HAZARD COMMUNITY AND TECHNICAL COLLEGE
Division of Sciences and Mathematics
CHE 233 Organic Chemistry Laboratory II
SEMESTER: Fall 2007
CLASS TIME: Mondays and Wednesdays, 12:30 to 3:30 p.m.
INSTRUCTOR: John F. Hoppe, Ph.D.
OFFICE LOCATION: Room JCC 258
OFFICE HOURS (Hazard Campus): Mondays and Wednesdays, 3:30 to 5:30 p.m.
Tuesdays and Thursdays, 2:30 to 5:30 p.m.
E-MAIL: John.Hoppe@kctcs.edu
OFFICE PHONE: (606) 487-3250
COURSE DESCRIPTION: Laboratory for CHE 232.
PREREQUISITE: CHE 231; PREREQUISITE OR CONCURRENT: CHE 232
TEXTBOOKS
J McMurry. Organic Chemistry, 6th Ed. Belmont, CA; Thompson Learning, 2004.
ISBN 0-534-38999-6
AM Schoffstall, BA Gaddis, and ML Druelinger, Microscale and Miniscale Organic
Chemistry Laboratory Experiments, 2nd Ed. Boston: McGraw-Hill, 2004.
ISBN 0-07-242456-7
Bound laboratory notebook with carbons and perforated pages
COURSE COMPETENCIES
1) Perform and explain the underlying principles for organic separation and purification
techniques such as column chromatography and sublimation.
2) Use the chemical literature to obtain information about the physical properties of
compounds.
3) Trace the fate of a synthetic compound through the techniques used to isolate and
purify the compound.
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4) Characterize an organic product using descriptive and physical methods including
melting point determination, boiling point determination, refractive index, solubility
density, and infrared spectra.
5) Keep an accurate laboratory notebook of observations made while performing a
laboratory experiment.
6) Prepare tables and graphs as needed to present experimental data in organized form.
7) Determine the theoretical yield and percent yield for a synthetic product.
8) Explain and interpret experimental results including possible causes for high and
low yields.
9) Having performed these reactions in laboratory, write chemical equations for
examples of Diels-Alder reactions, addition polymerizations, Grignard reactions,
reductions, oxidations, Wittig synthesis, aldol condensations, Fisher esterifications,
and electrophilic aromatic substitutions.
10) Use visible spectrophotometric measurements to monitor a reaction and to determine
its rate constant and half life.
Students will be assigned readings from the text and will be expected to summarize and
interpret this information in a written pre-lab report. Students will learn new laboratory
techniques by watching the technique demonstrated and by following written procedures
as they perform the technique. Upon satisfactory completion of a laboratory experiment
or exercise, students will submit a final written report. Student’s observations,
calculations, tables, graphs, discussion, and conclusions will be included in the report.
Attainment of these competencies will be assessed by observing the students work,
grading their laboratory reports, and by giving two written examinations.
GENERAL EDUCATION COMPETENCIES
I.
Communicate effectively
1.
Read and listen with comprehension.
2.
Speak and write clearly using standard English.
3.
Interact cooperatively with others using both verbal and non-verbal means.
4.
Demonstrate information processing through basic computer skills.
II.
Think critically
1.
Make connections in learning across the disciplines and draw logical
conclusions.
2.
Demonstrate problem solving through interpreting, analyzing,
summarizing, and/or integrating a variety of materials.
3.
Use mathematics to organize, analyze, and synthesize data to solve a
problem.
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III.
Learn independently
1.
Use appropriate search strategies and resources to find, evaluate, and use
information.
2.
Make choices based upon awareness of ethics and differing
perspectives/ideas.
3.
Apply learning in academic, personal, and public situations.
4.
Think creatively to develop new ideas, processes, or products.
IV.
Examine relationships in diverse and complex environments
1.
Recognize the relationship of the individual to human heritage and culture.
2.
Demonstrate an awareness of the relationship of the individual to the
biological and physical environment.
3.
Develop an awareness of self as an individual member of a multicultural
global community.
In a science course, communication competencies are usually measured indirectly.
Students who comprehend readings from the textbook, comprehend standard spoken
English, write clearly, and form study groups with fellow students usually perform better
in this course. Students will apply mathematics to solve science problems. To perform
well in this course, students will need to study individually as well as in class and with
others. Students should use any available resources and apply creative thinking to solve
the assigned problems. Choices students make regarding study time and intensity of
study will affect their grade.
Chemistry is central to the technological age in which we live. The development of
chemistry has been a global process and the applications of chemistry have become an
integral part of our human heritage and culture. Students studying chemistry develop a
stronger awareness of their common chemical selves as well as their unique individual
natures.
ATTENDANCE POLICY
Attendance is mandatory for laboratory sessions. A record of attendance will be kept by
the instructor. One makeup laboratory session is scheduled at the end of the semester.
Other makeup sessions may be held at the instructor’s discretion.
INCLEMENT WEATHER POLICY
When the start of classes is delayed because of inclement weather, all classes scheduled
before 9:30 a.m. will be cancelled. Because CHE 233 begins after 9:30 a.m., its meeting
time will not be affected by inclement weather delays.
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ACADEMIC HONESTY POLICY
KCTCS faculty and students are bound by principles of truth and honesty that are
recognized as fundamental for a community of teachers and scholars. When a student is
guilty of cheating or plagiarism, the faculty member has options ranging from assigning a
lower grade to the test or paper to recommending suspension or expulsion from the
college. The action taken is at the discretion of the faculty member. More information
about academic offenses and student's rights including the student's right to appeal is
described in the KCTCS Code of Student Conduct
(http://www.kctcs.edu/student/code.htm).
WITHDRAWAL POLICY
August 24 is the last day to withdraw from the course without receiving a grade. October
15 is the last day to withdraw and automatically receive a grade of W. Also, October 15
is the last day to change from credit to audit. December 7 is the last day a student may
withdraw and at the discretion of the instructor receive a grade of W. The student will
receive a W if the instructor is convinced that the student has made an effort to attend
class regularly and to complete all assigned work. Students who stop attending class and
do not officially withdraw will receive a grade of E.
ACCOMMODATIONS POLICY
Students needing special accommodations should contact the local disabilities service
representative (Doug Fraley on the Hazard campus) to complete an Accommodations
Plan. This Plan should ensure that the student receives the full benefits of this course by
making the instructor aware of any accommodations needed.
EVALUATIONS METHODS
A handout describing the format for written laboratory reports will be distributed at the
first laboratory session. Before starting a new lab, students are expected to read the
assigned readings and to write a pre-lab report. The pre-lab report is due at the beginning
of the laboratory session. Submitting the pre-lab report will cause 5% to be deducted
from the grade for the complete laboratory report. The Results and Summary sections of
the laboratory report are due at the beginning of the laboratory session following
completion of the lab. The required laboratory notebook has carbons and perforated
pages to allow the carbon copy to be submitted, while the original copy is retained in the
notebook. The laboratory reports will be graded. A zero will be assigned for missed
laboratory sessions which are not made up.
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Two laboratory exams will be administered. The exams will contain individual and
structured group work sections. Missed exams will be scored as zero
The course grade will be calculated from the scores obtained on laboratory reports (80%)
and lab exams (20%). The final grading scale will be as follows:
100 - 90
89 - 80
79 - 70
69 - 60
59 - 0
A
B
C
D
E
COURSE OUTLINE
Session 1:
Sessions 2-4:
Sessions 5-6:
Sessions 7-8:
Sessions 9-10:
Sessions 11-12:
Sessions 13-14:
Sessions 15-16:
Session 17
Session 18:
Session 19:
Sessions 20-21:
Sessions 22-23:
Sessions 24-25:
MSDS Video/Check in
Nuclear Magnetic Resonance Spectroscopy (McMurry, pp. 424-452;
Schoffstall et al., pp. 125-148)
Infrared Spectroscopy (McMurry, pp. 403-414; Schoffstall et al.,
pp. 110-121)
Diels-Alder: Reaction of 1,3-Butadiene with Maleic Anhydride
(Schoffstall et al., pp. 271-276, Part A)
Addition Polymers: Preparation of Polystyrene and Polymethyl
Methacrylate (Schoffstall et al., pp. 251-254, Parts A and C, use
10 mg benzoyl peroxide instead of tert-butyl peroxybenzoate)
Grignard Reaction: Synthesis of Triphenylmethanol from
Benzophenone (Schoffstall et al., pp. 351-358, Part A, oven dry
glassware before laboratory)
Reduction of Benzil by Sodium Borohydride (Schoffstall et al.,
pp, 364-366, Part A)
Mass Spectrometry (McMurry, pp. 394-402; Schoffstall et al.,
pp. 160-171)
Exam
Sublimation (Schoffstall et al., pp. 45-48, 50-51, Exercise F.5 or F.6)
Ultraviolet-Visible Spectroscopy: Kinetics of Chromic Acid Oxidation
Of Alcohols (McMurry, pp. 482-485; Schoffstall et al., pp. 154-159;
Pavia et al., pp. 234-240)
Wittig Synthesis: Preparation of trans-9-(2-phenylethenyl)anthracene
(Schoffstall et al., pp. 386-389, Part B)
Aldol Condenstion: Identification of a Mixed Aldol Product
Schoffstall et al., pp. 404-407, 410, Part C)
Separations Based on Acidity and Basicity (Schoffstall et al.,
pp. 200-203, Parts A and B, use p-nitroaniline instead of ethyl
aminobenzoate)
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Sessions 26-27: Fisher Esterification: Synthesis of Fruity Esters (Schoffstall et al.,
pp. 430-435, Parts A and B, General Procedure 1)
Sessions 28-29: Column Chromatography; Bromination of p-Methylacetanilide
(Schoffstall et al., pp. 97-99, 316-317, 319-320, Part B)
Session 30:
Exam/Check out