Houseknecht
Chemistry 302
Spring 2013
Chemistry 302 - Organic Chemistry II
Meeting Times
MWF 11:30 – 12:30 Science 262
W
12:40 – 4:40 Science 255C (Section 2, meet in Science 262)
Th
12:40 – 4:40 Science 255C (Section 3, meet in Science 262)
Instructor
Justin Houseknecht (house-neck), PhD
Science 245E, 327-6437, jhouseknecht@wittenberg.edu
Office hours
MWF 10:00 – 11:30, TTh 10:00 – 12:30
Please make use of this time if you have any questions or concerns. No new material will be discussed
during office hours, but as much assistance will be given as possible. If you prefer individualized
assistance or cannot make it during the hours listed above, please contact me to set up an appointment.
Required Textbooks and Resources
Organic Chemistry, John McMurry, Brooks/Cole Thomson Learning, 8th Edition, 2012.
Organic Chemistry OWL Access Code Card, Brooks/Cole Thomson Learning, 1st Edition*
* Available with new copies of Organic Chemistry or in the bookstore
The Organic Chem Lab Survival Manual, A Student’s Guide to Techniques, Zubrick, 8th Edition, 2009.
Organic Chemistry Laboratory Experiments, Hanson and Houseknecht, Spring 2013*
*Available on Moodle, http://moodle.wittenberg.edu/login/index.php
Laboratory Safety for Chemistry Students, Hill and Finster, 1st Edition, 2010.
Recommended Textbooks and Resources
HGS Molecular Model Kit 1013/ Organic Chemistry Set for Student*
*HGS has other kits available, the more extensive ones would also be okay
ThomsonNOW Printed Access Card, Brooks/Cole Thomson Learning, 1st Edition
Course website – On the class (Q) network drive, Q:\chemistry\Houseknecht\index.html
Chemistry Department Mission Statement
The mission of the Chemistry Department is to provide a challenging and supportive environment for
students to learn chemical principles and laboratory skills, enhance their critical thinking and
communication skills, and become responsible in their use of scientific knowledge.
Course goals and philosophy
Reinforce understanding of the basics of organic chemistry from Chemistry 201 and expand upon that
with more detailed understanding of spectroscopy, multistep synthesis, concerted reactions of alkenes,
reactions of aromatics and -carbonyl compounds. Additional techniques used in the synthesis,
purification and analysis of organic compounds are emphasized in the laboratory with a focus on multistep synthesis and spectroscopy. Every reasonable methodology will be used to promote learning.
Houseknecht
Chemistry 302
Spring 2013
Assumed Skills
To do well in Chem 302 you need to have some basic skills at your disposal. The following are many of
the skills that you have encountered in Chem 201 and in general chemistry. I assume that you are
proficient in the following:
Structure
VSEPR
Reactivity
Recognize acids and bases
Mathematics
Stoichiometry
Valency and formal charge
pKa
Balancing reactions (including redox)
Lewis dot structures
Nucleophiles and electrophiles
Calculation of percent yield
Resonance
Polarity
Arrow formalism (curved arrows)
Reaction kinetics and equilibria
Hybridization and bond angles
Representations of molecular structure
Line-bond structures
Stereochemistry
Nomenclature of non-aromatics
Students with disabilities
Wittenberg University and I are committed to providing reasonable accommodations for eligible students
with disabilities. If you are eligible for course accommodation due to a disability, please provide me with
your self-identification letter from the Academic Services Office, 206 Recitation Hall, so that we may
discuss your learning needs. Early identification at the start of the term is required to ensure timely
provision of services.
Grading criteria
Final grades will be determined by performance on homework assignments, quizzes, hourly exams, the
final exam, and laboratory assignments. The last day to drop without a “W” is Feb 8, 2011.
Homework
15%
Exams
50%
Final exam
15%
Laboratory
20%
Grades will be assigned as detailed below. Scores within 2 – 3% of cut-offs will receive +/- modifiers as
appropriate. I do reserve the right to assign letter grades more leniently. All course grades will be
assigned based upon a class-wide scale, no individual exceptions will be granted.
A
90 – 100%
B
80 – 90%
C
70 – 80%
D
60 – 70%
F
0 – 60%
Homework
Daily preparation is essential for success in organic chemistry. As such, homework problems will be
assigned on a daily basis. Successful students will complete the problems assigned from the textbook
prior to the ensuing class period. Homework will also be assigned for the online program OWL. To
receive credit for each assigned exercise it must be completed by the due date. The website for OWL is
http://owl.cengage.com/owl-c/user/loginpage.cgi?Server=owl-wittenbergunivmcmurry7e&UserType=
Student. If you have any difficulty accessing or using this resource please ask for assistance
immediately. Up to fifteen homework extra credit points will also be available by completing
worksheets between the class in which they are distributed and the next class period.
Houseknecht
Chemistry 302
Spring 2013
Examinations
Exams will be given during the normal class meeting time. All exams will be cumulative, although
emphasis will be placed on material that has not yet been tested. Half the points on each exam will come
from the assigned problems in the text or worksheets. Sample exams from previous years are available
on the Q drive. Unexcused absence from an exam will result in a zero for that exam. Excused absences
will be rescheduled. To receive an excused absence from an exam you MUST receive a written excuse
from the instructor at least a day before the scheduled exam time or provide documentation of the
unavoidable, unforeseen emergency. Re-grade requests must be discussed with the instructor within one
week of the return of the exam. The final exam will be given on Friday, May 3rd at 8:00 am. The
final exam will be the American Chemical Society (ACS) organic exam. Study guides for this exam are
available through the ACS. The Chemistry Club will place an order for these in early February.
Laboratory
Laboratory is an essential component of this course. Therefore, you cannot pass Chem 302 if you do
not achieve a passing grade in the laboratory. Laboratory grades will be based upon pre-lab quizzes,
pre-lab exercises, post-lab reports, and performance in the laboratory. Organic chemistry lab is not
dangerous (e.g., an abandoned mine field), but failure to prepare properly can result in serious injury.
To avoid such unpleasantries, read the entire experiment (and any assigned reading) before coming to
lab and always come to lab in appropriate lab attire (lab goggles, long sleeves, closed-toe shoes, etc.).
Failure to do so can and will result in expulsion from that day’s lab and a zero on any related
assignments. You are, of course, also expected to know the location of safety equipment and refrain
from dangerous activities such as horseplay, eating, or drinking while in the laboratory.
Course schedule (tentative)
Unit
1
2
3
4
5
Approx. Dates
Jan 7 – Jan 30
Exam Feb 1st
Feb 4 – Feb 27
Exam Mar 1st
Mar 11 – Mar 25
Exam Mar 27th
Apr 1 – Apr 12
Exam Apr 15th
Apr 17 – Apr 29
Exam May 1st
Topics
Mass Spec and IR
NMR: 1H and 13C
Conjugated Polyenes, MO Theory, UV/Vis
Aromatics
Phenols
Aldehydes and Ketones
Carboxylic Acids and Derivatives
Sections
Chap 12
Chap 13
Chap 14
Chaps 15 and 16
Secs 17.1, 17.9, 17.10
Chap 19
Chaps 20-21
-Carbonyl Reactions
Chaps 22-23
Amino Acids and Peptides
Carbohydrates
Final Exam – Friday, May 3rd @ 8 am
Chap 26
Chap 25
Houseknecht
Chemistry 302
Spring 2013
Study habits
Organic chemistry has the reputation of being a difficult subject. There are certainly many reasons for
this, but the primary reasons are:
1. It is a vast subject area that requires a substantial amount of material to be processed in the course of
a semester.
2. It is one of very few subjects that is truly cumulative. A thorough understanding of the material
covered at the beginning of the course is essential for success throughout the semester. Similarly,
material covered later in the semester will further clarify material covered at the beginning of the
semester.
3. It is a subject that many approach from an unproductive perspective. Prior to the Information
Revolution, organic chemistry education consisted almost entirely of memorizing hundreds or
thousands of reactions. This may have been appropriate for the time, but ready access to computers,
the Internet, and powerful search engines, as well as advances in the field, have made rote
memorization an essentially worthless endeavor. Most instructors of organic chemistry now
emphasize the importance of understanding how and why a few essential organic reactions proceed.
This approach makes the course grow easier as it proceeds and is the method we will use in Chem
201. Unfortunately, many students of organic chemistry have continued to emphasize memorization
of as many reactions as possible. This usually becomes overwhelming by the midpoint of the
semester. The resulting consternation of students who have worked very hard is predictable.
So, what should a student of organic chemistry do to be successful? The short answer is to commit the
necessary time to learning the material, particularly the first few weeks, and to focus upon understanding
the processes of organic chemistry – not just the results. The long answer is to:
1. Always study material with the intent of understanding it. Another way to say this is to remember
that the journey is more important than the destination, particularly when studying.
2. Study for 60 - 90 minutes a day, 4 - 6 days a week. This is much more efficient than waiting until a
few days before the exam to begin studying.
3. Recopy your notes from lecture in a fresh notebook within 24 hours of lecture.
4. Complete the assigned homework problems within 48 hours. Waiting longer will leave you
unprepared for the next class and overwhelmed by the shear number of problems to be worked.
5. Do as many practice problems as possible, not just the assigned homework problems. Consult other
students, the instructor, or the solutions manual for every problem that you don't understand.
6. Avoid working problems with a solutions manual nearby. Using it to check your answers after you
have answered a group of 5-10 questions can be valuable, more frequent use will negatively impact
your understanding of the material and exam performance. If you are having trouble in the course
and feel like you are drowning DO NOT reach for a solutions manual. Seek out help from
classmates, the instructor, or the Chemistry Workshop (usually SMTTh evenings).
7. Study with several classmates on a regular basis. This time should be used to ask one another
difficult questions and review key concepts, not to read the text or work on simple problems from
the book. Finding a group of peers willing to prepare properly for group study should be a high
priority the first few weeks of the semester.
8. Take the advice of students who have been successful in organic chemistry. I have compiled a list of
suggestions and placed it on the Q drive.