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Los Angeles Mission College 13356 Eldgridge Avenue Sylmar, CA 91342 Phone (818) 833-3382; CMS-244 12890 Harding Street, Sylmar, CA 91342 E-mail: [email protected] Course Syllabus CHEM 212 ORGANIC CHEMISTRY II, SPRING 2016 Course Hours: Lecture TTh 8:15 am - 9:40 am in CMS-222 (section # 0170) Laboratory TTh 9:50 am - 1:10 pm in CMS-206 G. Godjoian, Ph.D. Monday/Wednesday 12:25 pm– 12:55 pm & 3:30 – 5:00 pm Tuesday/Thursday 7:25 am – 8:10 am & by appointment Instructor: Office hours: The best resource for help is the instructor. The purpose of office hours is to set aside a block of time for the instructor to be available for students. You are not interrupting something important when you go to an instructor's office hour. You and your questions are the most important thing! Please make use of this resource. You can stop by in person, or email me your questions. Try to get your questions answered as soon as possible. Course Prerequisites: A grade of C or better in Chem. 211 is required. It is assumed that you have command of the concepts covered in Chemistry 211. Chemistry 212: Organic Chemistry II Student Learning Outcome (SLO) At the end of Chemistry 212 course the student will be able to: 1) Demonstrate an understanding of the mechanism of organic reactions by proposing mechanisms for reactions of moderate complexity, and be able to predict patterns of reactivity on the basis of mechanistic reasoning. 2) Design multi-step synthesis for compounds of moderate complexity using conceptual models and retro-synthetic analysis strategies. 3) Analyze and interpret mass, ultraviolet, infrared and nuclear magnetic resonance spectra to propose the structure of organic molecule. Course Goals and Objective: Offered for students in physical and biological sciences, medical and dental professions and other majors concerned with the nature of organic substances. Chem. 212 is the second course sequence in organic chemistry. This first course provides the context for students to develop the analytical skills necessary for an understanding of the structure and reactivity of organic molecules. This second course provides the context for students to develop an understanding of organic reactions, how does product formation occurs (mechanism), and synthesis of organic molecules. It is with this knowledge that the student will be able to understand the role of molecular science in his/her own academic major and career objective. The course will be developed as discussions among the students and instructor, and will necessarily depend on the active participation by the student. The student should be reminded that the study of organic chemistry is a systematic one and that each new topic is based on what was learned earlier. ORGANIC CHEMISTRY CANNOT BE MASTERED BY ROTE MEMORIZATION, but must be approached from a thorough understanding of its basic principles. If you have trouble, please come to see me as early as possible. The objectives are to show the overall organization of classes of organic compounds, factors involved in classification, characteristic reactions of functional groups and subgroups, the application of physical and chemical methods of characterizing organic compounds. A mechanistic approach to reactions and a focus on multistep synthesis will be emphasized throughout the course. 1 Materials for the class: 1) Paula Yurkanis Bruice, Organic Chemistry 7th edition, ISBN-10: 0-321-80322-1 2) Weeks, Pushing Electrons: A Guide for Students of Organic Chemistry 4th edition, ISBN10: 1-133-95188-0 (Recommended) 3) Pavia, Lampman, Kriz, Engel, Introduction to Organic Laboratory Techniques, customized edition, ISBN-10: 0-495-08282-1 4) Colored pens/pencils or highlighters 5) Molecular Model Kit (Recommended) 6) Safety Goggles or Safety Glasses (Z-87 code) 7) Laboratory Coat (Recommended) 8) Disposable Gloves (Required for most experiments) 9) Laboratory Notebook: a bound notebook with carbon copies and page numbers throughout is required 10) Non-programmable scientific calculator COLLEGE RESOURCES FOR CHEMISTRY STUDENTS Admissions and Records: Students can register for classes, request transcripts, file petitions for graduation, and drop classes at this office. For more information call (818) 833-3322 or visit: http://www.lamission.edu/admissions/ Assessment Center: Offers student assessments in English, English-as-a-Second-Language (ESL) and Mathematics. Please contact the Assessment Center at (818) 364-7613 for more information or visit http://www.lamission.edu/assessment/ Science Success Center (SSC): Free tutoring and workshops are available for chemistry students in Room CMS 101. During Fallsemester the SSC is open Monday-Thursday from 10 am-8 pm, and Saturday from 10 am-2pm. For more information visit their Facebook page LAMissionSSC or call (818) 364-7600 x 7133. STEM Office: For information on free tutoring, resources, internship opportunities, and academic counseling for STEM (Science, Technology, Engineering, and Math) students visit the STEM Center in Room CMS 8 or http://www.lamission.edu/stem Bookstore: For hours of operation, book availability, buybacks, and other information call (818) 364-7767 or 7768 or visit http://eagleslanding.lamission.edu/default.asp Counseling Department: For appointments and information call (818) 364-7655 or visit http://www.lamission.edu/counseling/ Disabled Students Programs and Services (DSP&S): For appointments, eligibility, services, and information call (818) 364-7732 or visit http://www.lamission.edu/dsps/ Extended Opportunity Programs and Services (EOPS): For appointments, eligibility and information call (818) 364-7645 or visit http://www.lamission.edu/eops/ Financial Aid: For information and applications call (818) 364-7648 or visit http://www.lamission.edu/financialaid/ Library: For information on hours, resources, workshops, and other services contact (818) 364- 7106 or visit http://www.lamission.edu/library/ Tutoring Services in Learning Center: Laboratories for Learning, Writing, & some Math classes. Walk-in and appointments. Call (818) 364-7754 or visit www.lamission.edu/learningcenter/ 2 Student Code of Conduct & Academic Honesty: Students are expected to respect and obey standards of student conduct while in class and on the campus. Students shall demonstrate individual work in lecture, exams, homework/assignment, and laboratory data and reports. All students are required to follow “NO CHEATING AGREEMENT” which states if a student is caught cheating, the student will receive a "0" for the assignment or test and will be reported to the Dean of Student Affairs. If the student is caught a second time, the student will be reported to Vice President of Student Services. In addition, please note the following for this course: • Collaboration with other students in this course is encouraged for classwork/homework, lab reports and in-class activities. This means that you are encouraged to verbally discuss your thoughts, arguments, etc. on these assignments. You may not, however, copy another student’s work directly or submit the exact same answers as another student. For individual assignments, all problems must be worked out by you (work shown), and written answers must be in your own words. Failure to follow this policy will result in a zero for the assignment. • Collaboration of any kind is NOT allowed on quizzes or exams. • Any form of cheating (this includes copying lab reports, "dry-labbing", copying or allowing some one to copy answers on a laboratory activity, lab report, quiz, test, or giving information about the quiz or test to another student) is not tolerated. • Using, receiving, or providing unauthorized information during tests or on any written assignments. • Changing answers on assignments after work has been graded. • Having another student take an examination for you or taking an examination for another student, or using unauthorized electronic devices, such as cell phones, PDAs, electronic dictionaries, IPODs during examination are not allowed. • Plagiarizing or presenting someone else’s work as your own. • Violating any other standard that an instructor identifies as cheating in that particular course or subject area. To prevent academic dishonesty the following guidelines will be followed. You are allowed to bring colored pens, pencils, and a non-programmable calculator to quizzes, exams, laboratory, and the final. The following are not allowed during lecture and laboratory: headphones, audio recorders, image capturing devices (cameras, scanners, etc.), food, and drinks. Breaks during an exam are not permitted. Tardy: Arriving late disrupts the class. I expect all students to arrive on time and ready to work. If you are unavoidably detained, respect your fellow students and instructor by entering the classroom quietly. If you are late to a quiz or exam, no extra time will be granted. Showing up on time is especially important in the laboratory section as important safety information is discussed at the beginning of the lab period. For this reason, students arriving more than 10 minutes late to lab will receive a 10% penalty on their lab report. Assignments: Chapter assignments will be announced in lecture along with due dates. Assigned problems may come from your text (odd and even problems) plus some additional problems (not from textbook), or problems made by your instructor. These problems will be collected, graded, and returned to you. Assignments must be turned in at the beginning of the class period on the due date. Late assignments will not be accepted except for legitimate absences. All sheets must be stapled, problems written in the numerical order assigned, and neatness counts. It is your responsibility to successfully complete each assignment. You may also want to consider forming a study group with other class members, and attend tutoring available free of charge. Quizzes and Exams: Weekly quizzes will cover recent materials from lecture. They will be given in lecture time. There are no make-ups for missed quizzes. There are 13 quizzes total (starting second week of the semester, given on Thursdays; however, weeks 4, and 12 quizzes will be Tuesday). I will choose 12 best quiz scores out of 13 toward your final grade. Exams will be administered during the laboratory portion of the course (about 90-120 minutes, followed by laboratory work). All quizzes and exams will be closed book and closed notes. You may use a calculator on quizzes and exams (if necessary) but it must not have any stored information (no Visors, Palms, language translators, or cell phones). Three exams will be given during the semester. All exam dates are listed on the Schedule provided. It is important that you take 3 each exam on the assigned date. No make-up exams will be given unless there was a valid, verifiable reason for missing that exam. No make-up exams will be given after the test has been returned. If you are going to miss an exam, you should get in touch with your instructor as soon as possible and make arrangements to take the test earlier. All exams will be cumulative. Laboratory: The laboratory section is an important component of the course and worth 35% of your grade. Laboratory Quizzes 10% Laboratory Reports 15% Laboratory Written Final Exam 10% This is your chance to get “hands-on” experience with the topics covered in lecture and to learn/practice important laboratory skills that you’ll need in future science courses or employment involving laboratory work. It is essential that you keep your lab notebook current and that you enter all data directly into the notebook (using black or blue ink pen). To make sure of this your lab notebook will be checked periodically in the lab. Our goal is to make the laboratory a true learning experience and not just a test of your ability to follow directions. No late lab reports are accepted. Because important safety information is discussed at the beginning of the period, you must show up on time to lab. For your safety and the safety of your classmates, it is very important that you follow proper lab procedures at all times. Students who do not follow directions or otherwise engage in unsafe behavior in the lab will be dismissed from the laboratory and will be given a zero for that lab assignment. For safety purposes, students must dress appropriately when working in the laboratory. Goggles (Z87-code) and closed-toed shoes must be worn during all laboratory work. If you frequently wear sandals to school, you may leave a pair of close-toed shoes in your car. Body parts facing the lab bench/hood must be covered. This may be accomplished by wearing a lab coat or apron. Long hair must be tied back. Students who are not appropriately dressed for laboratory work will be dismissed from class and given a "0" for the scheduled experiment. It will be up to the student to schedule a make-up session for the experiment. Laboratory quizzes will be announced during laboratory time and will be given during laboratory section of the course. Laboratory quizzes and laboratory written final exam will be closed book, closed notebook and notes, covering the experimental techniques, laboratory reading materials, and all the experiments done in the laboratory. There are no make-ups for missed quizzes; however, one lowest quiz grade will be dropped at the end of the semester. Grading: Grades will be assigned based on the following percentages: Grading Scale: Assignments 5% 90-100% = A Exams 30% 80-89% = B Quizzes 15% 70-79% = C Final Exam -ACS 15% 60-69% = D Laboratory 35% 59 and below = F Important Dates: Friday, February 19th 2016 Sunday, February 21st 2016 Sunday, May 8h 2016 Last Day to Add Last Day to Drop with no “W” Last Day to Drop with “W” ABSOLUTELY NO BEEPERS OR CELL PHONES WILL BE TOLERATED IN LECTURE OR LABORATORY SECTIONS! YOU MUST COME TO CLASS ON TIME! 4 CHEM. 212 LECTURE TENTATIVE SCHEDULE* SPRING 2016 Week Date Lecture on Chapter Lecture Schedule Reading Assignments (Read Before Class) 1 2/9 2/11 Ch. 8 Ch. 19 Benzene and Aromaticity (8.1-8.3, and 8.7-8-12) Reactions of Benzene 2 2/16 2/18 Ch. 19 Ch. 19 Reactions of Benzene and Substituted Benzene Quiz #1; Reactions of Benzene and Substituted Benzene 3 2/23 2/25 Ch. 19 Ch. 11 Reactions of Benzene and Substituted Benzene Quiz #2; Alcohols: Properties and Reactions of Alcohols 4 3/1 3/3 Ch. 11 Ch. 11 Quiz #3; Reactions and Synthesis involving Alcohols Ethers: Properties & Reactions 5 3/8 3/10 Ch. 11 Ch. 11 Reactions of Epoxides, Thiols and Sulfides Quiz #4; Reactions of Amines 6 3/15 3/17 Ch. 16 Ch. 16 Reactions of Carboxylic Acids and Carboxylic Acid Derivatives Quiz #5; Reactions of Carboxylic Acids and Carboxylic Acid Derivatives 7 3/22 3/24 Ch. 16 Ch. 17 Reactions of Carboxylic Acids and Carboxylic Acid Derivatives Quiz #6; Reactions of Aldehydes and Ketones 8 3/29 3/31 Ch. 17 Reactions of Aldehydes and Ketones No Classes- Cesar Chavez Day SPRING BREAK (April 4th – 9th) 9 4/12 4/14 Ch. 17 Ch. 17 Reactions of α, β-Unsaturated Carbonyl Compounds Quiz #7; Reactions of α, β-Unsaturated Carbonyl Compounds 10 4/19 4/21 Ch. 18 Ch. 18 Reactions at the α-Carbon of Carbonyl Compounds Quiz #8; Reactions at the α-Carbon of Carbonyl Compounds 11 4/26 4/28 Ch. 18 Ch. 20 Reactions at the α-Carbon of Carbonyl Compounds Quiz #9; Amines and Heterocyclic Compounds 12 5/3 5/5 Ch. 20 Ch. 20 Quiz #10; Reactions of Heterocyclic Compounds Heterocyclic Compounds in Synthesis 13 5/10 5/12 Ch. 21 Ch. 21 Carbohydrates Quiz #11; Carbohydrates 14 5/17 5/19 Ch. 21 & 22 Ch. 22 Carbohydrate & Amino Acids, Peptides, and Proteins Quiz #12; Amino Acids, Peptides, and Proteins 15 5/24 5/26 Ch. 26 No Classes- Memorial Day Quiz #13; Amino Acids, Peptides, and Proteins FINAL EXAM: Tuesday, May 31st 7:30 -9:30 am (Comprehensive) *This schedule is tentative and subject to change as the class progresses. *Instructor reserves the right to change this schedule as class progresses. 5 CHEM. 212 Week Date 1 2/9 2/11 2 3 2/16 2/18 2/23 2/25 4 3/1 3/3 5 3/8 3/10 6 3/15 3/17 3/22 3/24 7 8 9 10 11 12 3/29 3/31 4/12 4/14 4/19 4/21 4/26 4/28 5/3 5/5 13 14 15 5/10 5/12 5/17 5/19 5/24 5/26 LABORATORY TENTATIVE SCHEDULE* SPRING 2016 Laboratory Schedule Review of Spectroscopy (IR & NMR Exercises); Laboratory Notebook & Locker Check-in Iodination of Vanillin Purification and Analysis of Iodination of Vanillin Product Molecule Synthesis of Methyl Orange Analysis of Methyl Orange by Visible Spectrum & Use of Methyl Orange as a Dye, and the Effect of a Bleach on Dye Dehydration of 2-Methylcyclohexanol and Analysis of Product by Spectroscopy and Chemical Tests Oxidation of Cyclohexanol Lecture Exam #1; Oxidation of Cyclohexanol & Product Analysis by Spectroscopy and Chemical Tests Introduction to Mass Spectroscopy Interpreting Mass Spectroscopy of Organic Molecules & Determination of Organic Molecule Structure by Combination Spectroscopy Mass Spectroscopy Exercises Introduction to Ultraviolet Spectroscopy Interpreting Ultraviolet Spectroscopy of Organic Molecules Williamson Ether Synthesis & Library Assignment Lecture Exam #2; Continue with Williamson Ether Synthesis No Classes- Cesar Chavez Day SPRING BREAK (April 4th – 9th) Synthesis of 1-Phenyl-3-butene-1-ol & Product Analysis Product Analysis of 1-Phenyl-3-butene-1-ol & Wittig Reaction: Synthesis of 1,4-Diphenyl-1,3-butadiene Wittig Reaction: Synthesis of 1,4-Diphenyl-1,3-butadiene, continues Identification of an Unknown by Fischer Esterification Identification of an Unknown by Fischer Esterification, continues Aldol Reaction: Synthesis, Purification and Analysis of 1,5-Diphenyl-1,4-pentadiene-3one Lecture Exam #3; Continue with Aldol Reaction Reaction of Acetophenone with Clorox Multi-step synthesis: First Step Multi-step synthesis: Second Step Multi-step synthesis: Third Step Analysis of Multi-Step Synthesis and Clean-up & Check-out Written Final Exam *This schedule is tentative and subject to change as the class progresses. *Instructor reserves the right to change this schedule as class progresses. *Use of cell-phones is not allowed during laboratory time. *Laboratory Quizzes will be announced during laboratory time. Students are required to wear safety goggles during laboratory. Failure to comply will be reflected in your laboratory grade. Food, Gum, or Drinks are not allowed in the laboratory at any time. grade. Food, Gum, or Drinks are not allowed in the laboratory at any time. 6