CHEM201: Organic Chemistry Duke University, Fall 2013 M W F 8:459:35 AM Location: FFSC 2231 Lecturer Professor Qiu Wang

(Office: 2102 FFSC; Phone: 660-1648; Email: qiu.wang@duke.edu) Textbooks 1. Organic Chemistry, 5 Edition, G. Marc Loudon, Roberts and Company Publishers, 2009. 2. Study Guide and Solutions Manual to Accompany Organic Chemistry, 5 Edition, G. Marc Loudon and Joseph G. Stowell, Roberts and Company Publishers, 2010. Recommended Materials 1. A Molecular Model Kit. The graduate organization PLU will be selling kits ($30 cash or check) on the lower level of FFSC near the organic lab hallway. Dates and times of sales to be announced. Most other model kits are also fine. Exams There will be three 50-minute examinations and a final examination. In the event of an excused absence from an hour examination, a normalized final examination score will be used to calculate the final grade. There will be no make-up examination. Hour Exam 1: Hour Exam 2: Hour Exam 3: Final Exam: Grading September 23, 2013 (Monday, 8:359:35 AM) October 21, 2013 (Monday, 8:359:35 AM) November 18, 2013 (Monday, 8:359:35 AM) December 13, 2013 (Friday, 7:00 PM 10:00 PM) = 450 points = 300 points = 250 points = 1000 points
th th

Three 50-minute Examinations @150 points Final Examination Laboratory TOTAL

Recitation Each student is scheduled for a 50-min recitation session each week, during which material & problems relevant to the lecture part of the course will be discussed. Problem sets for each recitation can be found in a folder in the RESOURCE section of the Sakai course site. The first recitation will be on Friday, August 30, 2013 (no problem set). Recitation TAs: Stacey McDonald stacey.turner@duke.edu, Megan Lanier megan.lanier@duke.edu

Recitation Schedule (Friday)

Recitation # 1 2 3 4 5 6 7 8 9 10 11 12 13 14

Date August 30, 2013 September 6, 2013 September 13, 2013 September 20, 2013 September 27, 2013 October 4, 2013 October 11, 2013 October 18, 2013 October 25, 2013 November 1, 2013 November 8, 2013 November 15, 2013 November 22, 2013 December 6, 2013

Problem set --1 2 3 --4 5 6 --7 8 9 --10

Laboratory A mandatory laboratory session accompanies this CHEM 201 course. There is no laboratory textbook; all general information including relevant experimental procedures and required materials will be posted on the Sakai CHEM 201 Laboratory site. In addition, enrollment in the online Sapling Learning system is required (see lab syllabus for details). The laboratory sessions are scheduled as a series of alternating hands-on (wet lab) and on-line (dry lab) meetings and assignments. The first lab meetings will take place the week of Sept 2-6 if you are in an odd-section of lab, or the week of Sept 9-13 if you are in an even- section. For complete details regarding meeting times, course structure, and how to determine whether you are in an odd or even section, please see the laboratory syllabus and relevant announcements posted on the lab Sakai site. While in lab, you are required to follow the prescribed laboratory safety rules contained in the laboratory handouts for the course. Appropriate attire and safety glasses must be worn at all times. Goggles can be purchased on the first floor of FFSC near the chemistry labs or the Duke Bookstore. Please read the assigned laboratory material and complete all required pre-lab preparations prior to each lab period. Chemistry 201 Laboratory Manager: Dr. Amanda Kasper (Office: 1225 FFSC; Phone: 660-1615; Email: amanda.kasper@duke.edu)

Chem201 Course Resources Sakai. This course will use Sakai for posting relevant course information and announcements, including recitation problems and answer keys, hour examination keys, and supplementary course information. Laboratory information will be available at a separated Sakai Lab site managed by Dr. Kasper. Recitation. Each student is scheduled for a 50-min recitation session each week, during which material & problems relevant to the lecture part of the course will be discussed. Problem sets for each recitation can be found in a folder in the RESOURCE section of the Sakai course site. Recitation TAs: Stacey McDonald and Megan Lanier Resource Room. The Resource Room will be staffed by graduate students. It will be open several times each week on a schedule to be announced. If you plan to attend a session of the Resource Room, please sign up on the sheet posted outside of the room 1218 FFSC at least 15 minutes prior to the session you wish to attend so that the tutor will know to be present. Announcements concerning the resource room times and policies will be posted on the CHEM 201 Lab Sakai site. Office Hours. I will generally be available in 3232 FFSC to answer questions on Tuesdays and Wednesdays from 4:005:00 PM. Deviations in this schedule for a given week will be posted Sakai or by e-mail. Individual appointments can be scheduled as needed by email or after class. Peer Tutoring. The Peer Tutoring Program offers tutoring from screened and qualified former organic chemistry students. http://web.duke.edu/arc/peer_tutoring/index.php Academic Skills Instructional Program. This program provides assistance to students whose study skills may need refining for them to achieve their full potential in CHEM201. Assistance specific to organic chemistry and other science courses is available. http://web.duke.edu/arc/academic_skills/index.php Problems in textbook. Each student is responsible for all of the problems that are embedded in the text of the chapters corresponding to material covered in class. The problems at the end of the chapters are also very useful. A subset (10/chapter) of the end-of-chapter problems has been selected as a representative starting point for your studying. The remaining unselected problems are valuable as well. Problems will not be turned in for grading. Chapter 1 Chapter 2 Chapter 3 Chapter 4 Chapter 5 Chapter 6 Chapter 7 Chapter 8 Chapter 9 Chapter 10 Chapter 11 Chapter 12 Chapter 13 24, 25, 27, 28, 31, 32, 39, 46 27, 29, 30, 31, 33, 35, 37, 38, 39 30, 31, 32, 33, 36, 39, 42, 45, 48, 50 39, 44, 45, 46, 50, 51, 54, 56, 63, 66 27, 29, 32, 33, 35, 36, 37, 38, 48, 49 27, 30, 31, 32, 36, 41, 42, 45, 48, 51 36, 37, 40, 43, 50, 52, 55, 61, 63, 64 33, 39, 40, 41, 44, 45, 53, 54, 55, 61 34, 36, 37, 38, 39, 46, 51, 57, 64, 67 35, 36, 45, 53, 54, 55, 56, 57, 58, 61 44, 46, 47, 50, 54, 56, 58, 61, 75, 78 22, 23, 29, 33, 39 35, 36, 37, 39, 43, 45, 51, 52, 53, 60 Note: The problems at the end of the chapters of the textbook are also very useful. Problems in other textbooks, particularly those texts authored by Dr. Paula Bruice and Dr. John McMurry, provide additional perspective and experience.

Copies of old exams and answers. These documents will be available in the REOURCE section in the Sakai course site.

Chem201 Course Policies Missing an exam or lab. The course policy for a graded exercise (exam or lab) missed due to a shortterm illness will be consistent with the university policy. A discussion of the policy, its relationship to the Duke community Standard (DCS), and the link to the Short Term Illness Notification Form can be found at http://trinity.duke.edu/academic-requirements?c=class-attendance-and-missed-work Regrade request for any exam. 1. A regrade process will involve the re-evaluation of the entire exam document and the regrade of all the questions/answers. 2. A student must submit a written request to list specific questions requiring a regrade and the reasons. 3. Use of pencil in answering the exam can forfeit the chance to request a regrade. Class Attendance. Each student is responsible for all information disseminated during lectures and you must accept the consequences of failure to obtain this information. Set your cell phone so that they will not ring during the class lectures, lab and recitations. Policy on dropping back after the First Hour Exam. A first-year student taking their first semester of chemistry has the opportunity to drop back to the next lower level chemistry course after the first exam if they feel that they are not performing at a comfortable level. The following steps must be taken in order to make the drop back request of the Registrar: 1. Set up a meeting with Dr. Roy after the first hour exam (within three days of receiving your score) in order to discuss whether dropping back makes sense. 2. The student must have the time slot available in their schedule for the next lowest level chemistry course. Once the meeting has been set with Dr. Roy and the progress of the student has been discussed, if the student has the time slot available in their schedule, the request will be made of the Registrar to drop the student back to the correct chemistry course, and there will be no record of this on the students transcript. They will be excused from any work from the new course up to the drop back date.

Chem 201 Fall 2013 Tentative Class Schedule Lecture 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 Day M W F M W F M W F M W F M W F M W F M W F M 22 23 24 25 26 27 28 29 30 31 32 W F M W F M W F M W F Date 08/26 08/28 08/30 09/02 09/04 09/06 09/09 09/11 09/13 09/16 09/18 09/20 09/23 09/25 09/27 09/30 10/02 10/04 10/07 10/09 10/11 10/14 10/16 10/18 10/21 10/23 10/25 10/28 10/30 11/01 11/04 11/06 11/08 Topic Introduction/Atomic Orbital, Chemical Bonding Lewis Structure, Molecular Orbital Theory Alkanes Alkanes Acids and Bases, the Curved-Arrow Notation Acids and Bases, the Curved-Arrow Notation Alkenes Alkenes Alkenes Addition Reactions of Alkenes Addition Reactions of Alkenes Addition Reactions of Alkenes Exam 1 Addition Reactions of Alkenes Chirality Chirality/Diastereomers Diastereomers Cyclic Compounds Cyclic Compounds Stereochemistry of Reactions Stereochemistry of Reactions Fall Break Alcohols and Ethers Alkyl Halides Exam 2 Nucleophilic Substitution and Eliminations SN2 Reaction SN2 Reaction/E2 Reaction E2 Reaction SN1 Reaction and E1 Reactions Alcohols Alcohols Alcohols Chapter 9 Chapter 9 Chapter 9 Chapter 9 Chapter 9 Chapter 10 Chapter 10 Chapter 10 Chapter 8 Chapter 8 Chapter 5 Chapter 6 Chapter 6 Chapter 6 Chapter 7 Chapter 7 Chapter 7 Chapter 7 Chapter 1 Chapter 1 Chapter 2 Chapter 2 Chapters 3 Chapter 3 Chapters 4-5 Chapters 4-5 Chapters 4-5 Chapters 5 Chapters 5 Chapter 5

33 34 35 36 37 38 39

M W F M W F M W F

11/11 11/13 11/15 11/18 11/20 11/22 11/26 11/28 11/30 12/03 12/05 12/06 12/13

Ethers, Epoxides, and Sulfides Ethers, Epoxides, and Sulfides Ethers, Epoxides, and Sulfides Exam 3 IR and MS IR and MS/NMR NMR Thanksgiving Break Thanksgiving Break NMR NMR Wrap-up Final Exam 7:00 PM10:00 PM

Chapter 11 Chapter 11 Chapter 11

Chapter 12 Chapter 12-13 Chapter 13

40 41 42 43

M W F F

Chapter 13 Chapter 13 Chapters 1-13

Recitation Schedule (Friday) for TA

Recitation # 1 2 3 4 5 6 7 8 9 10 11 12 13 14

Date August 30, 2013 September 6, 2013 September 13, 2013 September 20, 2013 September 27, 2013 October 4, 2013 October 11, 2013 October 18, 2013 October 25, 2013 November 1, 2013 November 8, 2013 November 15, 2013 November 22, 2013 December 6, 2013

Topics on problem sets --1 2 3 --4 5 6 --7 8 9 --10