Objective:
CHE 232
Organic Chemistry II
The goal of this course is to build upon the concepts put forth in the first semester of organic
chemistry and apply them towards the study of various classes of organic compounds.
Mechanisms, organic reactions, and multi-step syntheses will be emphasized.
Prerequisites:
Successful completion CHE 231 (or equivalent) preferably with a grade of at least C-.
Textbook:
Organic Chemistry,11th Edition, T. W. Graham Solomons, Craig B. Fryhle, and Scott A. Snyder,
Wiley, 2014 (required).
Sapling Learning Interactive Homework (required).
Molecular Model Kit for Organic Chemistry (strongly recommended).
Study Guide and Solutions Manual for Organic Chemistry, 11th Edition (strongly recommended).
Requirements:
Satisfactory performance on online homework, quizzes, hourly exams, and a comprehensive
American Chemical Society (ACS) final exam (which will cover material from the entire year).
Attendance
Policy:
Attendance will not count towards the final grade obtained in this course. You are, in effect,
paying me to lecture to you about organic chemistry. If you chose not to show up, that is your
prerogative. However, be aware that the exams will be based on material covered in lecture, and
that you are responsible for any announcements (homework assignments, exam dates, etc.)
mentioned in lecture. If, for some reason, you cannot attend a lecture, be sure to obtain notes and
other important information from another student. Office hours will not be used to cover material
missed by an unexcused absence.
Evaluation
Policy:
There will be ten quizzes administered on Thursdays throughout the semester.
If your online homework grade is higher than your quiz sum, then your Quiz/Homework score will
be a 50/50 average of your quiz grade and your online homework grade. If your online homework
grade is lower than your quiz sum, then your Quiz/Homework score will be the sum of your
quizzes (the homework will not count). There will be three hourly exams (approximately one
every four weeks). Either your Quiz/Homework score (scaled to 100%) or your lowest exam
score (whichever is lower) will be dropped. Offline problem sets (from the textbook) will be
assigned in class (one per chapter) but will not be collected. It is your responsibility to keep up
with the material, know the areas that are giving you problems, and get help. The final multiple
choice exam (which will be a standardized ACS exam) is cumulative for the entire semester. The
portion of the grade allotted to each of these items is as follows:
(Quiz/Homework Average and Hourly Exams) (best 3/4)
..........75%
Final Exam
……….........................25%
Academic
Honesty:
For questions regarding Academic Dishonesty, the No-­‐Grade Policy, Sexual Harassment, or the
Student Code of Conduct, students are encouraged to refer to their major department’s handbook,
the Undergraduate Course Catalogue, the Rams Eye View, or the University Web Site. Please
understand that improper conduct in any of these areas will not be tolerated and may result in
immediate ejection from the class. Exams will be photocopied before they are returned.
Makeup Policy: If you know in advance that you will be missing a quiz or an exam, you must notify me as soon as
possible. If you are sick enough to miss a quiz or exam, you are sick enough to see a doctor and
get documentation for your illness. Again, you must notify me before the quiz/exam of the
situation. You will have until 2:30 PM the following Tuesday to complete a makeup. It is your
responsibility to contact me in order to arrange the makeup. No after-the-fact makeups for quizzes
or exams will be given.
Subject Matter:
CHE 232 will cover Chapters 11-21 (not necessarily in order). Supplemental material may be
assigned as well. Although only a few problems will be assigned per chapter for the homework
sets, you should work out all of the in-chapter and end-of-chapter problems as well, since these
problems will likely form the basis for exam questions. A general non-binding course outline is
attached.
ADA Policy
Statement:
West Chester University will make accommodations for students with disabilities.
Consult the Office of Services for Students with Disabilities (ext. 3217) and bring the resulting
documentation to the instructor.
Emergency
Information:
In case of an emergency that occurs during class, contact Public Safety at 610-436-3311, or
X-3311 on a campus telephone.
Excused
Absences
Policy for
UniversitySanctioned
Events:
Undergraduate students participating in University-sanctioned events such as, but not limited to,
the Marching Band, musical ensembles, theatre group, athletic events, forensics competition, etc.,
will be granted an excused absence(s) by the respective faculty members for class periods missed.
Students will be granted the privilege of taking, at an alternative time to be determined by the
professor, scheduled examinations or quizzes that will be missed. The professor will designate
such times prior to the event. Professors can provide a fair alternative to taking the examination or
quiz that will be missed. Students must submit original documentation on University letterhead
signed by the activity director, coach, or adviser detailing the specifics of the event in advance.
Specific requirements include the following:
1. Responsibility for meeting academic requirements rests with the student.
2. Students are expected to notify their professors as soon as they know they will be
missing class due to a University-sanctioned event.
3. Students are expected to complete the work requirement for each class and turn in
assignments due on days of the event prior to their due dates unless other arrangements
are made with the professor.
4. If a scheduled event is postponed or canceled, the student is expected to go to class.
5. Students are not excused from classes for practice on nonevent days.
The following are specifics for the student athlete:
1. The student athlete is expected, where possible, to schedule classes on days and at
hours that do not conflict with athletic schedules.
2. Athletes are not excused from classes for practice or training-room treatment on
nongame days.
Course Outline
Subject Matter
# Lectures
Reading Assignments
Alchohols and Ethers: Nomenclature, Synthesis of
Alcohols and Ethers, Epoxides, Williamson Synthesis
3
Chapter 11
2
Chapter 12
3
Chapter 13,
Parts of Chapter 10
Aromatic Compounds: Failure of Resonance Theory,
More Molecular Orbital Theory, 4n + 2 Rule,
Aromaticity vs. Antiaromaticity, Annulenes,
Nomenclature of Aromatic Compounds, NMR of
Aromatic Compounds
2
Chapter 14
Reactions of Aromatic Compounds: Electrophilic
Aromatic Substitution, Substituent Effects, Sidechain
Reactions, Oxidations, Blocking Groups, Synthesis
Problems
3
Chapter 15
Aldehydes and Ketones I: Nomenclature, Synthesis,
Nucleophilic Addition, Hemiacetals, Acetals, Imines,
etc., Wittig Reactions
3
Chapter 16
Carboxylic Acids and their Derivatives: Acyl
Compounds, Acidity, Spectroscopic Properties,
Synthesis, Acyl Transfer Reactions, Acyl Chlorides,
Anhydrides, Esters, Amides, Nitriles, Decarboxylation
3
Chapter 17
Reactions at the α-Carbon of Carbonyl Compounds:
Enolate Ions, Tautomerization, Acetoacetic Ester
Synthesis, Malonic Ester Synthesis, Alpha
Halogenation
3
Chapter 18
Condensation and Conjugate Addition Reactions of
Carbonyl Compounds: Claisen Condensations, Aldol
Reactions and Condensations, Michael Additions,
Robinson Annulations, Stork Enamines
2
Chapter 19
1
Sections of Chapters 20 and 21
Redox Chemistry of Alcohols and Carbonyl
Compounds, Organometallic Compounds (Grignard
Reagents, Organolithium Reagents, Dialkyl Cuprates)
Conjugated Unsaturated Systems: Allyl radicals,
Molecular Orbital Theory Revisited, Free Radical
Reactions Revisited, Resonance Theory Revisited,
Polyunsaturated Hydrocarbons, Thermodynamic vs.
Kinetic Control, Diels-Alder Reactions
Exam I
Exam II
Exam III
Crash Course on Amines, Phenols, and Aryl Halides