CH 318N Spring,2005

Chemistry and Biochemistry Majors

PROFESSOR NATHAN L. BAULD

COURSE SYLLABUS

TABLE OF CONTENTS

Note: The Final Course Curve and the Final Exam Key are Both Posted Below Under the Table of Contents

1. Course information
2. Meeting time and location
3. Instructor
4. Assistants
5. Course Topics
6. Required textbook
7. Course Philosophy
8. Exams
9. Review Sessions
10. Grading system
11. Scholastic dishonesty policy
12. Additional information and Emphasis Topics
13. Class Notes
14. ORIENTATIONAL CURVE FOR EXAM #1(A Previous Exam)
15. ORIENTATIONAL CURVE FOR EXAM #1(Spring, 2005)
16. Answer Key for Exam 1 (Previous Exam)
17. Answer Key for Exam 1 (2005)
18. ORIENTATIONAL CURVE FOR EXAM #2 (Previous Exam)
19. ORIENTATIONAL CURVE FOR EXAM #2 (2005)
20. Answer Key for Exam 2 (Previous Exam)
21. Answer Key for Exam 2 2005)
22. ORIENTATIONAL CURVE FOR EXAM #3 (Previous Exam)
23. ORIENTATIONAL CURVE FOR EXAM #3 (2005)
24. Answer Key for Exam 3(Previous Exam)
25. Answer Key for Exam 3(2005)
26. FINAL CURVE (Previous Exam)
27. FINAL CURVE (2005)
28. Final Exam Answer Key (Spring,2002) (Previous Exam)
29. Final Exam Answer Key (2005)
30. Link to BI(Movies of the aldol, claisen, aromatic substitution, and Diels-Alder Reactions
31. Review of TS Modelling and Competing TS's

CH 318N

Meeting time and location

Instructor

Name: Professor Nathan L. Bauld
Office: Welch Hall 5.232
Office Hours: Tu,Wed 2-3
Phone: (512)471-3017
E-mail: bauld@mail.utexas.edu

Teaching Assistant

Teaching Assistant: Ms. Kristin Procko

e-Mail Address: kprocko@mail.utexas.edu

Office Hour: Tu 1-2 (Welch 1.3 Hallway, Cubicle C):

Teaching Assistant: Ms. Suvi Simila

e-Mail Address: suvisimila@mail.utexas.edu

Office Hour: Tu 10-11, Cubicle A

Course Topics

1. Unit 1: Chapter 16. Aldehydes and Ketones
2. Unit 2:Chapter 17. Carboxylic Acids
3. Unit 3: Chapter 18. Functional Derivatives of Carboxylic Acids (Esters, Amides,etc.)
4. Unit 4: Chapter 13: NMR Spectroscopy
5. Unit 5: Chapter 19.Enolate Anions.
6. Unit 6: Chapter 20. Aromaticity.
7. Unit 7: Chapter 21.Reactions of Aromatics .
8. Unit 8: Chapter 22.Amines.
9. Unit 9: Chapter 23. Conjugated Dienes.
10. Unit 10: Chapter 24.Organic Polymer Chemistry.
11. Unit 11: Chapter 25. Carbohydrates.
12. Unit 12: Chapter 26. Lipids.
13. Unit 13: Chapter 27.Amino Acids and Proteins.

Required Text

• "Organic Chemistry", Third Edition, by Brown & Foote, Saunders College Publishing, 2002. (The same text as was used in the first semester.)
• The Study Guide and Solutions Manual for this text.

Course Philosophy

This course strongly accentuates reaction mechanisms and theoretical understanding of organic chemical reactions. On exams, mechanisms must be written out exactly (for full credit), with rate-determining steps specified as "rds" or slow steps as "slow" over the reaction arrows. The student should be able to rationalize why the appropriate step is rate determining or slow, also. All steps known to be equilibria ( as mentioned in class) must be so indicated by the use of equilibrium arrows. Theoretical explanations of structure, rate, specificity, etc. must be logical and complete to the level expounded by the instructor in class. Great emphasis is placed upon the specific material discussed in the lecture, understood at the level at which it is presented and demonstrated appropriately on the exams..

Transition state models are often required and must be derived from resonance theory, not simply written down as dotted line/partial charge structures. Transition states are characterized by various characteristics such as carbocation or radical or alkene character and often this must be refined to a more specific sub-character, such as primary or secondary or tertiary carbocation character or arenium ion character or monosubstituted or disubstituted alkene character. The characterization is then extended by the use of the Hammond postulate, whenever it is applicable, to indicate whether the transition state has much or a little of the specified character. It will usually be necessary to explain the specific application of the Hammond postulate and how it is being applied.

The Method of Competing Transition States must be used in many cases to explain the results of competing reactions such as orientation in electrophilic aromatic substitution, or relative rates, or reaction specificity.

Exams

• Exam 1:Wednesday, February 16, 2005 in GEO 2.216 (7-9 P.M.).
• Exam 2: Wednesday, March 23, 2005 in Welch 1.316 (7-9 P.M.)
• Exam 3:Wednesday, April 20, 2005 in Welch1.316 (7-9 P.M.).
• Final Exam: Wednesday, May 11, 2005 (9-12n).

Exam Answer Keys

• Exam 1
• Exam 2
• Exam 3
• Final Exam

Exam Orientational Curves

• Exam 1
• Exam 2
• Exam 3
• Final Curve

Review Sessions [In Class]

Grading System

• Each exam counts 100 points; the final exam counts 150, for a total of 450 possible points. Homework does not contribute to the grade.
• Exam papers, except for the final exam, will be handed back in class.
• Regrade requests must be handed in within one week of the day on which the exam paper is returned. The right of regrading the entire exam is reserved. Our standard procedure must be followed. This consists of attaching a cover sheet to the exam in question which specifies which questions and answers are at issue and why, as succinctly as possible. The exam with the attached cover sheet is brought to the lecture and given to the TA . Regraded exams will be returned in the same way, i.e.at class time.
• No exam can be regraded which is done in pencil or in which there are extensive cross-outs or white-outs.
• Calculators are not permitted.
• At the time that each exam paper is returned, an orientational curve will be presented. These are not intended to represent formal letter grades, but only an approximate indication of your standing with respect to the class. The final course grade will be curved, but the student should understand that the A and B ranges will still be approximately in the 90's and 80's, respectively, give or take a few points (most likely one or two). The "C" range usually extends down to about 60 as the lowest "C", and anything below 50 will undoubtedly be failing.

Scholastic Dishonesty Policy

Additional Information

1. Emphasis Topics for the 1st Exam
2. Emphasis Topics for the 2nd Exam
3. Emphasis Topics for the 3rd Exam
4. Emphasis Topics for the Final Exam

Class Notes

1. Chapter 16 (Aldehydes and Ketones) :
2. PRACTICE PROBLEMS for Aldehydes and Ketones GROUP1;** GROUP2.:**GROUP3** ANSWERS : GR1** GR 2**GR3
3. Chapter 17(Carboxylic Acids) :
4. Exercises for Chapter 17
5. Chapter 18 (Derivatives of Carboxylic Acids)
6. Exercises for Chapter 18
7. Chapter 13 : NMR, Mass Spectrometry (DON'T FORGET TO DO PRACTICE EXAMPLES OF SIMULATING NMR SPECTRA GIVEN A SPECIFIC STRUCTURE: YOU COULD USE THE STRUCTURES IN THE THREE EXAMPLES ON PP488,489, AND 491 OF THE TEXT. WITHOUT LOOKING AT THE SPECTRA PROVIDED, TRY TO SIMULATE THE EXPECTED SPECTRA JUST ON THE BASIS OF THE STRUCTURE AND THEN COMPARE THEM WITH THE SPECTRA GIVEN.)
8. Chapter 19(Enolate Anions)
9. Chapter 19 (Continued)
10. Exercises on CH 19
11. Chapter 20(Aromatics and Aromaticity)
12. Exercises on Aromaticity
13. Chapter 21(Aromatic Substitution)
14. Chapter 21: Aromatic Substitution(Continued)
15. Aromatic Substitution:Exercises
16. Chapter 22(Amines)
17. Chapter 22: Amines(Continued)
18. Chapter 22 (Revised)
19. Amines: Exercises
20. Chapter 23: Dienes:
21. Chapter 23: Dienes (Continued)
22. Dienes: Revised
23. Dienes: Exercises
24. Chapter 24: Polymers :
25. Chapter 24: Polymers (Continued)
26. Exercise: Chapter 24
27. Polymerss: Revised
28. Chapter 25: Carbohydrates:
29. Chapter 25: Carbohydrates(Continued)
30. Exercises: Carbohydrates
31. Carbohydrates: Revised
32. Chapter 26: Lipids
33. Lipids: Revised (2005)
34. Chapter 26: Exercises.
35. Chapter 27: Amino Acids and Proteins
36. Chapter 27: Amino Acids: Continued :
37. Chapter 27: Amino Acids(Last)
38. Ch27 Exercises.
39. Peptides: REVISED

Spring Term, 2005