Chemistry 2312: Organic Chemistry Lab II
Spring, 2007

Instructor: Tim Soderberg
Office: Sci 1320
Phone: (320) 589-6331
email: soderbt@morris.umn.edu
Reference Text: Pavia, Lampman, Kris, and Engel. Techniques in the Organic Laboratory: Microscale and Macroscale.   Harcourt College Publishers, 2002.
Lab Manual: Carpenter, Nancy E., Soderberg, Tim Organic Chemistry Lab II Manual (University of Minnesota, Morris, 2002)
Office Hours: see my weekly schedule

Link to Chemistry Discipline Web Page

SCHEDULE OF EXPERIMENTS

ANNOUNCEMENTS

Download prelab assignments here (PDF files)

Exp 1 prelab (benzoin)
Exp 2 prelab (fragrant ester)
Exp 3 prelab (camphor reduction)
Exp 4 prelab (benzil)
Exp 5 prelab (TPCPD)
Exp 7 prelab (Grignard) part I
(You do NOT need to calculate how many grams of dry ice are needed (you don't have the necessary information). But you do need to calculate the other quantities in this question. When calculating the volume of ether needed to make a 1.5M bromobenzene solution, you should take into account the volume of the bromobenzene.)
Exp 7 prelab part II
Exp 8 prelab (combinatorial chemistry)

GRADING

Grade totals: Download an Excel file showing assignment grades and totals (with code names).

Grades in Chem 2312 will be based on an (approximately) 250 point scale. The breakdown is as follows:

Note: this is an approximate breakdown only - total points may be off a bit by the end of the semester, but each category will be normalized to the point values above before final grades are calculated.

The translation to a letter grade will be based on the traditional percentage scale:

93-100%: A
90-92: A-
87-89: B+
83-86: B
80-82: B-

. . .and so on. A 60% (300 points) is the minimum for a passing grade. These are scores that will guarantee you the given grade, and it is possible (but not certain) that I will either curve grades upward at the end of the semester, or adjust the curve by making extra credit assignments available. Typically the median grade in this class is in the B range.

Prelab assignments:

Prelabs will be due at the beginning of the lab period, and will generally cover the entire experiment if it is a two-parter. Often, prelabs will involve a number of calculations necessary to start the procedure. There will also be conceptual questions. Straightforward information such as physical data will not be part of the prelab assignments, but these should still be in your notebook before you start the lab. Occasionally, I may give you an assignment to complete after you have finished a lab.

Prelab quizzes:

Every time you walk into lab, you need to be prepared to take a short (10 minute) quiz on the experiment we are currently carrying out. We probably will not have a quiz every week, but there probably will be at least six or seven over the semester. I do not intend these quizzes to be horribly difficult - they will be relatively straightforward questions that you should be able to answer if you have read and understood the experiment. It is not necessary for you to memorize reagents or procedures - but you should be prepared to answer questions like "why are we adding the acid during the workup? ", or "what is the precipitate that is forming in the aqueous layer?" In other words, you need to show that you are thinking - not just blindly following instructions. Of course, you should also be familiar with the background information, and with techniques that will be involved. You should also be able to perform calculations and/or answer questions similar to those you did in that week's prelab assignment.

If we are in the first week of a two-week lab, you need to be prepared to answer questions about both parts of the lab. If we are wrapping up one experiment and starting another, you should be ready to answer questions on both. For the multi-step synthesis, however, you will not be responsible for the entire synthesis, just the current experiment. I will not hand back the quizzes (so I can reserve the ability to use the questions again), but a key will be posted in lab immediately after you take them so you will know your result right away. If you are unsure about anything that you got wrong on the quiz, be sure to ask me.

Lab notebooks

As with Chem 2311, there will be no lab worksheets in this course. Your lab reports will consist entirely of your notebook - for this reason your notebook grade is a large part of the total grade for the course. It is assumed that by now you know how to keep a proper laboratory notebook. Refer to the appendix in your lab manual for more specific instructions - note that I do not expect seperation schemes in your notebook this semester. Unlike in the fall semester, I will not collect notebook carbons, so you may use any bound (NOT spiral) notebook with pages pre-numbered. The notebook grade will be determined in two ways. On the next-to-last lab meeting, before check-out, there will be a notebook exam. You will have ONLY your notebook (not this lab manual or the Pavia text) to refer to. In the exam you will be asked to provide specific information that you should be able to find somewhere in your notebook. Here are a few example questions that I could have asked in a similar exam covering the fall semester lab:

What did you use to recrystallize your caffeine?
What is the literature melting range of benzoic acid?
What is the density of dichloromethane?
How many equivalents of phosphoric acid did you use in the dehydration of cyclohexanol?
Draw the structure of 2-napthol

This notebook exam will be worth 30 points.

I will collect your notebook at the end of the the semester for grading (out of 50 possible points).This will be done on a 'spot check' basis: I may, for example, evaluate the introduction from Experiment 3, the discussions from Experiments 4 and 8, the separation scheme from Experiment 2, etc. I will also be checking for procedural and observational details: Did you sketch your TLC plate (including starting material, product, and standards, if available) from experiment XXX? Did you record how many times you extracted your aqueous layer in experiment YYY, and with what? Did you note the appearance of the product in experiment ZZZ? You get the idea.

Products:

You will turn in your products in a labeled glass vial when everyone is completely finished collecting data. I will let you know when I would like to collect each product. Labels on your glass vial should have:

Your name
The date
Your section#
Product name

In the linear synthesis, you will only turn in your final product (TPCPD), NOT your intermediates (benzoin and benzil). Some of the experiments will not have products to turn in. Product grading (5 points each for experiments 2, 3, 6, and 8; 10 points for the product from experiments 1/4/5) is based upon yield, purity, and of course proper labeling and punctuality. If a disaster occurs and you spill all of your product on the bench, do not despair - we will figure out a way for you to continue the lab, and you will still get half of the product points as long as you actually do the experiment.

Review: what is due when? (see the announcements section for up-to-date deadlines)

At the beginning of lab when we start a new experiment:

Prelab assignment
Possibly a quiz

One week after an experiment is completed, at the beginning of the lab period:

Any extra postlab questions that were assigned
Product in labeled glass vial

At the end of the semester:

Notebook
Notebook exam