Chemistry 220
Instructor: Dr. James Cormier
Office: PSC 3063
Text:
Telephone: 867-5080 (o); 863-9167 (h) e-mail: jcormier@stfx.ca
Organic Chemistry, 8 th
ed., Wade. The book and study guide are available in the bookstore. In the first term, we will cover (approximately) Chapters
1-11, and bits of a few other chapters. In the second term, we will go up to about Chapter 23. Not all topics in all Chapters will be covered, so it is important to stay current. The idea is to have a survey of functional groups and an understanding of reaction mechanisms. This leads to the ability to do elementary synthesis.
Lectures: There will be three lectures each week, in P block. This is a 6 credit (two semester) course.
Labs: There will be one three hour lab period each week (either Tuesday or
Wednesday afternoon).
Topics: Chapter 1: Introduction and a review of bonding, Lewis structures, electronegativity and polarity, resonance, structural formulae, Lewis and
Brønsted-Lowry acids and bases
Chapter 2: Structure and properties of organic molecules; atomic and molecular orbitals, hybridization, molecular shapes, single and multiple bonds, polarity of bonds and molecules
Chapter 3: Alkanes; structure and stereochemistry, general properties and reactions, conformations, cyclic alkanes and their conformations, isomerism
Chapter 4: Chemical reactions; free-radical halogenation as an example of mechanism
Chapter 5: Stereochemistry; chirality, optical activity, R/S nomenclature, racemates, optical purity, Fischer projections, enantiomers, diastereomers, meso compounds, resolution
Chapter 6: Alkyl halides; properties, preparation, reactions (Sn1, Sn2, E1,
E2)
Chapter 7: Alkenes; properties of the double bond, physical properties of alkenes, preparation (elimination reactions)
Chapter 8: Alkenes; reactions, electrophilic addition, catalytic hydrogenation, oxidation
Chapter 9: Alkynes; structure, preparation, reactions
Chapter 10: Alcohols; structure and preparation, use of organometallics in synthesis,
Chapter 11: Alcohols; reactions, acidity, oxidation, nucleophilicity
Chapter 14: Ethers, epoxides; properties, preparation, reactions

Chapter 15: Conjugated systems; allylic ions and radicals, conjugated dienes, 1,2- and 1,4-addition
Chapter 16: Aromaticity; structure and properties of benzene and derivatives, aromaticity, antiaromaticity, Hückel’s rule
Chapter 17: Reactions of aromatic compounds; electrophilic aromatic substitution, halogenation, nitration, sulfonation, Friedel-Crafts alkylation and acylation, directive and activating/deactivating effects
Chapter 13: Nuclear magnetic resonance spectroscopy
Chapter 12: Infrared spectroscopy (very briefly)
Chapter 18: Carbonyl compounds; ketones and aldehydes, properties and preparation, nucleophilic acyl addition, Wittig reaction, hemiacetals, acetals, aldol reaction
Chapter 20: Carboxylic acids; properties and preparation, acidity, reactions, nucleophilic acyl substitution
Chapter 21: Carboxylic acid derivatives; esters, anhydrides, amides, acid halides
Chapter 19: Amines; properties and preparation, basicity, reactions
Assignments: There will be an assignment posted on my web page each Friday, along with some suggested practice questions from the text. The following
Friday, there will be a short (10 minute) quiz in class based on the assignment and recent lecture topics. The quiz is to be written at that time . Answers to assignments will be posted on the same web page.
There may also be occasional demonstrations done in class on which you will be asked to answer some questions. This will form part of the assignment mark.
Marking Scheme: Final
October quiz (Oct. 16) 5%
November quiz (Nov. 20) 5%
December exam (TBA) 20%
February quiz (Feb. 12)
March quiz (Mar. 26)
5%
5%
Christmas
15%
15%
40%
----
----
April exam (TBA)
Assignments
Laboratory
*
40%
10%
----
15%
10% 15%
*The lab section of the course is required . You cannot pass the course without passing the lab and lecture components separately. Labs cannot be made up. If you have any medical condition which may interfere with your ability to do the labs, or if you are pregnant, or think you might be, please let us know as soon as possible. If you have previously completed the lab portion of the course, that part of the grade will be distributed by evenly increasing the proportion from midterms.
Plagiarism and Cheating:

Copying or other forms of cheating will not be tolerated. This includes copying of labs from students who took the course previously. Read the
Section of the Calendar on plagiarism (Sec. 3.9).
A link is provided in
Sec.3.9 (f) of the Calendar. Read it!
Lab Exercises: You will be sold a set of exercises at the lab, along with two folders.
Each week, you will hand in the previous week’s lab to be marked, in one folder, and receive the lab from the week before, marked, in the other.
Labs are to be handed in at the beginning of the next lab period. Late labs are penalized at the rate of 20% per day, and there are no makeup lab days. You will be given general information on lab procedures and safety at the first lab, and specific information at the beginning of each subsequent lab. Safety glasses are required , contact lenses and open-toed shoes/sandals are not permitted. Lab coats are required. Loose hair should be tied back. Pants are recommended over shorts or skirts.
Tutorial: There will be an evening tutorial session held weekly. You should take advantage of this. Other tutorials may be scheduled as need arises.
Missing Tests: Tests and exams may be missed for medical reasons, if an appropriate note is supplied. A missed test should be made up as soon as possible.
Tests and exams may not be missed because of travel plans. In particular, plan to be here for the whole Christmas and Final exam period.
Remember that that the exam schedule given here and in the timetable is tentative.
Unsolicited Fatherly Advice:
This course requires a lot of attention to detail. It is important not to fall behind. Attend lectures, do assignments and labs independently and attend tutorials. Ask questions in class; you won’t look stupid and it’s unlikely you’re the only person having trouble with that particular point. Above all, if you are having trouble, get help immediately. See me first . I may be able to solve the problem or find someone who can. We can have a regular appointment, find a tutor, or whatever is necessary. Remember, you’ve already paid for it! Students tend to wonder what I want you to learn in the course. The short answer is “Everything”. The long answer is that, at the end of the course you should have a general understanding of the structures of organic compounds, and how structure relates to their properties. Inherent in that is the understanding of the reactivity of organic compounds. Reactivity can best be understood in terms of the mechanisms of the reactions. When we understand reactions, we can understand how to manipulate them to create new molecules of our choosing; that is, we can do synthesis. Thus, synthesis, reactivity and mechanism are all bound together.