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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 2019

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Schedule of Experiments

Lab Experiment
Thursday . . .
Special Notes and Reading
What is due, in addition to the pre-lab?
Check-In and Column Chromatography: The Separation of Two Organic Compounds
January 24
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
Acetominophen to Phenacetin: A Williamson-Ether Synthesis of an FDA Banned Substance
January 31
Review Wade, 11-14 and 14-5. Review Sn2
Column Chromatography (non-formal report)
Triphenylmethanol Synthesis via a Grignard Reaction
February 7 and 14
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 7th
Nitration of Methyl Benzoate
Februrary 21

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: Wade, Chapt 17, especially 17-3, 17-7

Grignard
Set up week zero of the multi-step synthesis of tetraphenylcyclopentadienone

February 28 and March 7, 21

Syntheses from Chapters 53, 55, 51 and chemical literature.  Benzaldehyde to hydrobenzoin via benzoin and benzil intermediates. Spring break begins Sunday the 10th.

Nitration due March 7

Macroscale Esterification
March 28
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
Tetraphenylcyclopentadienone
April 4, 11
Review the Wittig reaction (Wade pp. 918-921). Review NMR and IR (Wade chapters 12 and 13). On the 11th, before any lab works begins, you will be taking the departmental Level 2 curriculum exam. This is nonoptional and in exchange for your participation, it will count as a 2.5% jump in your final grade percentage.
Esterification

Identification of an Unknown and Qualitative Organic Analysis

April 18
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
Luminol Activity, check-out
April 25
Finish and submit all remaining work. Check out and return equipment drawer key.
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