CHEMISTRY 2320-2 Organic Chemistry II

Fall 2012 – MWF 10:30-11:20AM MPC 110


Dr. Steven Bachrach


115 Oakmont, Room 205




Office Hours

MWF 1:00pm-2:00pm, Java City or by appointment

Help Sessions

To Be Determined

Peer Tutor

Ruth Hahn (our section),, MW 8:00-9:30pm Java City (MT 8:00-9:30pm on weeks of the exams)
Helene Nepomuceno, ST 8:00-9:30 pm in CSI 337,


John McMurry, “Organic Chemistry” Eighth Edition (required)
Susan McMurry, “Study Guide and Solution Manual” (recommended)
David Klein, “Organic Chemistry II as a Second Language” (recommended)


This is the second semester of a two-semester sequence of organic chemistry. In this course, we will build upon your foundation in organic chemistry by introducing many more functional groups and learning how to interconvert them. The goals will be to increase your skills in nomenclature, understanding reaction mechanisms, functional group transformation, and multi-step synthesis.


We will have 3 exams and a comprehensive final exam. Your grade for the course will be based on your highest two exam scores, the final exam, and one of the following two options, whichever is higher: your score on the remaining exam or the sum of your quiz scores. Each exam is worth 100 points. Each quiz is worth 10 points; the quiz grades will be summed together and scaled to 100 points. The grade scale will be discussed in class after each exam; the scale will be no more severe than >90% A, >80% B, >70% C, >60% D, <60% F. Exam dates are listed in the course outline; quiz dates will be announced in class.

Top 2 Exams:

200 points

Remaining Exam or Quizzes

100 points

Final Exam:

150 points


450 points


Exams can only be made up in cases of excused absences, including religious holidays, death in the family, extreme documented illness, and for students representing the university off-campus such as in sporting events.  For regular season athletics, students must arrange for makeups as soon as the schedule becomes available.  In all cases, failure to arrange a makeup as soon as possible will preclude the arrangement. An option for make-up is to substitute the quiz grades for the missed exam. No make-ups will be offered for the quizzes; we will be dropping 2-4 quizzes in determining the quiz total.

Web Site


Homework problems for the class are listed below. Homework will not be collected nor graded, however, I am available to check/discuss your answers in office hours and help sessions. Your peer tutors can also help with the homework.

Chapter 16

28, 30, 32, 35, 39, 43, 45, 47, 49, 51

Chapter 17

25, 29, 35, 37, 45, 48, 51, 60, 67, 70

Chapter 18

23, 24, 27, 35, 39, 44, 51, 56, 58, 61

Chapter 19

30, 32, 35, 36, 38, 40, 46, 50, 55, 58, 63, 68, 70, 73

Chapter 20

21, 22, 26, 31, 32, 34, 36, 39, 45, 48, 52, 56, 57, 61

Chapter 21

31, 34, 38, 39, 48, 51, 55, 61, 68, 70, 73

Chapter 27

14, 17, 22

Chapter 22

20, 22, 25, 27, 29, 33, 36, 38, 43, 45, 48, 50, 55

Chapter 23

27, 28, 31, 35, 37, 41, 43, 48, 49, 53, 57, 60, 64

Chapter 24

30, 31, 34, 35, 36, 40, 44, 47, 48, 54, 66, 70, 74, 75

Chapter 25

30, 33, 38, 40, 42, 43, 50, 52, 57, 58, 68

Chapter 26

26, 27, 50, 53

Chapter 30

15, 16, 20, 21, 24, 30

Additional problems can be found on the textbook’s web site:

Honor Code Policy:

All students are covered by a policy that prohibits dishonesty in academic work. The Academic Honor Code covers all those who entered the fall of 2004 or later. Under the Code, a faculty member will (or a student may) report an alleged violation to the Academic Honor Council. It is the task of the Council to investigate, adjudicate, and assign a punishment within certain guidelines if a violation has been verified. Students who are under the Honor Code are required to pledge all written work that is submitted for a grade:  “On my honor, I have neither given nor received any unauthorized assistance on this work” and their signature.  The pledge may be abbreviated “pledged” with a signature.

You may use previous exams as study tools. Collaboration is encouraged for homework assignments and studying for exams and quizzes. Exams and quizzes are to be taken without assistance from notebooks, books, calculators, computers, other students, or any other source of assistance. You are allowed to use molecular models during exams and quizzes.

Tentative Course Outline





Review of organic I, electrophilic substitution

Ch. 16.1-2


Aromatic substitution and polysubstitution
Oxidation and reduction of aromatics

Ch. 16.3-16.7
Ch. 16.9-11


Alcohols, spectroscopy, synthesis Reactions, Phenols

Ch. 17.1, 17.11,17.2
Ch. 17.6-17.10


Ethers, Spectroscopy, Reactions of Ethers, Thiols

Ch. 18.1-18.9


Aldehydes and ketones, spectroscopy
Exam 1 (Wednesday Sept. 19)
Preparation, Nucleophilic substitution

Ch. 19.1, 19.14
Ch. 19.4-19.6


Grignard rxn, Reductions
Wittig, Conjugate addition

Ch. 19.7, Ch. 17.5, Ch. 17.4
Ch. 19.8-19.13


Carboxylic acids
Carboxylic acid derivatives

Ch. 20.1-20.8
Ch. 21.1-21.3


Reactions of acid derivatives, esters, amides
Soaps and waxes

Ch. 21.4-21.10
Ch. 27.1-3


α-Carbon reactions
Exam 2 (Wednesday Oct. 17)

Ch. 22.1-22.6


Enolate reactions
Condensation Reactions

Ch. 22.7-22.8
Ch. 23.1-23.11


Amines, basicity, spectroscopy

Ch. 23-11-23.13
Ch. 24.1-24.6, 24.10


reactions of amines, heterocycles
Carbohydrates: reactions, disaccharides

Ch. 24.7-24. 9
Ch. 25.1-25.5


Carbohydrates, reactions, disaccharides
amino acids

Ch. 25.6-25.10
Ch. 26.1-26.4, 26.7-26.8


Exam 3 (Monday Nov. 19)



Coupling Reactions
Enantioselective synthesis



Pericyclic Reactions

Ch. 30


FINAL EXAM – Thursday, December 13, 8:30am – 11:30am

Please note that I will try very hard to follow this schedule. However, the only rigorously maintained items on the schedule are the dates of the exams (listed in bold).

Tips for Success in Organic and Bioorganic Chemistry

  1. The material from the first semester is still applicable and necessary for this class. Organic chemistry continually builds upon itself. If you don’t remember topics from last semester, you absolutely must spend some time early in the semester to get up to speed.
  2. The pace of this class will be even more relentless than last semester. You cannot fall behind at all. Come to class having already read the material from the text before I discuss it. Do the homework problems as we go along; don’t wait until right before the exams.
  3. Do at least all of the problems I assign as homework. Do more if you are having difficulty. Don’t keep repeating the same problems. There are lots of other organic chemistry textbooks and web sites that offer many alternative (and useful) problems.
  4. Be real careful in using the answer book. Do not come to rely on it!
  5. If you are having difficulties, don’t wait to get some help. You are welcome to see me as often as you need, whether it is during my office hours, at the help sessions or at some other time that we arrange. Come to the help sessions with questions to ask. I am available for assistance at pretty much any other time during the day. I am happy to help via email but this is somewhat limited by not being able to easily include chemical structures. Make use of the peer tutor, they have been through this class and can be of great help!

Some online resources

Test answers

Quiz answers

Office Hours and Help Sessions for the end of the semester

Ruth Hahn