CHEM 2212 Organic Chemistry II - Summer 2009

Laboratory Program

Course Goal / Exp Obj / Experiment Objective Description / Assignment
Exp H. Preparation of Aldehydes and Ketones by Oxidation of Alcohols: Oxidation of 4-Chlorobenzyl Alcohol to 4-Chlorobenzoic Acid
8-14
Dates
Jan 14
Jan 28 / h1 / Conduct an oxidation of an alcohol to a carboxylic acid. / 1. Read: pp. 525-530 (oxidation of alcohols); pp. 535-537-chlorobenzyl alcohol and microscale procedures)
2. Complete Exercises: pp. 538-539 questions 2, 3, 4, 10, 15
h2 / Isolate the product.
h3 / Characterize and analyze.
h4 / Present, analyze, and discuss results in a written report.
Exp I. Reactions of Carbonyl Compounds: Synthesis of (Z)- and (E)-Stilbenes by a Wittig Reaction
8-14
Dates
Feb 4
Feb 11 / i1 / Synthesize a mixture of stilbenes by a phase-transfer Wittig reaction. / 1. Read: pp. 585-589 (Wittig reaction); pp. 590-593 (synthesis of stilbenes and microscale procedures)
2. Complete Exercises: pp. 596-598 questions 3, 6, 12, 14
i2 / Isolate the product.
i3 / Characterize and analyze.
i4 / Present, analyze, discuss results in written a report.
Exp J. Aldol Condensations to Produce α,β-unsaturated Carbonyl Compounds: Synthesis of trans-p-Anisalacetophenone
8-14
Dates
Feb18
Feb 25 / j1 / Synthesize an α,β-unsaturated carbonyl compound. / 1. Read: pp. 601-603 (aldol condensations); pp. 603-605 (trans-p-anisalacetophenone and microscale procedures)
2. Complete Exercises: pp. 605-606 questions 2, 6, 7, 13
j2 / Isolate the product.
j3 / Characterize and analyze.
j4 / Present, analyze, and discuss results in written a report.
Exp K. Fischer Esterification Reaction of a Carboxylic Acid Derivative: Preparation of Benzocaine
8-14
Dates
Mar 3
Mar 17 / k1 / Conduct an acid-catalyzed esterification of a carboxylic acid with an alcohol. / 1. Read: pp. 651-655 (Fischer esterification); pp. 655-658 (preparation of benzocaine and microscale procedures)
2. Complete Exercises: pp. 658-659 questions 7, 11
k2 / Isolate the product.
k3 / Characterize and analyze.
k4 / Present, analyze, and discuss results in written a report.
Exp L. Preparation of Amides from Carboxylic Acid via Acid Chloride: Preparation of N,N-Diethyl-m-toluamide (DEET) - NEED TO KNOW GLASSWARE SETUP BEFORE COMING TO LAB!
8-14
Dates
Mar 24
Mar 31 / l1 / Conduct synthesis of an amide from a carboxylic acid via the corresponding acid chloride. / 1. Read: pp. 661-663 (amides and insect repellents); pp. 664-668 (preparation of N,N-diethyl-m-toluamide and microscale procedures)
2. Complete Exercises: pp. 668-669 question 12
l2 / Isolate the product.
l3 / Characterize and analyze.
l4 / Present, analyze, and discuss results in a written report.
Exp M. Synthesis Exam
5
Date
Apr 7 / m1 / Understand and apply techniques to synthesize organic molecules. / All course material
Exp N. Qualitative Identification of Organic Compounds by Functional Group Differentiation
15
Date
Apr 14 / n1 / Use qualitative functional group tests to identify and match 6 unidentified compounds to a list of 6 known compounds. / 1. Read: pp. 817-821 (qualitative analysis); pp. 867-868 (ceric nitrate test for alcohols); pp. 840-842 (2,4-DNP test for aldehydes and ketones); pp. 844-846 (chromic acid test for 1o/2o alcohols and aldehydes); pp. 846-848 (iodoform test for aldehydes and ketones with α-hydrogen); pp. 843-844 (Tollen’s test for aldehydes); pp. 851-852 (bromine test for unsaturation); pp.853-854 (silver nitrate test for alkyl halides)
All experiments:
1. are microscale.
2. are 2 laboratory sessions of 3 hours each for a total of 6 hours per experiment, except Exp M & N, which are 3 hours each.
3. have assignments refer to Gilbert and Martin, Experimental Chemistry: a Miniscale and Microscale Approach, 4th ed. (except as noted).