Organic Chemistry I
Laboratory Program
Summer 2008
Course Exp Experiment Objective Description
Assignment
Goal
Obj
Exp A. Introduction to the Organic Laboratory and Characterization Techniques
8-12
a1
Identify the safety features and physical layout of the
1. Scan: Ch 1-2.
organic laboratory.
2. Read: instructor provided
procedures; pp. 93-97
a2
Locate and operate instruments and equipment in the
(recrystallization); pp. 106-107
laboratory.
(benzoic acid); p. 108
a3
Recrystallize a pure sample of either benzoic acid or
(naphthalene); pp. 113-117
naphthalene.
(melting points); pp. 118-119
a4
Characterize benzoic acid, naphthalene, and a mixture
(capillary-tube melting points);
of these two by melting point analysis.
pp. 175-180 (thin layer
a5
Characterize common household products (Anacin,
chromatography)
Excedrin, Tylenol, aspirin, caffeine) using thin layer
3. Complete Exercises: pp.
chromatography.
110-113 questions 8, 18, 31; pp.
a6
Present, analyze, discuss results in a written report.
119-121 questions 3, 4, 14, 15;
p. 184 questions 2, 3, 7
Exp B. Extraction of a Natural Product: Isolation of Trimyristin from Nutmeg
8-12
b1
Use extraction techniques to isolate a natural product.
1. Read: pp. 149-152 (theory
of extraction); 167-168
b2
Characterize and analyze.
(extraction of a natural product);
b3
Present, analyze, discuss results in written a report.
pp.168-170 (trimyristin and
microscale procedures)
2. Complete Exercises: pp.
170-171 questions 2, 4, 5, 7, 8
Exp C. Acid-Base Extraction: Extract Components of a Mixture of an Acid (benzoic acid), Base (4nitroaniline), and Neutral (naphthalene)
8-12
c1
Use extraction techniques to isolate an acid, base, and
1. Read: pp. 152-157 (base and
neutral compound.
acid extractions); p. 162 (acidbase extraction microscale
c2
Characterize and analyze.
procedures)
c3
Present, analyze, discuss results in a written report.
2. Complete: instructor
provided pre-lab questions.
Exp D. Bromination of Alkenes: Bromination of (E)-Stilbene
8-12,
d1
Conduct an electrophilic addition reaction of alkenes.
1. Read: pp. 333-334 (alkenes
14
introduction); p. 372
d2
Isolate the product.
(bromination of alkenes); pp.
d3
Characterize and analyze.
372-374 (stilbene and
d4
Present, analyze, discuss results in written a report.
microscale procedures)
2. Complete Exercises: pp.
374-375 questions 1, 2, 9, 15
Exp E. Electrophilic Aromatic Substitution: Friedel-Crafts Alkylation of p-Xylene
8-12,
e1
Conduct an electrophilic aromatic alkylation of an
1. Read: pp. 481-484
14
activated arene.
(introduction, Friedel-Crafts
alkylation), pp. 485-488
e2
Assess the relationship between carbocation
(alkylation of p-xylene and
rearrangement and arene nucleophilicity.
microscale procedures)
e3
Isolate the product.
2. Complete Exercises: pp.
e4
Characterize and analyze.
488-493 questions 1, 3, 7, 10
e5
Present, analyze, discuss results in a written report.
Exp F. Nucleophilic Substitution Reactions: SN1 vs SN2
8-12,
f1
Review SN1, SN2, E1, E2 reactions and mechanisms.
1. Read: pp. 451-455
14
(nucleophilic aliphatic
f2
Compare and contrast the effect of the leaving group
CHEM 2211L
Georgia Gwinnett College
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School of Science & Technology
Organic Chemistry I
Laboratory Program
Summer 2008
and the substrate structure on nucleophilic substitution
reactions of primary, secondary, and tertiary alkyl
halides and aryl halides.
Present, analyze, discuss results in a written report.
substitution); Review McMurry
pp. 371-389 (SN2 & SN1
reactions); pp. 392-400
(elimination reactions)
f3
2. Complete instructor provided
pre-lab questions.
Exp G. Spectroscopy: Mass Spectroscopy (MS), Infrared Spectroscopy (IR), Ultra-Violet and Visible
Spectroscopy (UV-Vis), and Nuclear Magnetic Resonance Spectroscopy (NMR)
8-12,
g1
Learn to use the IR and UV-Vis instrumentation in the 1. Scan: pp. 233-238.
13
lab
2. Review: McMurray
Chapters 11-12.
g2
Understand and apply concepts and techniques from
3. Complete instructor provided
MS, IR, UV-Vis, and NMR to analyze individual
pre-lab exercises.
spectra of each type.
g3
Access spectra on web databases.
g4
Integrate analysis of MS, IR, UV-Vis, and NMR to
determine structure of unknown compounds
g5
Present, analyze, discuss results in written report
All experiments:
1. are microscale.
2. begin with a written quiz.
3. are 2 laboratory sessions of 3 hours each for a total of 6 hours per experiment.
4. require an individual student written report.
5. and assignments refer to Gilbert and Martin, Experimental Chemistry: a Miniscale and Microscale
Approach, 4th ed. (except as noted).
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Georgia Gwinnett College
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2/15/2016
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