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 2018
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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 2018 |
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Schedule of Experiments
Lab Experiment |
Thursday . . . |
Special Notes and Reading |
What is due, in addition to the pre-lab? |
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January 25 |
None |
Nothing |
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February 1 |
Read Chpt 28 and pp. 190, 191 (HPLC) . Review Recrystallization (Chpt 4, especially macroscale recrystallization), MP (Chpt 3), and TLC (Chpt 8). Do Exp 2, “Macroscale Nitration …”. MP, TLC, and IR will be used to analyze products. Ref: Loudon, Chapt 16 |
None |
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February 8 |
Read Chpt 32. Do Microscale Procedure, p. 440. Purify the product by column chromatography as follows: Column Chromatography. Read Chpt 9, pp. 185-190, follow procedures on pp. 200, 201 and p. 440, "Column Chromatography" and "Elution". (Basically to purify the acetylferrocene do Exp 4, p. 200, but use the acetylferrocene that you prepared, not a 50:50 mixture as described in Exp 4.) Analyze final product by IR as a mull. |
Nitration of methyl Benzoate |
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February 15, 22, March 1 |
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: Loudon, Chapter 19, section 19.9. |
Acylation of Ferrocene due on Feb 15. |
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March 8 |
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: Loudon Chapt 20, Sec 20.8. For IR, Chapt 12, For NMR, Chapter 13. |
Triphenylmethanol Synthesis |
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Continue: Multi-step Synthesis of Tetraphenylcyclopentadienone |
March 29, Apr. 5 |
Syntheses from Chapters 53, 55, 51 and chemical literature. Benzaldehyde to hydrobenzoin via benzoin and benzil intermediates.
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Wittig due March 29 |
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Identification of an Unknown |
April 12 |
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: Loudon Chapt 19, and for spectra, chapt 12 and 13. |
Mulit-Step Synthesis |
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Luminol Activity, check-out |
April 19 |
Finish and submit all remaining work. Check out and return equipment drawer key. |
Unknown ID |