CHM 1321 – Section B
Organic Chemistry I
Professor:
Telephone:
Email:
Blackboard:
Dr. Alison Flynn
DRO 407
D’Iorio Hall
613-562-5800 ext: 6342
alison.flynn@uottawa.ca *Please put CHM 1321 in the subject line*
https://uottawa.blackboard.com/webapps/login/?action=login
Office Hours: Mondays 1:30 – 2:30 pm
Tuesdays 11:30 am – 12:30 pm
(If you can’t make it during these hours, please make an appointment by e-mail)
Prerequisite:
CHM1301 or CHM1311 or 4U chemistry or OAC chemistry or equivalent.
Classes:
Tuesdays
Thursdays
DGDs:
NEW Mondays
17:30 – 19:00 FSS 1006
Wednesdays
16:00 – 17:30 MNT 203
Thursdays
13:00 – 14:30 TBT 333
You can attend either (or both!)
TAs:
Alexander Foo
Evan Haidasz
Kyle McClymont
Daniel Pau
10:00 – 11:30 MRN Aud
8:30 – 10:00 MRN Aud
afoo013@uOttawa.ca
ehaid045@uOttawa.ca
kmccl069@uOttawa.ca
dpau011@uOttawa.ca
Course format: This course is flipped! Here’s how it works: Watch video or read
•  MODULES on
Blackboard
Pre-class test
•  Sapling
•  Due Tuesdays at 8 am
Classes (2)
•  Tuesdays at 10 am
•  Thursdays at 8:30 am
•  MRN Aud, TopHat
DGDs
•  Wednesdays 16:00 17:30 pm MNT 203
•  Thursdays 13:00-14:30
TBT 333
LAB
•  Once every 2 weeks
•  Pre-lab quiz
•  Lab report
Assignment
•  Sapling
•  Due Tuesdays at 8 am
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Have questions?
Discussion
forum
Email (Prof
Flynn)
Office hours
(Prof Flynn)
• Use for confidential
questions
• Use to set up an
appointment
• Ask questions
• Individual or small
groups
• DRO 407
• Tuesdays 11:30 am –
12:30 pm
• Thursdays 10:00 am
– 11:00 am
DGDs (TAs)
• Blackboard
• Use for most
course-related
questions
• Ask conceptual
questions here
• Answer your
classmates'
questions
• Do not post answers
to Sapling questions
until after the due
date
Assessment: • Problem-solving
• Ask about difficult
concepts
• Wednesdays 16:00 17:30 pm MNT 203
• Thursdays
13:00-14:30 TBT
333
Lab questions
• Lab teaching
assistant (TA)
• Lab coordinator Dr.
Venkateswaran:
vrashmi@uottawa.ca
TopHat* (participation):
Pre-class tests (due Tuesdays 8 am):
Assignments (due Tuesdays 8 am):
Lab***
Midterm 1 (cumulative): Tues, February 4, in class
Midterm 2 (cumulative): Tues, March 11, in class
Final Exam (cumulative):
5%
5%
10%
15%
10% – 20%**
10% – 20%**
25% – 45%**
Total: 100%
* Participate 80% of the time and receive 100% for TopHat
**The weighting that gives you the best result will be used to calculate your final mark.
***You must pass BOTH the lecture and the laboratory sections in order to pass the course.
TopHat:
TopHat is a classroom response system: I ask questions, you answer using your cell phone
(text), smart phone, tablet, or laptop—we see how well concepts are understood. Marks are
based on participation in class (i.e., 100% for an answer, 0% for no answer). A TopHat final
mark of 80% will correspond to 100% (i.e., you can miss 20% of TopHat questions without
penalty). TopHat questions will be used in class starting on Thursday, January 9 and in every subsequent
class.
Top Hat course name: CHM 1321 Winter 2014
Direct URL: https://app.tophat.com/e/046205
6-digit course code: 046205
Cost: $5 (a $15 discount will be applied upon checkout)
Registration: Enter your student # for “Student ID”
Technical support: Use TopHat’s technical support
Do not contact Prof Flynn about technical issues—
you are responsible for getting them resolved)
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Sapling Learning:
Sapling's chemistry questions are delivered in a web browser to provide real-time grading,
response-specific coaching, improvement of problem-solving skills, and detailed answer
explanations. Dynamic answer modules enable one to interact with 3D models and figures,
utilize drag-and-drop synthetic routes, and draw chemical structures - including
stereochemistry and curved arrows. Altogether, Sapling is cheaper than a tutor, provides
more value than a solutions manual, and goes beyond a mere assessment exercise to give a
learning experience. To get started:
1.
2.
3.
4.
Go to http://saplinglearning.ca.
a. If you already have a Sapling Learning account, log in and skip to step 3.
b. If you have Facebook account, you can use it to quickly create a SaplingLearning account. Click
the blue button with the Facebook symbol on it (just to the left of the username field). The form
will auto-fill with information from your Facebook account (you may need to log into Facebook
in the popup window first). Choose a password and timezone, accept the site policy agreement,
and click "Create my new account". You can then skip to step 3.
c. Otherwise, click "create account”. Supply the requested information and click "Create my new
account". Check your email (and spam filter) for a message from Sapling Learning and click on
the link provided in that email.
Find your course in the list (listed by subject, term, and instructor) and click the link.
University of Ottawa - CHM 1321 - Winter14 - FLYNN
Select your payment options and follow the remaining instructions.
Work on the Sapling Learning training materials! The activities, videos, and information pages will familiarize
you with the Sapling Learning user environment and serve as tutorials for efficiently drawing molecules,
stereochemistry, etc. within the Sapling Learning answer modules. These training materials are already
accessible in your Sapling Learning course.
During sign up – and throughout the term – if you have any technical problems or grading
issues, send an email to casupport@saplinglearning.com explaining the issue. The Sapling
Learning support team is almost always faster and better able to resolve issues than your
professor.
Pre-class tests: Sapling pre-class tests assess your basic understanding of the weekly reading/video
assignment. They are marked on correctness (not participation).
• Go to Blackboard and watch the assigned video (or read the associated textbook
sections).
• Complete the pre-class test on Sapling: Saplinglearning.ca. The tests are due on Tuesdays at
8 am. The first test is due at 8 am Tuesday, January 14th.
Assignments:
Sapling assignments assess your comprehension of the course to date. Assignments are due
Tuesdays at 8 am. The first assignment is due at 8 am Tuesday, January 14th.
Problem sets:
Keeping up with the problem sets (on Blackboard) will help you succeed in the course. No
marks are given for completing problem sets, but the midterms and final exam will closely
resemble the types of questions asked on the problem sets and assignments.
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Re-grades:
IF there is an error in the marking of your midterm, you may request a re-grade. Please
attach a piece of paper indicating the questions you would specifically like to have reevaluated (or write “addition” if there is an addition error). Do not write anywhere on your
exam after it has been marked! Exams that have been altered in any way will be forwarded to
the academic fraud committee.
Requests for midterm re-grades must be submitted to me in class or to my office no later
than one week from the first day midterms are available for pick-up. Submissions after the
deadline will not be considered.
The entire exam will be re-graded; your new score could be lower than your original score.
Textbook:
Organic Chemistry, 4th Edition, Janice Smith (optional)
Ebook (including free trial): http://connect.mcgrawhill.com/connect/shortUrl.do?accessUrl=smith4e
OR
Organic Chemistry, 8th Edition, L.G. Wade Jr. (optional)
Mastering Chemistry (access to ebook and text’s study area):
http://www.masteringchemistry.com/site/register/new-students.html
Course code: MCFLYNN64925
You can also get earlier editions of the text or similar textbooks (e.g., Solomons).
If you will be taking CHM 3120 (3rd year organic), you can use that text, Organic Chemistry,
2nd edition by Clayden, Greeves, and Warren in this course, too.
Both optional textbooks are available on reserve (4 h loan) at the Morisset library.
Molecular models are required. Darling Molecular Models are recommended. These can be purchased in
MRN 308. Please buy your models soon and bring them to class starting in week 3. We will
be using them regularly in class, and you will need them for the second experiment.
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Laboratories: Schedule:
You will perform one experiment every two weeks. Please consult your personal timetable for
your schedule. You will have to learn some laboratory material independently. You can use the
lab manual and textbook to help you with this. ODD-numbered sections do the experiment in
week 1; EVEN-numbered sections do the experiment in week 2. Experiments start the first
week back (i.e., Jan 6, 2014)!!
Pre Labs:
You must complete a pre-lab quiz with a mark of 80% or better at least 30 minutes before
entering each lab. You may do each quiz as many times as you’d like, but only the LAST grade
is recorded.
The link is on Blackboard: “Lab Space for CHM 1321 and CHM 1721”.
Lab reports:
Due the week after YOU perform the experiment. See the lab manual for additional details.
Requirements:
You must attend and hand in reports for at least five experiments to receive a grade for CHM
1321. Absence from an experiment without an approved exemption will result in a grade of 0
for the evaluation and report for that experiment.
Avoid academic fraud Take advantage of the resources available AND maintain academic integrity!
http://web5.uottawa.ca/mcs-smc/academicintegrity/students.php
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Course Outline: see the learning objectives of each module for more details
Nomenclature: Do it yourself. You are responsible for naming chains up to 12 carbons long for the following
classes of compounds: alkanes, alkenes, alkynes, alcohols, thiols, halides, amines, aldehydes, and ketones. You
will also be responsible for R/S and E/Z nomenclature once it has been taught in class.
Part A: Structure
1) Organic molecular structure
a) “Organic” periodic table
b) Electronegativity and periodic trends
c) Drawing organic structures: Lewis & compressed (line) structures
d) Formal charge method
e) Polarity
f) Atomic and molecular orbitals, molecular orbital theory, bonding and antibonding orbitals
g) Orbital shapes, hybridization, bond angles and structure
h) σ and π bonds, geometries, relative energies
i) Dipoles, Van der Waals forces, H-bonding, molecular structure and bulk properties (review/learn on
your own)
2) Alkanes
a) Properties
b) Line structures
c) σ bond rotation, conformations, energy potential diagrams, Newman projections, sawhorse
projections
d) Cycloalkanes, ring strain, conformations, configurations, syn/anti and cis/trans terminology.
e) Chair conformation, axial and equatorial bonds, chair interconversions
f) Stereochemistry, chiral compounds, configuration and R/S nomenclature, enantiomers, diastereomers
and meso compounds, racemic mixtures
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Part B: Reactivity
1) Organic reaction mechanisms
a) Curved arrow notation
b) Reaction coordinate diagrams
c) Transition state approximations
2) Acids and bases
a) Mechanisms of acid-base reactions
b) Terminology: acid, base, conjugate acid, conjugate base, protonate, deprotonate
c) Acidity of organic compounds: explain by comparing the relative stability of bases using inductive
effects, resonance, electronegativity, atom size, or hybridization.
d) Predict the direction of an equilibrium
e) Meaning and use of pKa values.
f) Relationship between predominant species at equilibrium, pKa, and pH (i.e., Henderson-Hasselbalch
equation)
3) π bonds as electrophiles
a) Polarity of bonds. Carbonyl compounds. Effects of resonance. Concept of mechanism, nucleophiles,
electrophiles.
b) Reduction of carbonyl groups. Additions “across” bonds. Sodium borohydride and lithium aluminum
hydride.
c) Imines. Acid catalysis. Sodium cyanoborohydride.
d) Cyanohydrin formation. Reversal of the reaction. Acid and base catalysis
e) Grignard reagents. Preparation. Polarity. Acid/base reactions. Carbonyl displacements.
f) Organo-lithium reagents. Acid/base reactions. Carbonyl displacements. Alkynyl and vinyl
nucleophiles.
g) Hydrate formation. Equilibrium with carbonyl forms. Hemi-acetal formation. Intramolecular reactions
and ring formation.
h) Acid and base catalysis in carbonyl additions. Oxonium ions. Additions to oxoniums.
i) Microscopic reversibility. Molecular orbitals and reactivity.
4) π bonds as nucleophiles
a) Markovnikov additions. Hydration. Oxy-mercuration. Regioselectivity
b) Anti-Markovnikov additions. Hydroboration-oxidation. Stereochemistry.
c) Radical hydrohalogenation. Chain reactions and initiation.
d) Epoxide formation. Concerted mechanisms. Stereochemistry.
e) Halogenation. Stereochemistry. Halohydrin formation. Regiochemistry.
5) Aromatic compounds as nucleophiles
a) Aromaticity. Huckel’s rule. Antiaromatic compounds. Ions and heterocycles.
b) Allyl groups and resonance. Allyl cation and anion.
c) Electrophilic aromatic substitution. Directing groups. Electrophiles. Heterocycles.
d) Manipulations of directing groups. Reductions. Hydrolysis.
e) Multi-step synthesis. Retrosynthetic analysis. Disconnections.
f) Directed metallation. Directing groups. Strong bases. Electrophiles.
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Success in Organic Chemistry 1. Read the relevant sections in the text before the class.
2. Review notes as soon as possible after each class (drawing the structures and mechanisms is much
more effective than simply reading the material)
3. Write the key concepts in your own words.
4. Practice regularly: Do the assignment questions (not the night before the exam)
NOTE: attempt each question BEFORE looking at the answer. It is much easier to understand
the question with the answer in front of you. The challenge is knowing how to approach the
problem—this comes with practice!
5. Attend tutorials (DGD’s) and extra help sessions.
6. Group study is extremely useful as discussions help to cement concepts.
7. Ask questions!
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