Chemistry 235 Organic Chemistry Spring 2009
This course is a continuation of Chemistry 231 (Introductory Organic Chemistry). It completes
the second half of a full academic year of introductory organic chemistry, and is intended for
those students in programs that require further chemistry courses. In addition to completing a
survey of organic functional groups, synthetic methodology involving carbanions will be
introduced, as well as concepts in π-conjugation, aromaticity, and the chemistry of benzene.
Prerequisites: Chemistry 102 and Chemistry 231 are the prerequisites for this course. Students
must ensure that they have the proper prerequisites; they will be deregistered without warning at
any time if found not to have the required courses. Chemistry 213 is recommended, principally
for the lab component, but you will not be deregistered if you do not have Chemistry 213.
Textbook: Organic Chemistry, Seventh Edition, John McMurry, Thompson*Brooks/Cole,
2007. Students who already have the sixth edition may continue to use it for this course. The
library has other introductory organic chemistry texts that offer a (somewhat) different
perspective on the topics covered in Chemistry 235. A study guide is highly recommended, as is a
molecular model kit.
Laboratory: You are required to be co-registered in a laboratory section of Chemistry 235 while
you are registered in the lecture. A current laboratory manual (green cover) is required,
and is available in the bookstore. Laboratories start the week of January 5. Students who
have previously passed the laboratory portion of either Chemistry 232 or 235 may apply
for a passed lab credit by registering in section LS99.
Lecturer: Dr. Devin Mitchell, Elliott 327, (devinpm@uvic.ca).
Office hours will be announced during the first week. You can also contact me by e-mail. The
second year drop-in centre (Ell 038) can also provide help, check their website for a schedule
(http://web.uvic.ca/~berryde/2ndyrdropin/index.htm).
Web site: Lecture: http://members.shaw.ca/devinmitchell/chemistry235/, the link to the lab web
site for thelaboratory portion is at the top of that page.
Grading: The grading formula consists of three components; laboratory, quizzes and final exam.
The percentage component of each is shown in the table below. Both the lecture and laboratory
portions of the course must be passed independently of each other in order to successfully
complete the course.
Laboratory
Quizzes
Final Exam
Total
33
25 (5 x 5%)
42
100
1) Quizzes will be written in class, and ALL quizzes count towards the lecture grade. Quizzes are
compulsory. The final exam mark will not, under any circumstances, be taken as a replacement
for the lecture mark calculated from the percentages listed above.
2) The mark for any quiz or exam which is not written, and for which no official medical excuse
is provided will be zero. The excuse must be dated within the week of the quiz and must be
handed in within two weeks of the quiz date. The medical excuse must provide sufficient
information to establish that the student was not able to write the quiz or Component %
exam due to his/her medical condition on the date of the quiz or exam in question. The
student will also be required to give written consent for information about her/his medical
condition to be disclosed to the instructor. Any such information obtained is treated as
confidential. Certain other types of personal or family circumstances may be considered
as equivalent to a medical excuse if accompanied by appropriate documentation. There
is no requirement for us to provide make-up quizzes. Students with medical excuses for
missed quizzes will have their quiz scores averaged on the remaining quizzes written.
Quiz writing time is 20 minutes during a regular lecture period.
3) Quizzes will test your knowledge of the material covered over a short span of chapters/
sections. The fi nal examination will cover the entire course.
4) Conversion of numerical percentage scores to letter grades will be based on the following
approximate scale.
A+
> 90
A
8589.9
A8084.9
B+
7579.9
B
7074.9
B6569.9
C+
6064.9
C
5559.9
D
5054.9
F
< 49.9
5) Quiz dates (and chapter coverage) are as follows: Friday, January 23 (Chapters 5, 10
& 14), Friday, February 6 (Chapters 15 & 16), Friday, February 27 (Chapter 19), Friday,
March 13 (Chapters 20 & 21), Friday, March 27 (Chapters 22 & 23).
6) It has been departmental practice to post a list of course marks and quiz marks by student
number. If you desire that your grade and student number NOT be posted, notify your
instructor.
7) The date of the final examination is set by Records Services. Students are advised not to
make travel plans until their exam schedule is known. Exceptions/exemptions based on
travel plans will not be made.
Course Topics and Suggested Problems
Organic Chemistry can only be learned by actively engaging in the course material. This requires
attending the lectures, laboratories, and doing the suggested problems. Keeping up with the
course material will make studying for the quizzes and exams easier. Use the learning resources
available (second-year drop in centre, textbook web site (see the front of the book), etc.). Organic
chemistry is a subject that cannot be crammed the night before the exam. It is imperative that you
try as many problems as possible —the lists below are a suggested minimum. The key to learning
is to find insight and realize that certain principles are being followed in what appear to be
unrelated reactions.
Chapter 5; An Overview of Organic Reactions
This chapter is intended as a review chapter, no specific problems are assigned. The topics
in this chapter are fundamental to the rest of the course. The material will be on the first
quiz.
Chapter 10; Organohalides
All sections are covered as review topics, the material will be on the first quiz.
Problems: 6th edition: 10.3 - 10.13, 10.17, 10.23, 10.35, 10.37, 10.39, 10.42.
Problems: 7th edition: 10.3 - 10.13, 10.17, 10.23, 10.33, 10.35, 10.37, 10.39.
Chapter 14; Conjugated Compounds
Covered sections: 6th edition: 14.1 - 14.6, 7th edition: 14.1 - 14.5.
Problems: 6th edition: 14.1 - 14.10, 14.20 - 14.23, 14.27, 14.33, 14.34, 14.40, 14.43, 14.44, 14.55.
Problems: 7th edition: 14.1 - 14.10, 14.21 - 14.23, 14.26, 14.32, 14.33, 14.40, 14.43, 14.44, 14.55.
Chapter 15; Benzene and Aromaticity
Covered sections: 6th edition: 15.1 - 15.8, 7th edition: 15.1 - 15.7.
Problems: 6th edition: 15.1 - 15.8, 15.10, 15.11, 15.25, 15.26, 15.30, 15.33, 15.37, 15.40, 15.41.
Problems: 7th edition: 15.1 - 15.8, 15.10, 15.11, 15.25, 15.26, 15.29, 15.32, 15.36, 15.41, 15.42.
Chapter 16; Chemistry of Benzene: Electrophilic Aromatic Substitution
All sections are covered.
Problems: 6th edition: 16.1 - 16.24, 16.30, 16.31, 16.34, 16.35, 16.36, 16.54, 16.73.
Problems: 7th edition: 16.1 - 16.24, 16.31, 16.32, 16.35, 16.36, 16.37, 16.55, 16.73.
Chapter 19; Aldehydes and Ketones: Nucleophilic Addition Reactions
Covered sections: 6th edition: 19.1 - 19.12, 19.14, 7th edition: 19.1 - 19.11, 19.13.
Problems: 6th edition: 19.1 - 19.20, 19.28, 19.32, 19.33, 19.41, 19.48, 19.49, 19.53, 19.56, 19.58.
Problems: 7th edition: 19.1 - 19.22, 19.30, 19.34, 19.35, 19.42, 19.50, 19.51, 19.54, 19.57, 19.59.
Chapter 20; Carboxylic Acids and Nitriles
Covered sections: 6th edition: 20.1 - 20.9, 7th edition: 20.1 - 20.7, omit 20.3.
Problems: 6th edition: 20.1 - 20.13, 20.23, 20.24, 20.33 - 20.36, 20.49, 20.50.
Problems: 7th edition: 20.1 - 20.4, 20.6 - 20.13, 20.25, 20.26, 20.36 - 20.39, 20.52, 20.53.
Chapter 21; Carboxylic Acid Derivatives
Covered sections: 6th edition: 21.1 - 21.7, 7th edition: 21.1 - 21.7.
Problems: 6th edition: 21.1 - 21.11, 21.13 - 21.22, 21.36, 21.37, 21.42, 21.54, 21.55, 21.57.
Problems: 7th edition: 21.1 - 21.21, 21.36, 21.37, 21.43, 21.56, 21.57, 21.62.
Chapter 22; Carbonyl Alpha-Substitutions
All sections are covered.
Problems: 6th edition: 22.1 - 22.9, 22.11 - 22.17, 22.21, 22.24, 22.37, 22.44, 22.48, 22.49.
Problems: 7th edition: 22.1 - 22.16, 22.20, 22.23, 22.35, 22.44, 22.49, 22.50.
Chapter 23; Carbonyl Condensation Reactions
Covered sections: 6th edition: 23.1 - 23.13, 7th edition: 23.1 - 23.12.
Problems: 6th edition: 23.1 - 23.22, 23.28, 23.39, 23.42, 23.43, 23.45, 23.54, 23.56.
Problems: 7th edition: 23.1 - 23.22, 23.28, 23.39, 23.42, 23.43, 23.45, 23.56, 23.57.
Chapter 24: Amines
Covered sections: 6th edition: 24.1 - 24.8, 7th edition: 24.1 - 24.8.
Problems: 6th edition: 24.1 - 24.19, 24.29, 24.30, 24.32, 24.38, 24.39, 24.41, 24.45, 24.57, 24.59.
Problems: 7th edition: 24.1 - 24.19, 24.33, 24.34, 24.36, 24.42, 24.43, 24.47, 24.52, 24.63, 24.64.