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Chemistry 262H; S. J. Meek
Honors Organic Chemistry II – Chem 262H
Spring 2015
Instructor:
Professor Simon Meek ([email protected]); Venable 1307 (919-962-0359)
Class:
Monday, Wednesday & Friday 9:05 am –9:55 am; Venable G307
Pre/Co-requisites:
A grade of C- or better Chem 261 or 261H. It is an Honor Code violation to be enrolled
in a course lacking the proper pre- and co-requisites.
Q & A Sessions:
Monday
Friday
Textbook:
“Organic Chemistry”, Bruice, 7th Ed.
“Organic Chemistry Student Study Guide and Solutions Manual”, Paula Bruice
Course Website:
All course materials will be posted at: sakai.unc.edu
4:00-5:00 pm
3:00-4:00 pm
Venable 1301
Venable 1301
(CHEM262H.001.SP15)
Course Description: Chemistry 262H is the second half of a two semester, cumulative overview of organic
chemistry. We will examine the chemistry of carbonyls, carboxylic acid derivatives,
aromatics, and amines as well as biological molecules: carbohydrates, proteins.
Foremost, students in this course should endeavor to develop an understanding of the
properties and reactivity of important functional groups in organic chemistry. Grappling
with unfamiliar mechanisms, predicting the products of organic reactions, and applying
reactions to chemical synthesis will be significant and recurring themes. Implicit in this
undertaking is an aggressive approach toward problem solving and pattern recognition.
As you learned in 261, organic chemistry challenges you to wrestle with new concepts, to
retain a large volume of information, and to apply these tools in unfamiliar settings.
Expect to work hard in this class.
Exams:
Hour Exam I
Hour Exam II
Hour Exam III
Final Exam
2/4
3/6
4/10
5/4
(Wednesday)
(Friday)
(Friday)
(Friday), 8:00-11:00 am
Final exam rescheduling policy: http://www.unc.edu/ugradbulletin/procedures1.html
A request to reschedule your final exam time will not be considered in the absence of (a)
a written examination excuse from the Dean of your school; or (b) an "Official Permit to
take Final Examination to remove grade of AB” from the Office of the Registrar (this can
be obtained if the student is on the Infirmary List).
I want to grade your best effort. If your mean-adjusted final exam score is better than
any of your mean-adjusted hour exam scores, I will replace your lowest mean-adjusted
hour exam score with the mean-adjusted final exam score. In the event that you must
miss a single hour exam for medical reasons or other emergencies circumstances, the
score on your final exam will be inserted as your missed hour exam score. An absence
from a second hour exam will result in a score of 0 for that exam. No makeup hour
exams will be given; there will be no exceptions to this policy.
Grading:
Three hour exams (50%); Final exam (40%); quizzes (10%).
Final letter grades will be assigned in accord with the Academic Polices in the College of
Arts and Sciences, which describes the meaning of grades as follows
(http://advising.unc.edu/AcademicPoliciesProcedures):
Chemistry 262H; S. J. Meek
A - Mastery of course content at the highest level of attainment that can reasonably be
expected of students at a given stage of development. The A grade states clearly that
the student has shown such outstanding promise in the aspect of the discipline under
study that he/she may be strongly encouraged to continue.
B - Strong performance demonstrating a high level of attainment for a student at a given
stage of development. The B grade states that the student has shown solid promise in
the aspect of the discipline under study.
C - A totally acceptable performance demonstrating an adequate level of attainment for
a student at a given stage of development. The C grade states that while not yet
showing any unusual promise, the student may continue to study in the discipline with
reasonable hope of intellectual development.
D - A marginal performance in the required exercises demonstrating a minimal passing
level of attainment for a student at a given stage of development. The D grade states
that the student has given no evidence of prospective growth in the discipline; an
accumulation of D grades should be taken to mean that the student would be well
advised not to continue in the academic field.
F - For whatever reasons, an unacceptable performance. The F grade indicates that the
student's performance in the required exercises has revealed almost no understanding
of the course content. A grade of F should warrant an adviser's questioning whether the
student may suitably register for further study in the discipline before remedial work is
undertaken.
The final grading scale (“curve”) will be created to reflect these assessments.
Honor Code:
“Since all graded work (including homework to be collected, quizzes, papers, mid-term
examinations, final examinations, research proposals, laboratory results and reports,
etc.) may be used in the determination of academic progress, no collaboration on this
work is permitted unless the instructor explicitly indicates that some specific degree of
collaboration is allowed. This statement is not intended to discourage students from
studying together or working together on assignments which are not to be collected.”
As you know, the Honor Code (http://honor.unc.edu/) is a cornerstone in maintaining
academic integrity at Carolina. I take it extremely seriously and expect you do as well.
While I do not anticipate problems, you should know that I have no hesitations about
reporting Honor Code violations.
Class Rules:
Please be respectful of both the instructor and your classmates:
Be early. It is disrespectful and disruptive to your classmates and to me to be late.
No mobile phone use. You may leave your phone on vibrate in the event there is an
Alert Carolina broadcast message, but your mobile is not to be used otherwise.
No laptop use without explicit instructor permission. If you want the materials that
have been posted on Sakai, you should print them before coming to class. Drawing
chemical structures is a key component of organic chemistry and you can’t do this on a
laptop.
Chemistry 262H; S. J. Meek
APPROXIMATE COURSE OUTLINE
Problems at the end of chapters are required insofar as you are responsible for all of the included material on
exams.
Date
Topic
Reading Assignment
Assigned Problems (Minimum)
9-Jan
Introduction; NMR
15.1–15.5
Ch15:3–6,11–14,16,18,19,20,23,24,26,27,33,46,48–
55,58,60,61,64,65,66,70,73
12-Jan
15.6–15.11
14-Jan
15.12–15.15, 15.17
Examples
16-Jan
19-Jan
No class
21-Jan
Aldehydes & Ketones
17.1–17.6
23-Jan
17.6–17.12
26-Jan
17.12–17.16
17.16–17.19, 12.1–12.3
28-Jan
30-Jan
Organometallics
Ch17:2,5,6,13,14,18,20,28,33–35,37,39,40,41,44,47,49–
52,54,56,58,59,61,62,66,69,70,71,75,79
Ch12:1,4,8,9,10,20,24,25,26,27,28,34,35,36
12.3–12.5
2-Feb
4-Feb
Exam 1
6-Feb
Carboxylic acids
16.1–16.22
Ch16:3,4(a,c,e,g),6,11,13,15,16,18,23,24,28,30–32,41,43–
45,47,56,57,58,60,63,64,70,71,75–78,81,86,89,93
Reactions at the α-carbon
18.1–18.20
Ch18:4,5,7,8,10,11,12,14,16-24,26-42,47,52-56,5862,64,65,67-74, 79,81,87
9-Feb
11-Feb
13-Feb
16-Feb
18-Feb
20-Feb
23-Feb
25-Feb
Synthesis
27-Feb
2-Mar
Aromaticity
Reactions of benzene
4-Mar
Reactions of benzene
6-Mar
Exam 2
9-Mar
No class
11-Mar
No class
13-Mar
No class
16-Mar
Reactions of substituted
benzenes
18-Mar
8.1–8.2; 8.7–8.12; 8.15
19.1–19.9
Ch19:4,6–9,13,15,16,18–29,32,34,35,42,43,44,48,52,53,
55,56,57,59,60,62,63,69,73,74,86,86,87,91
19.10–19.18
19.21–19.24
20-Mar
23-Mar
Amines
25-Mar
Amines
20.1–20.8
Ch20:4,5,6,9,22,23,24,25,27
Chemistry 262H; S. J. Meek
27-Mar
Carbohydrates
21.1–21.11
1-Apr
Carbohydrates
No class
21.12–21.17
3-Apr
6-Apr
Amino acids, proteins
Ch21:1–5,7–14,19–23,25,31,37,66
Ch22:2,5–8,10,11,21–23,27,28,33,35,38,47,50,55,62,63,70
22.1–22.7
8-Apr
10-Apr
22.8–22.17
13-Apr
15-Apr
8.19–8.20;
28.1–28.7
Ch8:48,50,51,52,56;Ch28:1–3,5–10,12–15,19–20,23–
Ch23:1–6,8–16,18,25–27,29–31,33–34,38–40,42–43,46
Exam 3
Pericyclic reactions
27,32,34,37
17-Apr
20-Apr
Catalysis
23.1–23.7
22-Apr
24-Apr
To be determined
4-May
Final - 8 am
Studying: Organic chemistry is a course that builds upon key concepts throughout both semesters. In this
course, you will be asked to learn additional concepts, to recall and to apply these concepts to solve
problems. It is vital to your success that you review reactions and concepts from Chem 261 at the
beginning of the semester in order to be adequately prepared for Chem 262H. To aid in
understanding the material, it is advisable that you review your notes daily as opposed to waiting
until the night before the exam to study. In addition to reviewing your notes, you are strongly
encouraged to work through the assigned problems in the text and to come to my Q & A sessions* if
you have any questions. The best advise for obtaining a good grade in this class: practice, practice,
practice.
*Individual Meetings: These are intended to address big picture questions: deeper understanding of concepts,
connecting topics, course studying, etc.
About This Course
Understanding organic chemistry is not unlike learning a foreign language. Gifted linguists do not develop
without daily practice of the art. If you wish to learn organic chemistry, be proactive and industrious in your
approach to it. I recommend the following at a minimum:
i. Come to class prepared. This is a no-brainer. Much of organic chemistry is conceptually new and if you’ve
introduced yourself to key ideas before I lecture on them, they will sink in faster. If you are prepared, it will be
easier to thoughtfully consider the content of the lecture rather than passively scribble down the notes, trying to
digest them later. I will do what I can to make the class time an active, rather than passive information exchange.
In this context, you should be prepared to think about and answer questions that I pose.
ii. Do something for this course every day. You will learn and retain more if you spend some time each day
reading the text, studying notes, doing Mastering Chemistry or working problems, rather than doing (e.g.) five
hours once a week (or twelve hours the night before the exam). To let more than two days pass without a
substantial out-of-class effort is courting disaster.
iii. Do all the problems. Do not skip working the problems, look at the answers, and say “Oh, I understand that
now.” Chances are good that you don’t, at least not to the degree needed. Hold off on checking the answers
until you have wrangled, wrestled, and discussed. Look up related material in the notes and the appropriate text
chapter. You will only learn the content by adopting a thorough and aggressive approach toward problem
solving.
iv. Get help early. If you are having problems with the material, seek help early in the semester. Halfway
through the course is way too late.
Chemistry 262H; S. J. Meek
v. Use summary sheets/flash cards. As new reactions and concepts are introduced, prepare a summary
sheet or flash card that contains:
(a) the name of the reaction
(b) general example (use R groups); include all necessary reagents, solvents, and reaction conditions. Include
workup conditions where appropriate.
(c) Specific examples
(d) Step-by-step mechanism showing electron movement with curved arrows
(e) Stereochemistry of the reaction (if applicable)
(f) Any electronic or structural effects on the reaction
For studying purposes, grouping reactions by category is helpful.
vi. Studying in groups can help. Group studying can be effective when everyone is working hard and at a
similar level of understanding. It can also give a false sense of understanding if the group comes up with an
answer that is not completely obvious to the individual. If you study in groups, do not fall into the trap of feeling
that your understanding of the material is more advanced than it is.
vii. The purchase of a molecular model set (Student Stores) is strongly recommended. Much of what you
will learn requires visualizing molecules in three dimensions. Constructing molecular models is one of the best
ways to understand the shape and conformation of organic molecules. You will be able to use your model sets
on exams.
viii. Chemistry Resource Center (M-Th 1-6 PM; Kenan Laboratory C143). Free chemistry help when you
need it or cannot make it to my office hours.
NOTES AND CLASS TIME
This will be a lecture-based course and you will be responsible for taking notes during class. Although
attendance is not factored into your final grade, it is highly encouraged that you do not miss any classes.
If you miss a class, it is your responsibility to copy the notes from one of your classmates. Reading
assignments for each section are given above, as are the hourly exam dates. The final exam date is scheduled
by the University Registrar.
Course Structure
Introduction:
Some of this course will be taught using team-learning techniques. A growing body of evidence
indicates that active, collaborative learning is the most effective method of information transfer.
Most, if not all, of the science courses you have taken rely heavily on lectures as the mechanism
of information transfer. While lecture remains an important and indispensable teaching tool,
exclusive reliance on it has been documented to be less effective with respect to understanding
and retaining material presented in the course.
Student Responsibilities:
Team learning in this course will entail group problem solving sessions conducted in class under
my “supervision”. At the end of a given class period, I will make available online a handout on
material that will be covered in the next class period. This material will be supplemented with
material from your text. It is the student’s responsibility to carefully study this material before
coming to the subsequent class period. This “background” information will be employed as the
basis for an in-class problem session that will augment your understanding of the material you
covered outside of class. For team learning to be effective, you must come to class prepared.
To promote this, we will have brief (5-10 minute) quizzes at the beginning of class periods.
These quizzes are intended to be simple if you have studied the assigned material. Your quiz
scores will count toward you final grade.
Problem Solving Class Sessions:
The Monday/Wednesday/Friday course schedule lends itself well to a format wherein we have a
problem-solving sessions during the Monday/Wednesday class and a “normal” lecture on
Wednesday/Friday. In this way, you will have three days (Friday to Monday) to assimilate the
Chemistry 262H; S. J. Meek
new material before a problem session. The problems I will distribute after your quiz on
Monday/Wednesday will be something akin to a problem set. You will be working in groups of
three/four. The following things are important in the group setting:
• Each group member must be vocal and contribute. There will be disagreement on how
to solve a given problem. This format provides a forum to discuss your opinion and
provide the evidence to support it. You know you have a strong grasp of material when
you are able to explain it to someone else!
• Each group member should feel an obligation to your colleagues. If you come to class
unprepared, you will hinder your own development, and the progress of your colleagues.
• Respect your colleagues. Listen to what they have to say and learn from them. It is an
important skill to be able to voice your opinion while respecting the opinions of others.
Summary:
This format has been used successfully and with very positive student response in the past.
You will learn the same material that has been taught in previous years. You will additionally
begin to develop a skill, “scientific self-expression” if you will, that is necessary whatever your
career goals and underdeveloped by more passive learning techniques. I encourage your
feedback at any point and am willing to listen to any concerns you might have.
Further Reading:
If you wish to learn more about team learning techniques in organic chemistry, I encourage you
to consult the following literature on the subject:
(1)
Dinan, F. J.; Frydrychowski, V. A. "A Team Learning Method for Organic Chemistry." J. Chem.
Educ. 1995, 72, 429-431.
(2)
Birk, J. P.; Foster, J. "The Importance of Lecture in General-Chemistry Course Performance." J.
Chem. Educ. 1993, 70, 180-182.
(3)
Gosser, D. K.; Cracolice, M. S.; Kampmeier, J. A.; Roth, V.; Strozak, V. S.; Varma-Nelson, P. PeerLed Team Learning: A Guidebook; Prentice Hall: Upper Saddle River, NJ; 2001.
(4)
Bradley, A. Z.; Ulrich, S. M.; Jones, M. J.; Jones, S. M. "Teaching the Sophomore Organic Course
without a Lecture. Are You Crazy?" J. Chem. Educ. 2002, 79, 514-519.
(5)
Paulson, D. R. "Active Learning and Cooperative Learning in the Organic Chemistry Lecture
Class." J. Chem. Educ. 1999, 76, 1136-1140.
Disclaimer:
The professor reserves the right to make changes to the syllabus, including project due dates and tests
(excluding the officially scheduled final examination), when unforeseen circumstances occur. These changes will
be announced as early as possible so that students can adjust their schedules.