"Study Guide and Solutions Manual to accompany Organic Chemistry" 5th edition
ISBN 0-13-196328-7 by Paula Yurkanis Bruice; Pearson/Prentice Hall.
Oakland University
College of Arts and Sciences
Department of Chemistry
ORGANIC CHEMISTRY I CHM 234 FALL SEMESTER 2007 4 Credits, Section 41667 Tu, Th 10:00 - 11:47 am, ODH 204 Roman Dembinski
COURSE CATALOG DESCRIPTION Introduction to the structure, properties, and reactivity of organic compounds. PREREQUISITE CHM 158 or 168 (General Chemistry or Honors General Chemistry) Important: Each student is expected to have a thorough command of all material in the general chemistry sequence. A poor background is a leading cause of failure in this course. The general chemistry texts used last year was "General Chemistry" 8th edition by Ebbing, Gammon. Especially important are chapters covering electronic structure and the periodic table, covalent bonding, thermochemistry, rate of reactions, acids and bases, equilibria in acid-base solutions, spontaneity of reaction. TEXT "Organic Chemistry" 5th (new) edition ISBN 0-13-196316-3 by Paula Yurkanis Bruice and "Study Guide and Solutions Manual to accompany Organic Chemistry" 5th edition ISBN 0-13-196328-7 by Paula Yurkanis Bruice; Pearson/Prentice Hall 4th (old) edition ISBN 0-13-140748-1 contains almost identical material and can be used Textbook and study guide are essential for passing this course. Purchase them right away. Every problem is assigned as homework unless otherwise stated. Read the section "For the Student" carefully. None of the special topics will be covered. MOLECULAR MODELS Good sets were available from the bookstore, and are essential for passing this course. The instructor will refuse office hour help to students who do not have models. BULLETIN BOARD Handouts, exam keys, etc. will be posted on a bulletin board at the end of the hallway that runs east in the SEB building (Chemistry Department, 2nd floor, across the room SEB 216). LECTURES Lectures must by necessity be rapidly paced in order to cover all of the material required for chemistry 234. Questions are welcome at any time. In fairness to all, questions of the type “what will be on the exam?” will be entertained only in class so that all students will have the benefit of the response. Over the discussion part of lectures, homework problems will be reviewed and worked out in detail. Examinations will be discussed and analyzed. You are encouraged to come with specific questions from lectures, the text, and assigned problems. OFFICE HOURS Office hours for the instructor (SEB 225) are Tu 12:00 – 1:00 pm, Th 1:00 – 2:00 pm, F 12:00 – 1:00 and 4:30 – 5:30 pm. All students are welcome at any of these. The instructor is also available on weekends (call in advance) but not later than 7:00 pm for any reason whatsoever. Office hours can be rescheduled when in conflict with Supplementary Instruction (if any). Office Phone: 248-370-2248.
CONTENTS OF LECTURES Chapter 1. Electronic structure and bonding. Acids and bases. Chapter 2. An introduction to organic compounds. Nomenclature, physical properties, and representation of structure. Chapter 3. Alkenes: structure, nomenclature, and an introduction to reactivity. Thermodynamics and kinetics. Chapter 4. The reaction of alkenes. Chapter 5. Stereochemistry: the arrangement of atoms is space; the stereochemistry of addition reactions. Chapter 6. The reaction of alkynes. An introduction to multistep synthesis. Chapter 7. Delocalized electrons and their effect on stability, reactivity, and pKa. More about molecular orbital theory. Chapter 8. Substitution reactions of alkyl halides. Chapter 9. Elimination reactions of alkyl halides. Competition between substitution and elimination. Chapter 10. Reactions of alcohols, amines, ethers, epoxides, and sulfur-containing compounds. Organometallic compounds. Chapter 11. Radicals. Reactions of alkanes. Chapter 12. Mass spectrometry, infrared spectroscopy, and ultraviolet/visible spectroscopy. Chapter 13. NMR spectroscopy (only introduction, time permitted). SCHEDULE OF LECTURES and EXAMINATIONS average pace of lectures: one chapter/2 lectures Week #1 (2-September); Week #2 (9-September); Week #3 (16-September); Week #4 (23-September); Week #5 (30-September); examination #1: Week #6 (7-October); Week #7 (14-October); Week #8 (21-October); Week #9 (28-October); examination #2: Week #10 (4-November); Week #11 (11-November); Week #12 (18-November); Week #13 (25-November); examination #3: Week #14 (2-December); final examination:
R lecture 1 T,R lectures 2-3 T,R lectures 4-5 T,R lectures 6-7 T,R lecture 8 Tuesday 2-October (chapters 1-3), followed by a short lecture T,R lectures 9-10 T,R lectures 11-12 T,R lectures 13-14 T,R lecture 15 Tuesday 30-October (chapters 1-7(6)), followed by a short lecture T,R lectures 16-17 T,R lectures 18-19 T lecture 20 (Thanksgiving recess) T,R lecture 21 Tuesday 27-November (chapters 1-10), followed by a short lecture T,R lectures 22-23 Thursday, 13-December, 8:00-11:00 am OTHER EXAMINATION DETAILS
(1) A grade of 0 (zero) is assigned for missed exams. There are no make-up exams. Any circumstances involving illness or deaths must be (a) communicated in advance of the exam, and (b) fully documented, with signed statements from a medical doctor (not a chiropractor) or a county coroner. Voice mail may be left at (248) 370-2248. (2) Students are responsible for checking their exams for blank or missing pages (the number of pages and problems will be indicated on the face page). (3) Errors can occur in grading. If you have grading questions on your exam, take the following steps: (a) check your answers vs. those on the key that is posted on the bulletin board; do not write on or mark your exam; (b) meet with the instructor. No regrading will be allowed five working days after the return of an exam. Some graded exams will be copied prior to their return. Any and all incidents of cheating will be referred to Academic Conduct Committee. (4) ID checks will be required at the examinations. -2-
COURSE GRADING Each midterm will count as 20% of the course grade, and the final will count as 40% of the course grade. Grades will not be assigned to individual exams, but rankings (distribution curves) will be posted. "Wild Card Rule": The instructors reserve the right to factor "surprise quizzes" into the final grades (up to 15% total). Grade distributions (%) previously given by the instructor in Chemistry 234 and 235 include: A
B
C
D
0(zero)
10 25 28 23 13 20 25 26 16 36
36 21 11 21 18 8 28 13 16 13
17 18 44 33 38 39 27 42 34 23
14 18 11 21 23 31 12 16 9 17
23 18 6 2 8 2 8 3 25 11
Incompletes: The official University policy will be rigorously followed, which means it will be almost impossible for anyone to be given an incomplete. Withdrawals: The official University policy will be rigorously followed. The following grading was used for this course recently (points out of 500) 0.0 1.0 1.1 1.2 1.3 1.4 1.5 1.6 1.7 1.8 1.9 2.0 2.1 2.2 2.3 2.4
99 and below 100 and above 110 and above 120 and above 130 and above 140 and above 150 and above 160 and above 170 and above 180 and above 190 and above 200 and above 210 and above 220 and above 230 and above 240 and above
2.5 2.6 2.7 2.8 2.9 3.0 3.1 3.2 3.3 3.4 3.5 3.6 3.7 3.8 3.9 4.0
250 and above 260 and above 270 and above 280 and above 290 and above 300 and above 310 and above 320 and above 330 and above 340 and above 350 and above 360 and above 370 and above 380 and above 390 and above 400 and above
ASSIGNMENTS It is expected that the following will be completed in advance of the specified chapter lectures: Read the chapter, complete all problems within the chapter, complete all additional problems at the end of the chapter.
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CHEMISTRY 234 STUDY GUIDE FALL SEMESTER 2007 Instructor Roman Dembinski GENERAL INFORMATION Chemistry 234 is the introductory semester of a two-semesters sequence of classes (234, 235) specifically designed to provide the chemistry major with the necessary organic chemistry background for study and work in advanced chemistry courses. Since a number of other academic areas require their students to take Chemistry 234-235, the course also provides basic background for entry into graduate and professional schools. In Chemistry 234, we will begin to acquire the information and language of organic chemistry and begin to develop the concepts and theories involved. It is important to stress that memorization of “organic chemistry” is not sufficient and perhaps not even possible. Understanding and being able to use and apply the concepts and theories upon which this field is based is a key to a successful experience throughout the year. As a student you may find these courses different than the others you have taken. You may need to develop new ways of thinking about and applying knowledge to important scientific problems. When you start Chemistry 234 it is assumed that you have successfully completed Chemistry 158 or 168 (or the equivalent) and that you have retained a thorough mastery of this material. Some students with poor background may encounter conceptual difficulties with portions of the topics in Chemistry 234 and end up investing more time than is usual for a four credit course. It is important for the student to realize that one cannot approach the subject of organic chemistry from the point of view of “short term learning.” “Cramming” for one exam can lead to disaster later on since point builds upon point, idea upon idea, and knowledge upon knowledge. As you proceed through the year, you must master and retain the material as it is encountered in reading, lectures, and working of problems. While organic chemistry has a reputation of being a very difficult subject, there is not a real basis for this. Average good students can quite readily do B to A work. Being aware of the following can be of help in achieving success: (1) recognize that organic chemistry may be different than other classes you have encountered before; (2) approach organic chemistry with a positive attitude and high enthusiasm; (3) have or develop good study habits for this course; (4) read so that you are ahead of lectures and discussions, identify new key terms and ideas, and listen for the lecture discussion of these; (5) take good, detailed notes, review these notes and fill in any missing details as soon after the lecture as possible; (6) do not get behind, as being behind even one or two weeks can result in calamity; (7) work enough problems (see below); (8) be willing to put in the time and effort to master the material (the time required often exceeds 3 hours for each hour spent in lecture). WORKING PROBLEMS The working of an extensive number of problems is so essential to being successful in organic chemistry that it cannot be overemphasized. If you work enough problems, and fully understand why the answers are what they are, you should be able to do well in the course. You are assigned to work all of the problems in and at the end of each chapter. As encouragement for this endeavor, you will find that the chapter problems will provide the basis for a significant number of questions on the midterm and final exams. Some hints on problem solving are in order. It is profitable to look over the problems in a chapter and attempt to work some of them after you have carefully read the subject material, but before it is covered in lecture discussions. This approach will help you identify subject matter you do not understand or that you did not retain. When the topics have been covered in lecture, work all of the problems as soon as possible. When you cannot solve a problem, do not hurry to the study guide. Instead, re-read the chapter and study your lecture notes, being alert to identify the parts that are pertinent to answering your problem(s), and then work on solving the problem(s) again. Turn to the study guide only to check answers you are certain of, or as a last resort. It is important for you to identify any new information given in a problem and make it a part of the chemistry that you have already learned. -4-
