Chem201DL.

001
Instructor

Organic Chemistry

Prof. Dorian Canelas

Teaching Assistants

Contact Info

Spring 2015

Office: 1223 FFSC

Email: [email protected]

Katie Bitting, Brett Hemric, Brittany Morgan, Jacob Timmerman

Class Hours

Lectures: Mondays and Wednesdays, 10:05am-11:20am

Laboratory: various
th
Recitation: Mondays or Tuesdays (starts week of January 12 )

Office Hours

Mondays 1:30-3:30 pm with Prof. Canelas in 1223 FFSC

Prerequisite

Credit for any of the following courses: Chem19, Chem21, Chem22L, Chem31L,
Chem43L, Chem101DL, Chem110DL

Course Description
Official synopsis from the Bulletin: The structures and reactions of the compounds of carbon and the
impact of selected organic compounds on society. Laboratory: techniques of separation,
organic reactions and preparations, and systematic identification of compounds by their
spectral and chemical properties.
Welcome to organic chemistry! It is an exciting topic that has direct applications to your environment and
health. Chem201DL is the first half of an integrated two-semester course sequence, and the material is
challenging and builds upon itself. For this reason, you are urged to employ all of the resources listed
below to maximize your comprehension of each section while it is being discussed in class.
Tips for success: Staying current with readings and problems as each topic is discussed in class is
critical to being successful in organic chemistry! Falling behind even a few sections will make it difficult to
synthesize the material in a way that will allow you to solve complex problems. On the calendar page, the
course pace is roughly sketched out so that you can read the appropriate chapter(s) for each week. I
want you to maximize your success and learning in this course, so please plan to spend 1-2 hours or
more per day, every day, working problems, reading the sections, viewing online material, and working
through examples and problems in the book. In addition to your personal study efforts, meeting with a
study partner or study group on a regular basis to discuss problem solving is another strategy that many
students use with great success. Be sure to use all of the resources available on a regular basis:
resource room, walk-in tutoring, instructor office hours, etc. Reminders about these will be given in class.
Resources
Required Course Materials:
Textbook
Loudons Organic Chemistry ISBN 9780981519432
Companion Study Guide and Solutions Manual ISBN 9780981519449
As an alternative, these can also be purchased together ISBN 9780981519456
Materials

Chemistry model kit

Safety glasses for laboratory

Internet

The web page for this course can be accessed through https://sakai.duke.edu
using your NetID and password to login. The syllabus, lecture notes, problem
sets, keys, content videos, and laboratory information will be available as
needed. There are separate sakai sites for lecture and laboratory. Sapling
Learning will also be employed for drill homework problem sets and some
laboratory work: http://www.saplinglearning.com.
Sapling access must be
purchased online.

Recitations:

Recitations provide you the opportunity to discuss organic chemistry topics and
solve challenging problems. You will work in small groups under the guidance of
a TA who has an excellent understanding of the material. Problem sets for
recitation will be periodically posted on sakai, and these need to be printed prior
to your recitation meeting.

Chem201DL-001
More Resources:

DMS

Spring 2015
Schedules/locations will soon be announced in class and on Sakai:
1) Chemistry Resource Room (free!) staffed by Duke students working towards
their PhD in Chemistry. Dont wait until the week of the test for the best help!
2) Walk-In Tutoring (free!) staffed by undergraduate Duke students who have
previously excelled in organic chemistry.
3) The Chemistry Department also keeps a list of graduate students who are
willing to tutor privately for a fee; each tutor sets his or her own rates.
http://www.chem.duke.edu/undergraduates/tutors.php
4) The Peer Tutoring Program offers free private undergraduate tutors for
students who do not do well on the first test. http://duke.edu/arc/peer_tutoring/

Students with disabilities are invited to register as soon as possible with the Disability
Management System--Student Access Office. Students who are currently registered with
the Disability Management System--Student Access Office should visit during faculty
office hours or email to schedule an appointment to discuss accommodations. This
should be done well in advance of the first exam.

Grading
Scores for the laboratory, online problem sets, three in-class tests, and final exam will be used to
calculate your total number of points as shown:
Tests 1, 2, & 3 (125 points each)
Online Homework
Final Exam
Laboratory
Total

375
75
300
250
1000

To encourage collaboration and study groups, the final grades for the course will not be curved this
semester. Instead, based upon average point total grade cut-offs over the past five years, the following
approximate minimum point cut-offs will be applied in course letter grade assignment: A+ 970, A 870, A820, B+ 790, B 740, B- 710, C+ 680, C 610, C- 560, D+ 540, D 520, D- 500.
If you miss one of the tests for any reason OR if you attend all tests but your final exam percentage
correct exceeds your percentage correct on any of the in-class tests, then your ONE lowest in-class test
score (out of 125 points; a zero in the case of a missed test) will be automatically replaced by more
heavily weighting your final exam. There are no make up tests after the date that the test has been given
in class.
Homework
Homework on a daily basis is the best way to learn the material and perform well on the tests. It
consists of reading the textbook, working through examples and problems at the ends of the chapters,
recitation activities, and online problems such as those posted on the Sapling learning website and the
course website. Sapling problems will contribute towards the points earned in the course.
Work and understand as many problems as you can; it is a great way to spend your study time! Book
chapter problems and recitation worksheets will not be collected and graded, but will serve as a good
study aid for you to measure your understanding of the material on a daily basis. Read each chapter to
solidify your understanding of the material; work ALL sample problems as you read. Please make an
effort to organize and categorize new material into the grand scheme of all material in the course to
find patterns. This might seem challenging at first; in the long run, this is a much better strategy than
trying to memorize by rote the huge volume of information that will be presented in this course.
Tests
Tests will be given on the dates shown on the calendar page. Each of these will cover approximately one
third of the course material. The comprehensive final exam will cover all of the course material. Tests
result in earning points rather than a letter grade. There is absolutely no make up for a missed
test after it has been given in class. It is strongly recommended that you attend every test or make
arrangements in advance for absences. If you will be absent for an test due to a planned event such as a
religious observance, court appearance, athletic event, military duty, or family obligation, you must clear

Chem201DL-001

Spring 2015

this with me in person at least one week in advance so that you can take the test prior to the regularly
scheduled class date.
If a question arises concerning the grading or point tally on a test, then the test in question should be
turned in for review within seven days of the date the graded tests were returned in class. Do not write
anything on the graded test itself. A separate regrade request form, which can be obtained from Prof.
Canelas, must be completed and attached to the test. Please read the academic integrity section below
and note that tests are often photocopied between the time of the grading and return to students in class.
Laboratory
A laboratory session will accompany the course. There is no laboratory textbook; general laboratory
information and procedures for each experiment are posted on the Laboratory Sakai site. Enrollment in
the online Sapling Learning system is required for lab. Students are responsible for reading assigned
material and completing a Pre-Lab assignment before each lab period. The laboratory is scheduled as
alternating dry and wet labs. Dry labs are done independently and wet labs are performed in the
laboratory room assigned. Students are required to follow the prescribed laboratory safety rules
contained in the laboratory syllabus for the course. Safety glasses must be worn at all times while in lab;
they can be purchased either in the Duke bookstore or for $5 at the base of the large staircase in the
FFSC at times TBD. Further information regarding meeting times, course structure, and requirements can
be obtained in the lab syllabus, available on the main lab Sakai site.
Laboratory Manager: Dr. A. Kasper (FFSC 1225, [email protected])
Attendance
Regular lecture, lab, and recitation attendance is expected.
Please see http://t-reqs.trinity.duke.edu/attendance.html and links therein for information regarding
absences that are considered excused. If a lecture is missed because of a short-term illness, a student
should submit an excuse that day on-line at the web address http://www.aas.duke.edu/trinity/treqs/illness/. Similar online forms are available for religious observances and athletic participation.
Regardless of the reason for absence, NO make up tests will be given after the scheduled due
date or class time. Please make arrangements with course faculty to complete online assignments
before the due dates if you will have a pre-planned absence for any reason. If you have an unexpected
absence during a test due to a non-planned event such as sickness, car trouble, or family emergency,
then please refer to the information in the grading section. A student who misses the final exam due to
severe illness, injury, or unexpected and tragic family event must provide documentation of the reason for
their absence to his or her Dean as soon as possible. The opportunity to make up the final exam (and
timetable for completion of the course) is at the discretion of the Dean in consultation with the instructor.
Academic Integrity
Students are expected to abide by the principles outlined in the Duke Community Standard:
Duke University is a community dedicated to scholarship, leadership, and service and to the principles of
honesty, fairness, respect, and accountability. Citizens of this community commit to reflect upon and
uphold these principles in all academic and nonacademic endeavors, and to protect and promote a
culture of integrity. To uphold the Duke Community Standard: I will not lie, cheat, or steal in my
academic endeavors; I will conduct myself honorably in all my endeavors; and I will act if the Standard is
compromised. In this spirit, each student must sign an Honor Pledge (I have neither given nor received
unauthorized aid on this exam.") on his or her test or final exam. Students found to be in violation of the
Honor Pledge will receive a zero for that test, exam, or assignment, and the incident will be reported. In
this case, the student also forfeits his or her right to replacement of the lowest in-class test score with the
final exam percentage. In some situations, assignment of a grade of F for the course may be deemed
the most appropriate grade sanction, and the instructor reserves the right to take this action in cases
where the student has been found responsible for an academic integrity violation by the Undergraduate
Conduct Board. Additional sanctions, including, but not limited to, suspension and expulsion, can be
implemented at the discretion of the Office of Student Conduct. Please see http://www.integrity.duke.edu/
and/or http://judicial.studentaffairs.duke.edu/index.html for more information about this policy.

Chem201DL-001

Spring 2015

Projected Course Calendar (Subject to Revision)

Week
#
1

Jan 7

Jan 12

W
M
W

Jan 14
Jan 19
Jan 21

M
W

Jan 26
Jan 28

Feb 2

4.7 4.9
14.1-2, 14.4,
14.6
5.1 5.4

W
M

Feb 4
Feb 9

5.4 5.5

W
M

Feb 11
Feb 16

5.6 5.7

Feb 18

Feb 23

Feb 25

Mar 2

Mar 4

10
11

Mar 16

12

W
M

Mar 18
Mar 23

Mar 25

Mar 30

W
M
W
M
W
M
W
Th

Apr 1
Apr 6
Apr 8
Apr 13
Apr 15
Apr 20
Apr 22
Apr 30

13

14
15
16

Date

Read Loudon
Chapters/Secs
1.2C1.4,
1.71.9,
15.6 to15.7A-C
2
3.1 3.3
No Class
4.1 4.7

8.9A, 17.2
12.1 12.6
13.1 13.7,
13.8 13.10
6.1 6.7
6.11 6.12
24.2
7

March 9 13
3.4 3.6, 14.7A
8.1 8.8

9.1 9.4
9.4 9.8,
14.7B
10.1 10.4

10.5 10.7
10.8 10.11
11.1 11.4, 14.8
11.5, 11.9-11.10

Topics and Remarks

Review Bonding, Resonance, Formal
Charge, Benzene
Alkanes: Structures, Conformations,
IUPAC Nomenclature, Combustion
Drawing Structures, Curved Arrows
Dr. Martin Luther King, Jr. Day
Alkenes and Alkynes: Nomenclature,
E/Z, CIP Rules, Addition of HX, Mechs,
Carbocations, Free Energy Diagrams
Catalytic Hydrogenations,
Nomenclature and Addn to Alkynes
Hydrations, Halogenations, Halohydrin
formation, Regiochemistry:
Markovnikov vs. anti-Markovnikov
More Alkene Addition Reactions:
Hydroboration-Oxidation, Ozonolysis
TEST 1
Radical reactions: HBr + peroxides
Free Radical Polymerization, Polymers
Radical Halogenations of Alkanes
Infrared Spectroscopy, Mass Spect.
13
C NMR, Chemical Shift, Proton NMR
Review Proton NMR, Coupling
Stereochemistry, Enantiomers, R&S,
Racemates, Diastereomers, Meso
Compounds, Fischer Projections
Cyclohexane, Conformational Analysis
Disubstituted Rings, Bicyclic Cmpds
Stereochemistry of Reactions on Rings,
Drawing a Reaction Map
Spring Break (No Classes)
Relative Acidities & Basicities, Grignard
& Organolithium Reagents, Acetylides
Nomenclature, Structure, and Solvation
of Alkyl Halides, Alcohols, Ethers, etc.
TEST 2
Nucleophilic Substitution & Elimination,
Rxn Rates, SN2 for Alkyl Halides
Substitution & Elimination, SN2 & E2,
SN1 & E1, -Eliminations
Review Substitution and Elimination
Reactions of Alcohols and Thiols
Sulfonate Esters,Thionyl Chloride, PBr3
Redox in Organic Chemistry
Designing Multistep Organic Syntheses
Ethers, Epoxides, Alkynes in Synthesis
TEST 3
Selected Glycol & Alkyne Reactions
Jeopardy & Review for Final Exam
Final Exam (Cumulative) 9:00 am

Recitation Topic
(Mondays/Tuesdays)
Review: Structure,
Bonding, Resonance,
and Formal Charge
1. Alkanes

No Recitation Monday
or Tuesday this week
2. Alkenes, Additions

3. Mechanisms

4. More Mechanisms,
Review for Test 1
5. Radical Mechanisms

6. Spectroscopy, NMR
Problem Set Rev

7. Stereochemistry

8. Cyclic Compounds,
Alkene Addn Reaction
Review

9. Acid & Base

Strengths

10. Substitution and

Elimination
11. Rxns of Alcohols,
Retrosynthesis Practice
12. More Practice with
Multi-step Synthesis

Chem201DL-001

Spring 2015

Please work ALL problems found within the assigned reading sections.
Suggested additional problems at ends of chapters (Loudon, 5th Edition)
These problems are suggested for your self study and will not be turned in.
Please do these in addition to the study problems, problems found throughout
the readings, recitation worksheets, and introductory drill problems in Sapling.
The problems below are, in general, more challenging than the examples and
problems found within the chapter readings. You need to work on these
gradually on a daily basis to be fully prepared for tests. Please feel welcome to
work additional problems if you are struggling with a concept; the list below
should be considered a minimum starting point.
Chapter Sections
1.2-1.4, 1.7-1.9
15.6-15.7C
2 (all)
3.1-3.3
4 (all)
14.1-2, 14.4, 14.6
5.1-5.5
Test 1
5.6-5.7
8.9A
17.2
12 (all)
13 (all)
6.1 6.9, 6.11-12
24.2
7 (all)
3.4 3.6
14.7A
8.1-8.5
Test 2
8.6 8.8
9 (all)
14.7B
10 (all)
11.1 11.4
14.8
Test 3
11.5 11.10
Final Exam

Problems
Ch 1: 25, 27, 31, 33, 41, 45-47
Ch 15: study problems 15.2 and 15.3, 27, 29, 38c-f
Ch 2: 26-30, 33, 35, 37, 40, 42, 45
Ch 3: 25, 26, 32, 33, 36, 37
Ch 4: 39, 41a, 42a, 44a-c, 46d, 50, 54, 57, 62, 63, 66
Ch 14: 28cd, 29a, 30, 26abcfg, 27abd
Ch 5: 27 not i&o, 31ab, 32acegi, 34-5, 46, 48abc, 52
Chapters 2&4 (all), sections of Chapters 1, 3, 5, 14, 15
Ch 5: 27io, 29, 31cd, 32bdfhj, 36, 48efg, 49, 51
Ch 8: 31, 32, 55
Ch 17: 18ab, 37ef
Ch 12: 22, 24a, 26, 28a, 35, 39
Ch 13: 35, 38a, 39d-e, 44, 49, 54
Ch 6: 28, 30-32, 36, 37, 42, 44-46, 51
Ch 24: 1-3
Ch 7: 34, 36, 37, 39, 40, 44, 47, 51, 53-55, 58, 63
Ch 3: 27, 31, 35, 39a&c, 40, 41a&c, 43, 44
Ch 14: 15, 16, 31
Ch 8: 33, 35, 36, 37ace, 38, 42, 47, 50, 56, 59a
Chapter 7, 12, & 13 (all), parts of 3, 5, 6, 8, 14)
Ch 8: 44ace, 48, 51, 52, 53, 62a
Ch 9: 35-37, 39, 40b, 41ac, 42, 47, 50-1, 58, 61, 63-4, 67
Ch 14: 18-22, 33acgh
Ch 10: 40ad, 41, 43ace, 45acf, 53, 54, 55, 59, 60
Ch 11: 1-22 (odd)
Ch 14: Study problem 14.2, 23, 34abe, 36
Chapters 9 & 10 (all), parts of 8, 11, 14)
Ch 11: 45, 47, 50, 52-54, 56, 60, 61, 68
Cumulative