Chem201DL.

002 Organic Chemistry Spring 2015

Instructors Prof. Amanda Hargrove Contact Info Office: 3219 FFSC

Email: amanda.hargrove@duke.edu
Prof. Dorian Canelas Contact Info Office: 1223 FFSC
Email: dorian.canelas@duke.edu
Teaching Assistants Katie Bitting, Brett Hemric, Brittany Morgan, Jacob Timmerman

Class Hours Tuesdays and Thursdays, 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

Tuesdays 3:15-5:15pm with Prof. Hargrove in 3219 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 Loudon’s 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
Personal response system: eclicker2
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
Chem201DL-002 Spring 2015

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.
More Resources: 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. Don’t 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/

DMS 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 and in-class 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) 375
Online Homework and In-Class Activities 75
Final Exam 300
Laboratory 250
Total 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, A-
820, 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
Chem201DL-002 Spring 2015

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
this with Prof. Hargrove or Prof. Canelas 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.
Hargrove or 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, amanda.kasper@duke.edu)

Attendance
Regular lecture, class activity, and recitation attendance is expected. In-class activities will
contribute towards the points earned in the course. The lowest two in-class activity scores (zero in the
case of a missed class for any reason) will be dropped before this portion of the grade is calculated.
Please see http://t-reqs.trinity.duke.edu/attendance.html and links therein for information regarding
absences that are considered excused. If class 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/t-
reqs/illness/. Similar online forms are available for religious observances and athletic participation.
Regardless of the reason for absence, NO make up class activity points will be given after the
scheduled class time. Please make arrangements with course faculty to complete 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
Chem201DL-002 Spring 2015

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-002 Spring 2015

Projected Course Calendar (Subject to Revision)

Week Date Read Loudon Topics and Remarks Recitation Topic
# Chapters/Secs (Mondays/Tuesdays)
1 Th Jan 8 1.2C–1.4, Review Bonding, Resonance, Formal Review: Structure,
1.7–1.9, Charge, Benzene Bonding, Resonance,
15.6 to15.7A-C and Formal Charge
2 T Jan 13 2 Alkanes: Structures, Conformations, 1. Alkanes
3.1 – 3.3 IUPAC Nomenclature, Combustion
Th Jan 15 Drawing Organic Structures
Curved Arrow Notation for Reactions
3 T Jan 20 4.1-4.7, Alkenes and Alkynes: Nomenclature, No Recitation Monday
14.1-2, 14.4 E/Z, CIP Rules, Addition of HX, Mechs,
Th Jan 22 Carbocations, Free Energy Diagrams
4 T Jan 27 4.8-4.9, Catalytic Hydrogenations, Hydrations, 2. Alkenes, Additions
Halogenation, Halohydrin formation,
Th Jan 29 5.1-5.4, 14.6 Markovnikov vs. anti-Markovnikov
5 T Feb 3 5.4 – 5.5 More Alkene Addition Reactions: 3. Mechanisms
Th Feb 5 Hydroboration-Oxidation, Ozonolysis
6 T Feb 10 TEST 1 4. More Mechanisms,
Th Feb 12 5.6 – 5.7 Radical reactions: HBr + peroxides Review for Test 1
Free Radical Polymerization, Polymers
8.9A, 17.2 Radical Halogenations of Alkanes
7 T Feb 17 12.1 – 12.6 Infrared Spectroscopy, Mass Spect. 5. Radical Mechanisms
13
13.1 – 13.7, C NMR, Chemical Shift
Th Feb 19 13.8 – 13.10 Proton NMR, Coupling
8 T Feb 24 6.1 – 6.7 Stereochemistry, Enantiomers, R&S, 6. Spectroscopy, NMR
6.11 – 6.12 Racemates, Diastereomers, Meso Problem Set Rev
Th Feb 26 24.2 Compounds, Fischer Projections
9 T Mar 3 7 Cyclohexane, Conformational Analysis 7. Stereochemistry
Disubstituted Rings, Bicyclic Cmpds
Th Mar 5 Stereochemistry of Reactions on Rings,
Drawing a Reaction Map
10 March 9 – 13 Spring Break (No Classes)
11 T Mar 17 3.4 – 3.6, 14.7A Relative Acidities & Basicities, Grignard 8. Cyclic Compounds,
8.1 – 8.8 & Organolithium Reagents, Acetylides Alkene Add’n Reaction
Nomenclature, Structure, and Solvation Review
of Alkyl Halides, Alcohols, Ethers, etc.
Th Mar 19 TEST 2
12 T Mar 24 9.1 – 9.4 Nucleophilic Substitution & Elimination, 9. Acid & Base
Rxn Rates, SN2 for Alkyl Halides Strengths
Th Mar 26 9.4 – 9.8, Substitution & Elimination, SN2 & E2,
14.7B SN1 & E1, α-Eliminations
13 T Mar 31 10.1 – 10.4 Review Substitution and Elimination 10. Substitution and
Reactions of Alcohols and Thiols Elimination
Th Apr 2 10.5 – 10.7 Sulfonate Esters,Thionyl Chloride, PBr3
Redox in Organic Chemistry
14 T Apr 7 10.8 – 10.11 Designing Multistep Organic Syntheses 11. Rxns of Alcohols,
Th Apr 9 11.1 –11.4, 14.8 Ethers, Epoxides, Alkynes in Synthesis Retrosynthesis Practice
15 T Apr 14 TEST 3 12. More Practice with
Th Apr 16 11.5, 11.9-11.10 Selected Glycol & Alkyne Reactions Multi-step Synthesis
16 T Apr 21 Jeopardy & Review for Final Exam
Th Apr 30 Final Exam (Cumulative) 9:00 am
Chem201DL-002 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 Problems

1.2-1.4, 1.7-1.9 Ch 1: 25, 27, 31, 33, 41, 45-47
15.6-15.7C Ch 15: study problems 15.2 and 15.3, 27, 29, 38c-f
2 (all) Ch 2: 26-30, 33, 35, 37, 40, 42, 45
3.1-3.3 Ch 3: 25, 26, 32, 33, 36, 37
4 (all) Ch 4: 39, 41a, 42a, 44a-c, 46d, 50, 54, 57, 62, 63, 66
14.1-2, 14.4, 14.6 Ch 14: 28cd, 29a, 30, 26abcfg, 27abd
5.1-5.5 Ch 5: 27 not i&o, 31ab, 32acegi, 34-5, 46, 48abc, 52
Test 1 Chapters 2&4 (all), sections of Chapters 1, 3, 5, 14, 15
5.6-5.7 Ch 5: 27io, 29, 31cd, 32bdfhj, 36, 48efg, 49, 51
8.9A Ch 8: 31, 32, 55
17.2 Ch 17: 18ab, 37ef
12 (all) Ch 12: 22, 24a, 26, 28a, 35, 39
13 (all) Ch 13: 35, 38a, 39d-e, 44, 49, 54
6.1 – 6.9, 6.11-12 Ch 6: 28, 30-32, 36, 37, 42, 44-46, 51
24.2 Ch 24: 1-3
7 (all) Ch 7: 34, 36, 37, 39, 40, 44, 47, 51, 53-55, 58, 63
3.4 – 3.6 Ch 3: 27, 31, 35, 39a&c, 40, 41a&c, 43, 44
14.7A Ch 14: 15, 16, 31
8.1-8.5 Ch 8: 33, 35, 36, 37ace, 38, 42, 47, 50, 56, 59a
Test 2 Chapter 7, 12, & 13 (all), parts of 3, 5, 6, 8, 14)
8.6 – 8.8 Ch 8: 44ace, 48, 51, 52, 53, 62a
9 (all) Ch 9: 35-37, 39, 40b, 41ac, 42, 47, 50-1, 58, 61, 63-4, 67
14.7B Ch 14: 18-22, 33acgh
10 (all) Ch 10: 40ad, 41, 43ace, 45acf, 53, 54, 55, 59, 60
11.1 – 11.4 Ch 11: 1-22 (odd)
14.8 Ch 14: Study problem 14.2, 23, 34abe, 36
Test 3 Chapters 9 & 10 (all), parts of 8, 11, 14)
11.5 – 11.10 Ch 11: 45, 47, 50, 52-54, 56, 60, 61, 68
Final Exam Cumulative