Organic Chemistry II, Chem 208

Summer 2008

Dr. Suzanne Theresa Mabrouk

General Information

• Class Schedule: Monday, June 30 - Tuesday, July 29 from 8:00 am until 9:45 am with Final Exam on Wednesday, July 30 from 8:00 am until 11:00 am in Byrd Hall room 302.
• Office Number: Byrd Hall room 401
• Office Hours: If you have difficulty with course concepts or have any questions, please feel free to drop by for help. If my office hours do not coincide with your free time, then schedule an appointment. Keep in mind that regular help will assist you in mastering the material. If you find that I am already helping other students during office hours, ask if you may join. I usually help more than one student at a time, with each student having the opportunity to interject questions. This method makes better use of everyone's time.
  • M - Th 1-2 pm
  • F 10 am - 12 pm
• Phone Number: 953-7788
• Email Address: mabrouks@citadel.edu
  If you need help at night, the best way to reach me is via email.

General Course Information

• Required Text: Organic Chemistry by Janice Gorzynski Smith, 2nd ed.

• Course Prerequisites:
  • Chem 151, 152, 207, and 217
  • Each student should understand the following key concepts from general chemistry: Lewis dot structures, the octet rule and its exceptions, atomic and molecular orbital theory, hybridization, molecular geometry, polarity, acidity and basicity, thermodynamics, and electronegativity. Each student should also fully understand the following key concepts from organic chemistry I: electrophilic addition, elimination, free radical, and nucleophilic substitution reactions and their mechanisms, stereochemistry, and spectroscopy.
• Co-requisite: Chem 218.

• Course Content: The exciting study of organic chemistry will continue in Chem 208 with the organic reactions and mechanisms (where available) of carbonyl alpha substitution, electrophilic aromatic substitution, nucleophilic acyl substitution, and oxidation-reduction. Additional examples of elimination and nucleophilic substitution reactions will also be discussed. Electronegativity of the atoms involved and/or the acidity or basicity of the class of compounds will used as the basis for mechanisms. As in Chem 207, synthesis will continue to be an integral part of the course. Future chemists, dentists, medical doctors, pharmicists, and veterinarians will find this course lays the groundwork for understanding the chemistry of living beings and pharmaceuticals, the preparation of polymers, etc.

• Course Objective: By the end of this course, students should be able to:
  1. deduce products to organic reactions
  2. deduce reasonable mechanisms to an organic reaction and
  3. devise reasonable syntheses for one organic compound from another.

   

• Lectures
  • Lecture notes have already been posted to WebCT. They can be accessed using the student's six-digit CIT number without the letters CIT or any dashes as the username. Initially the password is set to the last four digits of a student's social security number; the password can be re-set at any time by the student.
  • Prior to class, students must print and study the notes. Students must write each chemical reaction from the notes onto separate notecards (flashcards), with the reactants on one side of the card and the product(s) on the reverse side. Students must copy each mechanism from the notes five times. Students must study the reactions and mechanisms before each class meeting. The following materials must be brought to class each day: the notes from WebCT, the flashcards, and the sheets containing the copies mechanisms. If a student does not have the required items for class each day and is not prepared for class (except on three occasions), the student will be removed from classroom. The notes will be annotated during class when the professor makes remarks about particular reactions, mechanisms, or concepts. The students will solve representative problems at the whiteboard during most of the class time.

Date	Topic or Test	Suggested Homework Problems
June 30	Chapters 16 (16-16.11) and 17	Ch 16: 1-3, 5-17, 28-31, 33-41, 44, & 45.
July 1	Chapter 17	Ch 17: 1-4, 8, 10, 11, 13-19, 21, 22, 25-31, 33, 38, & 53.
July 2-3	Chapter 18	Ch 18: 1-24, 26, 28-30, 31a, b, 32-38, 40, 41, 44-46, 48, 54, 55, & 65.
July 4	HOLIDAY
July 7 (Monday)	Test #1: Chs. 16, 17, & 18
July 7-8	Chapter 25	Ch 25: 1-7, 11-21, 23-27, 29, 30b, c, 31, 33-35, 36a, 37-42, 44-48, 53, 55, 56, 57a-d, g, 59a-f, h, i, j, 61, 62, 64a-f, h, 66, 69a, 71, 73a, 74, 75a, b, e, 77, & 79e, f.
July 9	Chapters 25 and 20	Ch 20: 1-8, 10-33, 37, 38, 40, 41a, b, 43a-c, 47, 48a-f, 54-57, 60a, b, 61c-e, & 64a-c.
July 10	Chapters 20 and 21	Ch 21: 1-7, 11-15, 17-24, 26-35, 37-39, 43, 44, 46-50, 52-55, 58, 59, 61-69, 72, & 76.
July 11 and 14	Chapter 21
July 15 (Tuesday)	Test #2: Chs. 25, 20, & 21
July 15	Chapter 23 (23-23.7B)	Ch 23: 1-8, 10-14, 29-31, 35, 39, 40, 47g, i, 56b, & 57a.
July 16	Chapters 23 and 24 (24-24.4)	Ch 24: 1,2, 4-8, 10-13, 26, 27, 28a, 29-31, 43a-c, e-n, 44a, e, 47, 48, 50, 54a, b, 55, & 59a, b.
July 17	Chapter 19	Ch 19: 1, 2, 5, 6, 10-18, 28, 29, 31-40, & 43.
July 18 and 21	Chapter 22 (22-22.15 & 22.18)	Ch 22: 1-6, 9-31, 36-45a, 46-55, 57-60, 66, 68, 69, 71, & 73.
July 22 (Tuesday)	Test #3: Ch. 23, 24, 19, & 22
July 22-23	Chapter 27	Ch 27: 1-6, 9-26, 30, 39, 40, 43-47, 50-53, 55, 56, 58-61, & 63.
July 24	Chapters 27 and 28	Ch 28: 1-8, 13, 14, 16, 19, 20-25, 28-33, 35-39, 41, 42, & 48-57.
July 25	Chapter 28
July 28 (Monday)	Test #4: Chs. 27 & 28
July 29	Student Evaluations & Return of Test #4
July 30 (Wednesday at 8:00 am)	Final Exam: Chem 207 & 208

• Test Bank: Old tests have been posted to WebCT. Although topics may be grouped differently on the old tests, they can still be used for practice. Print the appropriate tests, give yourself one hour to work the test, and then consult your notes for assistance with any troublesome problems. The old tests will provide you experience for the in-class test.
• Electronic devices: PDAs and laptop computers are allowed in the classroom for note taking. Cell phones must be set on vibrate. No electronic devices may be used or in view during a test or the final exam.

Course Grading Policy

• Honor in the Class: All students will adhere to the Citadel honor code described in The Guidon, and as such will not cheat on any work submitted to the instructor for a grade. Cheating will not be tolerated!

• CLE Assignments: Students, working in groups of three to four, will devise one mutually acceptable solution to each assigned problem. The group will submit the assignment at the beginning of the next class, with each member of the group receiving the same grade. Any member of the class will be randomly selected to present the solution to a problem. When working these assignments, only students within a group may work together. It is a violation for groups to assist one another. At least three CLE assignments will be given in each testing period. All CLE's will be graded with the best one for each testing period counting. At the end of the course, the lowest CLE grade will be dropped and the remaining three counted for 5% of the course grade. For details about the operation of a CLE group see the associated handout.

• Tests: There will be a total of four required tests. At the end of the semester, the best three of the four tests will constitute 70% of the final course grade.

• Make-up Tests: All make-up tests must be taken by two days after the original test date. Failure to do so will result in a 0 on the corresponding test.
  1. Students who know that a test must be missed, must speak with the professor and establish a make-up test date prior to the absence.
  2. Ill students must contact the professor and make-up the test within two days of the original test date.
  
  
  Where special arrangements have been made regarding a make-up, this is a contract between the professor and that specific student. This student is not at liberty to pardon other students from taking the test on time.

• Final Exam: The final exam constitutes 25% of the course grade. The final exam is required for a final course grade. It will cover both Chem 207 and 208. Failure to take the final exam results in a final course grade of F. The final exam will only be given during the assigned time slot, Wednesday, July 30 at 8 am, regardless of circumstances.

• Laboratory: As the laboratory is offered as a separate course, the grade earned in Chem 218 will not affect the grade earned in Chem 208.

• Formula for Determining Course Grade: Since people have a bad day periodically, one CLE assignment and one test will be dropped at the end of the course.
  • Use the following equation to determine your final course grade.
    • Final Course Grade = (CLE Avg) (0.05) + (Test Avg)(0.70) + (Final Exam)(0.25)
    
    
  • CLE Assignments (best 3 of 4): 5%
  • Tests (best 3 of 4): 70%
  • Final Exam: 25%

• Scale for Final Course Grades: All lecture grades are awarded based on the following fixed scale. This scale does not apply to lab courses.
  • A: 100-87
  • B: 86-77
  • C: 76-67
  • D: 66-57
  • F: 57-0

LD Students

• It is the responsibility of these students to provide the professor with written documentation from OASIS regarding any special needs. According to Citadel policy, all letters addressing special needs must be processed by OASIS. Letters from OASIS must be received by this professor at least two days prior to the test and mutually acceptable arrangements must be made by this same timeframe between the professor and the student. All tests will be administered in the presence of this professor.

Teaching Style

A variety of teaching formats will be employed throughout this course, to more effectively transmit the subject of organic chemistry to the students. All of the following will be employed in addition to others as deemed necessary:

• interactive lecture style, lecture with questions for discussion
• group work
• board work

Class will meet each day from 8:00 am until 9:45 am with a ten minute break in the middle. On test days, there will be a ten minute break after the test followed by a half-hour of lecture.

Classroom Attendance and Etiquette (http://faculty.citadel.edu/mabrouk/etiquette.htm)

• Attendance at each class lecture is mandatory, as described in the college catalog p. 25.
  • Students should arrive on-time if not early.
  • Tardy students should enter class quietly and take their seat. They should not ask the professor to repeat previously stated material.
• Students are held repsonsible for learning all material discussed in class, even when a student is absent.  Absent students should copy the notes of classmates and discuss any difficulties with the professor.
• Students should not speak while the professor or a classmate is speaking.
• Students should speak respectfuilly to the professor and all classmates.
• When a student has a question, the student should raise their hand and wait to be recognized.
  • Record the question in the margins of your notes along with the professor's response. This information will be invaluable as you study.
    
• Sleeping is prohibited in this professor's classroom. The first time a student is caught sleeping the student will be directed to the back of the classroom. The second offense by any student will result in the removal of that student and any future sleeping student from the classroom. Sleeping during class prevents one from learning important concepts.
• You are responsible for the condition of your desk. Report any writing on the desk before class begins.
• Food, drink, smoking, and tobacco are prohibited in Byrd Hall.
• The use of profane language is unacceptable in the presence of this professor.

Student's Attitude

• be present, both in body and mind (the latter being most important!)
• be presentable (clean and kempt)
• have a positive attitude
• be friendly
• be outgoing
• ask genuine questions
• try to learn the material
• ask for help early
• make good and effective use of your time and the time of others
  
• have meaningful conversations
• choose your words carefully and wisely
  
• above all else be genuine
  

How to Study for Chem 208

• attend all classes and if you miss a class copy missed material from responsible and intelligent classmates and discuss any difficulties with the professor
• read the related chapter in the course textbook, jotting questions into the margins
  
• print and read class notes from WebCT before the next class meeting, jotting questions into the margins
• stop by the professor's office with questions; bring your notes, flashcards, and textbook with you
• ask questions during class
  
• prepare and study flashcards of each organic reaction in the WebCT notes using index cards (place reactants on one side and products on the reverse side of the card)
• re-write each mechanism from WebCT notes (with organic reaction at top of page and mechanism below) while talking it through (follow example of professor from class); write mechanism several times with notes beside you and then start writing it without any notes present
  
• review all  flashcards to date
• work CLE problems with groupmates
• study organic chemistry with CLE group, taking turns to quiz each other with flashcards
  
• work suggested homework problems (do not read the solutions manual, this does not count!), a few per day
• re-work all practice problems from the notes and past CLE problems (cover previous solutions and solve the problem fresh)
• make quiz questions for self by putting reactants from organic reactions in random order on sheets of paper; fill-in the products at a later time
• make mechanism questions for self by placing an organic reaction at the top of a sheet of paper and filling-in the mechanism at a later time without any notes
• stop by the professor's office to work additional practice problems
  
• prior to the test, print old tests from WebCT and work one test in one hour without notes or the textbook
  

Suggested Homework Problems

Homework problems are listed in the table above. These problems can be found in the course textbook, starting throughout the reading in a chapter and continuing at the end of the chapter. These problems will not be graded. However, some of these problems could appear on future tests. The homework will provide adequate experience solving organic chemistry problems.

Test Format

Tests will address material from the lecture notes, textbook, CLEs and suggested homework problems. The following types of questions will appear on tests, as appropriate:

• provide major organic products, 10-15 questions
• multiple choice questions on acidity/basicity, nomenclature, structural features, physical properties, etc.; 6-10 questions
• mechanisms, usually 2 questions
• syntheses, usually 2 questions
• other problems, 1-2 questions

Test/Final Exam Attendance and Etiquette

• Students should arrive early, since tests will start promptly at 8:00 am.
• Students should not ask the professor last minute questions before the test, since the professor will be trying to prepare test materials and to start the test on time.
  
• Regardless of any excuse, any student arriving late will only be allowed to work on the test until 9:00 am when time will be called.
  
• Tests will end promptly at 9:00 am, so any student remaining until this time should submit the test when the professor calls time.  No extra time will be given except to LD students as described above.
  
• The final exam will only be adminstered on Wednesday, July 30 at 8:00 am .  The exam will end promptly at 11 am, when time will be called.
  
• Tests and the final exam are closed book.
• Tests and the final exam will not be scaled, regardless of class performance.
• Students should bring a number 2 pencil to each test and the final exam.
• Do not use red pen to write your test, since the professor will be using red ink to grade the test/final exam. Pencil is best, since you can erase mistakes.
• Students may only use scrap paper provided by the professor.  All used scrap paper must be submitted to the professor at the end of the test.
• Students must be quiet during a test.
• If you have a question during the test, leave your seat, bring your test, and whisper your question to the professor. The only legitimate questions are those for which the student is seeking clarification of a test question.
  
• Students must print and sign their complete name on each test and the final exam and the accompanying scantron sheet in order for a grade to be awarded.
• After you have submitted your test, do not ask the professor to assess the quality of your test answers. Such discussions are distracting to classmates still writing the test. When time is called the professor is trying to vacate the room and prepare for other activities.
• Students are prohibited from discussing the test/final exam with any Chem 208 student who has not already take the test/final exam.  Discussions include any information pertaining to a test that a student would not have before taking it.  These discussions include the difficulty level as well as the content.
  
• Test scores will only be made available at the next class meeting and not before.  Tests will not be given to classmates in compliance with FERPA.
  

Test Taking Strategies

• Prior to starting the test, obtain scrap paper from the professor and jot down any charts or helpful information that may become mangled in your mind later.  Then you can consult this information while writing the test.
• Solve all problems that you know immediately, skipping all others at the present time.  Place a star beside any questions that you are skipping temporarily.
• After solving the easy problems, solve those with a star beside them.
• While answering multiple choice questions, place the answers directly on the scantron sheet.  No extra time will be granted at the end for the transfer of multiple choice selections.
  
• Throughout the testing period look at the clock so that you work with regard to the availability of time.  Do not expect nor demand extra time from the professor to complete your test.  No extra time will be granted.

© COPYRIGHT 1998 SUZANNE MABROUK mabrouks@citadel.edu (modified: 5/29/08).