CHEM 212B ORGANIC CHEMISTRY Fall 2008
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Lecture: |
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Laboratory: |
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Instructor: |
Dr. Raymond H. Fong |
Office Hours: |
M 9:30 - 10:30 |
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Office: |
S-236 |
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Phone: |
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Th |
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E-mail: |
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or by appointment |
Chemistry 212B (5 units) is the second semester of a one year course in organic chemistry for chemistry/biochemistry majors and many related majors. Fulfills requirements for all medical schools and other health related graduate programs.
Prerequisite:
Chemistry 208A or 212A with a final grade of C or higher.
Required:
- "Organic Chemistry", 5th. Or 6th Ed., Wade
- "Techniques in Organic Chemistry", 2nd Ed., Mohrig, Hammond, Sehatz, Morill
- Hardbound Laboratory Notebook
- Safety Glasses and Calculator
Recommended:
1. "Solutions Manual"; 5th or 6th Ed.
2. Molecular Models
Resources: Computer Lab(S-205) - Spartan, NMR software, GC/MS software, and internet access. Copy of Aldrich catalog in chemistry storeroom.
Grades: There will be 4 lecture exams and a comprehensive final examination. In addition, you will be graded in the laboratory on the basis of your laboratory reports, products, unknowns, laboratory notebook, and a lab final examination. You must pass both the lecture and lab portion of the course to pass the class. NO MAKE-UP TESTS WILL BE ALLOWED.
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Lecture Exams (4) |
600 points |
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Laboratory Score |
150 points |
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Final examination |
250 points |
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TOTAL: |
1000 points |
Approximate Letter Grades:>85% A; >72% B; >55% C; >45% D
Attendance: College regulations require that students be informed of attendance requirements for each course at the outset of the course. Any student who misses more than 3 successive meetings, or more than 5 class meetings, or 2 lecture tests, or 2 quizzes will be regarded as anon-participant and may be dropped.
Last day to DROP this course is
on
Assignments: For each chapter, read the assigned material and do the problem assignments. On occasion, I may give you additional problems to do. The intent of the problem assignments is only a suggestion. It will be for you to determine whether or not you need more practice on any given type of problem. If needed, you are expected to review any material from general chemistry or Chem 212A
Tentative Lecture Exam Schedule (subject to minor change)
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Exam 1 |
Thursday, September 11 |
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Exam 2 |
Thursday, October 9 |
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Exam 3 |
Thursday, November 6 |
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Exam 4 |
Thursday, December 4 |
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FINAL EXAM |
Friday, December 12 |
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Experimental procedures will be given in separate handouts and are part of the reading assignment. Almost all the techniques should have been learned in the first semester of organic chemistry and you are expected to review any techniques stated in the experimental procedures.
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DATE |
EXPERIMENT |
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Aug. 19 |
Orientation/Locker Check-in/NMR |
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Aug. 21 |
NMR training |
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Aug. 26 |
Diels-Alder Reaction and Molecular Modeling |
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Aug. 28 |
Diels-Alder Reaction and Molecular Modeling |
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Sept. 2 |
Nitration of Methyl Benzoatte |
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Sept. 4 |
Friedel Crafts Alkylation of 1,4-dimethoxybenzene |
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Sept. 9 |
Friedel Crafts Alkylation of 1,4-dimethoxybenzene |
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Sept. 11 |
Photoreduction of Benzophenone/Synthesis of Luminal |
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Sept. 16 |
Synthesis of Luminal/Rearrangement of Benzpinacol |
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Sept. 18 |
Wittig: Synthesis of trans-9-(2-phenylethenyl) anthracene |
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Sept. 23 |
Wittig: Synthesis of trans-9-(2-phenylethenyl) anthracene |
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Sept. 25 |
Preparation of |
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Sept. 30 |
Aspirin Synthesis and Isolation |
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Oct. 2 |
Aspirin Synthesis and Isolation |
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Oct. 7 |
Synthesis of Isopentyl Acetate |
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Oct. 9 |
Synthesis of Isopentyl Acetate |
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Oct. 14 |
2-Acetylcyclohexanone via the Enamine Reaction |
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Oct. 16 |
2-Acetylcyclohexanone via the Enamine Reaction |
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Oct. 21 |
2-Acetylcyclohexanone via the Enamine Reaction |
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Oct. 23 |
Dibenzalacetone by the Aldol Condensation |
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Oct. 28 |
Dibenzalacetone by the Aldol Condensation |
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Oct. 30 |
Esterification of Vanillin |
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Nov. 4 |
Esterification of Vanillin |
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Nov. 6 |
Mechanism Investigation |
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Nov. 11 |
Mechanism Investigation |
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Nov. 13 |
Qualitative Analysis |
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Nov. 18 |
Qualitative Analysis |
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Nov. 20 |
Qualitative Analysis |
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Nov. 25 |
Qualitative Analysis |
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Dec. 2 |
Soap Synthesis |
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Dec. 4 |
Polymers |
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You are required to read the experimental procedure before lab. In addition, you are required to have the following written in your lab notebook before the beginning of the lab:
1. Title and date of the experiment
2. Experimental Objective
3. Short outline of the procedure.
5. Table of physical constants for organic chemicals used:
molecular weight
melting point if chemical is a solid
boiling point if chemical is a liquid
density of liquid
hazards or dangers to be aware of
Grade for the course will determined by combining both lab total and the lecture total. Any changes in the lab schedule will be announced in advance. Lab reports are due one week after completion of the experiment. Points will be deducted for late lab reports. All lab reports and lab notebooks will include the following:
1. Title and date of the experiment
2. Experimental Objective
3. Procedure: short outline of the procedure. Also include any changes to the procedure.
4. Reaction and Mechanism(only for synthesis experiments)
5. Table of physical constants for organic chemicals used:
molecular weight
melting point if chemical is a solid
boiling point if chemical is a liquid
density of liquid
hazards or dangers to be aware of
6. Unknown Code if needed
7. Experimental Data and Observations - grams used, volume used, grams of product, etc.
8. Calculations: for example- moles used, theoretical yield, percent yield, etc...
9. Answers to any questions or problems assigned.
10. Conclusion of results and determination of unknown.
Poor lab technique will include the following: not wearing safety glasses or goggles in the lab, unprepared for the lab experiment, not finishing the experiment on time, not using your lab notebook to record data, and sloppy house keeping.
Locker Check in/Locker Check out: You will check into a laboratory locker during the first day of classes. You will be responsible for all equipment in the locker. If you should drop, withdrawal, or take a leave of absence from the course, you must also check out of the locker. If this is not done, there will be a HOLD placed on next semester's registration and all records at CCSF.
Reading and Problem Assignments
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Ch. 15 |
omit sections 15-13C and 15-13D Problems: 1, 2, 4, 5, 7ab, 8, 9, 11, 12, 14, 15, 16, 18, 19, 20, 25, 27, 29, 30, 31, 32, 33, 34, 35, 36 |
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Pericyclic Reactions |
Handout (McMurray – Ch. 30) Omit sections
30.10, 30.11, 30.12 Problems: 1, 2, 3, 4, 5, 6, 7, 8, 16, 20, 22, 24, 32, 33, 34 |
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Ch. 16 |
Problems:
4, 5, 7, 8 (assume all molecules are planar), 9ab, 10, 12 (assume all
molecules are planar), 13, 15, 16, 17, 18, 20bcd, 22, 24, 27, 28 (omit d and
h), 30, 32, 33, 34, 35, 36, 37, 38a, 41, 44abc, 45 (C10H4O) |
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Ch. 13 |
NMR of aromatic compounds: Problems 6b, 32 compound 1 (C8H11N), 38 |
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Ch. 17 |
Problems: 4, 5, 6, 7, 8, 9, 12, 13, 14, 15, 16, 17, 18ac, 21, 22, 25, 26, 29 (omit a), 30, 32, 34, 38, 40, 46, 47, 48, 49, 51, 57, 61, 64 |
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Ch. 18 |
omit section 18-5E Problems: 1ab, 2, 3, 4, 6, 7, 8, 9, 11, 12, 15, 17, 18, 19, 20, 22, 23, 24, 25, 27, 28, 29, 30, 33, 34, 35, 36, 37, 39 (except l), 40, 44, 45, 47, 49, 51, 52, 56, 66, 70 |
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Ch. 19 |
omit section 19-14 Problems: 2acef, 3a-e, 5, 6, 7, 8, 10, 11, 12, 13, 16, 17, 20, 21, 22, 24, 25, 26, 27, 28, 29, 30a-d, 31, 32, 34, 36, 37, 44, 47, 48, 49, 50, 51 |
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Ch. 20 |
omit section 20-7c Problems: 1bcdeg, 2 (only systematic name), 3, 8, 9, 11, 12, 13, 14, 16, 17, 22, 23, 24, 27abcefg, 29, 30, 32, 33, 35, 36, 39, 41, 42, 43, 47 |
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Ch. 21 |
Problems: 1a-h, l, n, p (systematic names only), 2, 5b, 6, 7, 8, 9, 10, 12, 13, 14, 15, 16, 17, 18, 19, 20, 22, 23, 25, 27, 28, 30, 31, 32, 34, 35, 37, 38, 39, 44a-j, 45, 46, 48, 49, 50, 53, 54, 55, 57bcd, 65 (C4H6O3), 66 (C5H7NO2) |
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Ch. 22 |
Problems: 1, 3, 4, 5, 7, 8, 9, 10, 12, 13, 14, 15, 16, 17, 18, 19, 21, 22, 23, 24, 25, 26, 27, 28, 29, 31, 32, 34, 35, 36, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 49, 50, 52, 53, 54, 56, 57, 58, 59, 61, 62, 63, 64, 65, 66, 67, 68, 69, 70, 71, 72, 73, 75, 76, 77, 78 |
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Ch. 23 |
omit sections 23-20 to 23-24 Problems: 1, 2, 3, 6, 8, 9, 10, 11, 12, 13, 14, 16, 17, 18, 19, 20, 21 (omit naming), 22 (omit naming), 23, 24, 26, 30, 31, 32, 33, 34, 35, 36, 38, 39, 40, 44, 45, 46 (omit naming), 55, 56, 57, 62, 64, 65, 68, 69 |
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Ch. 24 |
Problems: 4, 5, 6, 9, 10, 11, 12, 13, 14, 17, 18, 19, 20, 21, 23, 24, 25, 26, 27, 28, 29, 30, 31, 34, 36, 38, 39, 40, 41, 42, 43, 44, 45, 48, 51 |
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Ch. 25 |
1, 3, 5, 7, 8, 10, 11, 12, 13, 16 (omit f), 18, 20, 21, 22, 23, 26a, 27, 28, 29 |
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Ch. 26 |
1, 2, 3, 6, 8, 9, 10, 13, 16, 18, 19, 20 |
Exam 1
Exam 2
Exam 3
Exam 4
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