College of San Mateo
Course Outline
New Course
Update/No change
Course Revision (Minor)
Course Revision (Major)
Date: February, 2009
Department:
Chemistry
Number: 232
Course Title:
Organic Chemistry II
Units:
Total Semester Hours: Lecture: 48
5
Lab: 80 plus 16 recitation
Homework: 80
By
Arrangement: 16
Length of Course
Grading
Semester-long
Short course (Number of weeks
Letter
)
Open entry/Open exit
1.
Pass/No Pass
Grade Option (letter or Pass/No Pass)
Prerequisite (Attach Enrollment Limitation Validation Form.)
Chemistry 231 with a grade of C or better
2.
Corequisite (Attach Enrollment Limitation Validation Form.)
3.
Recommended Preparation (Attach Enrollment Validation Form.)
4.
Catalog Description (Include prerequisites/corequisites/recommended preparation.)
232 Organic Chemistry II (5) Minimum of 48 hours of lecture, 80 hours of lab, 16 recitation hours
plus 16 hours by arrangement per term. Prerequisite: CHEM 231. More rigorous treatment of
mechanisms, reactions and synthesis; structure determination using classical and spectroscopic
techiniques taught in Chem 231 including identification of unknown compounds and mixtures.
Extra supplies may be required. (CSU/UC)
5.
Class Schedule Description (Include prerequisites/corequisites/recommended preparation.)
More rigorous treatment of mechanisms, reactions and synthesis; structure determination using
classical and spectroscopic techiniques taught in Chem 231 including identification of unknown
compounds and mixtures. Extra supplies may be required. Prerequisite: CHEM 231. (CSU/UC)
6.
Student Learning Outcomes (Identify 1-6 expected learner outcomes using active verbs.)
Upon successful completion of the course, the student will be able to:
The student should be able to:
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A. Apply structure-reactivity principles to relate observable physical and chemical properties of
organic molecules to their three-dimensional structures and polarities. Extend these principles
to applications in related fields such as medicine and bioengineering.
B. Predict products of chemical reactions and propose a detailed reaction mechanism to
explain the experimental results observed; extend these mechanisms by analogy to similar
systems.
C. Use information from several sources and combine these data into a consistent model to
determine structures of unknown molecules.
D. Perform classical and modern analytical and purification techniques on more complex
mixtures. Record the experimental observations in a logical order.
7.
Course Objectives (Identify specific teaching objectives detailing course content and activities.
For some courses, the course objectives will be the same as the student learning outcomes. If
this is the case, please simply indicate this in this section).
See #6
8.
Course Content (Brief but complete topical outline of the course that includes major subject
areas [1-2 pages]. Should reflect all course objectives listed above. In addition, you may attach
a sample course syllabus with a timeline.)
Additional material on the last two topics listed in the Chem 231 Course Outline
COURSE LECTURE:
Reactions, reagents, and mechanisms:additional classes to be studied are aromatic hydrocarbons,
aldehydes and ketones, amines, carbolic acids and their derivatives, polyfunctional compounds,
organometallic compounds including modern reducing agents and their properties; concerted
reactions; natural and synthetic polymers. Modern analysis of compounds: NMR spectroscopy, IR
spectroscopy; simple mass spectral degradation patterns.
LABORATORY:
Topic: Multistep synthesis using a range of synthesis, isolation, purification and characterisation
techniques.
Students should be able to synthesis a series of organic compounds (benzaldehyde to benzoin,
then benzil, then tetraphenylcyclopentadienone and also benzilic acid) while maintain yield over
a multistep sequence.
Topic: Advanced Synthetic reactions
Coverage: Single or multi-step conversions from the standpoint of type of reaction and of
effective performance. Examples to elucidate lecture material.
Students should be able to understand the basis of, and carry out successfully, lab-manual type
conversions and subsequent work-ups. Examples of experiments include Grignard reagents,
Friedel-Craft Acylation and nitration of aromatic compounds, record the results in good order,
possibly in format suitable for journal publication.
Topic: Spectra
Coverage: Further uses of IR and nmr spectra.
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Students should be able to interpret simple spectra, and deduce structure. Take IR spectra.
interpret 1H nmr spectra with minimal instructor assistance.
9.
Representative Instructional Methods (Describe instructor-initiated teaching strategies that
will assist students in meeting course objectives. Include examples of out-of-class assignments,
required reading and writing assignments, and methods for teaching critical thinking skills.)
If hours by arrangement are required by this course, indicate the additional instructional
activity which will be provided during this time.
The course will include the following instructional methods as appropriate, in approximate order
- Lecture format used to introduce new concepts and information; time will be provided to
encourage student participation in question/answer period.
- Theory, purpose, and practice of the lab experiment will be outlined by the instructor during
the recitation period. Student will perform experiments on individual basis/ some experiments
are class projects that require assigned student groups.
- Class participation in the evaluation of data collected.
- Where appropriate, selected topics will be complemented by multimedia resources.
- Hours by arrangement activities are supervised and may include online search of science
databases and references, practice on using molecular models, group discussions on current
scientific affairs or relevance to course materials and peer-to-peer learning activities.
10.
Representative Methods of Evaluation (Describe measurement of student progress toward
course objectives. Courses with required writing component and/or problem-solving emphasis
must reflect critical thinking component. If skills class, then applied skills.)
- Frequent exams covering two or three chapters of the text. (short questions, multipart
questions, problem solving)
- Regular end-of-chapter quizzes
- Lab write-ups for each experiment, which include purpose, a detailed procedure, analysis of
results, and answers to questions designed to elicit critical thinking. Some experiments are
selected for more exhaustive treatment in a style appropriate for journal publication. For these
write-ups, the student clarifies the purpose of the experiment, develops and rationalizes the
experimental protocol, and justifies conclusions drawn from results.
11.
Representative Text Materials (With few exceptions, texts need to be current. Include
publication dates.)
LECTURE TEXT:
McMurry, Organic Chemistry, 7th Edition, publisher: Brooks Cole, 2007.
ISBN-13: 978-0495118374
Study Guide for McMurray’s Organic Chemistry 7th edition, 2007
ISBN-13: 978-0495112686
LABORATORY TEXT: Pavia, Kriz, Lampman, Engel, Micro and Macro Techniques in the Organic
Laboratory, Saunders College
Occasional topical articles assigned to maintain currency of lecture material.
Prepared by:
(Signature)
Email address:
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Submission Date:
CHEMISTRY 232 SPRING 2008
TEXT BOOKS AND COURSE MATERIALS
•
Carey, Organic Chemistry, 6th edition, McGraw Hill
•
Atkins & Carey, Student Solutions Manual to accompany Organic Chemistry, 6th edition, McGraw
Hill
•
Pavia, Kriz, Lampman, Engel, Micro and Macro Techniques in the Organic Laboratory, Saunders
College
•
•
Laboratory safety glasses or goggles that meet the ANSI Z-87.1 standard. If you
wear contact lenses you must use the goggles; if you wear prescription glasses,
the goggles may fit better over your prescription glasses than the safety glasses
do.
A laboratory notebook – Spiral bound Notebooks are NOT acceptable.
•
Molecular Model set (Instructor will give details first week of class).
•
ATTENDANCE AND CLASS RULES
•
Lectures begin at 11.10pm on M, W and F. Please be prompt. Repeated lateness will be not
tolerated. In return, I will finish lessons on time.
•
Please switch off cell phones during class.
•
Snack and beverages allowed during lecture – but please be reasonable.
•
Instructor will assign random seating during tests.
•
No talking or distracting other students during lectures.
•
You are free to leave if you do not want to attend lecture. But if you’re in the lecture room, you
may not do other assignments, read magazines, or anything that prevents you from paying
attention to the class.
GRADING
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Chem 232 has both a lecture and a lab section. A student earn points in
both the lecture and lab sections. Final course grade is based on points in
the lecture section only. Points scored in lab are NOT counted in your final
score, but a failure in your lab section will adversely affect your overall
course grade.
In the lecture section, points may be earned in required components or
bonus components. Approximately 700pts are allocated to required
components and approx 50pts may be earned from bonus categories. The
exact number of points varies from semester to semester. The final %
score is based on required components only. (ie: if a student earns 580pts
from required components, and 30pts from bonus components, her final
grade % is 610/700 = 87.1%).
Points earned in lab section are NOT counted in final course %, but a
student must earn a minimum of 70% in the lab section to pass. The
penalty for not meeting this requirement is the the lost of a grade in the
final course grade. (ie: if you score enough points for a grade “B” in your
lecture section, but gets less than 70% in your lab section, your grade for
the course will be “C”)
Final grade is assigned based on a class curve and the projected
boundaries are: Grade A - Approx. 85-90%, grade B: approx. 75-85%,
grade C: approximately 60-65%. Exact grade boundaries will be
determined after the final exam. Dishonesty will not be tolerated and will
result in points deducted. Make-up tests are not offered. It is your
responsibility to attend all required component testing. I will always give at
least 3 days notice for quizzes (20pts) and at least 1 week for midterms
(150pts).
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Required Components
Quizzes
Up to 10 x 20 pts each
Quizzes are approx 20 minutes and are short tests given at the completion of each chapter. Each
quiz is allocated 20pts. There will be a max of 10 quizzes through the course. You may be allowed
extra time at the lab instructor’s discretion. Quizzes are held during lab times.
Mid term Tests
2 x 150 pts
Two midterm tests will be scheduled (actually dates TBA – approx wks 6 and 12). 150 pts for each
test. Text books not allowed in tests, cheat sheet allowed in midterm 2 and final exam but not in
midterm 1.
Midterms will be held during lab times and allocated time is 2hrs. Midterm tests covers topics from
the most recent chapters covered. There are two parts: part A which are short questions
requirement simple written answers. All questions in part A must be answered. In part B, students
have a choice of various multi-part questions. Typically, you will choose 3 out of 5 questions. There
will be no essay questions and no multiple choice questions.
Final Examination
200pts
The 2 ½ hours final is comprehensive (covers all topics studied during the course). Examination
date is May 30th 2008 2.10pm to 4.40pm.
Poster
In the final 2 to 3 weeks of term, students may select from a number of topics for their own
research (literature and web based only. No lab work). They may present their results either in
essay or poster form. Guidelines on these topics will be given in due course.
WE WILL ONLY DO POSTERS IF THERE IS TIME TOWARDS THE END OF TERM
50pts
Bonus Components
Lab Tutorial Assignments and end-of-chapter assignments (EOC)
Up to 20 x 2pts each
There are EOC questions for each chapter we study. These are listed at the end of lecture
handouts. These questions are comprehensive and range from basic to quite challenging. You are
strongly advised to work through these EOC questions and to check your answers with Carey’s
student solution manual. You may earn bonus points by handing your answers to your lecture
instructor. Tutorial assignments are given on an as-need basis and will closely follow the chapters.
These are questions given in addition to the EOC questions. By turning in answers,a student may
earn bonus points. Both EOC and tutorial questions are designed to help you learn the topics
covered and prepare you for quizzes and tests. The key difference I will careful go through your
tutorial answers but NOT the EOC questions. You are strongly encouraged to ask for help from you
lab instructor – in addition to my office hours - on these assignments.
Miscellaneous Assignments
2 pts each
Occasionally, students are given the opportunity to undertake individual web-based research into
topics of scientific interest. These may be group work or individual assignments. These are again
voluntary and up to 2 pts per topic may be earned.
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Chem 232 SLO
1.
Students will develop an in depth understanding of chemical reactivity based on structure and chemical
properties (analysis/knowledge/comprehension)
This can include computer modeling program work and various laboratory and exam questions to ensure mastery.
2.
Students will learn the IUPAC nomenclature system and apply to range of simple organic compounds
(Knowledge/comprehension/application)
Various exams, quizzes, lab exercises, notebooks and reports will require application of this skill.
3.
Students should understand theories of retrosynthetic analysis in drug chemical synthesis
(Comprehension/analysis/application)
Exam and quiz questions along with computer structure analysis will be used for this skill.
4.
Analyze spectroscopic data to determine molecular structure (Application/analysis)
Various spectroscopic techniques will be used in lab involving combinations of instruments , textbook examples and
computer simulations will ensure mastery of this material.
5.
Comprehend, compare and contrast reaction such as electrophilic aromatic substitution, nucleophilic acyl
addition, nucleophilic substitution and various carbon-carbon bond formation reactions.
(application/analysis)
Exam, quiz and lab report work will be used to evaluate this skill.
6.
Develop laboratory skills with special reference to multi-step organic synthesis and structural determination.
(Synthesis/analysis)
Various laboratory exercises, computer simulations and exam questions will evaluate this skill.
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Chemistry 232 Lecture Schedule
Spring 2008
This is a tentative schedule, subject to changes depending on class progress. I hope
to finish the course at least a week before final exam.
Please note we will not have time to cover every section from each chapter. Exact
details of sections to be covered will be given with lecture handouts.
Week #
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
Chapter and Title
9- Alkynes
11 – Arenes and aromaticity
12 – Reactions of Arenes; EAS
14 - Organometallics
Catch up week
15 – Alcohols, diols and thiols
16 – Ethers, epoxides and sulfides
17 – Aldehydes and ketones; nucleophilic addition.
18 – Enols and enolates
Catch up week
19 – Carboxylic acids
20 – Carboxylic acid derivations; NuAcS
Catch up week
21 – Ester Enolates
21 – Ester Enolates
Poster week
Poster week
End of Term Review
Other key dates: (guideline only, exacts dates to be announced)
Late Feb/Early March: Midterm Test 1
Late March/Early April: Midterm Test 2
May 30th: Final Examination
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Chemistry 232 Laboratory – Spring 2008
The laboratory section is an integral part of the course. The focus is on laboratory techniques, competence, confidence
and organization skills.
Passing score is 70% for the lab section. Students who do not score a minimum of 70% will lose one grade from their
overall final course grade. (ie: if you score enough points for a grade “B” in your lecture section, but gets less than 70%
in your lab section, your grade for the course will be “C”).
Students attend two labs per week. Full attendance is required. Most lab classes will begin with technique demos and it
is important for students to attend lab sessions promptly.
Lab manuals are not available. Lab procedures are posted on instructor website approx. 1 week in advance.
Lab Rules
•
Students must be in lab on time.
•
Goggles to be worn at all times.
•
Please wear clothing with good coverage – no tank tops, shorts and open toe sandals.
•
Long hair must be tied back.
•
Please use the same fumehood each session.
•
All experimental work to be carried out in fumehood unless otherwise instructed.
•
Please use appropriate waste disposal container for all wastes.
•
All waste must be logged in book provided.
•
Most glassware should be cleaned with soapy water and rinsed with hot water, allowed
to drain on draining racks provided.
•
Please keep your fumehood and bench space tidy and safe at all times.
•
Chemical spills must be cleaned up immediately. Instructor will request students to clean
up during lab session as required.
•
Students are encouraged to keep a clear record of laboratory work. See separate sheet
on keeping lab book record.
•
Accidents must be reported immediately or as soon as it’s safe to do so.
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Lab Section Grading Components
Prelab Questions
5 to 10 pts each
Each lab procedure includes a prelab worksheet. This contains questions designed to help you prepare for the
experiment and to understand the chemistry background. Questions require short written answers. These must be
completed before each lab.
Post lab Questions
5 to 10 pts each
Within a week of completing an experiment, a postlab sheet must be completed. Questions typically ask for a summary
of experiment objective, chemical equations, results such as yield and analysis and well as short-answer questions
relating to the experiment.
Laboratory Exam
50 pts
The final experiment is a lab based project. Students are required to design and carry out an esterification synthesis and
then determine structure of the ester formed using a combination lab results and spectroscopic data. Assessment is
based on how well the experiment was carried out (30pts) and how the results are presented (20pts). More details will
follow.
General Lab Skills
60 pts
This is an evaluation of students’ performance in the lab throughout the semester. Areas include: safety, organization,
ability to follow procedure, practical skill, attitude/problem solving and overall ability to relate experimental and practical
situations to chemistry principles and theory.
Lab Book
(optional)
(no points)
You make have use of lab book for working notes during experiments. However, formal write-ups are not required (but
strongly recommended). Guidelines will be given on how to keep a good notebook.
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Chemistry 232 Lab Experiment Schedule
Spring 2008
General Outline
Expt 1 is a review of basic techniques from chem. 231: Mpt and Bpt determination, distillation,
recrystallization, solvent extraction, FT-IR and GC.
Expts 2 to 4 focus on using relatively simple, straightforward synthetic methods to perform a
multistep synthesis. A key challenge is to maintain yield and product purity through sequence.
Product characterization will be by mpt and IR in most cases.
Expts 5 to 7 are independent synthesis that require more advanced synthetic techniques. In all
cases, a minimum level of laboratory competence is necessary for success.
Expt 8 is an esterification procedure which is also good practice and preparation for the lab exam.
Expt 9 is a lab based project/exam. Students are required to design their own lab procedure to
carry out an esterification synthesis and then determine structure of the ester formed using a
combination lab results and spectroscopic data. Assessment is based on how well the experiment
was carried out and how the results are presented.
Experiment List
This is a tentative list, subject to changes depending on class progress:
Check in and lab familiarization.
Experiment 1: Re-familiarization with chem231 techniques: mpt, bpt, distillation, recrystallization,
solvent extraction, GC and FT-IR
Experiment 2: Multistep synthesis - benzoin
Experiment 3: Multistep synthesis - benzil
Experiment 4: Multistep synthesis – Tetraphenylcyclopentadienone
Experiment 5: Grignard Reaction
Experiment 6: Nitration of methyl benzene
Experiment 7: Friedel Craft acylation
Experiment 8: Esterification – banana oil
Experiment 9: Unknown Esterification – lab exam.
Lab times will also be used for quizzes, midterms and tutorial sessions.
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