Instructor:
Dr. Holly D. Bendorf Office: 209 HBC Phone: x4365 (office), 327-2888 (home)

Course Schedule:
            Lecture:     MWF 11:30 - 12:35
            Labs:         T 7:45 - 11:35 am, R 7:45 - 11:35 am, R 1:00 - 4:50 pm.

Office Hours: To be announced. Feel free to make an appointment or just stop by.

Evening Help-Session: To be announced.

Course Description: CHEM 221, Organic Chemistry II, is a continuation of CHEM 220. CHEM 221 will focus on the reactions of organic compounds and their mechanisms, the application of these reactions to organic synthesis, and the identification of organic compounds using modern spectrometric techniques.

Text and Materials:
• "Organic Chemistry" by George Schmid, Mosby Publishers, 1996.
• "Study Guide for Organic Chemistry" by Skonieczny and Schmid (Optional).
• Bound laboratory notebook (Freeman).
• CHEM 220-221 lab manual.
• Safety glasses or goggles (available at College Store).
• Calculator with logarithmic and exponential functions.

Materials in Chemistry Reading Room: Copies of several organic chemistry texts are available in the reading room. If you are not satisfied with Schmid's treatment of a topic in his text, feel free to consult one of the other textbooks--you may just find one you like. Also, these texts are excellent sources of extra practice problems.

Grading Criteria:       Quizzes           160 points     20%
                                    Exams            300 points     37%
                                    Laboratory     180 points     23%
                                    Final               160 points    20%
                                                            800 points 100%

Final letter grades will be assigned as follows: 720-800 A, 640-719 B, 560-639 C, 480-559 D.

Exams: There will be three in-class exams on the following dates: Friday, January 23; Friday, February 20; Friday, March 27. The final exam will be administered on the day and time announced in the final exam schedule. Exams cover lecture notes, assigned reading and problems from the text, and material from the lab.

Quizzes: Quizzes are an incentive to stay current with the course. They provide you with a means of evaluating your progress and allow you to identify any potential "trouble spots" before you get into an exam. The lowest quiz grade will be dropped.

Assignments From the Text: This syllabus lists assigned readings and problems from the text and it is your responsibility to stay current with these assignments. Quiz and exam problems may be taken directly from the text. Although they will not be collected, it is strongly suggested that you complete the assignments and have any questions answered before the next class period. Lectures, quizzes, and in-class assignments are prepared with the assumption that you have read and understand the assigned material and have completed the text problems.

Help-Session: The evening help session is an informal workshop where you will have the opportunity to ask questions, review lecture material, and work problems either individually or in groups.

Extra Credit: Extra credit points (3) can be earned by attending departmental colloquia. Extra credit points can also be earned by writing a brief research paper on a mutually agreed upon topic (up to 10 points). Other types of extra credit projects may become available during the semester.
Extra credit is limited to 20 points.

General Comments:
Attendance: Regular attendance at lecture is expected. Attendance at quizzes, exams and laboratory meetings is mandatory. You will be permitted to make-up a missed lab or exam only when the absence has received prior approval from me (usually a case of medical or family emergency which can be documented). You must be able to attend another lab section in order to make-up a missed lab. In the case of a missed exam, a single, cumulative make-up exam will be administered at the end of the semester. Quizzes cannot be made-up. In case of an emergency, I can also be reached at my home: 327-2888.

Participation: Participation is highly encouraged in lecture. Do not hesitate to stop me if I am going too quickly or have not explained something to your satisfaction.

Study Suggestions: The material covered in CHEM 221 builds upon the concepts covered in CHEM 220. Lectures, in-class assignments, and labs have been prepared with the assumption that everyone has a solid grounding in the material from CHEM 220. You are therefore responsible for the CHEM 220 material and should review when necessary. If you have any questions or would like some assistance in reviewing, don't hesitate to ask.

As you already know from CHEM 220, organic chemistry does not lend itself to memorization or cramming. This is true to an even greater extent in CHEM 221. The best approach for studying organic is to practice everyday: review your notes, study the text, discuss the material with your friends, quiz yourself, and most importantly, work lots of problems!

Finally, if you feel that you are having trouble in the course, come see me right away. I am always willing and (almost!) always available to help you.

Course Outline: The outline is tentative and subject to change.

Date	Subject	Text	Problems	Q/E
Jan. 5	Diene structure and properties	19.4-7	19.9, 25, 27, 28(a, c, d)
Jan. 7	Reactions of dienes, allylic species	19.1, 2, 8	19.1-5, 12, 33, 36
Jan. 9	Diels-Alder reaction	19.12.	19.16-19, 31(b, d, e), 38, 39
Jan. 12	Diels-Alder, UV spectroscopy	19.14-15	19.21, 22, 32
Jan. 14	Radicals, hydrogen abstraction	18.1-4	18.1-6, 8, 24, 25
Jan. 16	Radicals, rxn with alkenes	18.5, 6	18.9, 10, 26	quiz
Jan. 19	Polymerization, mass spectroscopy	18.8-10, 13-15	18.16-18, 28
Jan. 21	Benzene: prop.,structure, nomenclature	20.1-4; 21.1	21.1, 2
Jan. 23	Exam 1			exam
Jan. 26	Aromaticity	20.5, 7, 8	20.3-7, 18, 19, 23-25
Jan. 28	Side chain rxn, EAS	20.9-11	20.10, 12, 14, 16(except e)
Jan. 30	EAS of subst. benzenes	21.3-9	21.5-8, 10, 27	quiz
Feb. 2	More EAS	21.11-14	21.13-17, 22-25, 28, 32, 34
Feb. 4	Modification of nitrogen substitutents	22.15-18	22.22-24
Feb. 6	NMR-Theory, recognizing symmetry	5.9-13; 10.1-3	5.9-12; 10.1, 4, 5	quiz
Feb. 9	13C NMR	5.14.	5.16, 25-27; 10.23, 27; 21.4
Feb. 11	1H NMR	10.4-6, 11	10.6-9, 22, 24-26
Feb. 13	1H NMR	10.7-10, 12-14	10.10-14, 16, 28-34	quiz
Feb. 16	Alcohols: prop., struct., nomenclature	11.1-4, 15	11.1-6, 27, 35
Feb. 18	Oxidation and reduction, ROH prep.	11.5, 6, 9, 10	11.14-18, 28
Feb. 20	Exam 2			exam
Feb. 23	"Spring
Feb. 25	Break"
Feb. 27	No Classes
Mar. 2	Prep. of ROH: Grignard rxn.	11.7, 8, 11-14	11.9-13, 19, 21, 32-34
Mar. 4	Reactions of ROH	11.17-18	11.23, 24, 36
Mar. 6	Reactions of ROH	11.16, 19	11.39-42, 44	quiz
Mar. 9	Ethers	13.1-9	13.1-4, 6-11, 13, 15
Mar. 11	Epoxides	13.10-15	13.16-23, 29, 31
Mar. 13	Aldehydes & Ketones: prop., nom., prepn.	14.1-7	14.1-12, 44, 55	quiz
Mar. 16	Prep. & reactions of ald. and ket.	14.8-10,16,17	14.13-16, 29-31
Mar. 18	More reactions of ald. and ket.	14.11-15, 18	14.18-25, 35, 36, 38, 41, 42
Mar. 20	Carbohydrates	25.1-3,6-13	25.1,10, 18-21, 23, 34	quiz
Mar. 23	Acids and Esters: nomen., prop., acidity	15.1-4, 8-10	15.1-4, 6, 12, 22, 23
Mar. 25	Prep. and rxn. of acids and esters	15.5-7, 13-15	15.8-10
Mar. 27	EXAM 3			exam
Mar. 30	Fatty acids, waxes, and oils	15.10-12,16-7	15.14, 17, 28-32
Apr. 1	Phosphate esters and DNA	11.16, 27.1-4	27. 1, 2, 10, 11
Apr. 3	Acid derivs: prop., nomen., reactivity	16.1-7	16.1-3, 5, 7, 9	quiz
Apr. 6	Interconversion of acid derivs.	16.8-11	16.10-12, 16
Apr. 8	More reactions of acid derivs.	16.12-14	16.18, 20, 21, 29, 32, 34
Apr. 10	No Classes
Apr. 13	Amino acids, peptides, and proteins	26.1-8	26.3-6, 9-11, 14	quiz
Apr. 15	Enolate chemistry	17.1-5	17.1, 2, 4-6, 8
Apr. 17	Aldol, Claisen chemistry	17.6-8	17.9-14

Final Exam: The final will be administered during the final exam week at the time and place assigned by the Registrar. No exceptions.

Laboratory: It is imperative that you come to the lab fully prepared. Careful planning and preparation before you arrive at the lab will allow you to complete your experiments in an efficient and safe manner. It is your responsibility to read and understand the lab procedure before you arrive at prelab. Missing or arriving late to prelab will result in a reduced lab grade (up to 5 points per violation) and/or dismissal from the lab.

The laboratory grade is worth a total of 180 points. Late reports will be penalized 3% per school day.

Lab Safety: Unsafe behavior in the lab will not be tolerated and violations will be penalized. Repeated violations during a class may result in a zero for that lab. Keep in mind that lab safety includes laboratory hygiene. In the event that common areas are left dirty, (rotovaps, balances, melting point apparati, reagent hood) points may be deducted from the entire lab section. If you have any questions regarding lab safety, please do not hesitate to ask.

Lab Syllabus

Week	Dates	Lab	Required  Reading	Lab Due Week #	Point  Value
1	1/6, 8	Check-in
2	1/13, 15	Diels-Alder	Chp. 12, 29	4	20
3	1/20, 22	Radical Polymerization	Chp. 41	5	20
4	1/27, 29	EAS / Rad. Polym.	Chp. 31
5	2/3, 5	EAS	Chp. 19	6	20
6	2/10, 12	Nitration	Chp. 27, 30	7	20
7	2/17, 19	QOA	Chp. 33	12	20
8	2/24, 26	Spring Break
9	3/3, 5	QOA
10	3/10, 12	QOA
11	3/17, 19	Chemical literature	Chp. 32	13	40
12	3/24, 26	Synthesis Project	Chp. 37 or 40	14 (part 1)	20
13	3/31,4/2	Synthesis		15 (part 2)	20
14	4/7, 9	Synthesis
15	4/14, 16	Check-out

* There will be two write-ups due for the synthesis project.