Chem52 - Organic Chemistry II

Chem52 - Organic Chemistry II Summer 2013 Instructor: Dr. Catherine O. Welder Office: 113 Burke (603-646-9096) E-mail: [email protected] Tentative Office Hours: Monday 3:30-5 and Thursday 2-3:30 or by appointment Please plan to ask academic questions in person, not by e-mail. It is very difficult to communicate effectively by e-mail and misunderstandings could result. Lectures: Steele 006, MWF 11:15-12:20 and Tues. 12-12:50 (X-hours will be used for lecture.) Course Web Page: Some of the lecture course material can be found on Blackboard. Other material is posted online: http://www.dartmouth.edu/~welderco/Chem52/index.html Required Text: McMurry, Organic Chemistry, 8th ed., Thomson Brooks/Cole, 2012. Strongly Recommended Aides:  McMurry, Study Guide and Solutions for McMurry’s Organic Chemistry, 8th ed., Thomson Brooks/Cole, 2012.  Klein, Organic Chemistry II as a Second Language, 2nd ed., Wiley, 2006.

Exam Schedule/Grading Scheme Quizzes/Homework Exam 1 Exam 2 Exam 3 Final Exam (cumulative)

Dates Various, TBD Mon. July 8, during class Thurs. July 25, 4-6 pm Fri. Aug. 9, 4-6 pm Sat. Aug. 24, 8-11 am

Percent of Grade 10% 20% 20% 20% 30%

If you have an academic conflict with one of the exam periods, you will need to inform me in writing (by e-mail is fine) no later than July 1st to make other arrangements to take the exam. (Please specifically indicate the conflict.) Contact me as soon as possible to make up a missed exam due to illness or family emergency. Some students may wish to take part in religious observances that occur during this academic term. If you have a religious observance that conflicts with your participation in the course, please meet with me by July 1st to discuss appropriate accommodations. By its nature organic chemistry is cumulative. You will be expected to understand and use material covered in Organic I in addition to material covered earlier in the Chem52 term. Each exam will be cumulative, though the midterm exams will emphasize the material from current chapters. Attendance: Regular attendance is expected. The lectures will build on one another. If you miss several lectures, you may find it difficult to catch up with the class.

Students with Disabilities: Students with learning, physical, or psychiatric disabilities enrolled in this course that may need disability-related classroom accommodations are encouraged to make an office appointment no later than July 1st. All discussions will remain confidential, although the Student Accessibility Services office may be consulted to discuss appropriate implementation of any accommodation requested. Grading Policy: The approximate median grade will be a “B,” derived by curving the final scores in the class. If you are not satisfied with how an exam was graded, you must submit your detailed complaint in writing, along with your graded exam, directly to Dr. Welder not more than one week from the day the graded exam was made available for pick up. A convincing argument that the work was under evaluated must be presented. The entire exam will be subject to regrading, so it is possible that your exam grade may be lowered upon reevaluation. Labs: Labs begin the week of June 24th. Please see Blackboard for details on what must be done prior to the first lab meeting. The laboratory grades assigned & their effect on the overall grade are as follows: H

Exceptional Work raises a course grade at least one letter grade (for example, B to B+) and may earn a citation. This grade is reserved for the truly exceptional lab student. An H in lab will add 5% to your lecture grade.

S+

Consistently superior work may raise a course grade one letter grade (for example, B to B+), particularly in borderline cases and when the grade otherwise would be relatively low. An S+ in lab will add 3% to your lecture grade.

S

Satisfactory work in all respects has no direct influence on a course grade. Most Chem 52 students receive this grade.

S-

Laboratory work consistently below average or deficient in some particular respect may lower a course grade at least one letter grade, particularly in borderline cases. Failure to submit one lab report could result in a grade of S- in the lab. An S- in lab will subtract up to 3% from your lecture grade.

U

Unsatisfactory work occurs when a student fails to complete prelab assignments, misses prelab lectures, fails to turn in lab reports, or fails to demonstrate minimally acceptable laboratory competence. Having an unexcused absence for one lab period could result in the assignment of a U grade. The assignment of a U grade in lab results automatically in a failing grade (E) for the organic chemistry course.

Quizzes: 10-15 min. quizzes may be administered at the beginning of some class periods. I plan to announce most (but not necessarily all) quiz dates in advance. If you are late to class on the day of a quiz, you will not be allowed to take it. Online quizzes may also be used. Homework: Homework problems will be assigned on a regular basis. You will have required problems (to turn in) and recommended problems. To make sure you have a good understanding of the material presented in the text and lectures, complete both the required and the recommended homework problems. Write out your answers to the problems and then check the answer guide. Collected homework problems assigned from the text will be graded based on effort, not exclusively on having the correct answers. It would be easy for someone to copy answers to the problems onto a piece of paper and turn them in. That approach to the

assignments will not prepare you well for exams. I will be looking for class weaknesses in the homework, not at every question for every student. Assigned problems that are not from the text may be graded based on having the correct answers. Late homework will receive a penalty of 10% per day. Honor Principle: You will be expected to abide by the Academic Honor Principle. All exams and quizzes should reflect only your own work and are closed book/closed notes. However, you are free to work in groups on any assigned homework problems. Group study is recommended. Electronic devices with camera and/or e-mail capabilities are not to be used under any circumstance during a quiz or an exam. Review Guides: Course objectives are posted on my web page by chapter and are listed in the order that topics are covered in lecture. Most students find the objectives to be extremely useful as they very clearly list what you should be able to do on an exam. Online Resources: Lots of helpful material, including course objectives, old exams, and tutorials are linked through Blackboard. Take a look! Want to excel in this class? Keep up with the material! ORGANIC CHEMISTRY IS CUMULATIVE. At this point, you should have a good understanding of acid/base chemistry, electron pushing, resonance, formal charges, bond angles, molecular orbital hybridization, and a few synthetic reactions. It is a good idea to review the Organic I material. My course objectives for Organic I are available in Blackboard. You might want to take a look. Flash cards or your own review sheets are also a good idea. Organize the reactions in a way that makes sense to you. You are not trying to simply memorize reactions, but instead, to recognize how different reagents act (for example, electrophile, oxidizing agent, or acid). You might want to put reagents on one side of a card and products and the name of the reaction (if appropriate) on the other side of the card. You should understand MECHANISMS of reactions as they are introduced. Mechanisms will help you classify reagents (i.e. base/nucleophile) and predict the products of a given synthesis. If you find that you are having trouble with some of the concepts, please seek help (quickly). You can talk to classmates, the lab teaching assistants, study group leaders, tutors, or me. Feel free to contact me by phone or e-mail to make an appointment. A tentative calendar of when topics will be covered in lecture is posted on my web site. The calendar will be updated as necessary as the course progresses. As a courtesy to me and your classmates, please leave cell phones, pagers, etc. at home or turned off during class. Phones that ring during class may be confiscated for the day.

Material to be covered this term (tentative): Ch. 16 Ch. 17 and 10.7-8 Ch. 18 Ch. 19 Ch. 20 Ch. 21 Ch. 22 Ch. 23 Ch. 24 Ch. 25 Ch. 26 Ch. 27 Ch. 28

Chemistry of Benzene: Electrophilic Aromatic Substituion Alcohols and Phenols Ethers and Epoxides; Thiols and Sulfides Aldehydes and Ketones: Nucleophilic Addition Reactions Carboxylic Acids and Nitriles Carboxylic Acid Derivatives: Nucleophilic Acyl Substitution Reactions Carbonyl Alpha-Substitution Reactions Carbonyl Condensation Reactions Amines and Heterocycles Biomolecules: Carbohydrates Biomolecules: Amino Acids, Peptides, and Proteins Biomolecules: Lipids (if time permits) Biomolecules: Nucleic Acids (if time permits but unlikely)