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

WileyPlus1. 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. It is not possible to learn every facet of organic chemistry. 2. Persistence, repetition, and practice are necessary. You may

not understand it the first time. Do the assigned problems.3. Some problems in organic chemistry have exact solutions;

others have more than one correct answer. 4. Organic chemistry is based on a relatively small number of

basic principles. Difficulty arises due to DIVERSITY of structures and reactions.

5. The aim is to teach you to recognize, understand, manipulate, and build organic compounds. DRAWING molecules in one form or another is essential.

6. 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

PharmaceuticalsSome important examples:Lipitor, Tamiflu, IbuprofenAspirin, Allegra, AZT, CialisCelebrex, Risperidone, SingulairL-DOPA*, Fentanyl, Insulin*, Morphine*Oral contraceptives, Prozac, Quinine*Tagamet, Taxol*, Viagra(* naturally occurring)

Polymerspolycarbonatepolyethylene, PVCpolyacetylene, polypyrrole, polythiophenesNylon, Teflon, Kevlar, Nomex

MiscellaneousSunscreens, anti-oxidants, nutritional supplements, sugar and fat substitutes, alcohol, nicotine, paints and coatings, liquid crystals, OLED, gasoline, biofuels, natural gas, PCBs, dioxins

Illicit DrugsMethamphetamine, Ecstasy, Cocaine, LSD, Mescaline, Heroin, Morphine, GHB, Tetrahydrocannabinol (THC)

Relevance of some simple organic compounds

CO2H

CH3

CH3 CH3

Ibuprofen (Motrin, Advil)

HO

CH3 R

H

Vitamin D

O

O Cl

Cl

Cl

Cl

Dioxin

CH3O

HOHN

O

CH3

CH3

capsaicin

methamphetamine(watch Breaking Bad for synthesis)

HN

CH3

CH3

(from Solomons)

(from web)

Organic Chemistry can be conveniently divided into four main subtopics:

1. Structures2. Reactions3. Mechanisms4. Synthesis

3 4 5 6 7

Valence electrons:

What do you need to remember from Chem 101?

(from Solomons)

The Octet (8) Rule for Lewis Structures

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 IsomerismAn example of stereoisomerism (stereoisomers have the same molecular formula and same bond connectivity but differ in the arrangement of atoms in space)

Formal Charges

“move only non-bonding electrons and electrons in bonds to adjacent positions”

Resonance StructuresOrganic 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.

contributes more contributes less

Drawing Molecules

Perspective FormulaHow 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.