your lowest score will be dropped!

· There will be no make-up labs! All of the organic lab sections are completely full. Even if you have an excused absence, you will be unable to make-up the lab you missed. This will be your dropped lab.

Safety and Honesty

During the first week of classes, safety regulations will be reviewed. You are expected to follow them. When in doubt, ask your GTA or lab instructor. Do not, under any circumstances, use fabricated data or data from another student. Fabrication of data is academic misconduct: you will receive a grade of zero on the tainted work and will be reported to the Chief Academic Officer of your academic unit. Serious and/or repeat offenders will receive an F grade for the course and face disciplinary action from the University. It is your responsibility to know and uphold the UMKC rules of academic conduct (http://www.umkc.edu/umkc/catalog/html/append/policy/0020.html).

During the check-in week of the lab, you will be asked to sign a statement that you understand the safety regulations and academic honesty policy, and agree to adhere to them. A copy of these regulations is provided.

Laboratory

You must provide a padlock for your glassware drawer. You are responsible for maintaining the glassware clean and in good condition and for keeping your equipment drawer clean. Even though you are expected to take appropriate care with equipment and glassware, it is reasonable to expect a small amount of breakage. Notify the GTA as soon as possible if something is broken; you will be issued a replacement. No student will receive a grade for the course until he/she has checked out at the end of the semester.

Lab Reports

The due dates for lab reports are listed in the class schedule accompanying the syllabus. Lab reports must be turned in at the beginning of the pre-lab lecture prior to entering the laboratory. Late lab reports will never be accepted. No exceptions will be made.

If, and only if, you miss a lab period, you have three business days to turn the previous week’s lab into my office to avoid a grade penalty.

Regrade and Grievance Policy

Regrade requests for the lab reports should be submitted to the GTA as soon as possible, and no later than within one week of receiving the graded lab report. The GTA may decide to pass certain regrade requests to the instructor. Any other grievances about the class should be first taken up with the instructor. After contact with the instructor, further comments and complaints may be addressed to the Chemistry Department Chair.

LAB NOTEBOOKS

· Reread pages 30-33 in Mohrig et al.

· Each experiment should begin on a new page.

· Put your name, your section, your TA’s name on top of every page in every experiment.

· Make every entry in your notebook in ink, never in pencil. Do not erase or black out entries. Instead, ~~draw a line through the error~~ and add the new information.

· Record all laboratory observations and data directly in the lab notebook at the time they are observed. Do not use scratch paper. Do not expect to transcribe any information into your notebook at a later time. Carbon copies of your notebook entries should be stapled and handed in at the end of every laboratory session. Your typed reports must draw on data and observations recorded in your lab notebook.

· Organize your lab notebook using headings such as Title, Purpose, Procedure, Observations, Apparatus or Glassware set-up, Balanced reaction or Mechanism, and Purification.

· Do not, under any circumstances, use fabricated data or data from another student.

LAB REPORTS

For each experiment you will hand in (1) the carbon copies of pre-lab and data and observations pages from your lab notebook before leaving the lab and (2) a completed lab report on the scheduled due date, before leaving the pre-lab. Your report will consist of these two submissions and a pre-lab quiz, if applicable.

Your lab notes will be hand-written; all other submitted work should be type-written, with the exception of structures and figures, which should be hand-drawn in ink. Anything written in pencil will not be graded.

The individual lab handouts will be available for download at the course website and will be up the Monday before the week of that lab.

Before lab Þ Pre-lab

You will need to write in the procedure fully in your lab notebook because the handouts will not be allowed in the lab. You should be thorough enough so that you can perform the experiment from what you have written. Any changes to the lab will be announced in the pre-lab lecture and need to be noted in your lab book. When you arrive in lab, your GTA will sign your notebook pages ensuring that you have completed the required pre-lab. If not, you will not be allowed to start the experiment. You will have to leave the lab, complete the pre-lab, and then return to the lab but all labs will stop by the end of the lab section. No time extensions are allowed.

The pre-lab in your notebook at a minimum should contain the following

· Title

Begin each experiment on a new page with a title, your name, the date, your TA’s name and your lab section.

· Purpose

A brief statement of the experimental objectives

· Net equation and/or mechanism of reaction (for preparative experiments)

Include for all important reactions.

· Table of quantities and physical constants

Collect in tabular form the name, structure, formula, molecular weight, and density of any substance whose mass or volume you must measure (make sure you include units where appropriate!). Some of this information can be found in the handouts. That which is not in the handouts can be looked up in The Aldrich Chemical Company Catalog, The Merck Index, The CRC Handbook of Chemistry and Physics, and on‑line at http://chemfinder.camsoft.com or http://webbook.nist.gov/chemistry or http://www.inchem.org/.

· Theoretical yield (when necessary)

Calculate the theoretical yield of all reactions, showing all calculations.

· Procedure

Provide an outline of the experimental procedure to be carried out. Do not simply copy what is written in the handouts; use your own words and diagrams. It is often useful to construct a flow chart of the procedure.

During lab Þ Data and observations (hand-written in your lab notebook)

Maintaining good experimental records is an essential part of the laboratory work. For all experiments, record what was done, including amounts (in g or mL, and in mol or mmol) of the compounds used, and your observations (i.e., changes in appearance, color, temperature, precipitation, evolution of gas). Also, where applicable, include work-up, isolation, and purification techniques used, isolated yields (in g or mL and in percents), and appearance of the final product (physical state, color, texture, smell).

Carbon copies of these pages will be stapled together and submitted before leaving the lab. Failure to turn in those pages counts as an absence. If an absence for a lab is recorded, a grade of “0” is unavoidable.

After lab Þ Summary of results and lab report (typed; CANNOT be hand-written)

You will receive a list of what is required for that lab during your pre-lab lecture. You will need to type all of the information required. All calculations must be explicitly included and type-written. If your handout includes post-lab questions, type the answers to them in the appropriate space in “Post-lab Report”. Figures, structures and mechanisms are to be hand-drawn in ink (not in pencil). Your typed reports will be cross-checked against your lab notes. Spell-check and proof-read your typed work (see GRADING).

Your post-lab reports will be collected on the date they are due, in the pre-lab room.

Do NOT submit your lab reports to Chemistry Office!

Example of how to setup your lab notebook

Before the Experiment Begins.

Experiment Title:

Date:

Name:

Course: Chemistry 322L

Section:

GTA Name:

Purpose: (Purpose of the experiment; write a brief (1-3 sentences) statement of purpose for the synthesis or analysis, or state the question you are addressing)

Balanced Chemical Reaction: (Write balanced chemical equations that show the overall process, not a mechanism)

Table of Physical Quantities: (Include all reagents and solvents: name of reagent or solvent, molecular formula, molecular structure, molecular weight, melting point (solids) or boiling point (liquids), density, hazards). Water must ALWAYS be included!

Name (Other names)	Molecular formula	Molecular structure	Molecular Weight (g/mol)	Melting or Boiling Point (^oC)	Density (g/mL)
Magnesium	Mg		24.31	mp 648	1.74
Anhydrous Ether (Diethyl)	C₂H₅OC₂H₅		74.12	bp 34.6	0.706
Bromobenzene
Benzophenone
HCl
Sodium Sulfate
Petroleum Ether
Ethanol
Water

Name	Hazards (According to MSDS)
Anhydrous Ether (Diethyl)	Extremely flammable; May form explosive peroxides; Harmful; Repeated exposure may cause skin dryness or cracking; Vapors may cause drowsiness and dizziness.

Yield Calculations: Outline the formulas to be used in your experiment. Calculate the theoretical yield.

Procedure: (This is a procedural outline of what you are doing in the experiment. Remember, you will not be allowed to bring your lab report to class so it is important that you have the details of the experiment here. Leave space between lines here for any corrections that the GTA gives you to the procedures.)

During the Laboratory Session.

Observations: Record all observations that take place while you are performing your experiment. This includes:

Actual quantities of all reagents used.

Amounts of crude and purified products obtained

Mention measurements you took (temperature, time, melting point, and so on)

Smells

Color changes

Statement on Sexual Harassment

Recently there has been considerable media coverage of an alleged case of sexual harassment of a graduate student and an Associate Professor in the College. That case is under active investigation and no findings of fact have yet been made. It is important that we do not jump to conclusions of guilt in cases such as this; nor should we prematurely assume that the allegations are false. The presumption of innocence until proven otherwise is a cornerstone of the American justice system.

Please be assured, though, that the College and the University of Missouri-Kansas City have a zero tolerance policy for sexual harassment, intimidation, or discrimination of any kind. The faculty and the administration are committed to creating and maintaining an environment on campus that is free of all forms of harassment, intimidation, and discrimination.

Should you or a friend ever experience any action or speech that feels coercive or discriminatory, you should report this immediately to the department chair, the office of the Dean, and/or the Affirmative Action Office. The Affirmative Action Office will be responsible for investigating any complaint of discrimination or sexual harassment.

We are a community of learners dedicated to the pursuit of knowledge and the acquisitions of skills that will enable us to lead rich and full lives. We can pursue these ends only in a culture of mutual respect and civility. It is incumbent upon all of us to create a culture of respect everywhere on campus and at all times through our actions and speech. On behalf of the faculty of UMKC, I pledge to you that we will maintain a safe environment on campus that fosters respect for everyone.

Dr. Gary L. Ebersole

Professor of History and Religious Studies

Chair, UMKC Faculty Senate

Chemistry 322L Schedule of Labs

Week	Lab	Due Date
January 12-16	Check-in
January 19-23	No LABS! (Martin Luther King Holiday)
January 26-30	1. Grignard Reaction	February 2-6
February 2-6	2. Epoxidation of Cholesterol	February 9-13
February 9-13	3. Diels-Alder Reaction: Hexaphenylbenzene, Dimethyl tetraphenyl phthalate, 1,2,3,4-Tetraphenylnaphthalene	1. Extended write-up of experimental sections is due March 2-6. 2. Second (full) extended write-up is due March 30-April 3.
February 16-20	4. Diels-Alder Reaction: Triptycene
February 23-27	4. Diels-Alder Reaction: Triptycene	March 2-6
March 2-6	5. Acylation of Ferrocene	March 9-13
March 9-13	6. Alkylation of Biphenyl and Para-Dimethoxybenzene	March 16-20
MARCH 14 (Saturday)	LAB EXAM 1 (12:00pm-2:00pm in Royall Hall 111)
March 16-20	7. Nitration of Methyl Benzoate	March 30-April 3
March 23-27	No LABS! (Spring Break)
March 30-April 3	8. Wittig Reaction	April 6-10
April 6-10	9. Aldol Condensation	April 13-17
April 13-17	10. Synthesis of Banana Oil	April 20-24
April 20-24	Check-out
APRIL 25 (Saturday)	LAB EXAM 2 (12:00pm-2:00pm in Royall Hall 111)

A copy of this statement will be provided for your signature before the first experiment

CHEM 322L Laboratory Safety Regulations: Initial the items and sign the bottom.

Semester Spring 2009 Section ________ Room and Drawer#_______________

Instructor ______________________ Station # _______________________

1. I will prepare for lab by studying the experiment before class and by trying to anticipate potential hazards from the chemicals or procedures to be used.

2. I will wear approved safety goggles AT ALL TIMES in the laboratory unless the instructor gives specific approval to remove them.

3. I will not work in the lab unless an instructor is present.

4. I will not perform any unauthorized experiments.

5. I will notify the instructor of any allergies or other health conditions that may affect my ability to work in a chemistry lab.

6. I will not eat, drink, or smoke in the lab.

7. I will not use cellular phones or radios in the lab.

8. I will minimize my contact with chemicals by taking care to note odors, never tasting chemicals, using suction bulbs to fill pipettes, and washing any spilled chemicals off my person as soon as possible. I will wash my hands before leaving the lab.

9. I will not wear shorts, sandals, or other clothing in the lab that allows unnecessary exposure to spilled chemicals. I am also aware that certain chemicals can ruin clothing and that wearing a lab coat or apron adds some degree of protection.

10. I will secure long hair to keep it away from open flames and chemicals while I am working in the lab.

11. I will immediately report all cuts, burns, personal injuries, fires, chemical spills, or other accidents to the instructor.

12. I will keep my work area and the common areas of the lab clean.

13. I will NOT return unused chemicals to their original bottles.

14. I will consult with the instructor about the proper disposal of all waste chemicals.

15. I know the location, operation, and appropriate uses of the eye-wash stations, safety showers, fire extinguishers, fire alarms, and fume hoods; and I know the locations of all lab exits.

16. I agree to follow any specific or additional safety instructions that may be given for any experiments.

17. I will conduct myself in a professional and respectful manner. I will leave the lab after I complete my work.

I understand all of these statements and agree to observe them at all times in the lab. I also understand that if I fail to observe them, I will be expelled from the laboratory.

CHEM 322L Academic Honesty Statement

I will perform the work by myself and will adhere to the UMKC Academic Conduct Standards for Students (http://www.umkc.edu/umkc/catalog/html/append/policy/0020.html. It is my responsibility to understand the facets of academic honesty and to uphold them. If I am not sure, I will consult with the instructor.

Sign: Date: