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 2021
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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 2021 |
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Schedule of Experiments
Lab Experiment |
Date |
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 Acetominophen to Phenacetin: A Williamson-Ether Synthesis of an FDA Banned Substance |
Feb 4 |
Review Wade, 11-14 and 14-5. Review Sn2 |
Nothing |
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Feb. 11 & 18 |
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 18th to Gradescope by 11:59 PM |
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Structure Determination of an Unknown and Learn to use the benchtop NMR spectrometer.
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February 25
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Read LabText pp. 239 - 247, and 252 - 254. You will run an unknown and determine its structure. Also review Wade, Chapter 13.
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Grignard due to Gradescope by 11:59 PM
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March 4 |
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. |
Structure Determination (non-formal) due to Gradescope by 11:59 PM |
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March 11, 18
Read and understand section 20-15 (Synthesis and Use of Acid Chlorides) in Wade. Review SN2. Read pages 65-66 (macroscale recrystallization) and review pages 135-136 (mixing and separating layers with a sep funnel). Nitration due to Gradescope by 11:59 PM | |||||||
None!!!
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March 25
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Break Week. Lidocaine still due!!!
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Lidocaine due to Gradescope by 11:59 PM
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Click here to see which ester you will be synthesizing. |
April 1 |
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 |
None. |
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Identification of an Unknown and Qualitative Organic Analysis |
April 22 |
Read "Qualitative Organic Analysis" handout, pp. 762-768, 769-771 (b, alcohols, c, aldehydes, and g, ketones), and 779-783 (2, alcohols, 3, aldehydes, and 9, ketones). Read Chpt 36 (lab text, omit Exp 4, 7). You will be assigned to identify an unknown compound (it may be an alcohol, aldehyde, or ketone). For the prelab outline, devise a plan to do so. Ref: Wade, 18-16, 22-3A,B, and for spectra, 12-8, 12-9, 18-5A,B. |
Wittig due to Gradescope by 11:59 PM |
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Luminol Activity, check-out |
April 29 |
Check out and return equipment drawer key. |
Unknown ID due to Gradescope by 11:59 PM. All outstanding reports due by 11:59 PM on the first reading day. |