CHEM 234-Organic Synthesis and Analysis IV
Spring 2015
Laboratory Sections:
901:
902:
903:
904:
905:
MW 1:50-4:40 pm (Rm 2210)
TR 9:35 am-12:25 pm (Rm 2210)
TR 9:35 am-12:25 pm (Rm 2212)
TR 2:20-5:10 pm (Rm 2210)
TR 2:20-5:10 pm (Rm 2212)
Common Lecture:
F 3:00-3:50 pm (Rm 2104)
Instructors
901
Dr. Kenn Harding
Rm 2208 CHEM
E-mail: harding@mail.chem.tamu.edu
902
Dr. Amber Schaefer
Rm 412 HELD
845-6786
E-mail: aschaefer@chem.tamu.edu
903,
Dr. Tammy Tiner
Rm 2207 CHEM
904
Dr. Lin Jiang
Rm 35 CHEM
905
845-5433
862-4292
E-mail: tiner@chem.tamu.edu
845-3944
E-mail: lin.jiang@chem.tamu.edu
Instrumentation Manager
Vishruth Gowda
Rm 1116 CHEM
845-2232
E-mail: vishruth.gowda@chem.tamu.edu
Teaching Assistants
901
Jeffery Tharp
Rm 1223 CHEM
845-5229
E-mail: jeffery.tharp@chem.tamu.edu
902
Brendan Foley
Rm 1116 CHEM
845-2232
E-mail: brendan.foley@chem.tamu.edu
903
Brian Young
Rm 1116 CHEM
845-2232
E-mail: brian.young@chem.tamu.edu
904
Sasha Chihak
Rm 318 CHEM
905
Shogo Mori
Rm 1116 CHEM
Tammy H. Tiner, Spring 2015
845-2913
E-mail: sasha.chihak@chem.tamu.edu
845-2232
E-mail: smori@chem.tamu.edu
Course Description: Organic Synthesis and Analysis IV involves the synthesis of significant types of
organic compounds and study of their properties; laboratory separation of mixtures of organic substances,
identification of compounds through instrumental methods of separation, identification and analysis.
This is a writing intensive course.
Learning Objectives: The course will cover (1) the understanding and design of organic experiments, (2)
organic laboratory techniques, (3) the use , interpretation and presentation of analytical and spectroscopic
data, (4) the communication of scientific results by clear, concise, and precise writing, and (5) the
application of the scientific method to organic chemistry research, including the acquisition of results from
"failed" experiments, the use of data to support conclusions, proper documentation of observations in a
high-quality research notebook, and the formal reporting of results.
Prerequisites
CHEM 228 or registration therein; CHEM 237 or CHEM 231
Required Materials
Text:
“Experimental Organic Chemistry: A Miniscale and Microscale Approach” by John C. Gilbert and
Stephen F. Martin, 5th Edition, 2011, Cengage Learning,
Bundle: Custom CHEM 234 Organic Chemistry at TAMU, 5th + Custom Printed Access Card OWL
Gilbert Lab Skills/YouBook Organic Chemistry
ISBN-10: 1-285-91581-X, ISBN-13: 978-1-285-91581-4
The URL for online purchase is: https://owl.cengage.com/partners/tamu/
Students MUST have the electronic resource
Prelaboratory Assignments will be electronic.
package
since
Lab Notebook: NO handwritten notebook will be used in this course. We will use electronic
laboratory notebooks (ELN) through LabArchives that can be accessed by web browser on any
computer or tablet with internet access. You will enter pre- and post-lab information outside of lab
hours. During lab, you will enter your data using your own laptop or tablet (with wireless access to
internet) if you bring one with you. If you do not bring your own device, we will provide a
Chromebook for your use only during the lab period. Your lab reports will be graded electronically
by your TAs. Instead of purchasing a duplicating page notebook, you will need to purchase an online access code ($10) from LabArchives; we will help you get set up with both Cengage LabSkills
and LabArchives during the first lab Meeting.
Safety Goggles: These are available at the MSC bookstore and are usually sold the first week by GSAC.
After the first day, no one will be admitted without goggles.
Enclosing shoes: Sandals/flip flops are not allowed.
Long pants: Dresses, capris, and shorts are not allowed.
Optional Materials
Lab Coat: A lab coat is suggested to protect your clothing from chemical spills and splashes.
Tammy H. Tiner, Spring 2015
2
Recommended Text: “The ACS Style Guide: Effective Communication of Scientific Information”
3rd ed. Edited by Anne M. Coghill and Lorrin R. Garson (American Chemical Society, ISBN-13 :
978-0-8412-3999-9). Can be accessed from TAMU computers at
http://pubs.acs.org/isbn/9780841239999
Friday Lectures
Friday Lectures will be devoted to discussing theory, techniques, and topically interesting material related
to the laboratory you will be performing the following week and how experimental data is presented in
written formats. Writing Assignments will be introduced and discussed. Attendance at the Friday
Lectures is mandatory.
Course Grade
The total maximum points in this lab will be distributed as follows.
Searching the Literature Exercise
Laboratory Performance and Notebook
Prelaboratory Assignments
Writing Assignments
JOC Manuscript
Final Exam
1 x 50 pts
12 x 40 pts
12 x 10 pts
4 x 50 pts
100 pts
1 x 100 pts
=
=
=
=
=
=
Total
50 pts
480 pts
120 pts
200 pts
100 pts
100 pts
1050 pts
Searching the Literature Exercise
The first assignment in CHEM 234 is a Searching the Literature Exercise to acquaint students with
the various resources for accessing the chemical literature.
Laboratory Performance and Notebook
Advance preparation is very important in organic chemistry to promote optimum performance and
understanding and for the prevention of accidents. This is true not only for undergraduates in instruction
laboratories, but also students in graduate school and scientists working in various organic synthesis fields.
You should be very familiar with the reaction and techniques you will be performing or using in the
laboratory. A critical part of this preparation is the completion of a proper pre-laboratory section in your
Laboratory Notebook. Beyond this, it is imperative that you do the assigned readings, including
techniques sections that are pertinent to the reaction to be performed. Friday Lectures are crucial to your
pre-lab preparation. Students will receive a Laboratory Performance and Notebook grade for each
experiment in the course. A separate handout on Laboratory Performance and Notebook provides detailed
guidelines for the writing and the grading of the Laboratory Notebook.
Prelaboratory Assignments
The purpose of Prelaboratory Assignments, consisting of OWL LabSkills Prelabs and/or Prelaboratory
Quizzes, is to provide a student with adequate preparation for each main experiment. Prelaboratory
Assignments will be completed electronically and submitted no later than three hours prior to the
laboratory in which the experiment is started. Students who fail to submit a Prelaboratory Assignment
will NOT be allowed to work in the laboratory until the assignment is submitted. Prelaboratory
Assignments are worth 10 points each.
Tammy H. Tiner, Spring 2015
3
Writing Assignments
CHEM 234 is a ‘writing intensive course’ at TAMU. To achieve Learning Objectives (3), (4) and (5) (see
above), there will be four Writing Assignments specifically designed to instruct students in the preparation
of an article to be published in a scientific journal. Each assignment focuses on particular sections of a
journal article and is worth 50 points. Instruction for these writing assignments will occur in the Friday
Lectures and be accompanied with appropriate handouts and examples. These assignments will precede
the preparation of a complete manuscript, written in the style of a journal article.
JOC (Journal of Organic Chemistry) Manuscript
In addition to keeping a detailed Laboratory Notebook, which will be graded weekly, a formal JOC
Manuscript will be submitted towards the end of the semester. This manuscript will be written in the style
of a journal article.
After the completion of the four Writing Assignments, a formal JOC Manuscript will be prepared and
submitted for grading. Students will rewrite the previous four writing assignment submissions in
preparing this JOC Manuscript, which is worth 100 points.
Detailed instructions on the preparation of the JOC Manuscript will be provided during Friday Lectures,
with appropriate handouts and examples.
**NOTE: A student who fails the writing portion of CHEM 234 WILL fail the course.**
Performing Experiments
ALL experiments MUST be performed ONLY during scheduled laboratory hours including, but not
limited to, reactions, isolation, extraction, and purification of products by recrystallization, rotary
evaporation, flash chromatography or distillation. However, students may obtain characterization data
(NMR, IR, melting points ONLY) outside of normal laboratory time. Under no circumstances should
reactions or anything else besides NMR, IR, or melting points be performed without a TA present
because of safety considerations.
Absences
To prevent a University absence from being counted against you, you must notify an instructor prior to the
laboratory or lecture you will miss or, at the latest, prior to performing the next experiment. You will be
required to provide valid documentation regarding a University excused absence.
Make-up laboratory experiments may be scheduled with Dr. Tiner (who will coordinate with a TA from
another section to have you perform the experiment in their section) but only after providing
documentation to your instructor regarding the excused absence.
Final Exam
A mandatory 2-hour multiple choice/short answer final exam will be given at the scheduled time for
common lecture class time (Tuesday, May 12, 2015, 10:30 am-12:30 pm) in CHEM 2104.
Tammy H. Tiner, Spring 2015
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A Message About Copyright Infringement/Plagiarism/Cheating
The handouts used in this course are copyrighted. "Handouts" mean all materials generated for this class,
which include but are not limited to syllabi, quizzes, exams, lab problems, in-class materials, review sheets,
and additional problem sets. Because these materials are copyrighted, you do not have the right to copy
the handouts, unless permission is expressly granted.
Aggie Honor Code: "An Aggie does not lie, cheat, steal, or tolerate those who do."
Upon accepting admission to Texas A&M University, a student immediately assumes a commitment to
uphold the Honor Code, to accept responsibility for learning, and to follow the philosophy and rules of the
Honor System. Ignorance of the rules does not exclude any member of the TAMU community from the
requirements or the processes of the Honor System.
For additional information please visit:
http://aggiehonor.tamu.edu/
Suspected violations of the Aggie Honor Code will be referred to the Aggie Honor System Office for
appropriate action.
The main issues that arise in laboratories are Fabrication/Falsification, Plagiarism and Complicity.
Fabrication/Falsification: Definition of Fabrication: Making up data or results, and recording or reporting
them; submitting fabricated documents. Definition of Falsification: Manipulating research materials,
equipment, or processes, or changing or omitting data or results such that the research is not accurately
represented in the research record. These two areas are closely related in that one involves creation of
information and the other involves manipulating it. The key is that one is misrepresenting information
inaccurately.
Plagiarism: Definition: The appropriation of another person's ideas, processes, results, or words without
giving appropriate credit.
Examples:
•Intentionally, knowingly, or carelessly presenting the work of another as one’s own (i.e., without
crediting the author or creator).
•Failing to credit sources used in a work product in an attempt to pass off the work as one’s own.
•Attempting to receive credit for work performed by another, including papers obtained in whole or in
part from individuals or other sources. Students are permitted to use the services of a tutor (paid or
unpaid), a professional editor, or the University Writing Center to assist them in completing assigned
work, unless the instructor explicitly prohibits such assistance. If the student uses such services, the
resulting product must be the original work of the student. Purchasing research reports, essays, lab reports,
practice sets, or answers to assignments from any person or business are strictly prohibited. Sale of such
materials is a violation of both these rules and State law.
•Failing to cite the World Wide Web, databases and other electronic resources if they are utilized in any
way as resource material in an academic exercise.
•Other similar acts.
Tammy H. Tiner, Spring 2015
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Complicity: Definition: Intentionally or knowingly helping, or attempting to help, another to
commit an act of academic dishonesty. Showing your assignment to others or sending computer
file versions of your assignment to others can result in a complicity violation.
For more information on the Definitions of Academic Misconduct see:
http://aggiehonor.tamu.edu/RulesAndProcedures/HonorSystemRules.aspx#definitions
Americans with Disabilities Act (ADA) Policy Statement
The Americans with Disabilities Act (ADA) is a federal antidiscrimination statue that provides
comprehensive civil rights protection for persons with disabilities. Among other things, this legislation
requires that all students with disabilities be guaranteed a learning environment that provides for
reasonable accommodation of their disabilities. If you believe you have a disability requiring an
accommodation, please contact the Department of Student Life, Services for Students with Disabilities in
Rm 126 of the Koldus Building, or call 845-1637.
Tammy H. Tiner, Spring 2015
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CHEM 234 Tentative Schedule of Experiments
Wk.
1
Text References:
(Required Reading in GM
PRIOR to Lecture or
Laboratory)
Date
(Notebook
Due Date)
Day
Experiment
Jan. 19/20
M/T
MLK Holiday
Jan. 21/22
W/R
Check-In; Course Introduction, Inventory
Glassware, Bench Set-up.
-1H and 13C NMR and IR (sign-up for
training on instruments begins)
Jan. 23
F
Ch. 1, pp. 1-25
Ch. 26, pp. 905-920
-Course Introduction: Discuss Safety, Lab
Notebook Format
-Searching the Literature Exercise (SLE)
2
3
Jan. 26/27
M/T
Ch. 6: 6.1 (pp. 179-180), 6.3 (pp.
188—194)
Column Chromatography and IR (CC)
Ch. 2:2.6-7 (pp. 37-41), Ch. 3:3.3 -1H and 13C NMR and IR (sign-up for
(pp. 113-118)
training on instruments continues)
Ch. 8: 8.1-8.2 (pp. 237-261)
Jan. 28/29
W/R
Handout Provided
Ch. 8: 8.4 (pp. 297-303)
Feb. 2/3
M/T
Ch. 4: 4.1-2 (pp.127-129), 4.4
(pp. 135-143)
Ch. 2: 2.1-2 (pp. 27-29), 2.4-5
(pp. 31-37), 2.9 (pp. 43-51)
Liquid Unknowns: Separation and
Identification (LU)
W/R
Ch. 2: 2.14 (pp. 58-59)
Continue Liquid Unknowns
(CC Due)
Feb. 4/5
Ch. 8: 8.3 (pp.261-297)
(UV Due)
4
Feb. 9/10
M/T
Ch. 3: 3.1-3.2 (pp. 93-103), B. 4- Solid Unknown: Purification and
Identification (SU)
5. (p. 105-106)
Feb. 11/12
W/R
Ch. 2: 2.17 (pp. 66-71), 2.18 (p.
(LU Due)
5
UV of Sunscreens
Feb. 16/17
Continue Solid Unknown
72)
M/T
Handout Provided, Refer to Ch.
Fischer Esterification (FE)
20: 20.1-2 (pp.669-674)
Feb. 18/19
(SU Due)
W/R
Tammy H. Tiner, Spring 2015
Ch. 2: 2.11 (pp. 52-54)
7
Finish FE
6
Feb. 23/24
M/T
Ch. 18: 18.1-2 (pp.601-607)
Wittig Reaction (WR)
Ch. 2: 2.22 (pp. 81-83)
Feb. 25/26
W/R
(FE Due)
7
Mar. 2/3
Ch. 2: 2.13 (pp. 55-57), 2.21
(pp. 75-78)
M/T
Ch. 17: 17.1 (pp. 563-565), 17.4 Reduction of 4-t-butylcyclohexanone
(Red.)
(pp.581-584)
Mar. 4/5
Finish Wittig
W/R
Finish Reduction
(WR Due)
8
Mar. 9/10
M/T
Mar. 11/12
W/R
Handout Provided, Refer to Ch.
19: 19.1-2 (pp.639-643, 659-660) Grignard Reactions (GR)
Purification of Grignard Product
(Red. Due)
9
Mar. 23/24
M/T
Handout Provided for Procedure
Mar. 25/26
W/R
Ch. 18: 18.4 (pp. 625-627)
M/T
Ch. 15: 15.1 (pp. 491-492), 15.4
Michael + Aldol Sequence (M+A)
(GR Due)
10
Mar. 30/31
Nitration of Bromobenzene (NB)
A, B, C (pp. 513-519)
Apr. 1/2
Continue Nitration of Bromobenzene
W/R
(M+A Due)
11
Apr. 6/7
M/T
Handout Provided for Procedure
Friedel-Crafts Acylation and Vacuum
Distillation (FCA)
Apr. 8/9
W/R
Ch. 2: 2.15 (pp. 60-64), 2.23
Continue FCA
(NB Due)
12
Apr. 13/14
(pp. 83-84)
M/T
Ch. 21: 21.1-2C-E (pp. 703-
Sulfanilamide Synthesis (SS)
711, 714-718)
Apr. 15/16
W/R
Continue SS
(FCA Due)
Tammy H. Tiner, Spring 2015
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Apr. 20/21
M/T
Ch. 12: 12.1,2,3B (pp. 421-425, Diels-Alder Reaction (DA)
428-429)
13
14
Handout Provided
DA Molecular Modeling
Apr. 22/23
W/R
Apr. 27/28
M/T
Finish Up Everything
Apr. 29/30
W/R
Check out of Lab
(SS Due)
15
May 5
T
Friday Lecture - Redefined Day
T
Comprehensive Final Exam
Final Exam Review
(DA Due)
May 12
Tammy H. Tiner, Spring 2015
9
10:30-12:30 in Rm 2104