Chemistry 251 Laboratory Schedule
Spring 2010

Week 1 -- 1/19-1/22
No Lab

Week 2 -- 1/25-1/29
Unknowns -- The Power of Spectroscopy

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 -- 2/1-2/5
Diels-Alder Reaction With an Unexpected Product
Ester Formation from an Acid and an Alcohol
Check-In

Check into a lab drawer and start the Diels-Alder reaction of 2,4-Hexadien-1-ol with Maleic Anhydride. Is the product what you expected? This week you will also carry out an esterification reaction by condensing, under reflux, an alcohol and acid. After an aqueous work-up, you will store your product and purify it by distillation next week. This would be a good time to discuss your unknown 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 -- 2/8-2/12
Analysis of Diels-Alder Product
Distillation and Characterization of Esterification

Distillation is one of the most important purification techniques for liquids. You will purify your esterification product by distillation and then characterize it using IR, NMR, and GC-MS.

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

Week 5 -- 2/15-2/19
Searching the Chemical Literature & Introduction to Synthesis Projects

You will be introduced to sources of chemical information, including the use of SciFinder Scholar. You will also select a Synthesis Project and do literature research to develop a plan of attack for your synthesis.

• Your Diels-Alder and Esterification Lab Report is due at the beginning of lab this week.

Week 6 -- 2/22-2/26
Aldol Condensations Using Unknown Aldehydes and Ketones

This experiment gives you the opportunity to perform an aldol condensation and elimination. You will use recrystallization for purification. The structure of your product, and by inference the starting aldehyde and ketone, will be determined by melting point and spectroscopic techniques.

• Your reaction and compound literature searches are due at the beginning of lab this week.

Week 7 -- 3/1-3/5
Exploring the Stereochemistry of the Wittig Reaction

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 "Unknown Aldol" report is due at the beginning of lab this week.
• Your Synthesis Project Proposal must be turned in to the appropriate mentor (Bill Dasher, Eric Scharrer, John Hanson, or Tim Hoyt before Friday, March 5 at 4 pm.

Week 8 -- 3/8-3/12
Exploring the Sterochemistry of the Wittig Reaction: Results and Discussion
Synthesis Planning: Meet with your Project Groups and Mentor

In lab this week we will discuss the results from the Wittig Reaction experiment you performed in Week 7. You will also meet with your Project Mentor to discuss your Synthesis Project so that you will be ready to begin when you return from Spring Break.

Week 9 -- 3/15-3/20
Spring Break -- No Lab

Week 10 -- 3/22-3/27
No Lab

• Your Wittig report will be due Friday, March 26 in your lecture section.
  

Week 11 -- 3/29-4/2
Synthesis Projects

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

Week 12 -- 4/5-4/9
Synthesis Projects

Week 13 -- 4/12-4/16
Synthesis Projects

Week 14 -- 4/19-4/23
Synthesis Projects

• Your Synthesis Project Progress Report is due Tuesday, April 20 in your lecture class.

Week 15 -- 4/26-4/30
Check-out, Clean-Up, Presentations

Each group will make a short (10 minute) presentation on their project. Then we will clean-up and check-out of lab.