Organic Chemistry 2 (CHEM
212)
Spring 2008
Prof. W. P. Malachowski
Office: Park 270
Phone: Ext. 5016
e-mail:
web page: http://www.brynmawr.edu/chemistry/malachowski
course web page: http://www.brynmawr.edu/chemistry/malachowski/OChem2/OChem2.html
Class Meetings:
Section 1 (Undergraduates Only): Mon., Wed., Fri. 10:10-11:00 AM;
recitation: Fri. 2:10-3:00 PM (Park 25)
Section 2: Mon., Wed., Fri. 11:10-Noon; recitation: Fri. 9:10-10:00 AM
All class meetings will be held in Park 180 except as noted. Class
cancellations, i.e. for inclement weather, will be posted on the course website
and/or communicated via e-mail.
Office Hours: Wed.
Lecture Textbook: Organic Chemistry, Fourth Edition, by G. M. Loudon
Class Schedule:
|
Date (Lecture No.) |
Lecture Title |
Corresponding Text Sections |
Associated Questions |
|
Jan. 23 (1) |
"Introduction to Course" and "Dienes Introduction" |
15.1, 25.1A |
15.1, 15.2ab, 25.2abcdef, 15.4 |
|
Jan. 25 (2) |
"UV/vis Spectroscopy" and "Resonance" |
15.2, 15.6 |
15.10, 25-28, 34, 42ac |
|
Jan. 25 (3) |
recitation: "Diels-Alder Reaction" |
15.3, 25.3 |
15.11-18, 47, 49, 62bdf, 25.10 |
|
Jan. 28 (4) |
"Diels-Alder Reaction" cont. |
" " |
" " |
|
Jan. 30 (5) |
"Kinetic and Thermodynamic Control of Reactions" |
15.4 |
15.20-22, 35, 54 |
|
Feb. 1 |
recitation |
|
|
|
Feb. 1 (6) |
"Aromaticity" |
15.7 (16.6) |
15.29, 31, 32, 38, 39, 41bc, 60 |
|
Feb. 4 (7) |
"Benzene Introduction" and "Electrophilic Aromatic Substitution: Halogenation, Nitration and Sulfonation" |
16.1, 16.4A-D |
16.11, 16.57 |
|
|
"Friedel-Crafts Reactions" |
16.4EF (19.12) |
16.14ab, 16-19, 31de |
|
Feb. 8 |
recitation |
|
|
|
Feb. 8 (9) |
"Electrophilic Aromatic Substitution Reactions of Substituted Benzenes" |
16.5 |
16.20a, 21, 23acde, 24a, 27ab, 28, 29, 31abcf,
32, 38abcdegij, 39bc, 40b, 48, 53abdf, 55 |
|
Feb. 11 (10) |
"Allylic and Benzylic Reactivity" and "Nucleophilic Substitution and Oxidation of Allylic and Benzylic Sites" |
17.1-5 |
17.1a, 2a, 3a, 5, 6bc, 9, 10b, 16abc, 19, 20,
21acde, 23, 25, 31a, 32bcdefgi, 33ade, 39a, 40, 41 |
|
Feb. 13 (11) |
"Nucleophilic Substitution of Aryl Halides" |
18.1, 18.3, 18.4 |
18.1a, 3-6, 42ab, 56abde, 59, 65a, 68 |
|
Feb. 15 |
recitation |
|
|
|
Feb. 15 (12) |
"Resonance and Acidity" |
18.6 |
18.23ac, 38ae |
|
Feb. 18 (13) |
open |
|
|
|
Feb. 20 (14) |
"Introduction to Ketones and Aldehydes" |
19.1, 19.4-6 |
19.1aceg, 2 abcdf, 11ab, 13ab |
|
Feb. 22 |
recitation |
|
|
|
Feb. 22 (15) |
"Nucleophilic Additions to Ketones and Aldehydes" |
19.7-9 |
19.14, 15a, 17, 18ac, 19a-c, 20, 21a-df, 22,
37abdh, 38ab, 39a, 40a, 43e, 47abcefgh, 48, 54a, 55a, 56a, 57 |
|
Feb. 25 (16) |
"Carbohydrates" |
27.1, 2, 3, 10, 11A |
27.1, 2, 3cde, 4ab, 5, 7, 36bd, 37abc, 38c, 39ac,
62ab |
|
Feb. 27 (17) |
"Carbohydrates" (continued) |
|
|
|
Feb. 29 |
recitation |
|
|
|
Feb. 29 |
EXAM 1 |
Content: Ch. 15-18, and 19 (part) |
|
|
Mar. 3 (18) |
"Nucleophilic Additions to Ketones and Aldehydes: Part 2" |
19.10-12 |
19.23ab, 24ab,
25ab, 26, 27ac, 28, 30ab, 31, 37efgm, 38eg, 41, 43a-d, 46a, 47ikl, 50ab, 56d |
|
Mar. 5 (19) |
"Wittig Reaction" |
19.13 |
19.33ab, 34a-c, 37cil, 38d, 40b, 43fg, 47d, 56c |
|
Mar. 7 |
recitation |
|
|
|
Mar. 7 (20) |
"Introduction to Carboxylic Acids" |
20.1, 4 |
20.1a-f, 2a-df, 24b, 28ac, 38a |
|
Mar. 8-16 |
Spring Break |
|
|
|
Mar. 17 (21) |
"Synthesis and Reactions of Carboxylic Acids" |
20.6, 7, 8 |
20.9ab, 10ab, 11abcd, 12ac, 24afg, 25a, 36abc, 38c, 40, 45bfg, 48abf, 50a |
|
Mar. 19 (22) |
"Conversion to Acid Chlorides and Anhydrides" |
20.9 |
20.14a, 15b, 16, 17, 18a, 24ehi, 25cd, 44ac |
|
Mar. 21 |
recitation |
|
|
|
Mar. 21 (23) |
"Reduction of Acids and Decarboxylation" |
20.10, 11 |
20.19a, 20ab, 21ab, 24cd, 36def, 45a, 46a |
|
Mar. 24 (24) |
"Introduction to Carboxylic Acid Derivatives" |
21.1A-F, 2 |
21.1cdfh, 2abcf, 3 |
|
Mar. 26 (25) |
"Reactions of Carboxylic Acid Derivatives: Nucleophilic Acyl Substitution" |
21.6, 7 |
21.10a, 11, 14abd, 31ab, 32a, 40a, 52a |
|
Mar. 28 |
recitation |
|
|
|
Mar. 28 (26) |
"Reactions of Carboxylic Acid Derivatives: Nucleophilic Acyl Substitution" cont. |
21.8 |
21.15ab, 16abcd, 18bd, 31cfgh, 32bcfghi, 38ab, 40a, 41d, 44, 45a, 52bcdel, 55dg |
|
Mar. 31 (27) |
"Reduction of Carboxylic Acid Derivatives and Reactions with Organometallic Reagents" |
21.9-11 |
19abc, 20bc, 21, 24b, 25ab, 26, 28, 31de, 32de,
33c, 34, 36, 40b, 41abcef, 52fgij, 55ef |
|
Apr. 2 (28) |
"Enolates and Enols" |
22.1, 2 (14.5) |
22.1, 3, 6, 7abd, 9ab, 11a, 53, 55ab, 61a,
63ac, 64b, 82d |
|
Apr. 4 |
recitation |
|
|
|
Apr. 4 |
EXAM 2 |
Content: |
|
|
Apr. 7 (29) |
"Reactions of Enolates and Enols" |
22.3 |
22.12a, 14ab, 16ab, 57ab, 71f, 73k |
|
Apr. 9 (30) |
"The Aldol Reaction" |
22.4 |
22.19a, 20, 22abcdegh, 23, 36, 71e,
78a, 83a |
|
Apr. 11 |
recitation |
|
|
|
Apr. 11 (31) |
"Crossed and Intramolecular Aldol Reactions" |
22.4 |
|
|
Apr. 14 (32) |
"The Claisen Condensation" |
22.5 |
22.24bce, 25ab, 27b, 28abc, 29ab, 30ab |
|
Apr. 16 (33) |
"Alkylation of Enolates" |
22.7 |
22.33abc, 34, 35abc, 37ab, 38a, 71ab,
73dl, 78c, 79ac |
|
Apr. 18 |
recitation |
|
|
|
Apr. 18 (34) |
"Conjugate Addition Reactions" |
22.8A, B |
22.40a-d, 41a, 42ab, 43b, 47bcd, 48dfg, 69,
73e, 79f, 80a, 82h |
|
Apr. 21 (35) |
"Michael Addition and Organocuprate Conjugate Addition Reactions" |
22.8C, 22.9-11 |
22.44, 45ab, 46ab, 48ce, 49e, 73ab, 79bg |
|
Apr. 23 (36) |
"Introduction to Amines" |
23.1, 2, 5AB, 12 |
23.1abde, 2acd, 8ac, 38ab, 40abc, 43ab, 44, 49e,
53a |
|
Apr. 25 |
recitation |
|
|
|
Apr. 25 (37) |
"Synthesis of Amines" |
23.7AB, 11 |
23.14, 16a, 17, 20a, 21a, 22, 31, 32, 34, 39bg, 40dfgik, 49ab, 50d, 55ab, 59bc, 60cdhi, 71b |
|
Apr. 28 (38) |
"Reactions of Amines" |
23.8, 10AC |
23.26b, 38cefh, 39ae, 50ab, 53e, 60km |
|
Apr. 30 (39) |
"Amino Acids" |
26.1, 2, 3AB |
26.1, 2, 3a, 4, 5a, 6, 7, 8ac, 36a-d, 48, 62, 67a |
|
May 2 |
recitation |
|
|
|
May 2 |
EXAM 3 |
Content: |
|
|
May 8,
9:30 AM-12:30 PM |
FINAL EXAM in |
cumulative |
|
Book Sections Omitted: 14.1-4, 6-10; 15.5; 16.2, 3,
7; 17.6; 18.2, 5, 7-10; 19.2, 3, 15; 20.2, 3, 5; 21.1G, 3, 4, 5, 12;
22.6; 23.2, 3, 4, 5
Associated Questions: Questions are listed for your practice they will not be collected or graded. By working through the questions, you will be involved in "active learning", a proven method for success in academic studies. As we progress through the text, questions become more complex and will frequently draw upon multiple concepts to obtain the correct answer. Complex questions with multiple concepts have been placed in a lecture topic that I believe is the most important to obtaining the correct answer or understanding the essence of the problem. The answers to all assigned questions from your "Organic Chemistry" textbook can be found in the "Study Guide and Solutions Manual" that accompanies the textbook. A copy of the "Study Guide and Solutions Manual" is on reserve in Collier Library.
Exams:
There will be
-Molecular modeling kits may be used during an exam to assist you in answering
the questions.
-Exam answers will be posted on the course web page.
Final Exam: There will be a three-hour scheduled final exam from 9:30 AM-12:30 PM on Thurs. May 8 without lecture notes, textbook or any other associated course materials.
Laboratory: Dr. Maryellen Nerz-Stormes (Park 170) is in charge of the laboratory portion of the course.
Course Grading:
Lecture Assignments
|
Semester Exams |
100 pts. each (x 3) |
300 pts. |
|
Final Exam |
150 pts. |
150 pts. |
|
|
Total Points: |
450 pts. |
The Course Grade will be determined by the following
formula:
(Lecture Grade as a Percent of Total Points) x 0.70 + (Lab Grade as a Percent of Total Points) x 0.30= Course Percent
Approximate Grading Scheme:
|
93-100% 4.0 (A) |
70-73% 2.0 (C) |
|
89-92% 3.7 (A-) |
66-69% 1.7 (C-) |
|
85-88% 3.3 (B+) |
62-67% 1.3 (D+) |
|
81-84% 3.0 (B) |
58-61% 1.0 (D) |
|
77-80% 2.7 (B-) |
<57% 0.0 (F) |
|
73-76% 2.3 (C+) |
|
I reserve the right to make modifications to this scheme when I consider it necessary.
The grading scheme will be established based on the course averages of the undergraduate students only. After the grading scheme has been developed, all students will receive grades based on the undergraduate-only grade scheme.
Students with Disabilities: Students who think they may need accommodations in this course because of the impact of a disability are encouraged to meet with me privately early in the semester. Students should also contact Stephanie Bell, Coordinator of Access Services, at 610-526-7351 or sbell@brynmawr.edu, as soon as possible to verify their eligibility for reasonable accommodations. Early contact will help to avoid unnecessary inconvenience and delays.