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Chemistry 320M/328M Fall 2012

Organic Chemistry, Part I

Unique Numbers: 51845, 51965

MWF 10:00 - 10:50, Welch 2.224

Dr. Brent Iverson Office Hours: Tuesday 4 -5 PM Room: WEL 2.304 Thursday 5 - 6 PM Room: WEL 2.312 (Note these are not my real offices, they are classrooms)

Teaching Assistant: Brian Ikkanda Recitation: Monday 4-5 PM "Missed the Wave Recitation" Room: Welch 2.224 Office hours: Monday 5-6 PM, Room: TA Office Area B

Teaching Assistant: Amy Smith Office Hour: Wednesday 9-10 AM Room: Old Library (Welch 4.132B)

Teaching Assistant: Diana Zamora Office Hour: Tuesday 10-11 AM Room: TA Office Area B

Teaching Assistant: Mary Kim Office Hour: Tuesday 5-6 PM Room: TA Office Area B

Teaching Assistant: Wenzong Li Office Hour: Thursday 4-5 PM Room: TA Office Area B

Teaching Assistant: Cameron Peebles Facebook page TA

9-10 AM



Office Hours

Amy Smith

WEL 4.132B

10-11 AM

Office Hours

Diana Zamora

TA Area B

4-5 PM

"Missed the Wave" Recitation

Brian Ikkanda

WEL 2.224

Office Hours

Brent Iverson

WEL 2.304

Office Hours

Wenzong Li

TA Area B

5-6 PM

Office Hours

Brian Ikkanda

TA Area B

Office Hours

Mary Kim

TA Area B

Office Hours

Brent Iverson

WEL 2.312

6:30-7:30 PM

"Practice Problems" Recitation

All TA's

WEL 2.122

Weekly Recitation Sessions - these will be additional lectures given by the TA's. They will be designed to present the lecture material in a different context, from the point of view of the TA's, with the aim of helping you absorb the material and understand all of the key points.

Monday 4-5 PM Room: WEL 2.224 Brian Ikkanda "Missed the Wave Recitation" . This recitation is specifically reserved for those of you who feel you may be struggling. This recitation will encourage questions of all levels, especially older material that you are still uncertain about. If you are feeling comfortable with the material being presented in class, you should NOT attend this recitation. If you think you need to improve your background knowledge, this is specifically for you!

Tuesday 6:30-7:30 PM Room:WEL 2.122 Rotating scheduleof TA's presenting "Practice Problems Recitation" This recitation will focus on working problems so that you will become familiar with the format and expected answers for the types of questions asked on exams.

Review Sessions - I will be leading these review sessions which will be designed to help you as much as possible prepare for the exams.

Optional review sessions for the mid-term examinations will be given the Monday evening before each exam at on the following days and times:

Monday, September 24 Room: WEL 2.224 8:00 - 10:00 PM

Tuesday, October 23 Room: WEL 2.122 8:00 - 10:00 PM (Note room change)

Monday, November 12 Room: WEL 2.224 8:00 - 10:00 PM

An optional review session for the final will be given: TBA


Required Texts:

1. Brown, Foote, Iverson and Anslyn, Organic Chemistry, 6th Edition (Nautilus shell on the front cover), Brooks/Cole.

2. Study Guide for above text.

Note that the loose leaf version of these books, available directly from the publisher at tremendous savings, are also perfectly acceptable!

The 5th edition and the international edition are not the same and are not appropriate substitutes.

Course Prerequisites:

For CH320M: Chemistry 302 with a grade of at least C-, and credit or registration for Chemistry 204 or 317

For CH328M: Chemistry 302 and either Chemistry 204 or 317 with a grade of at least C- in each, and credit or registration for Chemistry 118K

Recommended Materials:

Molecular Models. These often make the difference between an A or B and C or lower. No kidding, buy them if you don't already have them, even though they are overpriced.


Additional Sources:

Selected old exams are posted on the web page.

Exam keys will also be posted on the course web page following the exams.


Homework: READ THIS

There will be two kinds of homework assigned in this class. There will be weekly homework sets that will be turned in BEFORE CLASS on the day it is due. These will be graded, and the points you earn will amount to extra credit that is added to your next exam grade as T-score points or Percentage points, whichever is in your best interest. The second type of homework will involve book problems that are assigned, but not collected. These are extremely important, as the only way to master organic chemistry is to work many, many problems over the course of the semester. Click here to see the homework assignment web page. The links will become active when the homework is assigned.


Facebook Page:

We have created a facebook page with the intent of facilitating communication between yourselves, as well as between yourselves and the TA's and I.

Search for "Where are the electrons" or click on this link if you have a Facebook account

We will be monitoring posts on the wall and will respond as our schedules allow. There are only two common sense rules:

1. All posts must be course content related.

2. We reserve the right to remove any post we feel is inappropriate in any way.

It is important to realize that this electronic mode of communication is to be used by you as an enhancement to the class, not a replacement for coming to Office Hours and Recitations.


Web Page Access:

This course will have a web page where we will place useful items including: a posting of the syllabus, Rules of the Day and homework assignments, Pictures of the day (this will make sense as the semester begins), links to the Class E-mail and a link to my chemistry movies. The page will be accessible from the Chemistry Department Undergraduate Course Home Page or you can get there directly using the following URL:


E-mail Access:

There will be E-mail access (under "E-mail Us" on the web page) to us if you want to ask a specific question electronically, and not on the public Facebook page. Be advised that during peak periods we may not be able to answer every question. However, I will be E-mailing you questions and answers that I think are particulalry important, along with any other class announcements.



Three mid-term exams will be given during the course of the semester. They will be held on Thursday evenings from 7:00 - 9:00 PM on the following days:

Thursday, September 27, 7:00 - 9:00 PM, Rooms: WEL 2.224, WEL 1.308, WEL 1.316

Those of you with last names starting with the letters A-J report to WEL 2.224, those with last names starting with K-Q report to WEL 1.308, those with last names starting with the letters R-Z report to WEL 1.316.

Alternate Time (for excused changes only*): 4:00 - 6:00 PM, WEL 1.308

Thursday, October 25, 7:00 - 9:00 PM, Rooms: Rooms: WEL 2.224, WEL 1.308, WEL 1.316

Those of you with last names starting with the letters A-J report to WEL 2.224, those with last names starting with K-Q report to WEL 1.308, those with last names starting with the letters R-Z report to WEL 1.316.

Alternate Time (for excused changes only*): 4:00 - 6:00 PM, Room: WEL 1.308

Thursday, November 15, 7:00 - 9:00 PM, Rooms: WEL 2.224, WEL 1.308, WEL 1.316

Those of you with last names starting with the letters A-J report to WEL 2.224, those with last names starting with K-Q report to WEL 1.308, those with last names starting with the letters R-Z report to WEL 1.316.

Alternate Time (for excused changes only*): 4:00 - 6:00 PM, Room: WEL 1.308

*An excused change is one caused by a regularly scheduled (in the course schedule) class or lab class. This list does NOT include an organization meeting, a job or a club sports activity. If you are going to have any of these conflicts, make plans now to be present at the mid term exams.

Final Exam: There are no makeup or alternative exams possible for the final. You must take it at the exact time and place listed.

Saturday, December 15, 9AM-12Noon, Rooms: WEL 2.224, WEL 1.308, JGB 2.218

Those of you with last names starting with the letters A-L report to WEL 2.224, those with last names starting with M-T report to WEL 1.308, those with last names starting with the letters U-Z report to JGB 2.218.




Course Outline

Unit 1: A Review of Molecular Structure and Bonding

Chapter 1 (Reviewed, not covered in depth)

Unit 2: Alkanes

Chapter 2


Chapter 3

Unit 4: Acids and Bases

Chapter 4

Unit 5: Alkene Structure

Chapters 5

Unit 6: Alkene and Alkyne Reactions

Chapters 6,7

Unit 7: Haloalkanes and Nucleophilic Substitution/Elimination Reactions

Chapters 8,9

Unit 8: Alcohols

Chapter 10

Unit 9: Ethers

Chapter 11

Unit 10: Nuclear Magnetic Resonance

Chapter 13


Proposed Exam Topics (Subject to Revision)

Mid-term Exam I: Units 1 - 5

Mid-term Exam II: Units 6 - 8

Mid-term Exam III: Units 9 - 10

Final Exam: All of the above (Yes, it is definitely cumulative)


Policy on Exam Coverage:

You will be responsible for all material covered up to the Friday lecture the week before each midterm. That way you will be able to think about the material for almost an entire week before you are tested on it. Also, the pace of the class can vary, so do not be concerned if we are not on the same schedule as descibed below under "proposed exam topics". The bottom line is that you are only responsible for the material covered in the previous Friday's lecture, NO MATTER WHAT THE SCHEDULE IN THE SYLLABUS SAYS ABOUT "UNITS" COVERED ON EACH MIDTERM.


What You Will Learn in Chem. 320M/328M

This course is designed around a simple idea. By the time a student has finished he or she should be able to simply look at a molecule and then predict how it will react under various conditions. In order to do this, you will learn about molecular three-dimensional structure and bonding, as well as the answer to the most important question in chemistry; where are the electrons? If you understand where electrons are located in three-dimensional space around a molecule, then you will be able to predict how that molecule will react under various conditions. Predicting reactions, based on a few fundamental principles, is vastly easier than trying to memorize all of the different reactions. Strive to understand and predict, not memorize and forget.

In addition, you will introduced to the Seven Golden Rules of Chemistry that explain almost everything you will learn about molecules in Organic Chemistry. Understanding the seven golden rules of chemistry will allow you to correctly predict the mechanism of a new reaction based on the relative energies of different possible reaction intermediates. You will also be able to predict which of the possible products will predominate. Finally, you will be able to make good guesses at the physical properties of new molecules, such as their solubilities, stabilities, reactivities, relative boiling points or melting points, etc.


You will be presented with chemical "tools" that are nothing more than the reactants needed to turn one type of molecule into another. By the time you have finished, you will have a relatively large "tool" kit, and you will be able to devise rather complex schemes for making a desired product out of a given starting material. The best way to study for this part of the course is to construct a road map that shows all of the different types of molecules we will be discussing (alkenes, aldehydes, carboxylic acids, etc.), and how the different "tools" are used to interconvert them. This "Big Picture" type of analysis will help you better understand what is going on. The key to success in this course will be the quality of your roadmap. Remember, the "tools" are not to be simply memorized, you must also understand how they work. Otherwise, you will be devastated by too much to memorize, and you will not be able to apply these "tools" to important new situations! In other words, mechanisms are important and must be learned and understood because they provide the detailed understanding that allows you to predict regiochemistry, stereochemistry, and when the reaction might not work (rearrangement, etc.). The mechanisms are very similar to each other so they are not that hard.

Do not memorize mechanisms, understand them by always asking yourself "why" each step occurs the way it does. Hint: almost all the steps in the organic mechanisms from 320M/328M can be viewed as one of the four fundamental mechanism elements described in chapter 6 of the textbook. Understanding the answer to the most important question in chemistry, namely where the electrons are located in a molecule, will allow you to predict accurately which groups on molecules will act as an electron-rich nucleophile and which groups will act as an electron-poor electrophile in a reaction. You will then be able to predict reaction mechanisms and thus reactions. You will understand organic chemistry and how to use it to build molecules!


Living systems are composed of molecules that can be understood using the same principles we will be talking about. A second emphasis on the class will be on the structure, properties, and reactions of molecules of living systems. This is intended to get pre health science students ready for subsequent courses in biochemistry and biology.


Organic Chemistry is a very hard subject and can only be mastered through very disciplined study. This means attendance at every class is among the minimum requirements for success. It will be virtually impossible to do well in this class if you do not attend the lectures faithfully. Successful students rely more on their lecture notes than the text, since the person giving the lectures is writing the exams. Okay, so I helped write the book as well, but you get the point.


How Can You Master Organic Chemistry?

Study the material every night, do all of the assigned problems and always try to relate new concepts and ideas to what you have already learned. Do not simply try to memorize the answers, in the hundred year history of Organic Chemistry classes, the memorization route has never, ever succeeded at the end of the semester, only the beginning when there is not that much to know. In the end, there are far too many things to memorize. You have to learn how things relate to each other, because then the whole picture is easy to remember. What is more, it becomes easy to figure out things you may have forgotten. Get behind at any time and you can kiss it good-bye....

How Should You Study Organic Chemistry? Click here to learn how best to study Organic Chemistry, and how to build the all-important roadmap for yourself. Learning how to study efficiently is perhaps the most important thing you could learn from this class.


To get a good grade you must do well on the tests. Duh. Since I try to emphasize important material on the test, you should focus your study on the important material. What is the important material you ask ? That is easy. The "Rules of the Day" highlight the important material discussed each lecture. Make sure you thoroughly understand the rules of the day, and why they are important. Second, I will say when something is important by playing my trumpet or drawing a little key next to a 'key' concept. Always write down these cues and use them as a study guide so you can focus your study time on the important stuff, not the less important details. We are not in the business of trying to trick people; if we say it is important, chances are it will be on the test. IT IS JUST THAT SIMPLE. (Of course this doesn't mean we can’t throw in a few mind benders to see how well you can apply what you know to new situations.)


How to Succeed in Chem. 320M/328M

If you were happy with your grade in previous chemistry classes: Keep up the good work!

If you were not satisfied with your grade in previous chemistry classes: You will have to change something! Find someone in the class who received the grade you wanted last semester, and ask them what they did differently than you. If you do not approach this class differently, then the result will probably be the same. The following is a top ten list of things you could change:

1. Never get behind, never get behind, never get behind

2. Strive to understand, not memorize the material

3. Come to class everyday.

4. Do all of the homework the night it is assigned.

5. Keep up with outlining your lecture notes and the book.

6. Keep up with updating your roadmap for each new reaction.

7. Understand, do not memorize mechanisms.

8. Practice predicting new reaction mechanisms, before you are told the mechanism.

9. Never get behind, never get behind, never get behind

10. Strive to understand, not memorize the material



The raw scores earned on each of the exams in this course will be converted to Standard T-Scores. The Standard T-Score is computed as follows:

T = [(x-X/s) 10] + 74


x = your raw test score

X = the class mean score = Sx/N

N = number of test scores

s = standard deviation = [S (x-X)2/(N-1)]1/2

Using Standard T-Scores allows an effective averaging of grades without introducing a bias in favor of tests with the greatest standard deviations. Since it is based on a normal (Gaussian) distribution, it generally represents the fairest way of grading. (Nearly all national exams such as the SAT, MCAT, and GRE use a similar form of Standard T-Scores)

Your final course grade will be calculated as 30% of your best midterm T-score, 30% of your second best midterm T-score and 40% of your final exam T-score. There will be three midterms during the semester, so this means that your lowest midterm exam T-score will be dropped OR you will be able to miss one midterm for any reason with no penalty.* The following conversion table will be used to calculate final course grades:

Score .............................Letter Grade

93.0000 < T ...............................A

90.0000 < T < 93.0000 ..............A-

87.0000 < T < 90.0000 ..............B+

83.0000 < T < 87.0000 ..............B

80.0000 < T < 83.0000 ..............B-

77.0000 < T < 80.0000 ..............C+

73.0000 < T < 77.0000 ..............C

70.0000 < T < 73.0000 ..............C-

67.0000 < T < 70.0000 ..............D+

63.0000 < T < 67.0000 ..............D

60.0000 < T < 63.0000 ..............D-

T < 60.0000 ...............................F

*Missing two midterms or the final exam without a documented, valid excuse will result in a failing grade.


*****Important Notice****** In general, using T-scores increases everyone's grades compared to using absolute percentages. Nevertheless, we will keep track of your percentage scores on every test. If the percentage scores are ever higher than your T-score, we will use the percentage score for your course grade calculation. Thus, if everyone does extremely well in this course, no grade will be lowered by using a curving system!


Academic Dishonesty:

The University of Texas at Austin has formally adopted the following academic honor code:

Honor Code

The core values of the University of Texas at Austin are learning, discovery, freedom, leadership, individual opportunity, and responsibility. Each member of the University is expected to uphold these values through integrity, honesty, trust, fairness, and respect toward peers and community.

Any violation of the above Honor Code that occurs during an exam or in the regrading process will result in a 0 being assigned for that exam and the student involved will be formally reported to the Dean of Students, where they will be subject to additional penalties or actions. The exam with the 0 will be automatically counted in the final grade calculation at the end of the semester.

To guard against altered exams being submitted for a regrade, we routinely copy a large number of exams following grading but prior to handing them back.



Exams can be turned in for regrades as long as they were taken in permanent ink, not pencil or erasable ink.  Regrades must be submitted within 7 days after the exam is handed back.  They can be submitted in the labeled class slot adjacent to WEL 2.212 or you can hand the exam to myself or one of the TA’s. You must indicate what problems need to be regraded, and provide a brief explanation for your concern.  The entire exam will be regraded. 


Exam rules: 

No notes or books are allowed used during the exams.  Because of recent incidents, you will not be allowed to interact with your cell phone in any way during exams.  No exceptions.  Turn them off, or leave them at home.  ***Interacting with a cell phone during an exam will be considered a violation of the Honor Code and will result in a 0 being recorded for your grade on the exam, no matter what you were actually doing with the phone.***



An incomplete (X) is a temporary delay in reporting the final course grade.  An X may properly be assigned for students who must miss the final due to illness or other imperative nonacademic reasons. An X may also be given when the student has not been able to complete all the required assignments for reasons other than lack of diligence but only if the student has a passing grade on the work completed. Documentation of non-medical excuses will be required. In general it is best for students to see a counselor in their Dean's Office regarding non-medical excuses for missing the finalJust to be clear, you will be required to have a written medical excuse signed by the person who treated you if the reason for the request for a postponed final is illness. Students have one long semester to make up an X and extensions are rare. After one long semester, the X converts to an F if no other grade is reported.

An X will not be assigned to allow the student an opportunity to repeat the entire course; the only assignments or exams that should be completed to resolve the X are those that were missed for legitimate reasons during the semester. In addition, the X should be assigned only if the student has been informed and the exact procedures by which the student will make up the work are agreed upon. The assignment of an X constitutes a contract between the student and the instructor. It is often helpful to have the arrangement in writing, specifying what the student is expected to do to complete the course, including due dates.


Drop dates:  

4th class day: Dropping courses electronically: During the first four class days, students may add and drop courses with the Registrar's online registration service, ROSE (September 4, 2012).

12th class day: Dropping a class with possible refund: During days five through twelve (September 14,
2012) students may drop courses online, but must go to the department offering the course to seek permission to add a course. Be advised that some departments do not allow adds/drops after the fourth class day. For those departments that do allow adds/drops, the add-transactions before the twelfth class day will be processed in the respective department. Students who wish to add a class after the twelfth class day should be required to go to the Student Division of the Dean's Office (first floor of W. C. Hogg) to provide justification for the proposed change. The student must have written permission and documentation of class attendance from the instructor and departmental approval.

49th class day: Last day to drop a course with approval: After the 12th day of class, and until the deadline for dropping courses (November 6, 2012), a student wishing to drop a course will get the forms from the Dean's Office (WCH 1.106) or their departmental advising center and ask the instructor to sign the drop form. Instructors are also asked to indicate on this form the grade (A-F) that the student has earned in the class up to this point. In contrast to previous years, instructors are not asked or able to assign a Q vs F on this form; henceforth the students are completing this paperwork for a Q-drop.

Nonacademic Q-drop: After the last day for academic Q-drop students with substantiated nonacademic reasons (as determined by the Dean's Office) may be allowed to drop a course. Faculty will be asked to provide information on student performance up to the time of the nonacademic Q-drop request but are not responsible for making the decision about assigning a grade of Q. Please encourage students who experience significant nonacademic problems such as extended health-related problems or family emergencies to contact the Dean's Office.

New One-time Drop Policy: Beginning this year, students have the option once in their undergraduate
degree to drop a class or drop out of all classes in a semester right up til the last class day. This new policy was proposed and approved by UT Faculty Council on May 9, 2011, and more information is available at According to the policy as approved by the Provost, a student who has completed at least two long semesters here at UT can drop a class only if he or she has an average grade of D+ or below in the class at the time of the request and if there are no pending investigations of scholastic dishonesty for the course in question.


Courses Taken on a Pass/Fail Basis (CR/NC)

The University defines a D- as a passing grade for undergraduate students. The instructor is obliged to assign a grade of CR (Credit) for a student registered on a pass/fail basis who has a D- or better in the course. It is important that the roster indicate the student is registered for the course on a pass/fail basis. Otherwise, a letter grade must be assigned. There is a time limit for students to change courses from a grade basis to pass/fail basis and vice versa. During the long session, it is the same as the final deadline for drop/withdrawal for academic reasons. See the current academic calendar for the exact date. After that deadline, students should see a counselor in the Student Division of the Dean's Office of their college.

For majors within the College of Natural Sciences, the College has instituted a minimum C- standard of passing grades for courses in order to progress to subsequent courses. For example, a grade of C- in M408N (calculus-I) is required to progress to M408S (calculus-II). This minimum standard applies to graduation requirements as well (see +/- grading below).


Students with Disabilities:

The rights of students with disabilities are protected under Section 504 of the Rehabilitation Act of 1973 and the Americans with Disabilities Act, which are civil rights provisions aimed at ending discrimination against persons with disabilities. Section 504 specifically refers to post-secondary and vocational education services. The legislation reads: "No otherwise qualified handicapped individual in the United States shall, solely by reason of his handicap, be excluded from the participation, be denied the benefits of, or be subjected to discrimination under any program or activity receiving Federal financial assistance." The University of Texas at Austin provides a wide variety of services to assist students with disabilities in becoming active members of the University community. These services vary according to the different types and severity of impairments.

The Services for Students with Disabilities (SSD) office of the Student Dean's Office is charged with assisting disabled students. They estimate that about 2000 students suffer from disabilities including mobility impairments, learning disabilities, visual impairments, hearing impairments, ADD and ADHD, and others. By law, these students are guaranteed a learning environment with reasonable accommodation of their disability.

We will provide any necessary and reasonable accommodation for students with disabilities, including accommodations for all of the exams. In order to qualify for accommodations, you will need to contact the Division of Diversity and Community Engagement, Services for Students with Disabilities, 471-6259, They will supply the documentation and recomendations needed for us to provide appropriate exam accommodations. This documentation must be provided prior to the first midterm exam. Because we administer night midterm exams, students requiring extra time must be prepared to either come earlier or stay later than other students on exam nights.


Absences due to Athletics or other University Activities:

Any athlete competing for UT on an NCAA team needs to notify me as soon as possible about any missed exams. Written documentation from the Athletic department will be required for accommodations to be given. An official team proctor must be provided to traveling team members by the athletic department, so that a copy of the exam can be administered outside of Austin at the same time as the students are taking the exam here. The sealed exam is then returned to me by the proctor, as soon as the team returns to Austin.

No other University of Texas at Austin organization or activity will receive consideration or accommodation for a missed exam. This includes all the "club" level teams (i.e. men's soccer or men's rugby, etc.) and any student organization or club.


Religious Holy Days:

A student who misses classes or other required activities, including examinations, for the observance of a religious holy day should inform me as far in advance of the absence as possible, so that arrangements can be made to complete an assignment or exam within a reasonable time after the absence. For reference, sections 51.911 and 51.925 of the Texas Education Code relate to absences by students and instructors for observance of religious holy days.