Welcome to the UMass Department of Chemistry
Organic Chemistry Laboratories - CHEM-268 - Organic Lab 2 for Chemistry Majors
Laboratory Director - Dr. Christopher McDaniel (mcdaniel[at]chem.umass.edu)
Spring 2020
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Welcome to the UMass Department of Chemistry Organic Chemistry Laboratories - CHEM-268 - Organic Lab 2 for Chemistry Majors Laboratory Director - Dr. Christopher McDaniel (mcdaniel[at]chem.umass.edu) Spring 2020 |
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Schedule of Experiments
Lab Experiment |
Week of . . . |
Special Notes and Reading |
What is due, in addition to the pre-lab? Due dates are all FRIDAY of that week |
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Check-In
and Column Chromatography: The Separation of Two Organic Compounds |
January 21 |
Read Chpt 9, pp. 185-190. For the experiment, it will be a combination of the handout and the text. This is a second semester technique experiment. The post-lab report is non-formal. Provide answers to questions 1, 2, 4 and 5 on page 204 of the manual. |
Nothing |
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Acetominophen to Phenacetin: A Williamson-Ether Synthesis of an FDA Banned Substance |
January 27 |
Review Wade, 11-14 and 14-5. Review Sn2 |
Column Chromatography (non-formal report) due to Gradescope by 11:59 PM |
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Triphenylmethanol Synthesis via a Grignard Reaction. On the last day (week of the 17th) of this experiment, ALSO setup "week 0" of the multi-step synthesis of tetraphenylcyclopentadienone |
February 3, 10 and 17 |
Read Chpt 38, pp. 490-494 and 501-504. Include the prelab exercise on p. 490 as part of your prelab outline. The apparatus will be modified slightly. Do Exp 4, 5, 7, pp. 501-504. The key word is DRY. Ref: Wade, 10-8, 10-9, 10-10, 18-12, and 14-2D. |
Phenacetin Synthesis due (the 14th) to Gradescope by 11:59 PM |
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February 24 and March 2
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Syntheses from Chapters 53, 55, 51 and chemical literature. Benzaldehyde to hydrobenzoin via benzoin and benzil intermediates.
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Grignard due (the 28th) to Gradescope by 11:59 PM |
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March 9 |
Review Recrystallization (Chpt 4, especially macroscale recrystallization), MP (Chpt 3), and TLC (Chpt 8). Do Exp 2, “Macroscale Nitration …”. MP, TLC, and NMR will be used to analyze products. Ref: Wade, Chapt 17, especially 17-3, 17-7. Spring break begins Sunday the 15th. |
Tetraphenylcyclopentadienone due to Gradescope by 11:59 PM (NOW DUE MARCH 23). |
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Click here to see which ester you will be synthesizing. |
Read Chpt 40, pp. 515-519, 524, 525. Review Extraction (Chpt 7). Read about macroscale extraction (Chpt 7, pp. 135, 136) and macroscale distillation (Chpt 5). You will be assigned to synthesize one of the following esters: ethyl heptanoate, ethyl hexanoate, methyl heptanoate, methyl hexanoate, methyl octanoate, propyl hexanoate. BEFORE YOU COME TO LAB, using the procedure of Exp 4, pp. 524, 525, plan the synthesis and write out the procedure for the preparation of 0.080 mol of your assigned ester. Use an 8-fold mole excess of the alcohol (carboxylic acid is the limiting reagent). Obtain the physical properties (e.g., BP, sol, density) of the product and reactants from a handbook. Describe the odor of your product and of the reactants. Check the odor of different esters made by your class mates. Analyze the product by IR and NMR spectroscopy and GC. Ref: Wade, 20-10, 21-2A. For IR, 12-8, 20-7A, 21-4A. For NMR, 20-7B, 21-4B |
Nitration due to Gradescope by 11:59 PM (NOW DUE APRIL 3) |
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This experiment is cancelled |
Wittig due to Gradescope by 11:59 PM (NOW DUE APRIL 30) |
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