Organic Chemistry I CHEM 211 Section 20299 Fall 2017 Instructor: Dr. Amer Hajjawi Email: hajjawa@lavc.edu Office Hours: MW 07:00 am-08:00 am and TTh 07:00 am-09:00 am, AHS 322 Class Meeting Times: Lecture: TTh 12:20 pm-1:45 pm, EST 109 Lab Section 20305: TTh 09:00 am-12:10 pm, AHS 342 Lab Section 27558: TTh 01:55 pm-05:05 pm, AHS 342 Course Description: This course is an introduction to the topological, physical and chemical properties of carbon-containing compounds. Laboratory emphasis is on the preparation, isolation, purification and analysis of organic compounds. Prerequisites: CHEM 102 (General Chemistry II) with a grade of C or better. Objectives (#1 9) and Student Learning Outcome (#10): Upon successful completion of CHEM 211, Organic Chemistry I, the student will be able to: 1. name organic compounds using IUPAC nomenclature rules, 2. draw correct structural representations of organic molecules, 3. compare organic compounds according to their relative physical or chemical properties, 4. predict the outcome of organic chemical reactions, 5. provide arrow pushing mechanisms of organic chemical reactions, 6. design synthetic routes to prepare organic molecules from simple starting materials, 7. assemble apparatus correctly for performing organic experiments, 8. demonstrate the ability to work effectively in teams, 9. follow the safety regulations and employ the procedures for the safe handling of chemicals, and 10. prepare, isolate, analyze and purify organic compounds. Required Materials: (1) Wade & Simek, Organic Chemistry, Books a la Carte plus MasteringChemistry with etext Access Card Package (9 th Ed) ISBN: 9780134183657 (bookstore) (2) MasteringChemistry access code (must be purchased separately if not packaged with your textbook) (3) Williamson, Macroscale and Microscale Organic Experiments (7 th Ed) ISBN: 9781305577190 (4) Hayden Mcneil, Organic Chemistry Laboratory Notebook, ISBN: 9781930882461 (5) Scientific Calculator (not graphing) (6) Safety Goggles (bookstore)* Optional Materials: (1) Wade & Simek, Organic Chemistry Solutions Manual, Books a la Carte (9 th Ed) ISBN: 9780134143224 (2) Organic Molecular Model Set (3) Lab Coat *Safety goggles (not safety glasses) must protect the eyes from the top and sides. Eye glasses or sunglasses are not appropriate eye protection. Safety goggles must be approved by your instructor. 1
Academic Integrity: Cheating, plagiarism, and falsification/fabrication of laboratory data are unacceptable practices, and are in violation of the Academic Honesty policy at Los Angeles Valley College. All students involved in an instance of academic dishonesty will be disciplined according to the actions outlined in the Los Angeles Valley College Catalog, pg. 196. In the least, all students involved in an incident will receive zero points for the assignment/exam. Additionally, the offender will be referred to the Vice President of Student Services for further disciplinary action, following due process. For further information, review the Los Angeles Valley College Policy on Academic Dishonesty and the Standards of Student Conduct and Disciplinary Action. Academic dishonesty includes copying the answers of homework and laboratory assignments. Students who allow their assignments to be copied are also guilty of violating the Academic Honesty policy at Los Angeles Valley College. Regardless of the extent of participation, all instances of academic dishonesty will result in the penalties described above. Disability Services: Los Angeles Valley College is committed to providing educational accommodations for students with disabilities upon the timely request by the student to the instructor. Services for Students with Disabilities (SSD) program functions as a resource for students and faculty in the determination and provision of educational accommodations. SSD is located in the Student Services Annex, Rm 175 and its contact information is: (818) 947-2681 or TTD (818) 947-2680 and Email: SSD@lavc.edu. If SSD has already sent the memo to instructor confirming accommodations required by student for this class, please meet with me to discuss arrangements. Emergency Response: In the event of an emergency, students must evacuate the building as directed by the instructor and must follow all safety instructions. Please take note of the safety features in and close to your classroom, as well as study the posted evacuation route. The most direct exit route may not be the safest because of the existence of roofing tiles or other potentially hazardous condition. Similarly, running out of the building can also be dangerous during severe earthquakes. During strong quakes the recommended response is to duck cover and hold until the shaking stops. Follow the guidance of your instructor. You are asked to go to the designated assembly area. Your cooperation during emergencies can minimize the possibility of injury to yourself and others. Important Dates: Last day to add and audit Last day to drop without receiving a W grade Last day to drop with a W grade Friday, Sep 8 th in-person and Sep 10 th online Sunday, September 10 th online Sunday, November 19 th Grading Policy: Regular attendance and participation is required for this course. You may be dropped from the course for excessive (8 or more hours) lecture or laboratory absences. Course Grade Breakdown* 1 : Online Homework (13) 20% Grading Scale: Lab Experiments (15) 20% 100 to 90 % = A Lab Quizzes (2) 5% 89 to 80 % = B Lecture Quizzes (12) 5% 79 to 65 % = C Lecture Exams (3) 30% 64 to 51 % = D Lecture Final Exam* 2 (1) 20% 0 to 50 % = F* 3 100% * 1 See attached schedule for dates. * 2 Failure to take the final exam will result in a letter grade of F in the course. * 3 If you fail the course, you must repeat all components of the course (lecture and lab) for course credit. 2
Online Homework: [ MasteringChemistry Course ID: MCHAJJAWI66188 ] Generally, it is not possible to succeed in an organic chemistry course without doing a significant number of problems. For this reason, homework assignments will be assigned for each chapter. The problems, found in your textbook, will be answered online at MasteringChemistry.com. Homework problems not submitted before the due date (and time) will be subject to a deduction of the available points. Although the problems are answered online, you should write out the work and answers to all of the problems in a notebook (or on loose sheets of paper). This will provide a record for you to study from, and it will help when asking questions, such as during help sessions or the instructor s office hours. Additionally, having a permanent record of the problems that you have solved will make it easier to prepare for the examinations. Laboratory: Please see below for a description of the laboratory portion of this course. Lecture Quizzes: A total of 12 quizzes will be given during scheduled lecture time. Students who arrive late will be allowed to complete a quiz with whatever time remains. Make-up quizzes will not be given; a missed quiz will be given a score of zero. Exams: You are expected to take all three exams and the final exam. Each exam will begin at the start of the lecture period and students will have the entire lecture class period to complete the exam. No Make-up exams will be given without a valid excuse approved by me; a missed exam will be given a score of zero. Final Exam: A cumulative final exam will be given during the last week of the semester. Refer to the attached schedule for the final exam date. You may submit your work to be re-graded if at any time you feel as though I have made a mistake or have graded you unfairly. Work that is to be re-graded must be submitted within one week; a written description of the mistake/complaint may be required for some assignments. All items submitted may be examined in their entirety. It should be noted that this could potentially result in a lower grade than given originally. All electronic communication devices must be put on silent mode during class and lab times. Failure to follow this policy will result in a verbal warning for the first offense and expulsion from the class for the duration of the day for the second offense. Suggested Problems (Answers are in Solutions Manual) Chapter 1: 40(c), 3(b-e), 45(a-f), 7(a,c,f,h), 41(a-c), 19(d), 22, 24, 25, 46(a-c), 52, 54(a-c), 58, 59. EC: 6(a,b,h,i), 8(b,d,f,g), 43(a-e), 14, 2(c,e,h,j), Chapter 2: 4, 6, 7, 14, 17, 21(b-g), 22(b-e), 27(a-f), 36, 42, 56, 57. EC: 5(a,b), 8, 10(b-d), 13(a-c), 35, 37, 38, 45. Chapter 3: 2, 3, 4, 5(a-c), 8, 10, 11, 12, 15, 16(a-c), 18, 22, 25, 30, 31, 34, 36, 41, 51(a). EC: 17, 28, 29, 39, 42. Chapter 4: 11, 19, 29, 30, 33, 35, 42, 45(d), 47(a). EC: 12, 26, 28, 31, 32, 40. Chapter 5: 3, 5, 6, 8, 12, 16, 19, 20, 22, 23, 28, 29(b,d). EC: 7, 17, 18, 21, 26, 27. Chapter 6: 2, 3, 5, 14, 15, 16, 18, 19, 23, 27, 33, 34, 37, 38, 40(a,b), 45(a-d,h), 58. EC: 6, 31(b,c,e), 32. Chapter 7: 4, 6, 8(a-d,f), 11, 15, 20, 25, 28, 29, 31, 41, 43(a-f), 49, 51(d,e), 50(d,e), 52(a-d), 55(a-d). EC: 14, 42(b,f), 46(a-c). Chapter 8: 4, 6, 8, 9, 10, 11, 21, 22, 23, 26, 29, 36, 48(b), 49, 51(a-f). EC: 13. Chapter 9: 1, 5(a-d,g,h), 12, 16, 18, 21(a,b,e), 24, 26(a,g,h,k), 29(a-f), 33(a-f,i-l), 36(a-g). EC: 34(e-j), 37(a-f). Chapter 10: 1, 31(a-d), 33, 34, 35, 8, 11, 12, 22, 23, 24, 25, 27, 28, 36, 39(a-f), 40, 41, 58. EC: 49, 37, 38, 43, 51. Chapter 11: 1(a-e,g), 2(a,c,g), 4, 5, 9, 10, 19, 31, 36, 42, 53. EC: 39, 43, 49, 52. Chapter 14: 15, 26, 28, 29(a-g), 33(a-g,j-m), 40. EC: 10(c-e), 13, 42. 3
Organic Chemistry I CHEM 211 Laboratory Guidelines The majority of the assigned lab grade will be based on student performance during each experiment and on the student s lab notebook. A tentative assignment of the lab grade will be based on the following breakdown, although the instructor reserves the right to modify the scheme as necessary. ASSIGNMENT Notes Each Total Lab notebook Observation checks Quizzes In-lab evaluation Total title, purpose, balanced reactions, table of reagents results, discussion, and answered questions short, unannounced checks of the observation sections of the lab notebook will be conducted. You will use your lab notebook to answer specific questions about the experiments that you have already performed. two quizzes will be given at the beginning of lab on weeks 9 and 15. The quizzes will be closed notebook and will cover the material on the most recent experiments. overall evaluation of the student s lab techniques/skills final grades will be assigned on a percentage scale (out of 25%); see course grade breakdown above. 15 pts 225 pts 10 pts 30 pts 25 pts 50 pts 3 pts 45 pts 350 pts Laboratory Notebook: Please refer to the Williamson textbook (Chapter 1) on keeping a lab notebook. When student notebooks are collected after an experiment, a grade is assigned based on the quality, organization, and completeness of the work contained inside. You must bring your lab notebook to all lab meetings and do all work directly into the notebook in ink. Never erase or use white-out. If you make a mistake, simply draw a line through the entry. Never write on loose notebook paper or paper towels. While discussion and exchange of ideas is encouraged, your lab write-up must be done in your own words. The following sections should be prepared each week BEFORE lab. Title, Purpose, Balanced reaction(s), Table of reagents and products, and Procedure: Each student must prepare his/her notebook with sufficient procedural details in order to perform the experiment. Textbooks and handouts are not allowed in the lab. It is highly recommended that students do not simply copy the procedure but think about what steps will be done and why. Also, students should consider what type of data will be collected during the experiment and prepare any tables that would be helpful. Observations should be completed each week DURING lab. Results and Discussion sections should be completed each week DURING or AFTER lab. Due Dates: The copies of your title, purpose, balanced reactions, and table of reagents are due at the beginning of lab. You will NOT be allowed to perform the lab experiment if you do not turn in this assignment. Late pre lab assignments will be accepted but a score of zero will be earned. The copies of your procedure and observations are due at the end of lab. The copies of the results and discussion are due the following lab 4
meeting unless otherwise stated. A lab report will be docked 20% of the total possible points for each day it is late. Results: A student s individual results will be evaluated for each experiment. For those experiments where a product is isolated, a sample will be submitted for grading. Products will be inspected visually, by physical properties, and for yield. In-Lab Evaluation: Evaluation of each student s laboratory skills will depend on several factors: a) independence, b) preparation, c) careful management of laboratory procedures, d) ability to adapt to unforeseen procedural changes, e) general neatness and safety consciousness in the lab. Laboratory Cleanliness: Each student is responsible for leaving his/her lab space clean and tidy. At the end of each lab, students should put glassware back into the lockers, wipe off hood stations with a damp sponge, and make sure all items in their lockers clean and ready for use the following lab. A student s in-lab evaluation points will be deducted for leaving a messy station. Attendance Policy: Attendance at your regularly scheduled lec/lab section is mandatory. Labs will begin promptly at the start of the lab period. There will be no make-up labs, and experiments may not be performed early. No student may enter the lab unless accompanied by an instructor. If you stop attending (or wish to drop the class), you must drop the class yourself officially over the Internet before the deadline (see Schedule of Classes). Failure to do so may result in a grade of "F" in the course. Safety Regulations: The safety of yourself and your classmates is of paramount importance during laboratory. Safety regulations must always be observed as it only takes one accident to cause a serious permanent injury. Safety in the laboratory will constantly be emphasized. In addition to viewing a video on laboratory safety, students will be required to read the laboratory safety rules in the Williamson textbook (Chapter 2) and Safety in Academic Chemistry Laboratories-Volume 1 (ISBN: 0841238634) and sign a laboratory safety agreement. Failure to follow the laboratory safety rules will result in the loss of points and/or dismissal from laboratory. -Always wear splash goggles when working in the lab. -Wear closed-toed shoes (no heels or sandals) in the lab. -Never remove materials from the lab. -No food or drink is allowed in the lab. 5
Organic Chemistry I CHEM 211 Lecture & Laboratory Schedule Week # and Start Date 1 08/28/17 2 09/04/17 Day 1 Lecture Day 1 Lab Day 2 Lecture Day 2 Lab CH 2 Acids and Bases; Functional Groups CH 3 Structure and Stereochemistry of Alkanes CH 1 Structure and Bonding CH 3 Melting Points CH 2 Acids and Bases; Functional Groups CH 3 Structure and Stereochemistry of Alkanes Safety/ Locker Check-In CH 1 Lab Notebook CH 3 Melting Points (EXPT 2, 4) 3 09/11/17 CH 4 The Study of Chemical Reactions Molecular Models: Organic Structures CH 5 Stereochemistry CH 4 Recrystallization 4 09/18/17 Exam 1 (CH 1 4) Sep 19 th CH 4 Recrystallization (EXPT 3, 5) CH 5 Stereochemistry CH 7 Extraction 5 09/25/17 CH 5 Stereochemistry CH 7 Extraction (EXPT 1) CH 6 Alkyl Halides; Molecular Models: Stereochemistry 6 10/02/17 CH 6 Alkyl Halides; CH 5 Distillation (EXPT 4A) CH 6 Alkyl Halides; CH 5 Distillation (EXPT 5A) 7 10/09/17 8 10/16/17 CH 7 Structure and Synthesis of Alkenes; Elimination Exam 2 (CH 5 7) Oct 17 th Reactions (Review) CH 8 Thin-Layer Chromatography CH 7 Structure and Synthesis of Alkenes; Elimination CH 8 Reactions of Alkenes 9 10/23/17 CH 8 Reactions of Alkenes CH 8 TLC (EXPT 1) CH 8 Reactions of Alkenes 10 10/30/17 CH 9 Alkynes 11 11/06/17 CH 10 Structure and Synthesis of Alcohols CH 9 Column Chromatography (EXPT 4) CH 16 S N 2 Reaction (EXPT 2) CH 9 Alkynes CH 10 Structure and Synthesis of Alcohols Elimination Reactions (Review) Lab Quiz I CH 9 Column Chromatography CH 16 S N 2 Reaction CH 17 S N 1/S N 2 Reaction 12 11/13/17 CH 10 Structure and Synthesis of Alcohols CH 17 S N 1/S N 2 Reaction (EXPT 1, 2) CH 11 Reactions of Alcohols CH 19 Alkenes from Alcohols 13 11/20/17 Exam 3 (CH 8 10) Nov 21 st 14 11/27/17 CH 11 Reactions of Alcohols 15 12/04/17 16 12/11/17 CH 14 Ethers, Epoxides and Thioethers Final Exam Dec 12 th (12:30 pm-2:30 pm) CH 19 Alkenes from Alcohols (EXPT 2) CH 11 Infrared Spectroscopy CH 58 Synthesis of Alkynes from Alkenes (EXPT 3) Holiday CH 14 Ethers, Epoxides and Thioethers Review Holiday CH 58 Synthesis of Alkynes from Alkenes Lab Quiz II Locker Check Out Review No Lab No Lecture No Lab "I reserve the right to alter the schedule above in any way that I feel necessary for providing effective instruction" 6