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Chemistry 231, Organic Chemistry I Syllabus Hofferberth, Fall 2011 Chemistry 231 – Organic Chemistry I Course Description: Organic chemistry is the study of the structure, properties, and reactions of molecules containing carbon. The prominence of carbon containing molecules, organic molecules, in our everyday life may explain why organic chemistry is such a rich discipline. Much of what we wear, smell, eat, build, burn, and touch during our lives is composed of organic molecules. We ourselves and all other life we know are based on compounds of carbon. Why has carbon adopted such a central role in our lives and life itself? One reason is that carbon is a versatile and promiscuous element. It is capable of bonding to itself and other elements in a multitude of ways. One indication of carbon’s versatility is the fact that more than 14 million organic compounds have been described and hundreds of novel compounds are being prepared or discovered every month. This course is the first of a two-course sequence designed to introduce students to the theoretical underpinnings of organic chemistry. We will begin by exploring how organic molecules are held together and learn to recognize the key functional groups. For the remainder of the year, we will take an in-depth look at the chemistry and properties of a number of functional groups. During our study you will acquire the tools to design a synthesis for simple organic molecules. You will also learn how to employ familiar concepts from thermodynamics and kinetics to predict both the products that are likely to form in an organic reaction and the detailed course of events that leads to their formation. Instructor and Resources: Instructor: Email: Office: Office Hours: Lecture Hall: Class Time: Text: Materials: Website: Dr. John Hofferberth [email protected] 312 Tomsich Hall Monday 2 – 4 PM, Wednesday 10 – 11 AM, Friday 2 – 4 PM Hayes 109 9:10 – 10:00 AM, MWF Organic Chemistry, 5th Ed, Vollhardt and Shore (optional study guide) HGS Molecular Structure Model (Kit C) moodle.kenyon.edu (search for Chemistry 231 once you have logged in) Course Policies and Expectations: Course Grade: Your grade in the course will be determined by your homework binder and performance on quizzes, midterms and the final. The point breakdown that will be used is provided below: Chemistry 231, Organic Chemistry I Syllabus Quizzes (10 × 5 pts) Midterm Exams (3 × 100 pts) Final Exam Homework Binder (3 × 20 pts) Participation and Preparation Total Points Hofferberth, Fall 2011 50 pts 300 pts 150 pts 60 pts 20 pts 580 pts The following absolute grading scheme will be followed to determine your final grade: Attendance: Grade Percent of Total Points Earned A (+/-) 100% - 90% B (+/-) 89% - 80% C (+/-) 79% - 70% D (+/-) 69% - 60% F < 60% Your attendance at every lecture is expected. You will be permitted three unexcused absences. Every absence thereafter will result in a grade reduction of 1/2 of a letter grade (29 pts) for the course. You will be expelled from the course after six unexcused absences. Preparation: The material in this course builds on itself. For that reason it is imperative that you keep up with the lecture. Strongly suggested study habits: 1) Neatly recopy and annotate course notes with material from the text, course web page, and other resources after every lecture. 2) Complete as many practice problems as you can. The suggested homework problems indicated on the course schedule represent the bare minimum preparation for the course. You will be required to maintain an organized homework binder which should contain all of the practice problems you work on. Revisiting practice problem from previous topics is a good way to assure that you have retained the key information. 3) Keep up with all aspects of the course and seek help quickly if questions arise. You can get help on any aspect of the course 6 days a week from: 1) The instructor (Office Hours, Sunday Review Sessions – see below) 2) The Math and Science Skills Center (101 Tomsich; Sunday, Tuesday, and Chemistry 231, Organic Chemistry I Syllabus Hofferberth, Fall 2011 Thursday 7:00 - 10:00 PM). There should always be a tutor able to help with organic questions available at the MSSC. We will also have a lead tutor for this class, Lars Matkin, who will hold two office hours each week at the MSSC (TBD). Sunday Evening Review Sessions: Dr. Hofferberth will lead a weekly review session on Sunday evenings between 6:00 and 7:00 PM in Tomsich 101. These sessions are entirely optional and the content will be directed by student questions. The review sessions will end promptly at 7:00 PM and students with additional questions can make use of the Sunday hours for the Math and Science Skills Center (7:00 – 10:00 PM). If these sessions are poorly attended the instructor reserves the right to discontinue them. Suggested Problems: The best way to master organic chemistry is to practice. A reading assignment and suggested problems will be indicated on the syllabus for each topic covered in lecture. You will organize all of the practice problems you complete into a ‘homework binder’ that will be collected at each midterm exam. The instructor will spot-check a few of the problems suggested since the last exam and will assign a grade out of 20 points based on the completion (10 pts) and correctness (10 pts) of the problems he checks. Mastering the suggested problems is key to success on quizzes and examinations. Revisiting suggested problems will increase comprehension, build confidence, and increase your speed in responding to exam questions. Working additional problems in the text (or in other organic chemistry texts) is a valuable use of your preparation time for this class. Suggested problems will appear on quizzes and exams. Quizzes: Ten quizzes will be given during the semester (dates indicated on the schedule). Each quiz will be composed of a suggested problem that has been assigned since the last quiz. Quizzes will begin at 9:10 AM and end at 9:15 AM. There will be no extra time or make-up quizzes given, however, your lowest quiz score for the semester will be replaced by your highest quiz score. Midterm Exams: Three in-class midterm examinations will be given during the semester (dates indicated on the syllabus). Seating for the in-class portion of the exam will be assigned by the instructor as students enter the exam room. Model kits may be used on all exams in this course. If you have a conflict with any of the exam times you must notify Dr. Hofferberth in writing at least one week prior to the exam to schedule an alternate exam time. Chemistry 231, Organic Chemistry I Syllabus Final Exam: Hofferberth, Fall 2011 The final exam for the course will be cumulative and closed-note. The final exam will be held on December 12th from 1:30 to 4:30 PM. Accommodations: In accord with Section 504 of the Rehabilitation Act of 1973 and the Americans with Disabilities Act of 1990: If you have a disability and need accommodation in order to fully participate in this class, please identify yourself to Erin Salva, Coordinator of Disability Services (PBX 5145, [email protected]). All information and documentation of disability is confidential. The instructor must receive information regarding the nature of the accommodation directly from Erin Salva and speak to you about the accommodation at least one week in advance of an exam or quiz so that arrangements can be made for the accommodation. Academic Integrity: Academic integrity is expected in all aspects of this course. A detailed description of academic integrity and the College policy regarding academic dishonesty can be found in the Course Catalog at the following link: http://www.kenyon.edu/x11747 Electronic Device Full engagement with the lecture portion of this course will be a key Policy: component of success. All electronic devices should be turned off before the beginning of every lecture. Tentative Schedule: Date 8/26 9/5 Topic Introduction, Bonding Review Bonding Models Resonance, Representations of Organic Molecules, and Functional Groups Kinetics, TD’s, Acids and Bases, Electrophiles and Nucleophiles Quiz 1 9/7 Alkanes, Nomenclature, and Conformational Analysis Alkanes 8/29 8/31 9/2 Reading (Suggested Problems) 1.1-1.4 (1.21-1.24, 1.29) 1.6-1.8 (1.31) 1.5, 1.9, 2.3 (1.25, 1.27, 1.32, 1.33, 1.35, 1.37, 1.39, 2.27, 2.39) 2.1-2.2 (2.22-2.24, 2.26) 2.4, 2.5, 2.7 (2.29-2.31) Chemistry 231, Organic Chemistry I Syllabus 9/9 9/12 9/14 9/16 9/19 9/21 9/23 9/26 9/28 9/30 10/3 Conformational Analysis Quiz 2 Bond Strength, Radicals Radical Halogenation, Hammond’s Postulate Radical Halogenation, Combustion Quiz 3 Cycloalkanes, Nomenclature, Ring Strain Cycloalkanes, Conformational Analysis Exam I Cycloalkanes Isomer Hierarchy, Chiral Molecules, Absolute Configuration and Optical Activity Diastereomers and Meso Compounds Quiz 4 2.8 (2.35-2.37) 3.1, 3.2, 3.4 (3.13, 3.14, 3.17) 3.5 – 3.7 (3.18 – 3.25) 3.8 – 3.10 (3.26, 3.27, 3.31, 3.32, 3.33) 4.1 – 4.3 (4.17 – 4.20) 4.5 (4.21 - 4.23) 4.6 (4.24 – 4.26, 4.30, 4.32) 5.1 – 5.3 (5.28-5.32) 5.5, 5.6 (5.34 – 5.36) 5.7 (5.38, 5.41 – 5.43) 10/7 10/10 Stereoselectivity Stereoselectivity and Enantioselectivity Fall Break Quiz 5 6.1 – 6.5 (6.27 – 6.29, 6.32, 6.34) 10/12 10/14 10/17 Haloalkanes/SN2 SN2 SN2 and SN1 Quiz 6 6.6 – 6.9 (6.35 – 6.38, 6.40 – 6.45) 7.1 – 7.3 (6.48 – 6.50) 7.4 – 7.5 (6.51, 6.52, 7.22 – 7.25) 10/19 SN1 E1 and E2 7.6 (7.26 – 7.32) 10/5 Hofferberth, Fall 2011 Chemistry 231, Organic Chemistry I Syllabus 10/21 10/24 10/26 10/28 10/31 Hofferberth, Fall 2011 Exam 2 Competition Quiz 7 11.9 – 11.11 (7.33-7.35, 11.45) (7.36 – 7.43) (11.47 – 11.49, 11.51, 11.52, 11.57, 11.58) 8.1 – 8.5 (8.21 – 8.25) Alcohols 11/2 11/4 11/7 11/19 11/11 11/14 11/16 11/18 11/28 11/30 12/2 12/5 Quiz 8 Reactions of Alcohols Reactions of Alcohols (Ethers) Reactions of Alcohols Quiz 9 Alkenes Rxns of Alkenes Exam 3 Quiz 10 8.6 – 8.9 (8.26, 8.30, 8.31) (8.32 – 8.35) 9.1 – 9.4 (9.25 – 9.30, 9.32) 9.5 – 9.9 (9.34 -9.37, 9.39, 9.40) 9.10 (9.41 – 9.44, 9.49, 9.55) 11.1-11.3 (11.26, 11.27, 11.30) 12.1-12.5 (12.27, 12.29, 12.31i, 12.32) 12.7-12.8 (12.33, 12.34, 12.36) 12.9-12.11 (12.37, 12.38) 12.12-12.14 (12.39-41, 12.45-47) 13.1, 13.2, 13.4, 13.5 (12.48, 13.21, 13.22, 13.25, 13.27, 13.30) Alkynes 12/7 12/9 12/12 13.6 – 13.8 (13.32, 13.33, 13.34) Study !! Wrap-Up and Evaluations Final Exam – 1:30-4:30 PM