CHEM 2212 Organic Chemistry II
Summer 2008
Laboratory Program
Course
Exp Experiment Objective Description
Assignment
Goal
Obj
Exp H. Preparation of Aldehydes and Ketones by Oxidation of Alcohols: Oxidation of 4-Chlorobenzyl Alcohol to 4-Chlorobenzoic
Acid
8-14
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
h2
Isolate the product.
Dates
procedures)
h3
Characterize and analyze.
Jun 24
2. Complete Exercises: pp. 538-539 questions 2, 3,
h4
Present, analyze, and discuss results in a written report.
Jun 25
4, 10, 15
Exp I. Reactions of Carbonyl Compounds: Synthesis of (Z)- and (E)-Stilbenes by a Wittig Reaction
8-14
i1
Synthesize a mixture of stilbenes by a phase-transfer
1. Read: pp. 585-589 (Wittig reaction); pp. 590Wittig reaction.
593 (synthesis of stilbenes and microscale
Dates
procedures)
i2
Isolate the product.
Jun 30
2. Complete Exercises: pp. 596-598 questions 3, 6,
i3
Characterize and analyze.
Jul 1
12, 14
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
j1
Synthesize an α,β-unsaturated carbonyl compound.
1. Read: pp. 601-603 (aldol condensations); pp.
603-605 (trans-p-anisalacetophenone and microscale
j2
Isolate the product.
Dates
procedures)
j3
Characterize and analyze.
Jul 2
2. Complete Exercises: pp. 605-606 questions 2, 6,
j4
Present, analyze, and discuss results in written a report.
Jul 7
7, 13
Exp K. Fischer Esterification Reaction of a Carboxylic Acid Derivative: Preparation of Benzocaine
8-14
k1
Conduct an acid-catalyzed esterification of a carboxylic
1. Read: pp. 651-655 (Fischer esterification); pp.
acid with an alcohol.
655-658 (preparation of benzocaine and microscale
Dates
procedures)
k2
Isolate the product.
Jul 8
2. Complete Exercises: pp. 658-659 questions 7, 11
k3
Characterize and analyze.
Jul 9
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)
8-14
l1
Conduct synthesis of an amide from a carboxylic acid via
1. Read: pp. 661-663 (amides and insect
the corresponding acid chloride.
repellents); pp. 664-668 (preparation of N,N-diethylDates
m-toluamide and microscale procedures)
l2
Isolate the product.
Jul 14
2. Complete Exercises: pp. 668-669 question 12
l3
Characterize and analyze.
Jul 15
l4
Present, analyze, and discuss results in a written report.
Exp M. Synthesis Exam
5
m1
Understand and apply techniques to synthesize organic
All course material
molecules.
Date
Jul 16
Exp N. Qualitative Identification of Organic Compounds by Functional Group Differentiation
15
n1
Use qualitative functional group tests to identify and match 1. Read: pp. 817-821 (qualitative analysis); pp.
6 unidentified compounds to a list of 6 known compounds. 867-868 (ceric nitrate test for alcohols); pp. 840-842
Date
(2,4-DNP test for aldehydes and ketones); pp. 844Jul 21
846 (chromic acid test for 1o/2o alcohols and
aldehydes); pp. 846-848 (iodoform test for
aldehydes and ketones with α-hydrogen); pp. 843844 (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, 4 th ed. (except as
noted).
CHEM 2212L
Georgia Gwinnett College
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7/16/2016
School of Science & Technology