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Fall 2005
Instructor: Office: Telephone: E-mail: Office Hours: Dr. Donovan Haines BE 2.518 (972) 883-4542 M 9:30am-10:30am; R 2:30pm-3:30pm

ORGANIZATION AND OBJECTIVES. This course is a continuation of CHM 2323 (Organic Chemistry

I). Fundamental organic reactions, mechanisms, synthetic strategy and structure determination techniques are reviewed in more depth and expanded upon. Relevance of the subject to biochemistry and other scientific and technological fields is explored.
PREREQUISTE: CHM 2323 (Organic Chemistry I). TEXTBOOK: L. G. Wade, Jr. Organic Chemistry. 5th. ed., 2003.

WHAT YOU SHOULD KNOW FROM ORGANIC I Essentially, you should already know the material from chapters 1-10 of your textbook (Note: Chapter 10 is also covered in Org. I but we will review it briefly). Because there is some variability in what is covered in Organic I versus Organic II from instructor to instructor and University to University, it is highly recommended that you review this material the first week of class and fill any gaps you may have. Especially important are the ability to draw Lewis dot structures, to assign formal charges, to draw resonance structures, write a chemical mechanism, and an understanding of reactions like the SN1, SN2, E1 and E2 because we will be extending this knowledge to more complex reaction mechanisms this semester.

WebCT Our course involves an online website that students can access at To access the website you must have an active NetID (the ID you use for nearly all campus resources) and password. Having a computer at home is not required, as you can access the site from the on-campus computer labs. The site is where you will obtain your grades, get lecture notes and overhead packs, get copies of assignments, and sometimes take quizzes. It also has links to useful sites on the internet. All students should make sure they can access the site the first week of class.

TESTS - There are four regular exams and a comprehensive final. Students can drop one of the

regular test grades, but the final exam cannot be dropped. If you miss an exam for any reason, it must count as your drop; no makeup exams will be given. Students who are unable to take the final exam as scheduled should file for an Incomplete by the last day of finals in order to avoid a grade of zero. During the exam you will be asked to put everything away and leave all bags in the aisles, not at your feet. For this reason, it is highly recommended that you do not bring valuables (cell phones, etc.) to the exams. You are responsible for any items that you bring. Exams may be held in a different room than lecture, this will be announced prior to Exam I. Prior to exam I you should bring four “ParScore Student Enrollment Sheets” (also known as a scantron) form #F-1712-PAR-L and turn them into Dr. Haines. This is the pink scantron you can obtain at the campus bookstore or at off-campus books. You will receive a scantron back with each exam you take. You are NOT to bring scantrons into the exams.
QUIZZES – Quizzes will be given at various times throughout the semester. Generally they will be

announced ahead of time, but not always. Your lowest quiz score for the semester will be dropped.
ASSIGNMENTS – Students are expected to work the problems given in the book as part of their

normal program of study. Problems from the text will also appear on quizzes, it is in your best interest to be familiar with them. There is no quiz rescheduling. Keys to quizzes are made available immediately after the quiz is taken. Any missed quizzes carry an automatic grade of zero. Exams will be rescheduled with documentation of an official University excuse (i.e. illness with a note from the doctor). Quizzes and tests are based exclusively on lecture notes and on the readings and exercises from the text. Quizzes and exams are written in mixed format, with questions involving multiple choice, short answers and the writing of structures and reaction mechanisms. The final grade is based on the following:
3 OF 4 REGULAR EXAMS QUIZZES & ASSIGNMENTS FINAL EXAM 60% (20% each) 15% total 25%

Your grade will be determined according to the scale below to the nearest whole percentage point. A+ A AB+ B BC+ 96-100 90-95 85-89 80-84 75-79 70-74 65-69 C CD+ D DF 60-64 55-59 50-54 45-49 40-44 39 or below

CLASSROOM ETIQUETTE. You are taking this class by your own decision in order to further goals that are important to you. The instructor and fellow students expect mature behavior from you at all times. Any behavior that is disruptive to class, inconsiderate, or offensive to anyone reflects poorly on the offender and is subject to disciplinary action. Examples of disruptive behavior are horseplay and loud speech or distracting other students when entering class late.

Use of cellular telephones in the classroom is prohibited. Please turn off your telephone before entering the classroom. If you must take a call during class time, please leave the classroom. Likewise, communication of any kind with anyone during tests is prohibited. If you have an emergency during a test, you must surrender your test and resolve the issue with your instructor at a later time. However, this does not carry any obligation on the part of the instructor to reissue the test or change the grading policy. Therefore,

the course. Failure to do so results in automatic failing grade.
INCOMPLETE GRADES are issued only if the student has satisfactorily completed all course work,

up until the drop with signature deadline. The student must also demonstrate a compelling reason. This process requires a contract signed by the student and the instructor specifying a deadline and the requirements for the completion of the course. Current regulations provide that if an incomplete grade is not removed within the following academic term, it automatically turns into a failing grade. If you are classified as a graduate student, be aware that some policies, including deadlines to remove incompletes, may be different from undergraduate policies.
PLEAS FOR SPECIAL TREATMENT. Unless you can demonstrate extraordinary circumstances such as

disabilities, emergencies, or undue psychological stress, refrain from making pleas for special treatment. Such requests are unfair to other students, place added burden on already overworked instructors, constitute unprofessional behavior, and therefore reflect poorly on the petitioner.
DISHONEST CONDUCT. Students found guilty of cheating on exams or quizzes will be allowed to

finish but will be referred to the Dean of Students for punishment. In the past this has normally involved failure of the course for a first-time offense.

ONE LAST HINT: Many students start out trying to memorize all the reactions in this course. Memorization is a necessary part of studying organic chemistry, and most students find flash cards helpful in this regard. A common mistake, however, is thinking memorization is enough. In some chapters of our text you will be presented with far too many reactions to memorize, but they will all occur through only a few common mechanisms. Learn those mechanisms and the fundamentals of what causes something to be reactive and you will not have nearly as much to memorize. Understanding mechanism is the key managing this course. Remember, Organic Chemistry is the behavioral psychology of electrons. Learn what they want to do and why and you have it made.

Tests are scheduled as below. The final exam follows the class schedule. All dates are subject to change.

Chapter 12: Infrared Spectroscopy and Mass Spec. Review of functional groups, fundamentals of infrared spectroscopy and identification of functional groups by IR, basic mass spectrometry with interpretation. Chapter 13: NMR Spectroscopy. Basic concepts in proton and carbon NMR, structure determination, and elements of unsaturation (p. 296-298). Chapter 11: Alcohol chemistry II. Oxidations, alcohols as Bronsted acids, nucleophiles, & electrophiles. EXAM 1 (Thur. 9-15-05) : Chapters 11, 12, 13

Chapter 14: Ethers, Epoxides and Sulfides. Properties, synthesis and reactions. Chapter 15 and p. 40-46: Molecular orbital theory. Conjugated systems, pericyclic reactions, UV spectroscopy. Chapter 16: Aromaticity. Aromatic, nonaromatic, and antiaromatic systems. MO theory of aromatics, heterocyclic aromatics, aromatic vs. aliphatic chemistry. EXAM 2 (Thur. 10-6-05) : Chapters 14, 15, 16

Chapter 17: Electrophilic Aromatic Substitution. Reactions of aromatic compounds. Chapter 18: Carbonyl group chemistry. Carbonyl groups as electrophiles, acetals as protecting groups, addition-eliminations, oxidation and reduction reactions. Chapter 19: Amines. Amines as bases, nucleophiles, and electrophiles; reactions of diazonium salts, oxidations & reductions. EXAM 3 (Tues. 11-1-05) : Chapters 17, 18, 19

Chapters 20 / 21. Carboxyl group chemistry. Carboxylic acids and their derivatives. Acidbase reactions, addition-eliminations, condensations, and reductions. Chapters 22. Alpha Substitutions and Enols. Description of enols and enolates, Adol condensations, Claisen condensation, Michael additions. EXAM 4 (Thur. 11-17-04) : Chapters 20, 21, 22

FINAL EXAM (11:00am – 1:00pm Thursday, December 1. The final exam IS comprehensive and will include chapters 11-22 as well as any additional material covered the last week of class.

(Chapters are listed in numerical order. Note that without prior notice you will not be asked to turn these questions in, but it is recommended you work them out to prepare for exams and quizzes.) It is highly recommended that you do all in-chapter problems for sections we cover in lecture.

5th edition: CHAPTER 10: 31, 32, 33 (b,c,g,h), 34(a,c), 35(b,d), 37(a,e), 38(a,c,g,i,k,m), 39(e,f,), 43(b) CHAPTER 11: 40, 41(a,c,e,g, more as you have time), 43, 44, 49, 53 CHAPTER 12: 15(c,d,e,f,g,h),16, 18, 20 CHAPTER 13: 33, 34, 35(a,b,c,e,f,h), 36, 38, 40, 46, 47 CHAPTER 14: 30(a,c,f,g,h), 32(a,e,f,g,h,i), 33(a,c,d,e,f,g,j,k,l,m,n), 37, 38(a,b,c), 44 CHAPTER 15: 24(a,b,c,d,e), 25(a,c,e,g,h), 26(a), 27(b,c), 28(a,b), 30(a,b,c,d), 33(a,c,f,h) CHAPTER 16: 27(b,c,h,i), 28(a,b,c,f,g), 32(a,b,c,d,e,f,g,h), 34(a,b,c,e), 41 CHAPTER 17: 44(a,c,j), 45(a,c,f), 47(c,d,h), 49, 50, 56, 58 CHAPTER 18: 39(a,b,c,d,e,f,g,h,I,j,k,l), 50(a,b,c,d,e), 51(e), 52(a,c,d,f), 53(b,d,e,f,h), 69 CHAPTER 19: 36(a,b,c,d,e,f,g,h), 37(a,c,d), 38(a,e,h), 39(a,c), 40(a), 41(a,b,c,d,h,j,k,p), 44(b,f,g), 52 CHAPTER 20: 26(a,c,e,g,h), 28(a,c,d,f,g,h,i), 29(a,c), 30(a,e), 31, 33, 34, 35(a,c,e,f,h,k), 42 CHAPTER 21: 44(a,c,e,f,k,l), 47(a,b,e), 49(a,c,e), 50(a,b,d,h,i), 52(a,b), 53, 58(a,e) CHAPTER 22: 61(a,d,e,h), 62(1), 63, 64(a,b,c,d), 65(a,c,e), 68(a,c,f), 70(b), 73(c,d), 79, 80

If you have 4th edition, the following problems are good choices (usually the same as above, just different numbering. I only have lists for these chapters): CHAPTER 14: 28(a,c,f,g,h), 30(a,e,f,g,h,i), 31(a,c,d,e,f,g,j,k,l,m,n), 35, 36(a,b,c), 42 CHAPTER 15: 24(a,b,c,d,e), 25(a,c,e,g,h), 26(a), 27(b,c), 28(a,b), 30(a,b,c,d), 33(a,c,f,h) CHAPTER 16: 25(b,c,h,i), 26(a,b,c,f,g), 31(a,b,c,d,e,f,g,h), 33(a,b,c,e), 39 CHAPTER 17: 42(a,c,j), 43(a,c,f), 45(c,d,h), 47, 48, 54, 56, CHAPTER 18: 37(a,b,c,d,e,f,g,h,I,j,k,l), 48(a,b,c,d,e), 49(e), 50(a,c,d,f), 51(b,d,e,f,h), 67