Advanced Organic Chemistry - I David M.

Birney
CHEM 5321 – Fall 2019 Office 232-C
806-834-7167
M. W. F 10:00 – 10:50 AM, English and Philosophy Room 164 david.birney@ttu.edu
Office Hours T, W, Th 1:00 – 2:00 PM or by appointment

This course is intended to provide graduate students with an in-depth and advanced perspective
on modern mechanistic organic chemistry. The first part of the course covers covalent bonding,
acid-base chemistry, and stereochemistry. The second part discusses energy surfaces, catalysis
and the experiments that provide mechanistic evidence. The third part looks in detail at the
mechanisms for several important classes of organic reactions, including organotransition metal
reactions.

Required textbook: “Modern Physical Organic Chemistry,” first edition, Anslyn and Dougherty,
University Science Books, Sausalito, California, 2006. Additional readings may be assigned
during the semester.

The following is a tentative schedule for our class meetings. Topics are subject to change; exam
dates are not.

Dates Lecture Topic Reading

Aug. 26, 28 Introduction to structure and models of bonding Ch. 1.1-1.3.3
Aug. 30, Sept. 4 Strain and stability Ch. 2.1, 2.3, 2.4
Sept. 2 Labor Day, no class
Sept. 6, 9 Acid-base chemistry Ch 5
Sept. 11-18 Stereochemistry Ch 6.1-6.4
Sept. 18 Review for Exam 1, 5:00 PM, room 113
Sept. 20 Exam 1
Sept. 23-27 Energy surfaces and kinetic analysis Ch 7.1-7.3, 7.8
Sept. 30-Oct. 4 Experiments related to thermodynamics and kinetics Ch 8.1-8.3, 8.8
Oct. 7-9 Catalysis Ch. 9.2
Oct. 11-28 Organic reaction mechanisms, part 1 Ch 10.1-10.9, 10.12-
Oct. 16 Review for Exam 2, 5:00 PM, room 113 10.20
Oct. 18 Exam 2
Oct. 30-Nov. 13 Organic reaction mechanisms, part 1I Ch. 11.1-11.5, 11.8.1,
Nov. 13 Review for Exam 3, 5:00 PM, room 113 11.9.4
Nov. 15 Exam 3
Nov. 18-Dec 4 Organotransition metal reaction mechanisms Ch 12.1-12.3
As time permits Special topics in mechanistic organic chemistry literature
Tues. Dec. 10 Final Exam, 7:30 – 10:00 AM, English and Philosophy Room 164

LEARNING OUTCOMES
The successful student will be able to:
1) Explain and utilize modern models of bonding, strain and acid base chemistry.
2) Explain stereochemical descriptors, experiments related to energy surfaces and chemical
kinetics.
3) Explain and predict a wide variety of organic and organometallic reaction mechanisms.

You are encouraged to ask questions during class. You are also welcome to ask them during
office hours or by E-mail.

CHEM 5321 Page 1 Fall 2019

 ASSESSMENT

Homework and exams; Pay close attention to the attached schedule; there will be no make-up
exams! If there is an excellent reason and it is approved in advance by me, one exam may be
excused. There will be three exams during the semester, in addition to the final exam. The final
exam will be a cumulative exam, covering material from the entire semester, but focusing on the
later material. There will be occasional take-home assignments that will count as part of the
exams. Answer keys will be posted. You will have a written report and an in-class presentation on
a selected reaction, at the end of the semester. This will be worth 40 points.

Grading: Three hour exams at 100 points each = 300 points

Oral and written report (5321 only) = 40
Final examination = 100
Total = 440

396 - 440 points = A The grade of incomplete will be given only

352 - 395 points = B
308 - 351 points = C
264 - 207 points = D
0 - 263 points = F
if you cannot continue in the course due to
circumstances beyond your control and
have been earning a passing grade up until
this point. You must meet with Dr. Birney to
discuss an incomplete.

Special Conditions: Any student who, because of a disability, may require special arrangements
in order to meet the course requirements should contact the instructor as soon as possible to make
any necessary arrangements. Students should present appropriate verification from Student
Disability Services during the instructor’s office hours. Please note instructors are not allowed to
provide classroom accommodations to a student until appropriate verification from Student
Disability Services has been provided. For additional information, you may contact the Student
Disability Services office in 335 West Hall or 806-742-2405. (TTU OP 34.22)

Academic Honesty: It is the aim of the faculty of Texas Tech University to foster a spirit of
complete honesty and high standard of integrity. The attempt of students to present as their own
any work not honestly performed is regarded by the faculty and administration as a most serious
offense and renders the offenders liable to serious consequences, possibly suspension. The use of
textbooks, notes, pagers, cell phones, and calculators are not allowed in any quiz or exam. (See
TTU OP 34.12 for more details)

Religious Holy Day: A student who intends to observe a religious holy day should make that
intention known to the instructor prior to the absence. A student who is absent from classes for
the observance of a religious holy day shall be allowed to take an examination or complete an
assignment scheduled for that day within a reasonable time after the absence. (TTU OP 34.19)

TTU Resources for Discrimination, Harassment, and Sexual Violence: Texas Tech
University is committed to providing and strengthening an educational, working, and living
environment where students, faculty, staff, and visitors are free from gender and/or sex
discrimination of any kind. Sexual assault, discrimination, harassment, and other Title IX
violations are not tolerated by the University. Report any incidents to the Office for Student
Rights & Resolution, (806)-742-SAFE (7233) or file a report online at titleix.ttu.edu/students.
Faculty and staff members at TTU are committed to connecting you to resources on campus.
Some of these available resources are: TTU Student Counseling Center, 806-742-3674,
https://www.depts.ttu.edu/scc/ (Provides confidential support on campus.) TTU Student

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Counseling Center 24-hour Helpline, 806-742-5555, (Assists students who are experiencing a
mental health or interpersonal violence crisis. If you call the helpline, you will speak with a
mental health counselor.) Voice of Hope Lubbock Rape Crisis Center, 806-763-7273,
voiceofhopelubbock.org (24-hour hotline that provides support for survivors of sexual violence.)
The Risk, Intervention, Safety and Education (RISE) Office, 806-742-2110, rise.ttu.edu (Provides
a range of resources and support options focused on prevention education and student wellness.)
Texas Tech Police Department, 806-742-3931, http://www.depts.ttu.edu/ttpd/ (To report criminal
activity that occurs on or near Texas Tech campus.)

CHEM 5321 Page 3 Fall 2019