Chemistry 355
Section 102

Course Syllabus, Fall 2007

Organic Chemistry I

Credit: 3 hours Prerequisite: C or better in CHM 212
Instructor: Dr. Gary D. Anderson Office: 498A Science
Email: anderson@marshall.edu Phone: 696-6594
Office Hours: Office Hours: T 1-2, W 2-5, R 1-2, other times by appointment – usually available on Monday and Friday afternoons

Required Texts:
Hornback, “Organic Chemistry”, 2nd Ed., Thomson Brooks/Cole, 2006
Straumanis, “Organic Chemistry: A Guided Inquiry”, Houghton Mifflin, 2004
WebAssign Access Code scratch card

Highly Recommended:
You will find that a set of molecular models will be very helpful when learning to visualize the three dimensional aspects of organic structures. The Molecular Visions Kit 1A is available in the bookstore.

Objectives

By the end of this course it is expected that the student will:

  1. Understand and be able to make predictions using structure-property relationships for organic compounds.
  2. Recognize conformers, constitutional isomers and stereoisomers and be able to determine their relative stabilities.
  3. Recognize and name compounds containing the important functional groups.
  4. Recognize the type of bonding involved in any molecule.
  5. Understand resonance structures and be able to utilize them to explain relative stability of compounds, intermediates, and transition states.
  6. Understand and be able to use the mechanisms of nucleophilic substitution and elimination reactions to predict which product(s) will be formed, predict relative reaction rates, and predict the conditions that would cause the desired product to be the predominant one.
  7. Understand and be able to use the mechanism of the electrophilic addition reaction to predict which product(s) will be formed, predict relative reaction rates, and predict the conditions that would cause the desired product to be the predominant one.
  8. Be able to combine reactions in such a way as to develop a reasonable synthetic approach to a target compound.

Grading

Quizzes: After the first week there will be a five minute quiz at the beginning of EVERY class period except exam days. This means that there will be 24 quizzes this semester. Quizzes will typically cover what you were supposed to learn during the previous class period. Quizzes the day after an exam will typically be the one or two most frequently missed questions from the exam.

Exams: There will be three hour exams. All exams are comprehensive and cover everything from the first day of the course up to the class period before the exam. Make-up exams will only be given for university excused absences as defined in the catalog.

Final Exam: The final exam will be the morning of Saturday, December 8, 2007. It will be comprehensive over the entire course and will be roughly double the length of the hour exams.

Computer Based Homework: There will be 14 computer graded homework sets. In most cases these will be administered through the WebAssign system but part or all of some sets will be administered through Vista. You will be able to redo the homework sets as many times as you like. You must score at least 75% on a given set or you will not receive credit for that set.

Calculation of Overall Average: The four lowest quiz scores will be dropped from the calculation. The average of the remaining quizzes will count the same as an hour exam.

The overall average will be calculated by two methods and the higher result will be used in determining the course grade.

Method 1. The quiz average, each hour exam score, and the final exam score will be added together and the total will be divided by 5. Thus, each exam counts 20%, the quizzes count 20%, and the final counts 20%.

Method 2. The lowest exam score is dropped from the calculation. The final exam counts double. The quiz average, the two best exams scores, and double the final exam score will be added together and the total will be divided by 5. Thus the quizzes count 20%, the final counts 40%, and the two best exam scores each count 20%.

Bonus/Penalty: An adjustment will be made to the final average based on the computer based homework. The amount of the adjustment will be (number of homework sets with score of 75% or better – one half of total number of homework sets assigned) time 0.2%. Since we will have 14 homework sets you will be able to earn a bonus of up to 1.4% on your average but you could also get a penalty of up to 1.4% if you fail to do the homework sets.

Grading Scale: Once the overall average has been calculated the course grade will be assigned on the basis of:

90 or better = A
80-89 = B
70-79 = C
60-69 = D
59 or less = F

Three Strike Rule

Effective January 2005 the Chemistry department has a policy (one that has been approved by the University Curriculum Committee and the Faculty Senate) that no one may take CHM 355 a third time unless they have successfully completed CHM 254. A withdrawal counts as an attempt. No student will be permitted more than two attempts to pass CHM 254.

This policy includes a “three strike” rule for CHM 355. After successful completion of CHM 254 the student will be given one final chance at CHM 355 but no one will be allowed more than three total attempts at CHM 355 at Marshall University.

POGIL Approach

This course will be taught using the Process Oriented Guided Inquiry Learning (POGIL) method instead of a traditional lecture. Students will be working in assigned groups and actively seeking answers to critical thinking questions as a way of learning the material. The POGIL materials are specially designed to use data and leading questions to guide the student towards the formulation of their own conclusions. The instructor serves as a facilitator to help the students in that process. In many instances, I may not answer a question directly but instead may ask you a question that will lead you to discovering the answer for yourself.

Communications

The Vista web server has a link for this course for all students registered for the course. The Vista page for this course will serve as a very important communications link between the students and the professor. The Vista page will be used to post answers to text book problems and to make announcements to the class. We may also use this resource as a way of encouraging group study.

You should check the Vista page daily for new announcements and course related information. To get to the Vista page you should use your computer browser to go to http://vista.marshall.edu. You will log in using your student ID number (the one that starts with 901) and the same PIN number you use for myMU and MILO. Once you are logged in you will see a link for all of your classes that have a Vista page. Click on a course and you will be taken to the materials for that course.

By far the best way to contact the professor is to either use regular internet email and send a message to anderson@marshall.edu or use the mail facility within the Vista page to send a message. The instructor is listed as Anderson, Gary fairly near the top of the list. If you use internet mail, be sure to put CHM 355 in your subject line so that I will know the message is from a student in my class and thus can give it priority over all the other email messages I get.

If you try to call me, I will answer the phone if I am in my office but if I am not in you will get the voice mail system. If you leave a message you should be sure to leave full information about how to get back to you (include the area code with your phone number). My policy is that I will make one attempt to return your call but if I don’t get through on that attempt I will not make any further attempts.

Attendance Policy

Students are expected to attend all classes. A large part of the learning process in this course is based on the in-class activities. If you are not here you will not have a chance to participate in those activities.

There will be no makeup quizzes – if you miss a quiz it will simply be one of the four that is dropped from the calculation. If you miss a class it is your responsibility to get class notes from another student in the class.

Academic Dishonesty

During exams you may not use your own paper or other materials except your pen or pencil and a set of molecular models.

Academic dishonesty will not be tolerated. Academic dishonesty includes unauthorized use of any materials, notes, sources of information, or study aids or tools during a quiz or exam. It also includes the unauthorized assistance of any person other that the course instructor during a quiz or exam, the unauthorized viewing of another person’s work during a quiz or exam, or the unauthorized securing of all or part of any quiz or exam before submission by the instructor.

The minimum penalty for academic dishonesty will be a failing grade for the course.

Electronic Devices

I do not have any objection to students taping my lectures but I doubt that it will help very much because the taped lecture will not be very meaningful without the blackboard materials that go with it.

Cell phones, pagers, and the like must be turned off before entering the classroom. Failure to comply with this can result in you being removed from the classroom, even during an exam.

Disability

Students requiring accommodation because of a disability must obtain appropriate documentation (from the Help Center or Sandra Clements) and contact me at least one week in advance of each test so that necessary accommodation can be made.

Problems

Working problems is an essential part of the process of studying organic chemistry. You should work all the problems that are within the text material since these are designed to allow testing yourself on understanding oft he section(s) just before these problems. The answers to these problems are in the back of your text book.

You should work all of the Exercises at the end of each ChemActivity in the Straumanis workbook. I will be posting the answers to these in the Vista course supplement.

You should also try to work most, if not all, of the problems at the ends of chapters in the Hornback text. This is time-consuming, but it will be of great benefit since the major objective of the course is learning to solve various types of problems. I have listed selected problems in the schedule portion of this syllabus. Even if you can’t find time to work all of the end of chapter problems you should, at a minimum, work at least those on this list. Answers to the selected problems will be posted in the Vista course supplement.

Schedule

Date Straumanis Chemactivity/Topic Hornback Sections Relevant Problems in Hornback
August 21 Introduction and Overview x x
August 23 01A Bond Angles
01B Molecular Shape
01-01 Field of Organic Chemistry
01-02 Simple Atomic Structure
01-03 Ionic Bonding
01-04 Covalent Bonding
01-09 Polar Bonds
01-10 Shapes of Molecules
01-11 Dipole Moments

1.21, 1.22, 1.28, 1.40

August 28 02A Lewis Structures
02B Formal Charge
01-05 Lewis Structures
01-06 Covalent Ions
01-07 Formal Charges
02-01 Common Bonding Situations
1.15,1.16,1.17, 1.18, 1.24,1.26,1.29,1.31,1.36
August 30 03A Resonance Structures
03B Curved Arrow Notation
01-08 Resonance
02-02 Bond Strengths and Bond Lengths
02-05 Physical Properties and Molecular Structure
02-06 Melting Points, Boiling Points, and Solubilities
03-08 Types of Resonance Interactions
03-07 Rules for Resonance Structures
03-08 Types of Resonance Interactions
1.23, 1.25, 2.29, 2.30, 2.31, 2.32, 2.37, 3.20, 3.21, 3.24, 3.25, 3.27, 3.36
Sept, 4 04 Conformers of Carbon Structures 06-03 Conformations 6.18, 6.19, 6.29
Sept. 6 05A Constitutional Isomers
IUPAC Nomenclature of Alkanes
02-03 Constitutional Isomers
05-01 through 05-04
2.17, 2.18, 2.21, 2.22, 2.24, 5.24a, 5.25a, 5.26, 5.27, 5.29b, 5.30a, 5.31h
Sept.11 05B Stereoisomers
IUPAC Nomenclature of Alkenes, Alkynes, Alcohols, etc
06-01 Cis-Trans Isomers
02-07 Introduction to Functional Groups
05-05 through 05-10
5.24 b-g, 5.25 b-f, 5.28, 5.29 a and c-i, 5.30 b-l, 5.31 a-g, 5.32, 5.34, 6.15, 6.31
Sept. 13 06A Energy Diagrams
06B Cyclohexane Conformations<
06-04 Conformations of Cyclic Molecules
06-06 Conformations of Other Rings
06-05 Conformations of Cyclohexane
06-07 Conformations of Cyclohexanes with One Substituent
06-08 Conformations of Cyclohexanes with Two or More Substituents
6.21, 6.22, 6.23, 6.25, 6.28, 6.32
Sept. 18 07A Chirality
07B Absolute Configuration
07-01 Chiral Molecules
07-02 Recognizing Chiral Molecules
07-04 Properties of Enantiomers
07-07 Resolution: Separating Enantiomers
07-09 Reactions That Produce Enantiomers
07-10 Other Chiral Compounds
06-02 Designating the Configuration of Cis-Trans Isomers
07-03 Designating Configurations of Enantiomers
07-05 Molecules with Multiple Chirality Centers
07-06 Stereoisomers and Cyclic Compounds
07-08 Fischer Projections
6.16, 6.17, 7.16, 7.17, 7.18, 7.20, 7.22, 7.23, 7.27, 7.29, 7.31
Sept. 20 Exam I x x
Sept. 25

08 Acid-Base Reactions
09A The Core Charge Effect

04-01 Definitions
04-02 The Acid-Base Equilibrium
04-03 Rate of the Acid-Base Reaction
04-06 Hydrogen Bonding
04-09 Tables of Acids and Bases
04-10 Acidity and Basicity of Functional Groups and Solvents
04-04 Effect of the Atom Bonded to the Hydrogen on Acidity
04-07 Hybridization

4.29, 4.30

Sept. 27 09B The Inductive Effect
10 Resonance Effects
04-05 Inductive Effects
04-08 Resonance
4.31, 4.32, 4.33, 4.36, 4.39
October 2 11A Orbitals and Sigma Bonds
11B Orbitals and Pi Bonds
03-01 Atomic Orbitals
03-02 Molecular Orbitals
03-03 Single Bonds and sp3 Hybridization
03-04 Double Bonds and sp2 Hybridization
03-05 Triple Bonds and sp Hypridization
03-06 Resonance and MO Theory
03-09 Molecular Orbital Energies
3.22, 3.26, 3.28, 3.29, 3.37
October 4 12A One-Step Nucleophilic Substitution-Leaving Group
12B One-Step Nucleophilic Substitution-Nucleophile/Electrophile
08-01 The General Reaction
08-02 Reaction Mechanisms
08-03 Bimolecular Nucleophilic Substitution
08-04 Stereochemistry of the SN2 Reaction
08-05 Effect of Substituents on the Rate of the SN2 Reaction
08-09 Leaving Groups
08-10 Nucleophiles
08-13 Intramolecular Reactions
8.22, 8.24, 8.37
Oct. 9 13A Carbocations
13B Two-Step Nucleophilic Substitution
08-07 Effect of Substituents on the Rate of the SN1 Reaction
08-06 Unimolecular Nucleophilic Substitution
08-08 Stereochemistry of the SN1 Reaction
08-09 Leaving Groups
08-11 Effect of Solvent
08-12 Competition between SN1 and SN2 Reactions
8.23, 8.25, 8.26, 8.27, 8.28, 8.31, 8.33, 8.36, 8.40
Oct. 11 14A Two-Step Elimination
14B One Step Elimination
09-01 The General Reaction
09-05 Unimolecular Elimination
09-06 Regiochemistry and Stereochemistry of the E1 Reaction
09-02 Bimolecular Elimination
09-03 Stereochemistry of the E2 Reaction
09-07 The Competition Between Elimination and Substitution
9.17, 9.18, 9.19, 9.20, 9.25, 9.26
Oct. 16 15A Alkene Potential Energy
15B Stereochemistry of E2 Reactions
09-04 Direction of Elimination
02-04 Degree of Unsaturation
08-13 Intramolecular Reactions
9.21, 9.22 9.23, 9.24, 9.28, 9.29, 9.30
Oct. 18 Exam II x x
Oct. 23 17A Electrophilic Addition
17B Carbocation Rearrangements
11-01 The General Mechanism
08-14 Competing Reactions

8.47, 8.53, 8.54
Oct. 25 17C Acid Catalyzed Electrophilic Addition
17D Electrophilic Addition to a Diene
11-02 Addition of Hydrogen Halides
11-03 Addition of Water (Hydration)
11-13 Additions to Conjugated Dienes
11.32, 11.40, 11.48
Oct. 26 Last Date to Drop an Individual Course x x
Oct. 30 18 Epoxide and Bromonium Ring Opening 11-04 Addition of Halogens
11-05 Halohydrin Formation
11.41, 11.42, 11.45, 11.51
Nov. 1 22A Hydroboration/Oxidation
22B Other Oxidation Reactions
11-07 Hydroboration-Oxidation
11-09 Epoxidation
11-10 Hydroxylation
11-11 Ozonolysis
11.34, 11.35, 11.37, 11.38, 11.52
Nov. 2 23 Electrophilic Addition to Alkynes 11-06 Oxymercuration-Reduction
11-07 Hydroboration-Oxidation
11.38, 11.39, 11.50
Nov. 8 Addition Reactions-Carbenes
Addition Reactions-Hydrogenation
Addition Reactions-Oxymercuration/demercuration
11-06 Oxymercuration-Reduction
11-12 Catalytic Hydrogenation
11-08 Addition of Carbenes
11.33, 11.36, 11.43, 11.46, 11.53
Nov. 13 Interconverting Functional Groups 10-01 through 10-07 x
Nov. 15 Interconverting Functional Groups 10-08 through 10-15 10.33, 10.34, 10.36, 10.37, 10.40, 10.41, 10.42
Nov. 27 Exam III x x
Nov. 29 Functional Groups and Nomenclature II 12-01 through 12-07 12.21, 12.22, 12.23, 12.24, 12.25, 12.31
Dec. 4 Review x x
Dec. 8 Final Exam (9:00 a.m.)
Location TBA
x x