CHEMISTRY 221

SPRING 2001 SYLLABUS

 

Instructors:                                                                                      

Dr. Holly D. Bendorf           Office: 209 HBC   Phone: x4365 (office), 998-8647 (home)

Dr. Chriss E. McDonald      Office: 233 HBC   Phone: x4186

 

Course Schedule:

            Lecture:            MWF  9:00 - 10:05

            Labs:                T  7:45 - 11:35 am,  T 2:00 - 5:50, and R  7:45 - 11:35 am.

 

Office Hours:  M 10:15 – 11:30, W 1:00 – 2:00, R 1:30 – 2:30 or just drop by.

 

Evening Help-Session:  Time and location TBA.

 

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," 5th ed., by John McMurray.

• Bound laboratory notebook (Freeman).

• CHEM 220-221 lab manual.

• Safety glasses or goggles (available at College Store).

• Calculator with logarithmic and exponential functions.

 

Other Useful Materials:  Copies of several organic chemistry texts are available in the reading room.  If you are not satisfied with McMurray'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.  Some useful web sites for NMR practice can be found at www.chem.ucla.edu/~webspectra/ and www.nd.edu/~smithgrp/structure/workbook.html.

 

 

Grading Criteria:                   Quizzes (6)                                 90 points          

                                                Exams (3)                                 300 points       

                                                Laboratory                               110 points       

                                                Final                                         100 points       

                                                                                                600 points

           

Final letter grades will be assigned as follows:  540-600 A, 480-540 B, 420-480 C, 360-420 D.         

 

Exams:  There will be three in-class exams on the following dates:  Friday, February 9; 

Friday, March 16; and Wednesday, April 11.  Exams cover lecture notes, assigned reading, problems from the text, and material from the lab.  The final exam is the American Chemical Society (ACS) standardized exam for organic chemistry and covers both semesters of organic chemistry.  It will be administered on the day and time assigned by the registrar.   

 

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:  Readings and problems from the text will be assigned throughout the semester.  It is your responsibility to stay current with these assignments.  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.  Quiz and exam problems may be taken directly from the text.  Answer keys will be posted on the Chemistry Department web site.

 

Help-Session:  The evening help session is an informal workshop where you will have the opportunity to ask questions, review the course 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 8 points, see me for more details).  Other types of extra credit projects may become available during the semester.  Extra credit is limited to 15 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, the grade earned on the final exam will be substituted for the missing exam grade.  Quizzes cannot be made-up.  In case of an emergency, I can also be reached at my home: 998-8647.

Participation:  Participation in class is expected.  Please let me know if I am going too quickly or have not explained something to your satisfaction.

Etiquette:  I try to encourage an informal, relaxed environment -- I want everyone to feel comfortable asking questions and discussing problems.  I will not, however, tolerate behavior that disrupts the class in any way.

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, please ask!

 

As you already know from CHEM 220, organic chemistry does not lend itself to memorization or last-minute 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.

Week	Date	Topics	Class Preparation	Q/E
			Read the following sections in the text:
1	Jan. 8	Radicals, Hydrogen Abstraction	Chapter 5.2-3
	Jan. 10	Radicals, reaction with alkenes	10.1-4
	Jan. 12	Polymerization, mass spectroscopy	7.10; 12.1-4
2	Jan. 15	NMR-Theory, recognizing symmetry	13.1-3
	Jan. 17	13C NMR	13.4-7
	Jan. 19	1H NMR - chemical shift	13.8-10	Quiz 1
3	Jan. 22	1H NMR - spin-spin splitting	13.11-13
	Jan. 24	NMR wrap-up and problems
	Jan. 26	Diene structure and properties	14.1-4, 11-13	Quiz 2
4	Jan. 29	Reactions of dienes, allylic species	14.5-7
	Jan. 31	Diels-Alder reaction	14.8-10
	Feb. 2	Benzene: prop's, structure	15.1-4	Quiz 3
5	Feb. 5	Aromaticity	15.5-10
	Feb. 7	Electrophilic Aromatic Substitution	16.1-4
	Feb. 9	EXAM 1		Exam 1
6	Feb. 12	EAS of subst. benzenes	16.5-7
	Feb. 14	Other reactions: NAS, benzyne	16.8-9
	Feb. 16	oxid'n and red'n of aromatic compounds	16.10-12
7	Feb. 19	Alcohols: prop., struct., acid-base chem.	17.1-3, 12
	Feb. 21	Prep. of ROH	17.4-5
	Feb. 23	Grginard Chemistry	10.8-9; 17.6	Quiz 4
	Feb. 26	Spring
	Feb. 28	Break
	Mar. 2	No Classes
8	Mar. 5	Reactions of ROH	10.7; 17.7-9
	Mar. 7	Ethers	18.1-5
	Mar. 9	Epoxides	18.7-10	Quiz 5
9	Mar. 12	Aldehydes & Ketones: prop., prepn.	pp 743-752; 19.1-2, 16
	Mar. 14	Prep. & reactions of ald. and ket.	19.4-6, 9, 11
	Mar. 16	EXAM 2		Exam 2
10	Mar. 19	More reactions of ald. and ket.	19.3, 7, 8, 12
	Mar. 21	Carbohydrates	25.1-3, 5
	Mar. 23	Acids and Esters: struct and props.	20.1-5, 9
11	Mar. 26	Prep. and rxn. of acids and esters	20.6-8
	Mar. 28	Fatty acids, waxes, and oils	27.1-3
	Mar. 30	Phosphate esters and DNA	28.8-9	Quiz 6
12	Apr. 2	Acid derivs: structure and reactivity	21.1-3
	Apr. 4	Interconversion of acid derivs.	21.4-5
	Apr. 6	Nucleophilic Acyl Substitution	21.6-7	Quiz 7
13	Apr. 9	More Nucleophilic Acyl Substitution	21.8, 11
	Apr. 11	EXAM 3		Exam 3
	Apr. 13	No Classes - Good Friday
14	Apr. 16	Amino acids, proteins, beta-lactams	21.11, 26.1, 5-6
	Apr. 18	Enolate chemistry	22.1-3, 5, 8
	Apr. 20	Aldol, Claisen chemistry	23.1-4, 6-8

 

                                                                

 

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) or dismissal from the lab, in which case you will receive a zero for that lab.

 

The laboratory grade is worth a total of 110 points and consists of 8 lab reports and one 15-point lab quiz.  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	Week Due	Lab Point
					Value
1	Jan. 9, 11	Check-In, Rad. Polym.	Chap. 41A	2	10
2	Jan. 16, 18	BF3 Reaction, lab quiz*	Chap. 28, 11, 12, 17	4	10
3	Jan. 23, 25	as above (NMR, IR)	Chap. 24, 27
4	Jan. 30, Feb. 1	Diels-Alder Cycloaddition	Chap. 29	6	10
5	Feb. 6, 8	EAS	Chap. 31, 19	7	10
6	Feb. 13, 15	Nitration of Methyl Benzoate	Chap. 30	8	10
7	Feb. 20, 22	as above (NMR, IR)	Chap. 24, 27
	Feb. 27, 29	Spring Break
8	Mar. 6, 8	Q.O.A.	Chap. 33	12	25
9	Mar. 13, 15	Q.O.A.
10	Mar. 20, 22	Q.O.A.
11	Mar. 27, 29	Synthesis Project	Chap 37 or 40	part 1: 13	10
12	Apr. 3, 5	as above		part 2: 14	10
13	Apr. 10, 12	as above
14	Apr. 17, 19	as above, check out
	*Lab quiz (15 points) will cover significant figures, stoichiometry, and IR.