Week 1 -- 1/15-1/19
No Lab

Week 2 -- 1/22-1/26
Unknowns -- The Power of Spectroscopy

Check-In

Check into a lab drawer. You will be assigned a solid and liquid unknown. Determine their structures using IR, NMR, GC-MS, mp, chemical tests, etc. You will be introduced to the use of the NMR and GC-MS this week.

Week 3 -- 1/29-2/2
A Diels-Alder Reaction With an Unexpected Product

Start the reaction of 2,4-Hexadien-1-ol with Maleic Anhydride. You can also continue to collect spectral data on your unknowns. This would be a good time to discuss your spectral data with your instructor and/or TA.

• A copy of your lab notebook pages describing your preliminary analysis of your unknown data, along with any spectra you acquired, must be turned in to your instructor during lab.

Week 4 -- 2/5-2/9
Searching the Chemical Literature & Introduction to Synthesis Projects

You will be introduced to sources of chemical information including computer searching using STN Easy on the Web. As part of your assignment you will search for a literature procedure for an esterification that you will run in Week 6. You will also select a Synthesis Project and do literature research to develop a plan of attack for your synthesis.

• Your Unknowns Report is due at the beginning of lab this week.

Week 5 -- 2/12-2/16
Exploring the Stereochemistry of the Wittig Reaction -- Part 1

This procedure will introduce you to the techniques used for working with strong bases under inert atmospheres. You will also observe how a seemingly minor difference in reaction conditions can produce a dramatic change in the stereochemistry of products.

• Your prelab for next week's esterfication lab must be turned in to your instructor at the beginning of lab this week.
• Diels-Alder report is due in your TA's box by Friday at 4 pm this week.

Week 6 -- 2/19-2/23
Devising an Experimental Procedure: Esterification

This week you will carry out an esterification using a procedure that you have obtained (and adapted) from the chemical literature. Use distillation as the method of purification.

• Your Literature Reports are due at the beginning of lab this week.

Week 7 -- 2/26-3/2
Aldol Condensations Using Unknown Aldehydes and Unknown Ketones

This experiment gives you the opportunity to perform an aldol condensation and elimination. You will use either recrystallization or flash chromatography for purification.

• The report on your esterification is due Friday, March 2 at 4 pm in your TA's mailbox.
• Your Synthesis Project Proposal must be turned in to the appropriate mentor (Bill Dasher, Tim Hoyt, or John Hanson) before Friday, March 2 at 4 pm.

Week 8 -- 3/5-3/9
Exploring the Stereochemistry of the Wittig Reaction -- Part 2

Design your own experiment to explore the stereochemistry of the Wittig reaction.

Week 9 -- 3/12-3/16
Spring Break -- No Lab

Week 10 -- 3/19-3/23
Synthesis Projects

These projects will give you some insight into the fun (and frustration) of research in organic chemistry.

• Your Unknown Aldol Report is due Thursday, March 22 at 4 pm in your TA's mailbox

Week 11 -- 3/26-3/30
Synthesis Projects

• Your Wittig Report is due Thursday, March 29 at 4 pm in your TA's mailbox

Week 12 -- 4/2-4/6
Synthesis Projects

Week 13 -- 4/9-4/13
Synthesis Projects

Week 14 -- 4/16-4/20
Synthesis Projects

• Synthesis Project Progress Report is Due Tuesday, April 17 at 4 pm in your TA's Box

Week 15 4/23-4/27
Check-out, Clean-Up, Presentations

Each group will make a short (10 minute) presentation on their project.

• Your Synthesis Project Report is due Friday, April 27 at 4 pm in the box in John Hanson's Office

Safety

As always, safety is the most important consideration in the lab. Please reread the safety information in the beginning of your laboratory text (pp 1-9). Failure to abide by safety rules may result in expulsion from the lab, and consequent failure in the course.

Laboratory Notebook

You may continue to use the laboratory notebook you used last semester. You should continue to follow the format described last semester. See pages 12-24 in your lab text. Again, you are responsible to have a detailed pre-lab prepared before you come to lab. This pre-lab should be detailed enough that you can perform the lab without reference to your lab text or handouts. The TA's will check for pre-labs and for recording of experimental information. Any potential hazards should be noted. More details will be provided at the first lab meeting.

Write-ups & Progress Reports

Lab write-ups will be similar to those used last semester. They should be typed and written in a clear and concise manner. The use of tables and figures is encouraged when this will clarify the presentation of information. Spelling, grammar, and clarity of the writing will be considered in grading laboratory write-ups. In general, the laboratory reports should follow the style of the Journal of the American Chemical Society. A general handout on report writing format is available on the web. Specific information on lab write-ups will be provided for each experiment.