University of Victoria CHEM 231
INTRODUCTORY ORGANIC CHEMISTRY
Course website web.uvic.ca/~chem231 (postings of course information,
midterm test dates and locations, course handouts, WileyPlus information,
important announcements, etc)
Pre-requisite: Chem 101 or Chem 150 (or equivalent).
Objectives Learn basic concepts in organic chemistry that explain the properties
of organic molecules: how and why they react, and how they are synthesized.
We will apply these objectives to alkanes, alkenes, alkynes, alkyl halides,
alcohols, and ethers. The course will also develop an appreciation and basic
knowledge of where and how organic chemistry impacts us in everyday life.
Website for online quizzes using WileyPlus
Detailed information will be provided in class on how to access the
WileyPlus website.
© Peter Wan 2014
WileyPlus
1. Purchase of WileyPlus is required to access the online quizzes for this
course. We have negotiated a discounted package price that also includes
the e-text, e-solutions manual, and the lecture book.
2. There are 7 online quizzes that covers the major chapters of this course. It
is worth a total of 7% of your course mark. The quizzes can be written
anytime before the end of the last day of classes.
3. The online quizzes should be regarded as minimal preparation for this
course. You should also do the assigned problems, past midterms and
final exams, etc.
4. Plan ahead: no excuse will be accepted for failure to complete the quizzes
by the end of the term.
5. WileyPlus is also more than a place to do your quizzes. It has extensive
resources such as the e-text, video presentations, sample lectures, worked
out problems, etc. Check it out!
6. Your access code for WileyPlus is good for one academic year. You can use
the same code for Chem 232 in Jan or May 2015.
Learning Organic Chemistry
1.
2.
3.
4.
5.
6.
It is not possible to learn every facet of organic chemistry.
Persistence, repetition, and practice are necessary. You may
not understand it the first time. Do the assigned problems.
Some problems in organic chemistry have exact solutions;
others have more than one correct answer.
Organic chemistry is based on a relatively small number of
basic principles. Difficulty arises due to DIVERSITY of
structures and reactions.
The aim is to teach you to recognize, understand, manipulate,
and build organic compounds. DRAWING molecules in one
form or another is essential.
The 3D nature of molecules (STEREOCHEMISTRY) present
one challenging aspect of organic chemistry. A molecular
model set will help immensely.
Examples of Important Organic Materials
Pharmaceuticals
Polymers
Some important examples:
polycarbonate
Lipitor, Tamiflu, Ibuprofen
polyethylene, PVC
Aspirin, Allegra, AZT, Cialis
polyacetylene, polypyrrole,
Celebrex, Risperidone, Singulair
polythiophenes
L-DOPA*, Fentanyl, Insulin*, Morphine*
Nylon, Teflon, Kevlar,
Oral contraceptives, Prozac, Quinine*
Nomex
Tagamet, Taxol*, Viagra
(* naturally occurring)
Illicit Drugs
Methamphetamine, Ecstasy, Cocaine, LSD,
Mescaline, Heroin, Morphine, GHB,
Tetrahydrocannabinol (THC)
Miscellaneous
Sunscreens, anti-oxidants, nutritional supplements, sugar and fat
substitutes, alcohol, nicotine, paints and coatings, liquid crystals,
OLED, gasoline, biofuels, natural gas, PCBs, dioxins
Relevance of some simple organic compounds
(from web)
(from Solomons)
Organic Chemistry can be conveniently
divided into four main subtopics:
1.
2.
3.
4.
Structures
Reactions
Mechanisms
Synthesis
What do you need to remember from Chem 101?
The Octet (8) Rule
for Lewis Structures
Valence electrons:
3
4
5
6
7
(from Solomons)
1. THE BASICS. Bonding and Molecular
Structure. (approx. lecture time: 1.5 hr)
Topics covered: 1.1-1.8, 1.10, 1.12-1.17.
Molecular structure of
ethylene
Drawing resonance
structures
The Structure of Ethane
The Structure of Ethylene
Cis-Trans Isomerism
An example of stereoisomerism (stereoisomers have the same molecular
formula and same bond connectivity but differ in the arrangement of atoms
in space)
Formal Charges
Resonance Structures
Organic compounds can have more than one valid Lewis structure. All
such structures (called resonance structures) must be considered in
order to better understand its true electronic structure.
“move only non-bonding electrons and
electrons in  bonds to adjacent positions”
contributes more
contributes less
Drawing Molecules
Perspective Formula
How to show 3D information using 2D representation:
You need to use lines and wedges (solid and hashed)
Some students have difficulty seeing these structures in 3D space.
This is when you should begin to use your molecular models.