CHEMISTRY 261: ORGANIC CHEMISTRY I, FALL 2015
001: TR 8:00 - 9:15 Chapman 211
002: MWF 11:15-12:05 Murray G202
Instructor: Dr. Jennifer Krumper
Text: Organic Chemistry (Bruice, 7th ed.)
Course webpage: sakai.unc.edu
Prerequisite: a grade of C- or better in 102
Other Materials: i>Clicker brand clicker (required; use any clicker made by this company), subscription to
ALEKS (required; available online), subscription to MasteringChemistry (required; bundled with your
textbook at the bookstore), HGS model kit (required), student solutions manual (optional).
CONTACT INFORMATION. To promote personal connection, reach me in person rather than by email. Use
email ([email protected]) only in emergency situations.
Bring science or course content questions to Q&A sessions. This way, all students have equal access to
help with tough topics in the class.
Q&A sessions: Locations: = Murray G202;  = Murray G307; = Kenan C143; $$= Chapman 211
Day
M
Tu
W
Th
Early
12:00-12:45 (Dr. K.; )
8:30-9:30 (261 mentors; )
Late Afternoon
2:30-3:15 (Dr. K.;
3:30-4:30 (Dr. C.;
2:30-3:15 (Dr. J.;
2:00-2:45 (Dr. K.;
)
)
)
)
Evening
6:00-7:00 (261 mentors; )
7:00-8:00 (261 mentors; $$)
6:00-7:00 (261 mentors; $$)
Office hours (non-science questions): Kenan C147F
W: 1:30-2:15
F: 2:45-3:30
or: catch me after class or a Q&A session
Office hours are set aside for questions about logistic matters, general strategies for success, or just to say
hello. I would love to meet you, so make it a point to drop by at least once during the semester.
If you wish to discuss an exam in office hours, bring: 1) the exam you wish to discuss, 2) your notes +
practice problems, and 3) a completed post-exam reflection survey (available on sakai).
COURSE DESCRIPTION
Chemistry 261 is the first half of a two semester, cumulative overview of organic chemistry. We will
cover the fundamental tools of organic chemistry and apply these to the reactions of alkanes, alkenes,
alkynes, alkyl halides, ethers, and alcohols.
You may find this course unusual for a science class, and surprisingly similar to acquiring a second
language. You will only be asked to perform simple mathematical operations, but you will learn many
reagents (nouns) and to develop a feel for the mechanisms (verbs) by which these reagents act.
Later, you will approach multi-step chemical synthesis, which is analogous to sentence construction.
Becoming fluent in the language of organic chemistry requires deep learning and long-term retention
of what you’ve learned. This can be achieved only by working a wide variety of practice problems and
by engaging deeply with the material every day.
THE CHEMISTRY 261 COMMUNITY
Our class emphasizes teamwork and good sportsmanship. Grading is on a flat scale, not a curve. In
Chemistry 261, therefore, ultra-competitive behavior is not only unattractive, it is also unnecessary.
ACADEMIC HONESTY
Cheating is NOT a part of the Chemistry 261 culture, nor does it benefit the cheater. Academic
dishonesty carries heavy consequences: http://instrument.unc.edu/instrument.text.html#IPreamble.
Some student work (e.g. exams, MasteringChemistry) must be completed individually and without
external aids. Other work (e.g. group questions in class) may be completed with help from peers
and/or selected external aids. If you are unsure whether a task is intended to be individual or group
work or whether you may use outside aids, ASK!
All course materials including notes and assignments are covered by University Copyright Policy:
http://www.unc.edu/campus/policies/copyright%20policy%2000008319.pdf
CHEMISTRY 261 IS AN ENGAGED-LEARNING CLASS
How well you learn depends largely on your choices: do you engage with the material every day, or do
you cram for exams? Do you think deeply about what you’re learning, or do you skim the surface? The
course structure of Chem 261 is designed to reward activities that support learning with class points.
These are called Daily Work Points, and they comprise 15% of your grade.
To earn Daily Work Points, you will prepare for each week of class with a pre-class assignment: video
lectures and/or selected textbook reading to do, followed by a graded ALEKS or MasteringChemistry
problem-solving activity. We will then check your understanding in class and delve into more
challenging topics with clicker quizzes and group work. Chemistry 261 mentors and I will rove during
these activities help you build the skills you need in the right way. After class, you will reinforce your
skills by doing textbook practice problems and graded online self-tests (in MasteringChemistry) to
ensure you have mastered the skills of organic chemistry. Each part of this class structure has been
shown to improve success in chemistry.
You may not earn a score higher than 100% on Daily Work, but many more Daily Work points will be
offered than are necessary to earn a 100% (see Daily Work grading chart). This will allow you to make
up points lost by the occasional missed class, dead clicker battery, or missed MasteringChemistry
deadline.
DAILY WORK AND ATTENDANCE
Your overall Daily Work score (15% of your grade) is roughly 50% based on in-class work. Excellent
attendance is required.
ALEKS: Course Code = JW9TN-TJF6L
We will use an online learning system called ALEKS for the first few weeks of the term. ALEKS is quite
different from other online homework systems: it assesses your skills and assigns specific tasks
catered to you. No two students will have exactly the same set of learning tasks in ALEKS. Work
individually in ALEKS. The program is designed such that collaboration of any kind will create a
significant amount of extra work for you. More information is available under “261 Startup” on sakai.
PRE-CLASS ASSIGNMENTS
Video lectures and/or reading will be assigned before each week of classes. ALEKS Objectives and/or
pre-class questions in MasteringChemistry (Course = KRUMPER261FA2015) will due each Sunday night
to hold you accountable for these Pre-Class Assignments. These assignments are graded and
required: their content will be tested on exams.
Pre-class assignments in MasteringChemistry and/or ALEKS will be due at 11:59pm on Sundays.
CLICKER ACTIVITIES
We will do a variety of problem solving activities in class using clickers. Some activities will test your
mastery of the Pre-Class Assignment. For these clicker quizzes, you will be instructed to work
individually, and your score will be based on your performance. You may use notes you have taken on
the Pre-Class Assignment on the clicker quiz, but other materials (e.g. your book) are excluded.
Throughout class period, we will learn new concepts and skills in lecture, then apply these to real
organic chemistry problems. You will work together with a team to master these tasks. You will earn
points for simply participating in these activities.
No makeups will be given for in-class clicker points. (See notes on Daily Work and Attendance above.)
PRACTICE PROBLEMS
A list of recommended practice problems from your text for each exam’s content will be posted under
“Daily Work and HWK” on sakai. These practice problems are the key to your success in Organic
Chemistry. Years of experience have shown me that successful students in the course do all of the
recommended textbook problems and they open their textbooks to solve problems every day.
SELF TESTS IN MASTERINGCHEMISTRY: COURSE = KRUMPER261FA2015
Self Tests will be assigned in MasteringChemistry on a weekly basis. Self Test problems are much like
end-of-chapter problems from the textbook, and they are intended to augment, rather than replace
textbook practice. Consider your performance on Self Tests as a measure of whether you have done
enough practice problems. You will have 90 minutes to complete each week’s Self Test.
No late work will be accepted in MasteringChemistry for any reason. The MasteringChemistry clock
will be used to determine the submission date/time. This clock may differ from yours, so submit your
work well in advance. You may use your book or other resources, but all MasteringChemistry
assignments are to be worked by you alone. No collaboration is allowed before the due date, but
discussion of MasteringChemistry content is encouraged after you’ve turned it in.
Self Tests in MasteringChemistry will be due at 8:00 am on Wednesdays.
QUIZZES, EXAMS, AND FINAL
See schedule for dates of midterms and the final. Unless you have a valid medical, emergency, or
university sanctioned excuse, a missed exam will be scored as a zero. Excused absences must be
accompanied by documentation for alternative arrangements to be made. If you know will need to
miss an exam in advance (e.g. for a medical procedure or University field trip), you may arrange to
take the exam early. Arrangements for early exams must be made at least two weeks in advance.
Email Dr.K. if you become ill on the day of the exam or have a last minute difficulty taking the exam.
Q&A SESSIONS
Attendance at Q&A sessions (see schedule on first page) will be encouraged with Daily Work points,
and you can collect these points by completing a weekly poll in sakai. If you are totally unable to
attend any of the Q&A sessions for a week, you may attest to this fact (on your honor) and be
awarded credit in absentia.
Weekly Q&A attendance polls will be due on sakai at 11:59pm on Sundays.
GRADING
Your Daily Work % score will be calculated as a % of 200 Daily Work points.
More than 280 points of Daily Work will be available, but your score may not exceed 100%.
Item
Points ea.
Number
Min. total pts.
36
MWF: 4
TuR: 6
1
~ 35
~23
36
~12
~12
~36
MasteringChemistry Self-Tests
3
3
Review Session Attendance (credit for 1 per week)
3
~12
~36
ALEKS
Clicker Activities (every class period)
MasteringChemistry Pre-Class assignments
Minimum Daily Work Points Available
Final Exam
Total
Grade Breakdown
Points Possible
Daily Work % score is
scaled to 75 points
300
(3 scores: 100 pts each)
125
500
~36
>280
200
Maximum Daily Work Points Applicable to Final % score
Item
Daily Work (more
info below)
Midterms
~ 140
% of Grade
15%
60%
(3 scores: 20% each)
25%
100%
Grade thresholds may be scaled down at the instructor’s discretion, but guaranteed minimum
values are listed below. (e.g. a score of 68% is guaranteed a C-)
Percentage Course
Percentage Course
Percentage Course
Percentage Course
score
grade
score
grade
score
grade
score
grade
93.0 – 100
A
87.0 – 89.9 B+
75.0 – 79.9 C+
60.0-66.9
D
90.0 – 92.9 A83.0 – 86.9 B
70.0 – 74.9 C
< 60.0
F
80.0 – 82.9 B67.0 – 69.9 C-
HOW TO SUCCEED IN ORGANIC CHEMISTRY
Be a good class citizen. Smile at your classmates and introduce yourself to them. Ask someone how
their day is going. Switch off all electronic devices (phones, computers, etc.) while in class.
Print up the list of recommended textbook practice problems and mark your progress on it. Keep a
spiral notebook or binder for your practice problems; it is useful for the purpose of review to have
them all collected in one location.
Do some organic chemistry every day. Complete all the Pre-Class Assignments before coming to
class. Complete all the recommended practice problems. Stay on top of your ALEKS work and Sapling
Homework.
A good study session feels like a hard workout; expect to be tired afterwards. Be well rested when
you start studying and study with focus + determination.
HOW TO SUCCEED IN ORGANIC CHEMISTRY, CONTINUED
Use the textbook wisely. While each student learns differently, be wary of over-reliance on the
textbook. We will not cover every topic presented in the assigned chapters in Bruice, and we may
cover topics with less or more detail than Bruice. As such, it can be a poor use of time to read the
textbook carefully. Student time is often better spent working problems and using the text for
reference, rather than to learn material. Specific sections that are important for you to read
thoroughly will be flagged in your pre-class assignment. If a section is not flagged, however, it is
suggested that you learn the content from the assigned video or lecture notes, rather than the text.
For non-flagged sections, you are urged to use the text for reference only.
Hand write your notes, both from the videos and in class. You may take notes on a tablet, but organic
chemistry requires a great deal of drawing; typing is not practical. Keep notes organized, and take
notes in more than one color. Color-coding greatly assists in tracking the movement of atoms in
organic reactions.
Review to the class notes posted on sakai after class. The class is fast-paced and clicker activities are
presented rapid fire. Your time is best spent working out solutions to questions rather than
transcribing question text. It is wise to take sketchy/partial notes on in-class questions: just enough to
flag the question in your notes and work out an answer. All notes and clicker activities presented in
class are posted on sakai immediately after class. Look these up and fill in the gaps in the notes you
took on in-class questions.
Attend Q+A sessions. There are many Q&A sessions offered each week, hosted both by mentors and
by Dr.K. Attend these sessions. Bring your questions and/or just bring your desire to learn.
Form a study group. Working with a study group outside of class will help you learn the material
deeply. Your in-class working group is a great place to form these connections. Exchange contact
information and follow up – call others and ask if they want to study together.
Make and study flash cards. It is extremely helpful to work with a shuffle-able deck of reaction flash
cards when we get into reaction chemistry (Chapter 6 and beyond). Flash cards train you to recognize
reactions without the context cues provided by seeing them on a page in your notes or the text. The
act of making the flash cards is also an excellent way to review the reactions we’ve learned.
Use non-assigned electronic resources. If you purchase a current version of textbook in the
bookstore bundle or an eText, you will receive free access to MasteringChemistry. Mastering offers a
“study area” with a host of practice multiple-choice problems. Google can provide a wealth of extra
practice problems, too.
Venues for extra help with 261:
1) The Learning Center coordinates free tutoring by appointment:
http://learningcenter.unc.edu/services/Math%20and%20Science/tutoring-for-math-and-sciences
2) The chemistry department recommends tutors for hire:
http://www.chem.unc.edu/undergrads/index.html?display=help___resources&content=tutoring
Tentative Schedule: Chemistry 261, Fall 2015, section 001 TR 8:00 am
Date
Day
#
Topics/Skills
Relevant Text Sections/Events
8/18
Tu
1
1.0 – 1.4, 2.8
8/20
Th
2
Chemistry 101 review: electronegativity, structural formulae, Lewis
Structures, formal charges, resonance
resonance, skeletal structures
8/25
Tu
3
Chemistry 101 review: atomic and molecular orbitals, hybridization
1.5 – 1.12
8/27
Th
4
Chemistry 101 review: hybridization & molecular geometry
1.13 – 1.16, 2.1 –2.6
9/1
Tu
5
Bronsted and Lewis; Alkane Nomenclature; Functional Groups
2.6 – 2.9, 2.12; 3.1 – 3.6; 5.5; 3.7
9/3
Th
6
Acyclic alkane conformations: C-C bond rotation
3.8 – 3.10
9/8
Tu
7
Cycloalkane conformations; Thermodynamics of equilibrium
3.11 – 3.15; pp. 206-207
9/10
Th
8
Chirality, enantiomers
4.1 – 4.6
9/15
Tu
9
Optical activity, multiple stereoisomers
4.7 – 4.14
9/17
Th
10
9/22
Tu
11
alkene structure, stereochemistry, kinetics, + thermodynamics in the
context of electrophilic addition of HX to an alkene
Exam 1
5.1 – 5.6; 6.1 – 6.3 (Background:
5.7; 5.9 – 5.12 (skip p.215))
Chapters 1-4
9/24
Th
12
Hammond Postulate, cation stability, hydration
6.4 – 6.5
9/29
Tu
13
Hydration and alcohol addition
6.5 – 6.7
10/1
Th
14
6.7 – 6.10
10/6
Tu
15
10/8
Th
16
carbocation rearrangements, hydroboration; X2 addition, peroxyacid
oxidation
ozonolysis, hydrogenation, alkene stability, stereochemistry review,
synthesis
Alkyne reactivity, Alkynes + HX, X2, Alkyne hydration
10/13
Tu
17
7.9 – 7.12
10/15
Th
Addition of H2 to alkynes, Alkyne deprotonation, C-C bond
formation, synthesis
Fall break
10/20
Tu
18
Additions to dienes, Review and Synthesis practice
8.17 – 8.18; 6.14-6.15, 6.18, and 7.12
10/22
Th
19
Exam 2
Chapters 5-7
10/27
Tu
20
Introduction to SN2; Factors and Trends for SN2, SN1
9.1 – 9.4
10/29
Th
21
SN1/2 competition, solvent effects
9.5 – 9.9
11/3
Tu
22
Intro to E2, intro to E1; E2 stereochemistry
10.1 –10.4; 10.6 – 10.7
11/5
Th
23
More on E1/2; SN1/2 vs. E1/2 and synthesis using these reactions
10.5 –10.11
11/10
Tu
24
Intro to alcohols
11.1 – 11.4
11/12
Th
25
Oxidation of alcohols, ethers, epoxides
11.5 – 11.8
11/17
Tu
26
Epoxides; intro to radicals
11.7 – 11.8; 13.1 – 13.3
11/19
Th
27
Exam 3
Chapters 8-11
11/24
Tu
28
13.4 – 13.5; 13.7 – 13.9
11/26
Th
Reactivity and selectivity in halogenation, Radical additions to
alkenes; Allylic and benzyllic halogenation;
Thanksgiving Break
12/1
Tu
synthesis with radicals and REVIEW
13.10
12/10
Th
29
Final Exam section 001: 8:00 am, Chapman 211
8.3 – 8.6, some 3.3
6.11 – 6.15; 6.18
7.1, 7.4 – 7.8
No class
No class
Tentative Schedule, Fall 2015, Section 002 MWF 11:15 am
Date
Day
#
Topics/Skills
Relevant Text Sections
8/19
W
1
1.0 – 1.4
8/21
F
2
8/24
M
3
Chemistry 101 review: electronic structure, electronegativity,
structural formulae, covalent bonds, Lewis Structures
Chemistry 101 review: Lewis Structures, formal charges, resonance,
skeletal sturctures
Chemistry 101 review: atomic and molecular orbitals, hybridization
8/26
W
4
Chemistry 101 review: hybridization & molecular geometry
1.10 – 1.14
8/28
F
5
hybridization practice, Bronsted Acids
1.15 – 1.16; 2.1 – 2.6
8/31
M
6
Bronsted Acids: structural factors
2.6 – 2.7
9/2
W
7
Bronsted and Lewis Acids; Functional Groups, Nomenclature
2.9, 2.12, 5.5, 3.1 – 3.4, 3.6
9/4
F
8
Physical properties, Acyclic alkane conformations: C-C bond rotation
3.8 – 3.10
9/7
M
Labor Day
No class
9/9
W
9
Cycloalkane conformations; Thermodynamics of equilibrium
3.11 – 3.15; pp. 206-207
9/11
F
10
Chirality, enantiomers
4.1 – 4.6 (skip Fischer projections)
9/14
M
11
R and S naming, Optical activity, and enantiomeric excess
4.7 – 4.10
9/16
W
12
Multiple stereocenters
4.11 – 4.14
9/18
F
13
alkene structure, stereochemistry, curved arrows
5.1 – 5.6
9/21
M
14
Exam 1
Chapters 1-4
9/23
W
15
9/25
F
16
kinetics, + thermodynamics in the context of electrophilic addition of
HX to an alkene
Markovnikov’s Rule, cation stability, Hammond Postulate
6.1 – 6.3 (Background: 5.7; 5.9 –
5.12 (skip p.215))
6.4 – 6.7
9/28
M
17
Addition of H2O and ROH
6.5– 6.6
9/30
W
18
Addition of ROH, carbocation rearrangements, hydroboration
6.6 – 6.8
10/2
F
19
hydroboration, X2 addition, peroxyacid oxidation
6.8 – 6.10
10/5
M
20
6.11 – 6.15
10/7
W
21
ozonolysis, hydrogenation, alkene stability, stereoselectivity in
addition rxns
Synthesis; Alkyne reactivity, Alkynes + HX, X2
10/9
F
22
Alkyne hydration + tautomerization,
7.7 – 7.8
10/12
M
University Day
No Class
10/14
W
7.9 – 7.12
10/16
F
Addition of H2 to alkynes; alkyne deprotonation, C-C bond
formation, synthesis
Fall Break
10/19
M
24
Dienes
8.17 – 8.18
10/21
W
25
Exam 2
Chapters 5-7
23
2.8, 8.3 – 8.6, some of 3.3
1.5 – 1.9
6.18; 7.1, 7.4 –7.6
No Class
Tentative Schedule, Fall 2015, Section 002 MWF 11:15 am, Continued
10/23
F
26
SN2 Introduction
9.1
10/26
M
27
SN2 Factors and Trends; SN1
9.2 - 9.4
10/28
W
28
SN1, SN1/2 competition
9.5 – 9.6
10/30
F
29
9.7 – 9.9
11/2
M
30
solvent effects, Intramolecular substitution reactions and biological
examples
E2 with stereochemistry
11/4
W
31
More on E2 stereochemistry, E1 with stereochemistry
10.3 – 10.7
11/6
F
32
SN1/2 vs. E1/2 and synthesis using these reactions
10.9 – 10.10
11/9
M
33
Intro to alcohols
11.1 – 11.2
11/11
W
34
More on alcohols
11.3 – 11.4
11/13
F
35
Oxidation of alcohols, ethers
11.5 – 11.6
11/16
M
36
Ethers and Epoxides
11.6 – 11.7
11/18
W
37
Intro to radical halogenation
13.1 – 13.3
11/20
F
38
Exam 3
Chapters 8-11
11/23
M
39
13.4 – 13.5; 13.7
11/2511/27
11/30
W
Reactivity and selectivity in halogenation, Radical additions to
alkenes
Thanksgiving Break
M
40
Allylic and benzyllic halogenation; synthesis with radicals
13.8 – 13.10
12/02
W
41
REVIEW
12/04
F
12:00 pm: Final Exam for section 002
10.1 – 10.2, 10.6 – 10.7
No class