Chemistry 310N Spring 2008

Organic Chemistry, Part II

Unique Numbers: 54365, 54370, 54375, 54385

MWF 11:00 - 11:50, Welch 2.224

Lecturer: Dr. Brent Iverson Office Hours: T Th 3:30 - 5:00 PM Room: Welch 3.422

Teaching Assistant: Chelsea Martinez Office Hours: TIPS sections MWF 2-3 PM

Teaching Assistant: Shagufta Shabbir Office Hours: Wednesday 9-10 AM Room: TA Area B

Teaching Assistant: Himali Hewage Office Hours: Thursday 10-11 AM Room: TA Area B (Just outside WEL 1.308)

Teaching Assistant: Brittany Gleason Office Hours: Friday 10-11 AM Room: TA Area B (Just outside WEL 1.308)

Teaching Assistant: Stevan Samuel Office Hours: Monday 4-5 PM Room: TA Area B (Just outside WEL 1.308)

Teaching Assistant: Shuhui Wan Office Hours: Tuesday 9-10 AM Room: TA Area A (Just outside WEL 1.308)

9-10 AM

Office Hours Shuhui Wan

TA Area A

Office Hours Shagufta Shabbir

TA Area B

10-11 AM



Office Hours Himali Hewage

TA Area B

Office Hours Brittany Gleason

TA Area B

11-12 AM
1-2:30 PM


Shagufta Shabbir

WCH 1.120

2-3 PM

TIPS Recitation 54365

Chelsea Martinez

WEL 2.308


TIPS Recitation 54370

Chelsea Martinez

WEL 2.312


TIPS Recitation 54375

Chelsea Martinez

WEL 2.308


3:30-5 PM

Office Hours Brent Iverson WEL 3.422

Office Hours Brent Iverson WEL 3.422

4-5 PM

Office Hours Stevan Samuel

TA Area B



5-6:30 PM

Practice Problems Recitation

Himali Hewage

GEO 2.324

6-7:30 PM


Stevan Samuel

WEL 2.246


Brittany Gleason

PAI 4.42


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. The recitations marked "Fundamentals" will be aimed at students who need more time to learn the basics, or those who feel they are struggling a bit (or a lot) in the class. The recitation marked "Problems Recitation" will be for those students who feel they understand the material, and want to see the material applied to additional exam type problems.

Sunday 1-2:30 PM Room: WC Hogg 1.120 (Fundamentals) Shagufta Shabbir

Monday 6-7:30 PM Room: WEL 2.246 (Fundamentals) Stevan Samuel

Tuesday 5-6:30 PM Room: WEL 2.312 (Practice Problems) Himali Hewage

Thursday 6-7:30 PM Room: PAI 4.42 (Fundamentals) Brittany Gleason

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 or Tuesday evening before each exam at on the following days and times:

Monday, February 18 Room: WEL 2.224 8:00 - 10:00 PM

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

Tuesday, April 22 Room: WEL 1.308 8:00 - 10:00 PM NOTE DATE AND ROOM CHANGE!

An optional review session for the final will be given:

Tuesday, April 29 Room: WEL 3.502 8:00 - 10:00 PM. Please bring a can of food or two to be donated to the Caritas House food pantry for the homeless here in Austin. As the stress of finals sets in, I think it is a healthy thing to remember what real stress is - not knowing where your next meal will be coming from.

Required Texts:

1. Brown, Foote, and Iverson Organic Chemistry, 4th Edition (Two enantiomers on the cover), Thomson.

2. Study Guide for above text.

Course Prerequisites:



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.  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.  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 final. 

Drop dates:  

Subject to the conditions below, an undergraduate may drop this course through February 12, 2007. The student must remain in conformity with the quantity of work rule and must obtain all required approvals. International students must obtain written permission from the International Office, in addition to other required approvals, to drop a course. On the recommendation of the instructor, and with the approval of the student's academic dean, a student may be required to drop a course at any time because of neglect or for lack of preparation. Dropping a course through the twelfth class day. The following rules apply from the first class day through the twelfth class day of a long-session semester and from the first class day through the fourth class day of a summer term: To drop a course during this period, the student must have the approval of the chair of the department offering the course. In some colleges and schools, the student must also have the approval of his or her adviser and dean; each student must consult the regulations of his or her college or school. If the student is allowed to drop the course, the course is deleted from his or her academic record and applicable fees are refunded. Normally, the approval of the chair of the department during this period is routine, and the student may initiate the drop through the registration system. However, in some circumstances a department may disapprove requests to drop certain courses. If a drop request is not accepted by the registration system, the student should consult the department that offers the course for more information. Dropping a course through the fourth week of classes. The following rules apply from the thirteenth class day through the twentieth class day of a long-session semester and from the fifth class day through the tenth class day of a summer term: To drop a course during this period, the student must have the approval of his or her dean. In some colleges and schools, the approval of the student's adviser is also required; each student must consult the regulations of his or her college or school. If the student is allowed to drop the course, the symbol Q appears on his or her academic record to indicate a drop without academic penalty. No refund is given. Dropping a course after the fourth week of classes. The following rules apply from the twenty-first class day through the midsemester deadline in a long-session semester and from the eleventh class day through the last class day of a summer term: To drop a course during this period, the student must have the approval of the instructor, the student's adviser, and the student's dean. If the instructor approves the drop, he or she will assign the symbol Q or a grade of F. The symbol Q indicates that the student has a grade of at least C in the course, that no final grade has yet been assigned, or that no academic penalty is in order because of the student's performance and the nature of the course. In compelling circumstances, the student's dean may assign the symbol Q for nonacademic reasons. Dropping a course after midsemester. After the midsemester deadline for dropping courses in a long-session semester, an undergraduate may not drop a course except with the approval of his or her dean, and then only for urgent and substantiated, nonacademic reasons..  

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.

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 question electronically. Be advised that during peak periods we may not be able to answer every question, so you might want to look at the "Already Asked Questions" section of the web page to see if your question has already been answered. In addition, I will be E-mailing you questions and answers that I think are particulalry important, along with any other class announcements.

Section Changes, Adds, and Drops:

All such business (involving either lecture or laboratory) will be handled during the first and second weeks of class by the Organic Division Secretary in Welch 2.212.


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:

Those of you with last names starting with the letters A-L report to WEL 2.224, those with last names starting with M-R report to WEL 1.308, those with last names starting with the letters S-Z report to WEL 1.316.

Thursday, February 21, 7:00 - 9:00 PM, Rooms: WEL 2.224, WEL 1.308, WEL 1.316

Alternate Time (for excused changes only*): 4:00 - 6:00 PM, Room: WEL 3.502

Those of you with last names starting with the letters A-L report to WEL 2.224, those with last names starting with M-R report to WEL 1.308, those with last names starting with the letters S-Z report to WEL 1.316.

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

Alternate Time (for excused changes only*): 4:00 - 6:00 PM, Room: WEL 3.502

Those of you with last names starting with the letters A-L report to WEL 2.224, those with last names starting with M-R report to WEL 1.308, those with last names starting with the letters S-Z report to WEL 1.316.

Thursday, April 24, 7:00 - 9:00 PM, Rooms: WEL 2.224, WEL 1.308, WEL 1.316

Alternate Time (for excused changes only*): 4:00 - 6:00 PM, Room: WEL 3.502

Final Exam:

Thursday, May 8, 2-5 PM,

Rooms: WEL 2.224, WEL 1.308, WEL 2.246

Those of you with last names starting with the letters A-L report to WEL 2.224, those with last names starting with M-R report to WEL 1.308, those with last names starting with the letters S-Z report to WEL 2.246.

*An excused change is one caused by a regularly scheduled (in the course schedule) class or lab class. NOT an organization meeting or job. If you have a job make plans now to be present at the mid term exams.

Taken together, the mid-term examinations will count for 60% of the final course grade. Plan NOW to be present for these exams! During the semester, however, one exam may be missed for any reason whatsoever without penalty. If you take all three exams, we will automatically drop your lowest grade. Failure to take two mid-term exams will result in an automatic F (or, in the case of justifiable excuse, an X) being assigned in 310M/318M. It is particularly important that students avoid any potential conflicts between these scheduled evening exams and any other activities such as laboratory classes. If unavoidable conflicts exist, please come see me immediately. Please note, I am sorry for any inconvenience these out of class two hour exams might cause, but we do things this way for your own protection because:

1) We can use rooms large enough to ensure no cheating is taking place during the exam.

2) The two hour format means we can administer tests that are comprehensive, yet do not have unreasonable time limits. Thus, you will have a chance to show what you know, not just how fast you can write.

Note that for the midterm exam grade that is dropped, the homework points for the weeks leading up to that exam do not count for any other exams. Also, for any exam for which you arrive after the official start time, you will only be allowed to enter the exam room is not a single student has already finished and left. BE ON TIME!!

The final exam, accounting for 40% of the course grade, will be comprehensive in its coverage of the material presented in Chemistry 310N. There will be no make-up exam for the final and it may not be taken at an alternative time for any reason. Specifically, failure to take the final exam at the scheduled time and place without an approved, documented excuse will automatically result in a failing grade being assigned for 310N. A documented, excused absence at the final will result in an Incomplete being assigned for the course. An example of a documented, excused absense is a note from a doctor that states you are physically UNABLE to attend the final. Simply not feeling your best is NOT considered to be an excused absence, as we all have days in which we are not feeling well but must take care of our responsibilities anyway. If you are up and walking around campus on the day of the final, you must take it. NO EXCEPTIONS.

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.


Requests for regrades will be accepted up to one week after each exam is returned. HOWEVER, TO BE REGRADED, THE EXAM MUST BE TAKEN IN INK, NOT PENCIL. In addition, we generally regrade entire exams, not just individual questions. When requesting a regrade on an exam, it is important to attach a brief note on the front of the exam indicating the problem in question, as well as your concern about the grading. Although we generally look over the entire exam, your note will help to direct our attention to where it is needed most. Tip: always check the addition of points on the back of your exam. Properly graded exams can sometimes have their points added incorrectly!!


Course Outline

The following schedule is only approximate, and subject to change during the semester. In other words, if we don't cover material before a test, it will not be on the test no matter what this schedule says.

Unit 1: A Brief Introduction to NMR

Chapter 13

Unit 2: Introduction to Organometallic Compounds.

Chapter 15

Unit 3: Introduction to Carbonyl Chemistry: Aldehydes and Ketones.

Chapter 16

Unit 4: Carbonyl Chemistry Continued: Carboxylic Acids and Derivatives.

Chapters 17,18

Unit 5:Formation of Carbon-Carbon Bonds with Carbonyl Compounds: Enolates

Chapter 19

Unit 6: Aromatic Compounds and Their Reactions

Chapters 20, 21, 22

Unit 7: Amines

Chapter 23

Unit 8: Carbon-carbon Bond Forming Reactions and Synthesis

Chapter 24, Selected sections

Unit 9: Biological Molecules: Lipids, Carbohydrates, Amino Acids and Nucleic Acids

Chapters 25-28, Various Sections

Proposed Exam Topics (Subject to Revision)

Mid-term Exam I: Units 1 - 3

Mid-term Exam II: Units 4 and 5

Mid-term Exam III: Units 6-8

Final Exam: All of the above plus Unit 9.

What You Will Learn in Chem. 310N

This course is designed around a simple idea. By the time a student has finished he or she should be able to 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. A major difference between CH310M/CH318M and CH310N is that CH310N introduces many more ways to make carbon-carbon bonds, so the synthesis possibilities are a great deal more interesting!

In addition, you will be referred 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 solubities, stabilities, reactivites, 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 310N can be viewed as nucleophiles attacking electrophiles, and when in doubt transfer a proton. 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!


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. 310N

If you were happy with your grade in CH310M/CH318M: Keep up the good work!

If you were not satisfied with your grade in CH310M/CH318M: 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] + 77


x = your raw test score

X = the class mean score = S x/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 calculated final course grades:

T-Score ........................Letter Grade

90.000 < T .............................A

80.000 < T < 89.999 ..............B

70.000 < T < 79.999 ..............C

60.000 < T < 69.999 ..............D

T < 60.000 .............................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!