CHEM 2212 Organic Chemistry II - Summer 2009
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
1. Read: pp. 525-530 (oxidation of alcohols);
acid.
pp. 535-537-chlorobenzyl alcohol and
Dates
microscale procedures)
h2
Isolate the product.
Jan 14
2. Complete Exercises: pp. 538-539
h3
Characterize and analyze.
Jan 28
questions 2, 3, 4, 10, 15
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
i1
Synthesize a mixture of stilbenes by a phase-transfer 1. Read: pp. 585-589 (Wittig reaction); pp.
Wittig reaction.
590-593 (synthesis of stilbenes and microscale
Dates
procedures)
i2
Isolate the product.
Feb 4
2. Complete Exercises: pp. 596-598 questions
i3
Characterize and analyze.
Feb 11
3, 6, 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-pAnisalacetophenone
8-14
j1
Synthesize an α,β-unsaturated carbonyl compound.
1. Read: pp. 601-603 (aldol condensations);
pp. 603-605 (trans-p-anisalacetophenone and
j2
Isolate the product.
Dates
microscale procedures)
j3
Characterize and analyze.
Feb18
2. Complete Exercises: pp. 605-606 questions
j4
Present, analyze, and discuss results in written a
Feb 25
2, 6, 7, 13
report.
Exp K. Fischer Esterification Reaction of a Carboxylic Acid Derivative: Preparation of Benzocaine
8-14
k1
Conduct an acid-catalyzed esterification of a
1. Read: pp. 651-655 (Fischer esterification);
carboxylic acid with an alcohol.
pp. 655-658 (preparation of benzocaine and
Dates
microscale procedures)
k2
Isolate the product.
Mar 3
2. Complete Exercises: pp. 658-659 questions
k3
Characterize and analyze.
Mar 17
7, 11
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
l1
Conduct synthesis of an amide from a carboxylic acid 1. Read: pp. 661-663 (amides and insect
via the corresponding acid chloride.
repellents); pp. 664-668 (preparation of N,NDates
diethyl-m-toluamide and microscale
l2
Isolate the product.
Mar 24
procedures)
l3
Characterize and analyze.
Mar 31
2. Complete Exercises: pp. 668-669 question
l4
Present, analyze, and discuss results in a written
12
report.
Exp M. Synthesis Exam
5
m1
Understand and apply techniques to synthesize
All course material
organic molecules.
Date
Apr 7
Exp N. Qualitative Identification of Organic Compounds by Functional Group Differentiation
15
n1
Use qualitative functional group tests to identify and
1. Read: pp. 817-821 (qualitative analysis);
match 6 unidentified compounds to a list of 6 known
pp. 867-868 (ceric nitrate test for alcohols); pp.
Date
compounds.
840-842 (2,4-DNP test for aldehydes and
Apr 14
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, 4 th ed.
(except as noted).