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The definitive source of course information remains the original (paper) syllabus distributed in class.


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CHEMISTRY 221

SPRING 2002 SYLLABUS

 

Instructors:

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

Chris Robbins Study Group Facilitator Phone: x4428

Course Schedule:

Lecture: MWF 9:00 - 10:05

Labs: T 7:45 - 11:35 am, T 1:00 - 4:50, and R 7:45 - 11:35 am.

 

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

 

Evening Review 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. A useful web site for NMR practice can be found at www.chem.ucla.edu/~webspectra/.

 

 

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 8; Friday, March 15; and Friday, April 12. 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. Some quiz and exam problems may be taken directly from the text. Answer keys will be posted on the Chemistry Department web site (exact URL TBA!)

Review Session: The evening review 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. Feel free to contact me at 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. I try to encourage an informal, relaxed environment -- I want everyone to feel comfortable asking questions and discussing problems.

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. 7

Radicals, Rad. Halogenation

Chapter 5.2-3

Jan. 9

Rad. Hal.; Rad. Add'n to alkenes

10.1-4

Jan. 11

Polymerization, mass spectroscopy

7.10; 12.1-4

2

Jan. 14

NMR-Theory, recognizing symmetry

13.1-3

Jan. 16

13C NMR

13.4-7

Jan. 18

1H NMR - chemical shift

13.8-10

Quiz 1

3

Jan. 21

1H NMR - spin-spin splitting

13.11-13

Jan. 23

NMR wrap-up and problems

Jan. 25

Resonance Review

handout

Quiz 2

4

Jan. 28

Diene structure and properties

14.1-4, 10-13

Jan. 30

Reactions of dienes with electrophiles

14.5-7

Feb. 1

Diels-Alder reaction

14.8-9

Quiz 3

5

Feb. 4

Benzene: prop's, structure

15.1-4

Feb. 6

Aromaticity

15.5-10

Feb. 8

EXAM 1

Exam 1

6

Feb. 11

Electrophilic Aromatic Substitution

16.1-4

Feb. 13

More EAS

16.5-6

Feb. 15

EAS of subst. benzenes

16.6-7

7

Feb. 18

oxid'n and red'n of aromatic compounds

16.10-11

Feb. 20

Multistep synthesis of benzene cmpds

16.12, pp 645-653

Feb. 22

Alcohols: prop., struct., acid-base chem.

17.1-3, 12

Quiz 4

Feb. 25

Spring

Feb. 27

Break

Mar. 1

No Classes

8

Mar. 4

Reactions of ROH

10.7; 17.4, 7-9

Mar. 6

Ethers

18.1-5

Mar. 8

Epoxides

18.7-10

Quiz 5

9

Mar. 11

Aldehydes & Ketones: properties

pp 743-752; 19.1-3, 16

Mar. 13

Prep'n of ald. and ket., Reactions

19.4-7, 17.5

Mar. 15

EXAM 2

Exam 2

10

Mar. 18

Reactions of A/K with nucleophiles

19.8, 17.6, 10.8-9

Mar. 20

Reactions of A/K with nucleophiles

19.6, 9, 11

Mar. 22

More reactions of ald. and ket.

19.12.

11

Mar. 25

Acids and Esters: struct and props.

20.1-5, 9

Mar. 27

Prep'n of acids and esters

20.6-7

Quiz 6

Mar. 29

No Classes-Good Friday

12

Apr. 1

Rxns. of acids and esters

20.8, 21.6

Apr. 3

Acid derivs: structure and reactivity

21.1-3

Quiz 7

Apr. 5

Interconversion of acid derivs-NAS

21.4-5

13

Apr. 8

Nucleophilic Acyl Substitution

21.6-7

Apr. 10

More Nucleophilic Acyl Substitution

21.8, 11

Apr. 12

EXAM 3

Exam 3

14

Apr. 15

Keto-Enol Tautomerization

22.1-3

Apr. 17

Enolate chemistry

22.5-8

Apr. 19

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 5% 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. 8, 10

Check-In, Rad. Polym.

Chap. 41A

3

10

2

Jan. 15, 17

BF3 Reaction, lab quiz*

Chap. 28, 11, 12, 17

4

10

3

Jan. 22, 24

as above (NMR, IR)

Chap. 24, 27

4

Jan. 29, 31

Diels-Alder Cycloaddition

Chap. 29

6

10

5

Feb. 5, 7

EAS

Chap. 31, 19

7

10

6

Feb. 12, 14

Acylation of Anisole

Chap. 45

8

10

7

Feb. 19, 21

as above (NMR, IR)

Chap. 24, 27

Feb. 26, 28

Spring Break

8

Mar. 5, 7

Q.O.A.

Chap. 33

12

25

9

Mar. 12, 14

Q.O.A.

10

Mar. 19, 21

Q.O.A.

11

Mar. 26, 28

Synthesis Project

Chap 40 or 43

part 1: 13

10

12

Apr. 2, 4

as above

part 2: 14

10

13

Apr. 9, 11

as above

14

Apr. 16, 18

as above, check out

*Lab quiz (15 points) will cover significant figures, stoichiometry, and IR.


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