City University of New York

Fall 2009

CHEM 26300/PR: Organic Chemistry II



Prerequisite: CHEM 26100, General Chem I & II

Meeting Place and Time: Marshak MR1, 2:00 PM – 3:50 PM Tue --Thu

Instructor:     Dr. Sean S. Boson

                        Office: Marshak 1018 Telephone: (212) 650-8386 E-mail:


Office hour:   Mon 12:00 – 1:00 PM, 4:00 – 5:00 PM

Tue 4:30 – 5:00 PM

Thu 12:00 – 1:00 PM, 4:00 – 5:00 PM


Course Description:


This course involves systematic study of organic compounds, nomenclature, methods of preparation, physical and chemical properties (reactions), and mechanisms. Emphasis will be given to solving problems in each chapter.


Required Textbook: Organic Chemistry, 7th Edition, by L.G. Wade Pearson-Prentice Hall

ISBN 978-0-321-59231-6.


Optional Study Aid: Study Guide/Solutions Manual, by Jan Simek (Recommended)

Molecular Model Set (Allyn and Bacon or other suitable one)


Course Objective and Expectations:


To study the structure, preparations, reactions and usage of different families of organic compounds including compounds of biological importance. Upon successful completion of the course, the students are expected to: (1) name common organic compounds, draw structures, (2) relate functional groups with their chemical and physical behaviors (3) propose reasonable methods for synthesizing different organic compounds, (4) predict reaction mechanisms, (5) distinguish organic compounds by simple chemical tests, and (6) understand chemical processes in biological systems.


Course Learning Outcomes

After completing this course, students should be able to:


1)    The reactivity of ethers and epoxides.

2)    Orbital conjugation and molecular orbital diagrams.

3)    The Diels Alder reaction mechanistically and strategically.

4)    Aromatic chemistry: including MO of benzene, Huckels rule, nomenclature, and associated physical properties.

5)    The reactions of benzene and other aromatic systems.

6)    The synthesis and reactions of aldehydes, ketones, imines, and amides.

7)    The properties and reactions of amines.

8)    The synthesis and chemical properties of carboxylic acids and their derivatives.

9)    Enolate chemistry and its use in organic synthesis.

10) The classification, structure, and reactions of carbohydrates.

11) The structures, properties, and reactions of amino acids, and how amino acids are used to synthesize peptides.

12) The chemistry of lipids and polymers




Exams and Grading Policies. There will be three 90-minute exams and a final exam. Best two of the three exam scores will be used for calculating final grade; the lowest one will be dropped. Make-up exams are not offered. If you miss an exam for any reason, it will constitute your dropped exam even if you have a medical excuse for the missed exam. The final exam is comprehensive and mandatory and may not be dropped. A pop-quiz may be given at/toward the end of each chapter (for a total of 9) without prior notification. No make-up quizzes can be offered. Final letter grades will be awarded only at the end of the semester after of all the tests and final exam are completed. Exam questions will comprise of all/mostly multiple choice type. Your overall course grade will be evaluated based on your performance and NOT on your effort or the time spent. There will be NO extra work of any kind to improve your grade, so you must study hard during the entire semester.


Best 2 exams (2x100) 200

Quizzes (8x10)          80

Final exam                             120


Grades will be determined by the percentage number of points accumulated out of a total of 400 points as follows:


            94% A+

90% A < 94%

89% A- < 90%

86%  B+ < 89%

81%  B < 86%

78%  B- < 81%

76%  C+ < 78%

72%  C < 76%

67%  C- < 72%

57%  D < 67%

            F < 57%



Homework Assignments: You are asked to do all problems inside the chapter and at the end of each chapter. Even though your homework will not be collected, it will be extremely difficult to pass the course without doing them. You are strongly advised to study 2 – 3 hours for each class hour of lecture. Make a study group with fellow students (2 – 3) and meet regularly for study sessions outside of classroom. This course is very time-demanding; you must spend lot of hours studying and solving problems in order to succeed. Once you are behind there will be little to no time to catch up. While selected problems will be worked during lectures, not all types of problems can, or will be covered. Exam questions will often be based on or similar to those of the text problems. You are strongly advised to buy molecular model set (may order through the campus bookstore, or internet).


Classroom Etiquette: Let's try to maintain a courteous, distraction-free learning environment. Please observe the following basic rules during lectures and exams:


       Obviously, turn off the cells and pagers. It's distracting when they ring. Also, it's rude to everyone else to have a private conversation during class. Yes, this is true even in the back of the classroom.


       Try not to pack up until class is completely over. It's rude and distracting to have notebooks closing and jackets and backpacks rustling while the professor is trying to finish up. I'll try my best to finish by the bell, and I hope you'll try your best to stay attentive until the bell.


       Please respect the wishes of your fellow students to listen to the lecture, and do not carry on conversations during class.


A little courtesy goes a long way. Thanks for the cooperation.



Student Responsibility. The job of the Instructor is to provide the best possible presentation of the material that he can, and to provide the best learning environment that is possible. It is not the Instructor's job to make the student study or to accommodate student by making the standards of the course lower so that they can pass. It is the student's responsibility to put forth the effort required to learn the material and to become competent with it. This means mastering the problems in the text, solving the problems at the end of each chapter, and using good study habits. Students are strongly advised to study in a study group. The Instructor will be happy to help you achieve these goals. The student should:


       preview the lecture material before coming to class;

       attend every class and take notes for later review;

       bring the text to class to follow the lecture;

       do all problems from the text (both inside and at the end of each chapter) until you are competent - the first step to learning is to find out what you don't know;

       make a list of what you don't understand and bring it to class and/or office hours;

realize that this is a skills building course and so will require considerable study outside of class.


Student Resources:


Aside from my office hours, chemistry tutors will hold office hours where questions on the subject material may be asked. I will try give you more specific details on this when they become available, or call the Chemistry Department office.



Cheating: Cheating is a serious offense that will not be tolerated in this course. I will take immediate action if I find any evidence of cheating. Please see the CCNY Policy on Academic Integrity at:










Tentative Lecture/Exam Schedule




Month / Day                          Chapter in Text                                                                   Exam


Sept     1, 3                             Ch 14. Ethers, Epoxides & Sulfides

Sept     8,10                            Ch 15. Conjugate Systems, Orbital Symmetry, Diels-Alder Rxn

Sept     15, 17                          Ch 16. Aromatic Compounds

Sept     22, 24, Oct 1               Ch 17. Reactions of Aromatic Compounds   


Oct      6                                  Chapter 14 - 17                                                                      Exam 1


Oct      8, 13                           Ch 18. Aldehydes and Ketones

Oct      15, 20                         Ch 19. Amines

Oct      22, 27                          Ch 20. Carboxylic Acids

Oct      29, Nov 3                   Ch 21. Carboxylic Acid Derivatives

Nov     5                                 Ch 22. Condensation and α-Substitution Reactions of                                                                      Carbonyl Compounds


Nov     10                                Chapters 18 - 21                                                                   Exam 2


Nov     12                               Ch 22. Condensation and α-Substitution Reactions of                                                                       Carbonyl Compounds


Nov     17, 19                          Ch 23. Carbohydrates and Nucleic Acids

Nov     24, Dec 1                    Ch 24. Amino Acids, Peptides, and Proteins

Dec     3, 8                              Ch 25. Lipids, Ch 26. Synthetic Polymers


Dec     10                                Chapters 22 - 26                                                                   Exam 3



Dec     15 or 17                      Chapters 14 – 26                                                                   Final Exam