Chemistry 231.02
Organic Chemistry I
Fall 2009
Lecture: MWF 9:30-10:50 Gregory 270
Lab: M,T,W,Th 1:00-3:50 T 8:00-10:50 Hedco 227
Barbara Murray
Office: Hedco 210
Phone: ext 8544
Email: barbara_murray@redlands.edu
Office Hours: T 12:30-2:00, W 12:30- 2, F 11:00-12:30
These are times when you are most likely to find me in my office, but feel free to come
around other times. When I'm not in class or in a meeting, I'll probably be in my office. If you want
to make an appointment, call or email me.
Required books and materials:
 Organic Chemistry, 7th edition by John McMurry
 Organic Chemistry: A Guided Inquiry, 2nd edition by Andrei Straumanis
 Laboratory Manual by David Soulsby
 Molecular Model Set – sold by Chemistry Club
 Safety goggles – You should have a pair from General Chemistry
 Hard bound laboratory notebook
Optional books:
The Solutions Manual for Organic Chemistry: A Guided Inquiry 2nd edition (Houghton
Miffline/Brooks-Cole/Cengage) ISBN: 978-0-618-97613-3 is available at
http://tinyurl.com/ExercisesAnswers Look for study Tool. But you really don’t need to buy it. You
are welcome to come to my office and check your answers using my copy if you must. The first
three ChemActivity Exercises answers will be up on Blackboard 2 days after we finish the activity.
Doing Organic Chemistry:
Imagine a coach who spends the entire lesson demonstrating good techniques but never lets her
students try out their new skills on the court. Would you want that person for your coach? We
learn by doing. This class is about doing organic chemistry yourself. We will be working on
problems each day in class. If you don’t get something right the first time, your classmates and I
will be right there to critique your form and help fix what’s going wrong. Research has found that,
at its best, organic chemistry is a team sport, so you will be working in groups of four or five.
The better your team works together, the more successful each individual will be.
The purpose of a science class is to teach students how to be scientists. So what is a
scientist? A scientist is a person who can a) look carefully at a situation that is new to her,
b) construct logical conclusions based on observations and c) discuss the merits of her
conclusions with peers. C is of particular importance in this era of collaborative research. These
days, no one makes a major discovery by him/herself; the abilities to communicate ideas and to
work within a team are essential.
Class Format:
 Most class periods will begin with a brief question and answer session based on the
previous day’s material.
 There will then be a ten minute quiz (taken individually) covering the previous day’s
material. This is to encourage you to keep up. Remember that if one member of a group
falls behind, the progress of the whole group is adversely affected.

The quiz is followed by group work on a ChemActivity Worksheet so you must bring your
workbook to class every day. During this time, I will walk around the class, observe, ask
and answer questions.
Groups:
 The bulk of class time is spent working in groups.
 I will assign group membership and will reshuffle groups frequently at first so you can get to
know everyone.
 You are strongly encouraged to work outside of class in groups. Find a study partner
or start a study group. Studies show most successful students do the bulk of their
homework in a productive group environment, and most students who fail are
 working alone. FIND A STUDY PARTNER! This is the single most important thing you
can do to make yourself successful in this course!!
 During the semester, you will each evaluate the other group members’ as well as your
contributions to the group based on the criteria to be handed out.
o
o
You will receive a zero for group performance if you do not submit an evaluation of the
students in your group within one week of the request.
Your assessment of your peers will be totally confidential. At the end of the semester, you
may receive your total performance score, but you will not know who gave you what score.
Out-of-class work:
 You must complete each day’s ChemActivity worksheet by the beginning of the next
class period, including the skill development exercises at the end of the activity.
 It is best to work through the assigned sections in the McMurray textbook after you have
completed the ChemActivity. (Assigned reading is found at the end of the syllabus.)
 ChemActivities will not be collected or graded.
 There will be selected, special, homework assignments periodically during the semester
that should be done individually and will be collected and graded.
 The problems suggested to be done at the end of the chapters in McMurray should be
done, and I encourage you to work on them with your study group. If you hand in copies of
all problems done on a regular basis (see  in class schedule for due dates), you will
receive points. These problems will count for a total of 50 pts in the course total.
 This course will use Blackboard. Answer keys, sample exams, useful links, and
announcements will be posted there. You should check there at least twice a week.
Grading Scheme:
3 exams (lowest one will be dropped)
final (comprehensive)
quizzes (constantly)
group work
homework
end of chapter problems
laboratory (50 pt exam)
200
200
200
50
50
50
300
1050 Total
The MAXIMUM percentages for a certain grade are listed below.
4.0
3.7
3.3
90
85
80
3.0
2.7
2.3
75
70
65
2.0
1.7
1.3
60
55
50
1.0 45
0.7 40
0.0 <40
Class Policy:
 Grades will be assigned on the basis of 1050 pts, as outlined above.
 There will be three hourly exams worth 100 pts each. The best two grades will be used to
compute your final grade.
 Any missed exam, regardless of the reason, will count as the dropped exam grade. Missing
more than one exam will result in scores of zero for the missed work.
 Make-up exams will not be given for missed work. There will be no make-ups for quizzes.
If you have a valid excuse (determined by me) to take an exam at another time, you must
make arrangements ahead of time or at least by the next day after the exam.
 The lowest three (or more, at my discretion) quiz grades will be dropped.
 No late homework will be accepted.
 Submit only your own work for your own credit. Any instances of suspected cheating in
this course will be dealt with according to the current Academic Dishonesty Policy.
The Science Center faculty strongly enforce the University’s Policy. You can not be a
scientist and not be ethical!
 Because the laboratory experience is an integral part of this course, concurrent enrollment
in lab is required, and a passing grade of 50% in lab is required to pass the course.
My view of organic chemistry:
Many students view organic chemistry as a cruel hurdle placed in their path to test their tolerance
for pain. Consistent with this view, many students’ main goal is to survive the course with a decent
grade. I encourage you to expect more from this course for two reasons:

I have found that students are more successful at organic chemistry when they enjoy it, so I
have worked hard to create a course that students can enjoy if they work hard.

Organic chemistry is an opportunity to hone skills like data analysis, problem solving, and
working effectively as part of a group. If you invest the time and energy you will learn skills
in this course that will make you more effective in your other courses and in whatever
career you choose.
Organic chemistry is not a hurdle; it is a staircase to a new and powerful way of dealing
with the world. That is why, more than any other course, admissions committees and future
employers care about your grade in organic chemistry.
Class Schedule:
Date
ChemActivity
W 9/9
Introduction and Syllabus
F
1: Bond Angles and Shapes
9/11
M 9/14
2: Lewis Structures
Reading JS (sections)
Assigned Problems
1.44
1.1-1.4
1.25, 2.32
W 9/16
3: Electron Orbitals
F
4: Polar Bonds, Polar Reactions
Part A
2.1-2.3, 2.13
9/18
1.5-1.12
1.26, .31, .33
2.22, .26, .31
M 9/21
Part B
2.7-2.8
2.40
W 9/23
Part C
2.9-2.11
2.38, .43, .44, .51, .53
2.4-2.6
2.33, .34
F
9/25
M 9/28

5: Resonance
Part A
Part B
2.54, .56
W 9/30
Nomenclature Worksheet 1
3.4, 4.1
3.38, .39, .40
F
6: Alkanes and Alkenes
Part A
3.6-3.7
3.47, .51
10/2
M 10/5
Part B
3.2-3.3 (6.2)
3.23, .24, .31
W 10/7
Part C
6.4-6.5
6.26, .29, .31

F 10/9
Review
M 10/12
Fall Break
W 10/14
Exam I over Activities 1 through 6
F 10/16
7: Cycloalkanes
Part A
Part B
M 10/19
Nomenclature Worksheet 2
W 10/21
8: Addition via Carbocation
Part A
F 10/23
M 10/26
Part B
4.2-4.3
4.4-4.8
LAST DAY TO DROP!
4.25
4.31,.32,.34,.37,.47,.48,.55,.56
6.3,8.1,10.1,17.1,18.1,24.1 10.17,17.26,18.24,24.31
5.1-.2, 5.4-.7, 6.6-.11 5.14,6.40,6.47,6.48,6.56
7.4
7.41a
9: Addition via Cyclic Intermediate
Part A
7.2-.3
Part B
7.6, 7.8
7.37
7.27
F 10/30
10: Oxidation and Reduction
Part A
Part B
7.5, 7.7
7.9, 17.7
7.25, .42
7.26,7.31,7.41bcd,17.30cd
M 11/2
11: Addition to Alkynes
8.3-.7
8.23,.25,.26,.36
W 11/4
Review
F 11/6
Exam II over Activities 7 through 11
M 11/9
12: Chirality
Part A
9.1-.4, .6-.7
9.29,.31,.32,.39
Part B
9.8-.9, 25.2
9.30,.43,.44,.50,.55,25.34
W 10/28
W 11/11

F 11/13
13: Substitution
Part A
M 11/16
Part B
W 11/18
Part C
F 11/20
Part D
M 11/23
14: Elimination
Part A
W 11/25
Thanksgiving Holiday
F 11/27
Thanksgiving Holiday
5.9-.10, 11.1-.3
11.25,.26,.29,.30,.31
11.37,.41,.42,.43
11.4-.5
11036,.57
11.7, .10
11.48

M 11/30
Part B
11.8
11.32,.45,.66
W 12/2
Part C
11.9, .12
11.47,.51,.55
5.3, 10.3-.4
10.19,.20,.21,.29
F 12/4
M 12/7
15: Radical Reactions
Part A
Part B
7.10
W 12/9
F 12/11
Review
Exam III over Activities 12 through 15
M 12/14
Final Review
Friday 12/18

Final Exam 9:00 am over all Activities
Advice from Past Students
Below are student answers to the question: What advice do you wish someone had given you at
the start?
 I really didn’t want to do group work at first because I have been successful taking notes
and studying by myself. But it works. Do not hesitate to talk and meet other students in and
out of class. They understand things you don’t, and vice versa.
 Don’t fall behind. Playing catch up is not fun. Don’t be afraid to ask questions and argue in
your group. That is the way learning is done in this class.
 Learn the reactions and read the textbook (McMurry).
 You may think (like I did) that group work in organic chemistry is a bad idea. (I thought it
would be the blind leading the blind.) But it really does work. I experienced both. I had
lecture for Organic 1, and I have really enjoyed the group work in Organic 2.
 Working together is the most important asset you have. Teaching others is an awesome
way to reinforce what you have learned.
 If you sit passively in your group, you don’t help anyone (especially yourself).
 Find people you work well with in and out of class. It helped me to find a study partner who I
could meet with twice a week outside of class.
 This format is much more fun and less intimidating than a lecture.
 You actually learn in class. In my lecture classes it was always about going home and trying
to figure it out later.
 I liked the idea of group work, but was afraid it would not prepare me for the final exam. My
advice to future students: Don’t worry. Fall into the format and it will carry you through.
 Don’t let yourself take the course lightly just because class is fun and relaxed. Do the
homework and reading.