CHEM 260 Course Syllabus

Organic Chemistry for Engineers

General Course Information

Instructor Information
Instructor Section Day/Start Time Assigned Lecture Office Email
Theatre Number
Dr. Jay Wickenden 109 MWF 9 AM SWNG 221 CHEM D346 [email protected]
MWF = Monday, Wednesday and Friday.
* Note that faculty may opt to hold office hours virtually. Please try to avoid arriving unannounced to my office (outside
of regularly posted office hours) unless directed otherwise.

Course Materials
Item Purchase Location Required or Cost
Recommended
CHEM 260 textbook ‐‐‐‐ Recommended Free (on Canvas)
Molecular model set Anywhere Recommended Varies
Canvas ‐‐‐‐ Required Free
Zoom** See Canvas link Required Free
** Zoom has been approved by UBC for remote exam invigilation and may be used. We may also need to use this for lecture
delivery due to technical difficulties. IF USED DURING AN EXAM, WE WILL NOT RECORD YOU. All exams are in person,
however this may change due to official announcements by UBC.

Grading Scheme
Item In‐person Open or Date Room Weight
or Online? Closed Book?
Midterm 1 In‐person Closed Tuesday October 10th – 6:30 – 8:40 BIOL 1000 20%
pm
Midterm 2 In‐person Closed Tuesday November 21st – 6:30 – 8:40 CHEM B250 20%
pm
Final Exam In‐person Closed Date TBA by UBC* TBA 45%
Quizzes Online Open (open Best 4/5 quizzes*** N/A 15%
internet**)
Total 100%
* The final exam date is announced by UBC. Course instructors have no say as to when the final exam will be
booked. As soon as the teaching team knows the date, it will be provided to you. Missing your final exam
because you have a flight booked is not an approved reason to miss a final exam.
** Students are not allowed to work together or communicate with another person, using any method, during
the quiz.
*** Your lowest quiz score will be dropped; best 4/5 quizzes. You do not need to do anything in this situation, it
is done automatically. So, each quiz is really worth 3.75% of your grade.

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 Course Content 2023

Number* Topics
1 General Concepts: hybridization, acid‐base equilibrium &
resonance
2 Structure & Bonding: Isomers, IUPAC nomenclature,
functional groups, conformational analysis, cycloalkanes
3 Stereochemistry
4 Bimolecular mechanisms (SN2 & E2)
5 Unimolecular mechanisms (SN1 & E1)
6 Additions to alkenes/alkynes (Bromination, HBr addition,
hydration, polymerization, reduction
7 Electrophilic aromatic substitution
8 Alkyl halides: Free Radical Reactions
9 Reactions of Alcohols: oxidation/reduction, conversion to
alkyl halides
10 Aldehydes and Ketones: Hydration, acetal
formation/hydrolysis, carbohydrates
11 Carboxylic acids, esters & amides: formation and
hydrolysis, peptides
* Topic numbers do not equal the number of lectures required to complete this topic.

Teaching Style and/or Delivery Method of Course Content

All UBC professors are afforded Academic Freedom, which means they can teach whatever they see as important,
however they see as appropriate. The material presented in CHEM 260 is typically a “blended teaching model”
which means your professor will more than likely lecture for a time, then expect you to work on problems
(individually, or as a group, or as in‐class exercise). Learning objectives are available for the CHEM 260 course,
which will provide students with a guide as to what we expect students to be able to do on examinations. Learning
objectives may be found at the beginning of each slide deck. Learning objectives are not a contract however.

Use of Zoom in CHEM 260

Some areas of the course, including office hours, may be held through Zoom, which is integrated with our Canvas
course. The section instructor may switch to another delivery method with notice to the students. Please note
that Zoom office hours will not be recorded. Review sessions will be held on Zoom and will be recorded to ensure
all students have the opportunity to view what took place. Do not distribute recordings of the class sessions as
doing so is a copyright violation as well as violation of your classmates' and instructor’s privacy. In the event we
are required to move online, we will not record students during the examination process.

ORC or Office hours: These sessions will be smaller, and therefore you can choose to activate your camera and
microphone and speak with your professor or a TA directly. When arriving into the virtual room, please follow
these instructions.

1. To get the attention of the TA, please use the “Reactions” button. A “raise hand” option is found in there.

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 2. Please wait until the TA calls your name, at which point, you may communicate to them however you wish.
We prefer if you use your microphone and camera, but it is not required. If you are more comfortable,
please use the chat feature.
3. Please allow other students to ask questions as well. Ask one, maybe two shorter questions and allow the
TA to answer. Then, lower your hand so that others can ask a question.

INAPPROPRIATE OR ILLEGAL BEHAVIOUR ONLINE

This will not be tolerated. During a lecture, the chances are minimized due to the size of the class. CHEM 260 has
taken numerous steps to ensure the security of our content delivery. However, in the unlikely event something
does occur, please note that all students are held to the Student Code of Conduct, including an online learning
environment. Abusive behaviour towards anyone (faculty, TA or fellow students) will not be tolerated, and you
will be reported.
Piazza
Piazza will be available via the course Canvas shell. While students will appear anonymous to each other, you must
register using the name we have as part of our class list. Students that are not identifiable will be removed from
this page periodically. This is done to enforce the UBC Student Code of Conduct. Piazza will be deactivated when
quizzes and examinations are available or currently happening.

Online Quizzes
Quizzes will be provided to students during the term using the Canvas quiz feature. Quizzes will be available for a
certain window of time, and you will be provided one attempt at the quiz. Quizzes are open‐book and open
internet. Students are not permitted to work or communicate with anyone, either in person or in the virtual world.
This means students are should not use Discord, Reddit, WeChat, or any other chat‐based programs. Chegg is also
screened frequently during quizzes. All students will get one attempt at each quiz. The quiz will be available to
open for a length of time. Once opened, you will have a certain amount of time to complete this quiz.

We will not scale quizzes. If you tell/show someone else what is on the quiz, their grade may be higher than yours.

For example: A hypothetical quiz is available on Monday all day. Once opened, a student would have 10 minutes
to complete the quiz.
Number of missed Quizzes What you should do…
Nothing! The grade for this quiz will be zero, and it will be dropped when we
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calculate your final grade. WE WILL NOT re‐weight to the final in this situation.
You should fill out an In‐Term Academic Concession From (available on Canvas).
The 2% assigned to this quiz will be re‐weighted to the final exam.
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You are required to fill out this In‐Term Concession Form for each missed quiz
after the first missed quiz. If we do not see a form, you will get a grade of zero.

Examinations (Midterms and Final) – MAY BE SUBJECT TO CHANGE

Delivery: Exams will be in‐person. Announcements will be made closer to the exam date(s) about location.

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Two‐Stage Exams in CHEM 260: Continuing with what was started in the fall of 2021, we will be using two‐stage
(collaborative) exams in CHEM 260 F2023. A two‐stage exam is a more active way of assessing a student’s content
knowledge. The exam has two‐stages, the individual portion, and the group portion. Operation of the exam occurs
as follows:
1. Students write the individual portion of the exam for the noted length of time.
2. Students submit all materials from the individual portion of the exam.
3. Students will be allowed time to form groups within the room they are wrote their individual exam. These
will be your group portion team members.
4. The exam booklet will have a group code on it. This is the code for everyone, and must be bubbled‐in on
your answer sheet. You must also write and bubble‐in every members ID on this answer sheet.
5. You will all discuss the questions and come to a consensus. Only one exam paper will be submitted from
any particular group, so you should all either agree, or have a majority vote on each question.

General Points Regarding Two‐Stage Exams

1. Two‐stage exams are not required. Meaning if you don’t complete the second stage, your exam grade is
100% based on your individual exam grade.
2. If you choose to write the second stage, your midterm grade is 85% based on your individual exam grade,
and 15% based on your group exam grade.
3. The group portion will either be identical, or very similar to the individual exam. It is a student’s
responsibility to identify changes that may have occurred between the two exams.
4. Your group exam grade can never hurt your overall performance. Meaning, if you were to achieve a
higher grade had you not written the group portion, we will award you that score.
5. If a regrade is requested for a group exam, and the grade changes (positive or negative), all members of
that group will be awarded this grade change automatically.
6. If one member leaves the exam early, or doesn’t participate at all during the group portion, you should
report them to the TA or Dr. Wickenden. Note there is a difference between someone that is quiet, versus
someone that is obviously not participating in the process at all. After the case has been reviewed by the
teaching team, the students’ grade may be based only on their individual exam.
7. The final exam will not be in the two‐stage format.

How to Calculate your Overall Exam Score

Let’s assume the individual and group exam were identical, and the total score was out of 63 points. A student
obtains the following grades:
Exam Type Score (out of 63) %
Individual Exam 45 71
Group 56 89
Overall Grade 46.7 74

To calculate the overall grade:

Overall grade = (individual score X 0.85) + (group score X 0.15)

Overall grade = (45 x 0.85) + (56 x 0.15)
Overall grade = 46.7
Is Individual score > Overall score? (No)
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 COVID Safety
For our in‐person meetings in this class, it is important that all of us feel as comfortable as possible engaging in
class activities while sharing an indoor space. Non‐medical masks that cover our noses and mouths are a primary
tool to make it harder for COVID‐19 to find a new host. Non‐medical masks are not currently required by either UBC
or Provincial Health Authorities, however this can change. If you have not yet had a chance to get vaccinated
against COVID‐19, vaccines are available for you. Please ask a physician. The higher the rate of vaccination in our
community overall, the lower the chance of spreading this virus. You are an important part of the UBC community.
Please arrange to get vaccinated if you have not already done so.

If you’re sick, it’s important that you stay home – no matter what you think you may be sick with (e.g., cold,
flu, other). If you think you might have COVID symptoms and/or have tested positive for COVID and/or are required
to quarantine: You can do a self‐assessment for COVID symptoms here: https://bc.thrive.health/covid19/en

Do not come to class if you are sick, have COVID symptoms, have recently tested positive for COVID, or are required
to quarantine. This precaution will help reduce risk and keep everyone safer. In this class, the marking scheme is
intended to provide flexibility so that you can prioritize your health and still be able to succeed. Missed
assignments are re‐weighted to the final exam. Recordings from class will appear on Canvas, as well as completed
notes from each section of the course.

If you do miss class because of illness:

● Make a connection early in the term to another student or a group of students in the class. You can help
each other by sharing notes. If you don’t yet know anyone in the class, post on the discussion forum to
connect with other students.
● Consult the class resources on Canvas. We will post [all the slides, readings, recordings …] for each class
day.
● Use the discussion forum for help
● Come to office hours
● See the marking scheme for reassurance about what flexibility you have.
● If you are concerned that you will need to miss a particular key activity due to illness, contact us to discuss.

If you are sick on a midterm exam day, please email the instructor as soon as you are confident you should not
come to the scheduled exam. We would strongly prefer that you contact us to make an alternate arrangement
than for you to come to the exam while you are ill. If you do show up for an exam and you are clearly ill, we will
make alternate arrangements with you. It is much better for you to email ahead of time and not attend.

If you are sick on a final exam day, do not attend the exam. You must apply for deferred standing (an academic
concession) through Science Advising no later than 48 hours after the missed final exam/assignment. Students
who are granted deferred standing write the final exam/assignment at a later date. Learn more and find the
application online: https://science.ubc.ca/students/advising/concession

If Dr. Wickenden is sick: We will do our best to stay well, but if we are ill, develop COVID symptoms, or test positive
for COVID, then we will not come to class. If that happens, here’s what you can expect:

● Any other professor can substitute.

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 ● One of the TA’s will substitute for one of us.
● If we are well enough to teach, but are taking precautions to avoid infecting others, we may have an online
session or two. If this happens, you will receive [an announcement in Canvas] telling you how to join the
class. You can anticipate that this would very likely be a last‐minute email. Our classroom will still be
available for you to sit and attend an online session, in this (hopefully rare) instance.

Missed Examinations
Missing an examination falls under two distinct categories:

1 – You know you can’t write the midterm examination ahead of the scheduled date. In this situation, you are
expected to rearrange your schedule to allow for the writing of the examination. This may require you to discuss
with your employer alternative shifts at work, or informing your volunteer organization that you will not be able
to attend on the particular day and time. If you play for a UBC Varsity team, you may have your coach write a
letter, and the examination is administered while you are on the road. If the examination falls on a religious
holiday which you observe, a letter from a religious figure stating that you are unable to write the examination
due to this conflict will suffice. All letters must include contact information of the individual writing, as well as an
organizational header. DOCUMENTATION MUST BE PROVIDED AHEAD OF THE MISSED EXAM. Having tickets
for a vacation booked is not an acceptable reason to miss an examination.

2 – You are unable to write the midterm examination due to illness or family emergencies (e.g., death/funeral,
etc.). Firstly, this is very sad and we (the teaching team) hopes this never happens to anyone. In these situations,
students must fill out a “Student Declaration of Academic Concession” form that is available on Canvas. This
form must be presented to your instructor within 2 days of the missed examination. Please note, PROVIDING A
DOCTOR’S NOTE OR DEATH CERTIFICATE, IS NOT REQUIRED. If you present us with more than one “Student
Declaration of Academic Concession” for in the term, we are required to refer your case to Science Advising and
the Dean’s Office.

The operational procedure in CHEM 260 is to push the weight of the missed exam onto the final examination.
You will not be provided with another midterm examination a week later. The means that your final exam
average will now be worth the weight of the missed midterm + weight of the final exam = new weight of final
exam. Failure to produce an acceptable reason for missing a midterm will result in a zero grade being assigned
for that portion of the course. We will not track students down to obtain this material, it is your responsibility
to provide the material.

If you begin to write an examination, and fall ill, you must continue to write the examination unless unable to do
so. Your grade stands regardless of how much of the examination you completed. You are not allowed to arrive
to the examination, look at it, and then decide you are too ill to write the exam. If you write an examination, and
then provide a “Student Declaration of Academic Concession”, your grade will stand. No exceptions.

If you miss the final examination for reasons such as illness or family crisis, you must inform the staff of your
Dean’s office of the reason for the absence in a timely manner (i.e. within a few days of the missed examination).
You may be required to provide a doctor’s note to support a claim of illness. Note that if you are ill for an
examination and choose to write the examination, then the grade obtained on that examination will stand. There
are no undocumented and approved re‐writes or make‐ups of final examinations.
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 Midterm Exam Re‐grading
Re‐grade Policy: Requests for exam re‐grades can be made within one week after they have been returned to
students. Generally, there are two types of re‐grade requests.

Calculation Error: In the case of a calculation or addition error on your midterm examination, bring the mistake
to our attention and, once confirmed, we will modify the grade accordingly. This should not be an issue as
Microsoft Excel does the math for us.

Requesting a regrade is done by using the form on Canvas. You can elect to ask for a regrade, at which point an
appointed professor will review your entire examination paper. This may result in your grade going down, as well
as up.

Final Examination
Final exam viewings will be held following the posting of your final grade, but not before January 15th 2024.
Please email your professor after the noted date to schedule a viewing or to review your final grade calculation.
Following a viewing, if you feel you require a re‐grade of your final examination you must apply for a ‘Review of
Assigned Standing’. Information on this process may be found by following the link below:

http://www.calendar.ubc.ca/vancouver/index.cfm?tree=3,49,0,0

Please note that viewing exams may result in finding a missed 0.5 point, maybe 1 point. This will more than likely
not change your grade. In addition, seldom does a grade change more than 1%. You will not find missing marks
on the final exam which will result in your grade moving 15% for example. In addition, remember that finding a
mistake that changes your grade from 85% to 86% means your grade letter does not change (you have an A).
Exam viewings are done in late January 2024. Please remember that faculty teaching CHEM 260 (or any course)
have families and take time off during breaks as well.

Academic Misconduct
For the definition and treatment of academic misconduct, please see the UBC Calendar. It is always expected
that all students complete their own exams, quizzes, including any online quizzes and homework. It is your
responsibility to know, understand and abide by the rules regarding academic misconduct at UBC. Again: graded
assignments are to be done only by you, individually, without guidance from anyone. The only exception to this
is if the instructor states that “this is to be done as a group.”

Doing your own work, acknowledging the contributions of others, and seeking help when you need it are all part
of what academic integrity means at UBC, as is avoiding tools and services that subvert these practices.

Academic integrity is a commitment to upholding the values of respect, integrity, and accountability in academic
work. It is foundational to teaching and learning and is a fundamental and shared value of all members of the
UBC community. UBC adopts an educative approach to academic integrity that supports students and instructors
around awareness and that values academic misconduct processes that are fair and effective.

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Academic integrity is a set of values and skills that must be learned and refined over time. Instructors are
responsible for setting clear expectations around academic integrity in their courses, modelling honest behaviour
as teachers and scholars, and creating a space for students to develop their understanding of academic integrity.
Students are responsible for meeting these expectations in their academic work, developing an understanding
of concepts, and seeking support when they have questions. UBC is responsible for creating and sustaining the
culture of academic integrity that makes all of this possible.

Everyone plays a part in supporting and enhancing academic integrity at UBC

A more detailed description of academic integrity, including the University’s policies and procedures, may be
found in the Academic Calendar at http://calendar.ubc.ca/vancouver/index.cfm?tree=3,54,111,0.

Generative AI (including ChatGPT)

The use of generative AI tools, including ChatGPT and other similar tools, to complete or support the
completion of any form of assignment or assessment (quizzes and exams) in this course is not allowed
and would be considered academic misconduct.

Pre‐requisites and Repeating

The specified pre‐requisites for entry into CHEM 260 are either CHEM 123, CHEM 130, CHEM 113 (very old course
at UBC‐V), CHEM 154 or SCIE 001. In some rare cases, APSC 182 and APSC 183 were accepted from UBC‐O by
special permission. Most students registered in CHEM 260 have the correct pre‐requisites. However, some
students took their first‐year chemistry courses at other institutions and the content of courses taught elsewhere
may not be the same as it is here at UBC. These students do have a year of general chemistry and have been
admitted to CHEM 260. CHEM 123/130 is offered during the summer in late July as a four‐week course or during
the January‐April semester of the normal academic year. There is a Faculty of Science regulation that stipulates
that a student may only attempt a course at UBC twice. If a passing grade is not obtained after two attempts,
the student cannot take that course at UBC for a third time. The student will have to consult with his/her faculty
advisor regarding possible alternatives that may include changing programs so that the problematic course is no
longer required. CHEM 260 assumes that you are thoroughly familiar with fundamental concepts of introductory
chemistry; specifically:
• Energy Levels
• Electronic Configuration
• Valence Electrons and Valence Shell
• Anions and Cations
• Description of chemical bonding in terms of valence bond theory (hybrid atomic orbitals, sigma and pi bonds,
etc,).
• Hybridization and Geometry: VSEPR and Orbital Geometry.
• Prediction of molecular geometry using VSEPR.
• Polar covalent bonds; dipole moments
• Relationship between molecular polarity and geometry
• Representation of molecules as Lewis, condensed, skeletal (=line‐bond) structures
• Wedges/dashed lines formalism
• Atoms with complete or incomplete octets
• Formal charge(s)/lone pairs of electrons
• Resonance Structures and Conjugation
• Intermolecular forces: London dispersion, dipole‐dipole, hydrogen bonding, ion‐dipole forces

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Except for formal charges and resonance, the above concepts will NOT be discussed again in CHEM 260.
Therefore, please review the corresponding CHEM 154 material:
Unit 2: The periodic table and atomic structure
Unit 3: Chemical bonding and molecular structure
Unit 4: Intermolecular interactions and phases of matter
It is also very helpful to review the following:
Unit 7 Energy and chemistry
Unit 8 Entropy and the second law of thermodynamics
Unit 9 Chemical equilibrium
Unit 10 Chemical kinetics
A general chemistry textbook has been posted in Canvas to help you review these concepts.

Missed Classes
It is up to the instructor to decide if graded items will occur during class time. The exact grading breakdown for
each section is typically covered during the first class. A recording of this class will occur, which will be posted to
Canvas as soon as possible. In addition, a complete slide deck (to the end of the discussion that day) or class
notes will be posted for you as well. This is at the discretion of the professor in charge of your section. There is
no need to contact your section professor to explain an absence from a regular class day/time (unless otherwise
noted by said professor).

We are working to have lectures recorded for several sections of the course. At least, and hopefully, one section
per professor will be captured and loaded onto Canvas. Please note we do not handle this feature, and we do
not know when a lecture will arrive for you to view. In all cases, class notes will be available for you, and we will
work to resolve the issue as best we can.

Pass Policy
It is essential that you demonstrate your mastery of the course material on course exams. There is no specific
pass policy beyond obtaining 50% or greater as your overall course grade.

No Special Treatment
Please do not ask us to alter the grading scheme for you. For example, if you do better on the final exam than
you do on the midterm that is wonderful, but we will not change the mark breakdown just for you. The reason
for this is that to do well in organic chemistry, you must keep up with the material. In addition, this isn’t fair to
students that have worked hard and done well the entire term. Thus, treat the midterms seriously because your
future understanding depends on your skills and abilities related to the midterm material.

Drop/Withdrawal Dates
Students should pay attention to the UBC calendar for internal deadlines for withdrawing from a course with, or
without a ‘W’ on their transcripts.

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 CHEM 260 Schedule (may be subject to change)
September 2023
Monday Tuesday Wednesday Thursday Friday Saturday Sunday
Sept 4* 5** 6 7 8 9 10
JW 4 – 5

11 12 13 14 15 16 17
ORC 6 – 7:30 ORC 4 – 5 JW 4 – 5 ORC 4 – 5 Quiz 1 DUE
11:59 PM
18 19 20 21 22 23 24
ORC 4 – 5 ORC 6 – 7:30 ORC 4 – 5 JW 4 – 5

25 26 27 28 29 30***
ORC 6 – 7:30 ORC 4 – 5 JW 4 – 5 ORC 4 – 5

* Labour Day – University closed

** Imagine Day – most classes are cancelled (CHEM 260 cancelled)
*** National Day for Truth and Reconciliation

Review sessions are via Zoom, and will be recorded

October 2023
Monday Tuesday Wednesday Thursday Friday Saturday Sunday
1
Quiz 2 DUE
11:59 PM
2* 3 4 5 6 7 8
ORC 6 – 7:30 ORC 4 – 5 JW 4 – 5 Review Session
6‐8 PM
9** 10 11 12*** 13 14 15
Thanksgiving MT 1 TA’s grading ORC 4 – 5
MT1
16 17 18 19 20 21 22
ORC 6 – 7:30 ORC 4 – 5 JW 4 – 5 ORC 4 – 5 Quiz 3 DUE
11:59 PM
23 24 25 26 27 28 29
ORC 4 – 5 ORC 6 – 7:30 ORC 4 – 5 JW 4 – 5

30 31
ORC 6 – 7:30

* Statutory Holiday in lieu of National Day for Truth and Reconciliation – University Closed.
** Thanksgiving Monday – University closed
*** This day operates as a Monday. Meaning, CHEM 260 has class on Thursday October 12th!

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 November 2023
Monday Tuesday Wednesday Thursday Friday Saturday Sunday
Nov 1 2 3 4 5
ORC 4 – 5 JW 4 – 5 ORC 4 – 5 Quiz 4 DUE
11:59 PM
6 7 8 9 10 11* 12
ORC 4 – 5 ORC 6 – 7:30 ORC 4 – 5 JW 4 – 5

13** 14 15 16 17 18 19
JW 4 – 5

20 21 22 23 24 25 26
Review Session MT 2 TA’s grading JW 4 – 5
6‐8 PM MT2
27 28 29 30
ORC 6 – 7:30 ORC 4 – 5 JW 4 – 5

*Remembrance Day – University closed? (It’s a Saturday, so not sure how this works)
**Statutory Holiday in lieu of Remembrance Day – University Closed.

December 2023
Monday Tuesday Wednesday Thursday Friday Saturday Sunday
Dec 1 2 3
ORC 4 – 5 Quiz 5 DUE
11:59 PM
4 5 6 7 Last day of 8 9 10
ORC 4 – 5 ORC 6 – 7:30 ORC 4 – 5 Classes*

11 12 13 14 15 16 17
Exam period
begins
18 19 20 21 22 23 24
Exam period
ends
25 26 27 28 29 30 31

* Additional ORC hours, office hours and a Review Session will be announced once the final exam has been set
by UBC.

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