Organic Chemistry, Paula Bruice; 7th Edition. Organic Chemistry Student Study
Guide and Solutions Manual, Paula Bruice. Mastering Chemistry, Pearson ...
CHEMISTRY 261, FALL 2015 CHEMISTRY 261, SECTION 003 FALL 2015: 10:10 –11:00 AM, MWF, MURRAY G202 INSTRUCTORS: DR. M.T. CRIMMINS, C640 KENAN LAB ; DR. J.S. JOHNSON, 220 CAUDILL LAB .
[email protected] [email protected] **PREREQUISITE: CHEMISTRY 102 OR EQUIVALENT**
SYLLABUS
Office Hours:
Crimmins: Monday, Thursday 3:30 -‐ 4:45 p.m. or by appointment Johnson: Tuesday, Friday 2:00 – 3:00 pm; 221 Caudill
Group question and answer sessions: held regularly, TBA. TEXT: Organic Chemistry, Paula Bruice; 7th Edition Organic Chemistry Student Study Guide and Solutions Manual, Paula Bruice Mastering Chemistry, Pearson, ALEKS subscription: free!! OTHER MATERIALS: i-‐ clicker (i-‐clicker + or i-‐clicker 2), HGS Molecular Models LECTURES AND EXAM DATES
DATE
BRUICE
August 19 August 21, 24, 26 August 28 August 31, September 2
Introduction; Chapter 1 Electronic Structure, Bonding Chapter 1 Electronic Structure, Bonding Chapter 8 Resonance Chapter 2 Acids and Bases
September 7 (M)
Labor Day
September 4, 9, 11 September 14, 16, 18, 21
Chapter 3 Nomenclature, Alkanes and Cycloalkanes Chapter 4 Stereochemistry
September 23 (W)
Exam I Chapter 1, 2, 3, 4 Bruice
September 25, 28 September 30, October 2, 5, 7, 9 October 12
Chapter 5 Alkenes: Structure, Reaction Dynamics Chapter 6 Alkenes: Reactions University Day: no class
October 14
Chapter 8 Additions to Dienes, Chapter 7 Alkynes
October 16
October 19, 21 October 23 (F) October 26, 28, 30, November 2 November 4, 6, 9 November 11, 13, 16, 18 November 20 (F) November 25, 27 November 23, December 30, 2 December 11 (F)
Fall Break Chapter 7 Alkynes, Synthesis Exam II Chapter 5, 6, 7 Bruice Chapter 9 Substitution Reactions of Alkyl Halides Chapter 10 Elimination Reactions of Alkyl Halides Chapter 11 Alcohols, Ethers, Sulfides and Epoxides Exam III Chapter 9, 10, 11 Bruice Thanksgiving break Chapter 13 Radical Reactions FINAL EXAM: 8:00 a.m. Murray G202
CHEMISTRY 261, FALL 2014 SYLLABUS STUDY TIPS FOR THE COURSE Organic chemistry is a two-‐semester sequence, which throughout builds sequentially on material presented earlier in the course. It is essential that you do not fall behind. It becomes extremely difficult to catch up. The best approach to mastering the material in this course is to keep up daily, therefore you should spend some time every day working on the course. Read the assigned sections and view assigned videos before class. It is significantly better to invest shorter amounts of time every day for seven days than to sit down and spend a large block of time one day a week on this course. Repetition is extremely important. It takes time to master some of the difficult concepts and going back over certain ideas will make them much easier to comprehend. In addition, new ideas that you learn later in a chapter will often make earlier concepts more understandable. This is why repetitive studying and working every day is so important. If you are having difficulty with the course, get help as soon as possible. Waiting until half way through the semester (or longer) is too late. As soon as possible (within the first month) you should MASTER the following: a. bonding (Bruice Chapter 1) b. formula writing (Bruice Chapter 1) c. structures and names of functional groups (Bruice Chapter 3) d. basic nomenclature rules (Chapters 3, Bruice pgs 97-‐108) e. arrow pushing electron movement e. stereochemistry (Bruice Chapter 4) MOLECULAR MODELS Molecular models are useful for much of the course, particularly the sections on bonding and stereochemistry. Since stereochemistry becomes an integral part of the course after its introduction, models will also be useful later. Models cannot be used during the exams, however. HONOR CODE Since all graded work (including homework to be collected, quizzes, papers, mid-‐term examinations, research proposals, laboratory results and reports, etc.) may be used in the determination of academic progress, no collaboration on this work is permitted unless the instructor explicitly indicates that some specific degree of collaboration is allowed. This statement is not intended to discourage students from studying together or working together on practice problems, which are not to be collected. It is a violation of the Honor Code to fail to comply with exam procedures. Exam procedures will be provided for each exam. These will include when you are allowed to begin the exam, when you should stop working on the exam and how to maintain the integrity of individual performance on the exam. It is a violation of exam procedure to look at another student’s exam during the exam period whether you use that information or not. It is also a violation of exam procedure to “allow” another student to look at your exam during the exam period. Each student is responsible for maintaining the integrity of the of exam by protecting their answers. Violations of the Honor Code and/or Exam Procedures will be vigorously pursued through the Honor System.
CHEMISTRY 261, FALL 2014 SYLLABUS ATTENDANCE AND DAILY WORK To create an active, engaged learning environment in this class, you will be asked to master some content before class by watching video lectures and/or reading. A daily quiz at the beginning of every class will help you assess your understanding of this pre-‐class material and/or the previous class. In this context, you should be prepared to think about and answer questions that are posed. During class, you will apply your knowledge also by solving problems in small groups. Excellent attendance is required. You will receive an overall “Daily Work” score (50 points: approximately 11-‐12% of your grade, see grade breakdown below) based on a mixture of pre-‐class quizzes, class participation, and online self-‐tests. More than 250 Daily Work Points will be available in the semester, your final total will be divided by 5 to obtain your Daily Work grade that is calculated into the final grade. A maximum of 50 points can be contributed toward your final grade. Because there is ample opportunity to collect points, no “make-‐ups” for clicker questions whether a result of a missed class, a forgotten or non-‐ functioning clicker, or whatever reason. If you know will need to miss an exam (e.g. for a medical procedure or University sponsored field trip), you may arrange to take the exam early. Arrangements must be made at least two weeks in advance. Exams missed for other reasons will be replaced by your final exam grade. DAILY WORK: CLICKER QUESTIONS AND CLASS PARTICIPATION (4 PT EACH) Numerous clicker questions will be posed during class that will test your understanding of the preceding class information or your understanding of the reading/video assignment for the class for the day. Points are awarded based on participation in at least 75% of the questions for the day. During some class periods, you will work on a set of problems together in groups. The problems will teach you how to apply the concepts you learned through class, reading, and videos. You may use your book and other notes to work the problems. DAILY WORK: PRE-‐CLASS MASTERING CHEMISTRY ASSIGNMENTS (2 PT EACH) There will be a short 2-‐3 question assignment in Mastering Chemistry due prior to 10:00 am before each regular class period (not before exams) that will focus on the reading and/or videos assigned for that class. DAILY WORK: MASTERING CHEMISTRY SELF TESTS (5-‐8 PTS EACH) Online Self-‐Tests will be assigned in MasteringChemistry at the end of each chapter. These will normally be due at 11:59 pm on Sunday of the appropriate week. Self-‐Test problems are much like end-‐of-‐chapter problems from the textbook. You will receive three chances to get the right answer for each question with 25% deduction for each incorrect answer. Correct answers are available after the due date. Please note: in order to earn credit for your work, you must click the “give up” button on multi-‐part problems where you do not achieve the correct answer. No late self-‐tests will be accepted for any reason. The MasteringChemistry clock will be used to determine the submission date/time. This clock may differ from yours, so submit your work well in advance. All graded self-‐tests are to be worked independently (by you alone) with no collaboration or outside discussion. Any collaboration will be treated as a violation of the UNC Honor Code. DAILY WORK: ALEKS (25 PTS) The ALEKs prep course will count 25 pts toward the Daily Work grade. The grade will be calculated based on the percent of your pie chart that is completed. 100% completion – 25 pts
CHEMISTRY 261, FALL 2014 SYLLABUS PRACTICE PROBLEMS Recommended practice problems from your textbook will also be assigned for you to work at your own pace. These assignments will not be graded, but questions from the practice problems may be on exams. Typically, the more problem solving you do, the better you will comprehend the concepts of the course. All the problems within the text of the chapter and at the end of the chapter are useful and will help if you work them. However, if time limitations prevent you from working all the problems, work only part of each problem such as the a and b part rather than a, b, c, and d. Problems that are representative of the material are listed below. Keep this list of problems in a handy location (e.g. cover of your three-‐ring binder). END OF CHAPTER PROBLEMS Chapter 1: 46 – 48, 50 – 62, 65, 66, 69, 73; also Chapter 8: 58, 62, 64, 67, 74b, 75, 77, 92 Chapter 2: 47 – 57, 59, 61, 64, 65 Chapter 3: 52(e,f,g,h,j,k,l), 54a (1-‐6, 10,11), 55 – 57, 59(b,e,g,h,I,j), 60(a-‐g), 61, 63, 64(a-‐h), 65 – 69, 70(a-‐f); 71 – 76, 78, 79, 82 Chapter 4: 53 – 63, 65, 69 – 74, 76, 77, 82, 83 Chapter 5: 36, 38 – 43, 45, 46, 48 – 54, 56 Chapter 6: 59 – 75, 77, 78, 80 – 93, also Chapter 8: 85, 87, 90, 99, 105 Chapter 7: 27 – 32, 34 – 37, 40 – 42, 44, 45, 47 – 49 52, 54, 56, 57 Chapter 9: 35 – 42, 44 – 48, 52 – 55, 59, 60 Chapter 10: 35 – 53, 57 -‐ 60 Chapter 11: 48 – 50, 52 – 56, 59, 60, 63, 64, 67b, 68, 76, 77 Chapter 13: 25 – 29, 32, 34, 35, 38, 39, 42, 43 GRADING Hour exams (300 pts); Final exam (100 pts); Daily Work (50 pts). Makeup up exams may be given under two circumstances: –If you know will need to miss an exam (e.g. for a medical procedure or University sponsored field trip), you may arrange to take the exam early. Arrangements must be made at least two weeks in advance. –Make-‐ups for exams missed for other reasons will require an official exam excuse. Exams missed without an official excuse will be replaced by the grade on the final exam. Final letter grades will be assigned in accord with the 2000 Educational Policy Committee Report, which describes the meaning of grades as follows: "A": Outstanding mastery of course material "B": Superior mastery of course material "D": Mastery of course material that is unsatisfactory "C": Adequate mastery of course material "F": Unsatisfactory mastery of course material If you miss an exam, the exam will be replaced by the final exam grade. Item Points Possible % Breakdown Daily Work Max = 50 (total/5 11.1% (>250 pts available) Midterms 300 66.67% (3 scores: 22.22% each) Final Exam 100 22.22% Total 450 100%
CHEMISTRY 261, FALL 2014 TENTATIVE CLASS SCHEDULE Lecture Class Day Date 1 8/19 W 2 8/21 F 3 8/24 M 4 8/26 W 5 8/28 F 6 8/31 M 7 9/2 W 8 9/4 F 9/7 M 9 9/9 W 10 9/11 F 11 9/14 M 12 9/16 W 13 9/18 F 14 9/21 M 15 9/23 W 16 9/25 F 17 9/28 M 18 9/30 W 19 10/2 F 20 10/5 M 21 10/7 W 22 10/9 F 23 10/12 M 24 10/14 W 10/16 F 25 10/19 M 26 10/21 W 27 10/23 F 28 10/26 M 29 10/28 W 30 10/30 F 31 11/2 M 32 11/4 W 33 11/6 F 34 11/9 M 35 11/11 W 36 11/13 F 37 11/16 M 38 11/18 W 39 11/20 F 40 11/23 M 11/25-‐7 W/F 41 11/30 M 42 12/2 W 12/11 F
Topics
SYLLABUS
Reading Assignment Bruice, Section: Introduction Chapter 1: electronic structure, electronegativity 1.1 – 1.3 Chapter 1: structural formulas, atomic orbitals 1.4 – 1.5 Chapter 1: covalent bonds, MO theory 1.6 – 1.10 Chapter 1: hybridization, bonding 1.11 – 1.16 Chapter 8: resonance 8.3 – 8.6 Chapter 2: acids and bases 2.1 – 2.9, 2.12 Chapter 3: nomenclature, physical properties 3.1 – 3.9 Labor Day Chapter 3: acyclic conformations 3.10 – 3.11 Chapter 3: cyclohexane conformations 3.12-‐ 3.14 Chapter 4: chirality, enantiomers 4.1 – 4.4 Chapter 4: enantiomers, stereoisomers 4.5 – 4.7 Chapter 4: optical activity 4.8 – 4.11 Chapter 4: multiple stereocenters, enzymes 4.12 – 4.16, etc. Exam 1 Chapters 1,2,3,4 Chapter 5: alkene structure, stereochemistry 5.1 – 5.6 Chapter 5: kinetics, thermodynamics 5.7 – 5.11 Chapter 6: electrophilic addition, cation stability 6.1 – 6.4 Chapter 6: addition of H2O, carbocation rearrange 6.5 – 6.7 Chapter 6: Other additions to alkenes 6.8 – 6.13 Chapter 6: stereochemistry of alkene additions 6.14 – 6.15 Chapter 6: enzymes and electrophilic addition 6.16 – 6.18 University Day, no class Chapter 8: additions to dienes, Chapter 7: alkynes 8.16 – 8.17, 7.1 – 7.7 Fall Break Chapter 7: alkynes – hydrogenation, acetylides 7.8 – 7.10 Chapter 7: alkynes – synthetic planning 7.11 – 7.12 Exam 2 Chapters 5,6,7 Chapter 9: SN2 substitution reactions 9.1 – 9.2 Chapter 9: SN1 substitution reactions 9.3 – 9.4 Chapter 9: SN1 -‐ SN2 competition 9.5– 9.6 Chapter 9: SN1 – SN2 solvent effects 9.7 – 9.9 Chapter 10: E2 and E1 eliminations 10.1 – 10.3 Chapter 10: Stereochemistry of eliminations 10.4 – 10.7 Chapter 10: elimination vs. substitution 10.8 – 10.11 Chapter 11: alcohols 11.1 – 11.3 Chapter 11: alcohol dehydration 11.4 – 11.5 Chapter 11: ethers, epoxides 11.6, 11.7, Chapter 11: thiols, sulfides; synthesis; bio examples 11.8, 11.11 -‐ 11.12 Exam 3 Chapters 9, 10, 11 Chapter 13: radical selectivity 13.1 – 13.5 Thanksgiving Break Chapter 13: radical additions 13.7 – 13.9 Chapter 13: synthesis; radicals in biological systems 13.10 – 13.12 Final Exam 8:00 am:
