We recognize and acknowledge that McMaster University meets and learns on the traditional territories of the Mississauga and Haudenosaunee nations, and
within the lands protected by the “Dish With One Spoon” wampum, an agreement amongst all allied Nations to peaceably share and care for the resources
around the Great Lakes.
CHEM 2OB3 – Organic Chemistry II
2023 Summer Term
Instructor: Anthony Rulo| E-mail rulloa@mcmaster.ca | Office: MDCL 4018
Coordinator: R. Turner | E-mail: orgochem@mcmaster.ca | Office: ABB 301
Course Description and Objectives
Nucleophilic substitutions at carbonyl centres, aromatic chemistry, carbohydrates, applications of
spectroscopic techniques in organic chemistry.
•
Two lectures (three hours), one lab (three hours) and two tutorials (one hour) every week; one
term
Prerequisite(s): CHEM 1A03 (or 1E03) and CHEM 1AA3 or ISCI 1A24 A/B and one of CHEM 2OA3, 2OC3,
2OG3 or CHEMBIO 2OA3, 2OG3
• Registration priority will be given to students for whom this course is a program requirement.
Antirequisite(s): CHEM 2OD3, CHEMBIO 2OB3, 2OD3.
• Not open to students registered in Honours Chemical Biology
Learning Objectives
CHEM 2OB3 is an introductory organic chemistry course intended to enable students to:
• Examine the chemical behaviour, structural chemistry and reactivity of a series of organic functional
groups including: alcohols, ethers, aromatics, carbonyls, carbohydrates, carboxylic acids and
enols/enolates
• Develop problem solving strategies to determine chemical structure and to assemble more complex
organic molecules
• Acquire laboratory skills and techniques required to investigate experimental problems in organic
chemistry
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Component Course Summary
Lectures
Tuesday and Thursday (starting June 25th)
6:00 – 8:50 PM
JHE 376
Tutorials
Tuesday & Thursday (weekly starting July 4th)**
12:00 – 12:50 PM
Laboratories
Tuesday through Thursday (weekly starting July 2nd)
8:30 – 11:20 AM OR 1:30 – 4:20 PM
→ Labs conducted on campus and submitted using Avenue2Learn
Office Hours
Course Instructor TBD
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Materials & Fees
Required Materials/ Resources
The following course materials are available at the Campus Store.
Textbook
•
Organic Chemistry – 4th edition by David Klein
Molecular Model Kits
•
MolyMod Molecular Model Set (By Indigo Instruments)
Lab Notebook **new**
•
this is a blue-bound notebook that students are required to purchase and bring to the lab for each
experiment. The link to purchase this item can be found here.
Safety Googles
•
UVEX Stealth safety googles
Lab Coat
•
Standard long sleeve lab coat (strongly recommended)
Virtual Course Delivery
To follow and participate in virtual classes it is expected that you have reliable access to the following:
•
A computer that meets performance requirements found here.
•
An internet connection that is fast enough to stream video.
•
Computer accessories that enable class participation, such as a microphone, speakers and
webcam when needed.
If you think that you will not be able to meet these requirements, please contact uts@mcmaster.ca as soon
as you can. Please visit the Technology Resources for Students page for detailed requirements. If you use
assistive technology or believe that our platforms might be a barrier to participating, please contact
Student Accessibility Services, sas@mcmaster.ca, for support.
Avenue to Learn
Avenue to Learn (A2L) will be used for electronic distribution of all course content including:
announcements; course information; lecture notes; live stream and recordings of lectures (via Echo 360);
problem-solving and student response sessions (via MS Teams); adaptive practice (via WileyPLUS); practice
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problems (via the question bank); term test answers keys, etc. Lab report submissions and grading will be
done on Avenue2Learn.
Crowdmark
Crowdmark (www.crowdmark.com) is an online platform available to all students within the course that
will be used for the electronic distribution of tests and examinations.
Microsoft Teams
Microsoft Teams will be used as a forum for discussion with the instructional team via a chat board and
virtual sessions (e.g., tutorials, office hours, help desks) throughout the semester. Microsoft Teams is
available for free via the Office 365 subscription accessible to all McMaster students.
Course Overview and Assessment
Course Content
In CHEM 2OB3, you will build on the foundation built during organic chemistry I. This course is designed
for non-chemists, particularly those whose interests are biological. Rather than consider systems, this
course examines how organic chemists manipulate functional groups to create and manipulate organic
molecules. There are two basic elements to the course: (1) extend your knowledge of and learn some new
ground rules of chemical behavior (e.g., solubility, acidity), structural chemistry (e.g., spatial and
electronic distribution in molecules, structural determination using spectroscopy) and reactivity (e.g.,
identify the most reactive sites within molecules, understand the driving forces behind organic reactions);
and (2) develop problem-solving strategies towards the transformation of a variety of functional groups,
the identification of reaction products, and the assemble of more complex molecules using the toolbox of
reactions studied within the course.
Lectures and course notes are the best resources to inform yourself on the topics that will be emphasized
in the course. The course textbook, Organic Chemistry − 4th edition by David Klein, should be used to
further your understanding of the course topics. The following list provides a general outline that will be
covered and the associated chapter information from the textbook. Make sure to stay up to date with the
lectures and course notes to know which topics will be emphasized in the course.
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The table below also contains a schedule that should be followed to prepare yourself for the laboratory
exercises, student response sessions and examinations.
SCHEDULE
TOPICS
CHAPTER (4th Edition)
Week 1
Radicals (Interlude)
10
Week 1
Alcohols and Phenols
12
Week 1-2
Ethers and Epoxides
13
Week 2
Pi Systems
16
Week 3
Aromatic Compounds
17
Week 3
Electrophilic Aromatic Substitutions
18
Week 4
Aldehydes and Ketones
19
Week 4
Carbohydrates
24
Week 5
Carboxylic Acids and Derivatives
20
Week 5
Amino Acids, Peptides and Proteins
25
Week 6
Enols and Enolates
21
Week 7
Amines
22
Course Evaluation
Assessment
Percentage (%)
Virtual Quizzes
5
Adaptive Practice
5
Labs
15
Term Tests
30
Final Examination
45
Total
100
In order to pass the course, the following criteria must be met: (1) a final grade ≥ 50 %; (2) the final
examination MUST be written; and (3) at minimum, 4 of 5 labs MUST be attended with lab reports
completed.
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Adaptive practice, student response and the term tests are OPTIONAL. Late assessments will not be
accepted, and rewrites of the term tests will not be allowed. If you elect not to take part in these
assessment(s), then the value of these assessment(s) will automatically be placed onto the final exam.
Students DO NOT need to obtain an MSAF for missing these assessment(s) as universal accommodation
grading schemes are in place for these assessments (see below).
Grade inquiry periods will be held within the semester for all midterm tests. Details will be posted
to A2L throughout the semester with respect to specific deadlines and item. Inquiries regarding lab reports
must be addressed within 5 business days of the return of the graded report unless explicitly specified
otherwise on A2L.
Final grades for CHEM 2OB3 will automatically be calculated using the following formulas and the
BEST final grade will be awarded for each student:
OPTION 1 AP (5 %) + Q (5 %) + MT (30%) + L (15 %) + F (45 %)
OPTION 2 AP (5 %) + MT (30%) + L (15 %) + F (50 %)
OPTION 3 Q (5 %) + MT (30%) + L (15 %) + F (50 %)
OPTION 4 MT (30%) + L (15 %) + F (55 %)
OPTION 5 AP (5 %) + Q (5 %) + L (15 %) + F (75 %)
OPTION 6 AP (5 %) + L (15 %) + F (80 %)
OPTION 7: Q (5 %) + L (15 %) + F (80 %)
OPTION 8 L (15 %) + F (85 %)
Abbreviations: Adaptive practice (AP), quizzes (Q), Midterm (MT), Lab (L), Final Examination (F)
Examinations
Midterm
Thursday July 17th
(15%)
6:30 – 8:30 PM (2 hours)
Final Examination
Thursday August 7th
(45 %)
6:30 – 9:00 PM (2.5 hours)
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All examinations will be conducted in-person. The McMaster standard calculator (Casio FX-991 MS or MS
Plus models) and molecular models kits (packaged in a clear plastic bag) are the ONLY acceptable aids
allowed during exams. The final examination MUST be written in order to pass the course.
A2L Quizzes
There will be 6 A2L quizzes, that will open at 12:00 pm (noon) on the weeks indicated in the schedule
below. These quizzes are due 48 hours after opening at 12:00 pm (noon) on the following Wednesday. All
students are provided with an automatic 48-hour grace period from Wednesday at 12:00 pm until Friday
at 12:00 pm (noon) to complete and submit their quiz. There are no penalties for quizzes submitted
during the grace period. Further extensions past Friday at 12:00 pm will not be provided. These quizzes
are designed to take one hour to complete, but there is no enforced time limit beyond the opening and
closing of the quiz.
It is strongly recommended but OPTIONAL that you take part in these quizzes. Student response quizzes
are worth 5% of your final grade and your grade will be determined by using the best 5 out of 6 virtual
quizzes.
Quiz Number
1
2
3
4
5
6
Date Open
June 30
July 7
July 14
July 21
July 28
Aug 4
Due Date
July 2
July 9
July 16
July 23
July 30
Aug 6
Date Closed
July 4
July 11
July 18
July 25`
Aug 01
Aug 8
Adaptive Practice (5%)
An adaptive practice homework platform available via WileyPLUS will be utilized in the course. WileyPLUS
is a part of the textbook package for Organic Chemistry – 4th edition by David Klein sold via the Campus
Store or can be purchased separately online from the Wiley website. It is strongly recommended but
OPTIONAL that you complete the adaptive practice homework. The adaptive practice problems are a
unique database of questions, with hundreds of questions per chapter, which are NOT found in the
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textbook. To take full advantage of using this self-assessment study tool, we advise that you work through
the lectures and in-text questions in the textbook, and then use the adaptive practice to evaluate your
overall comprehension of the chapter material.
Adaptive practice is worth 5% of your final grade and marks will be allocated based on the TOTAL number
of progress points obtained on ALL the WileyPLUS assignments throughout the semester. Adaptive
practice will include assignments for Chapters 10, 12, 13, 16-21, 24 and 25. Points are earned based on your
student progress through each assignment, which considers your response to each question, the difficulty
of the question and your history in responding to each learning objective included in the assignment. There
are no specific numbers of questions that must be completed for each individual chapter but points are
distributed based on your highest level of student progress achieved: 100% progress = 10 points, 80-99%
progress = 8 points, 50-79% progress = 6 points, < 50% progress = 0 points. The overall adaptive practice
grades will be calculated at the end of term according to the following table:
Total Progress Points (%)
Adaptive Practice Mark
80-100
5.0
65-79
4.0
50-64
3.0
35-49
2.0
< 35
0.0
Note – some chapter sub-sections have been excluded from the WileyPLUS assignments to limit the time
required to complete these assignments. The sub-sections included in the WileyPLUS assignments have
been selected to best develop the problem-solving skills needed in organic chemistry BUT DO NOT reflect
the sole content that you are responsible to know in the course!!!
All adaptive practice assignments are due on selected Fridays by 11:45 PM on the following dates:
Adaptive Practice Chapter
Due Date
10
June 27th
12
July 4th
13
July 4th
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16
July 11th
17
July 18th
18
July 18th
19
July 25th
24
July 25th
20
August 1st
25
August 8th
21
August 8th
Laboratories (15%)
In-person experiments are 3 hours in duration and will be held for Experiments 1 − 5 (starting the week of
July 2nd). Labs are held Tuesday through Thursday 1:30 – 4:20 PM. You MUST attend the lab section posted
in your timetable on Mosaic. If you have a conflict with your lab section, check on Mosaic to see if it is
possible to change to another lab section (before the add/drop deadline). If space is not available in another
section, contact the course coordinator as soon as possible with your documented conflict. Your lab section,
room number, bench number and teaching assistant (TA) will be posted in your gradebook on Avenue after
the add/drop deadline.
This semester, there will be a virtual lab manual used, and students will be required to purchase a lab
notebook (see introduction regarding required course materials). All lab related work will need to be
completed in the lab notebook in order for it to be graded. Further details will be discussed in lecture and
are available on A2L.
In-person lab reports will be submitted to Avenue for grading. All lab reports are due on the day of your
lab section by 11:45 PM. Student registered with Student Accessibility Services (SAS) with the
consideration for extensions accommodation will be permitted to submit their lab reports the day after
their lab section by 11:45 PM. A late penalty of 10% per day will be applied to lab reports submitted after
their due date. Reports later than 5 days will be given a grade of zero.
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The laboratory component is worth 15% of your final grade (1% PER pre-lab quiz, 2% PER lab report). To
pass the laboratory portion of the course, students MUST attend and complete at minimum 4 out of 5 lab
reports for the in-person experiments. Completion of each experiment involves the submission of a lab
report in which all required components (as detailed in the lab manual) have been completed. Lab reports
with significant components missing will NOT be considered complete and WILL NOT be accepted for
marks.
Please see the missed work policy on what to do if you miss a lab.
You are responsible for completing lab reports on YOUR OWN! Solutions CANNOT be completed within a
group collaboration, obtained from an online tutor website, copied from posts within a group chat, or
copied from students who have completed the course previously (see below for further information on
McMaster’s Academic Integrity Policy)!
Students unable to attend laboratory experiments due to illness or other valid reasons MUST obtain an
MSAF (see below for MSAF procedure). All missed laboratory experiments MUST be performed during the
Make-Up lab period at the end of the semester.
Lab Safety − In order to work in the lab, students MUST adhere to the following safety rules:
•
Safety goggles must be worn at all times in the laboratory.
•
Students must have their arms covered either by wearing a lab coat (strongly recommended) or a
long-sleeve shirt.
•
Students must wear long pants or a skirt. Shorts or capris are not acceptable attire.
•
Students must have shoes that completely cover their feet including the entire upper foot, toes
and heels. Sandals, open-toed shoes, ballerina shoes (flats) and shoes with cut-outs or openings
are not acceptable attire. Due to slipping hazards, shoes or boots with heels are strongly
discouraged.
Lab Exemptions – Students who have previously taken the course may be granted a lab exemption if they
meet the following criteria:
1. You MUST have attended all 5 experiments within the semester AND submitted all 5 lab reports
2. You must have taken Chem 2OB3 between Winter 2023 and 2025
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Both criteria must be met in order to qualify for a lab exemption consideration. If you meet those criteria
submit THIS FORM before June 25th at 12:00 PM (noon). Your lab exemption will be considered and you
will be notified of the result before labs begin in the semester.
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CHEM 2OB3 Course Schedule
Monday
Tuesday
Wednesday
Thursday
Friday
23
24
25
26
27
June/July
WEEK 1
Classes + Tutorials
begin
No Labs
30
WEEK 2
Exp. 1
WileyPLUS Chapter 10
Due Date
T01 12:00 − 12:50 PM
1
2
No Class – Canada
Day
**L02 Lab 1
rescheduled
3
4
WileyPLUS Chapters
12 + 13 Due Date
Quiz 1 Due 12:00 PM
WEEK 3
7
8
14
15
Exp. 3
WEEK 5
21
22
28
29
Due Date
18
16
17
Quiz 3 Due 12:00 PM
Midterm
WileyPLUS Chapters
17 + 18 Due Date
23
24
25
WileyPLUS Chapters
19 + 24 due
30
31
Quiz 5 Due 12:00 PM
Exp 5
11
WileyPLUS Chapter 16
Quiz 4 Due 12:00 PM
Exp 4
WEEK 6
10
Quiz 2 Due 12:00 PM
Exp. 2
WEEK 4
9
01
WileyPLUS Chapters
20 due
August
WEEK 7
Make-Up
Labs
4
5
Make-Up Labs TBD
6
Quiz 6 Due 12:00 PM
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7
8
Final Exam
WileyPLUS Chapters
25 + 21 Due Date
Requests for Relief for Missed Academic Term Work
McMaster Student Absence Form (MSAF): In the event of an absence for medical or other reasons,
students should review and follow the Academic Regulation in the Undergraduate Calendar “Requests for
Relief for Missed Academic Term Work”.
Course Specific MSAF Information
Missed work
MSAF Needed?
Result
Lab
One missed lab – NO
For one missed lab – the weight of the lab report
will be moved to the exam automatically and
students will not be able to attend a makeup
session. Please complete your pre-lab quiz still.
Two or more missed labs – YES
For two or three missed labs – students must
attend a makeup session for ONE or TWO makeup
labs respectively (such that 4/5 labs are
complete). Please ensure pre-lab quizzes are
completed.
Quiz
No
Test
MSAF not available
Adaptive practice No
Final Exam
For four or more missed labs please contact
orgochem@mcmaster.ca as soon as possible.
Only the best 5/6 quizzes will be used to calculate
your quiz grade.
If you are unable to attend the test, the weight of
the test will be moved to the final exam
automatically.
Not all wileyPLUS chapters need to be completed
in order to receive full grades on the adaptive
practice. Please review the wileyPLUS thresholds
listed above.
MSAF not available
If you are absent from the university for a minor medical reason, lasting fewer than 3 days, you may
report your absence, without documentation, using the McMaster Student Absence Form (MSAF).
Absences for a longer duration or for other reasons must be reported to your Faculty/Program office,
with documentation, and relief from term work may not necessarily be granted.
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When using the MSAF to report your second or third missed lab, report your absence to the course
coordinator using the following email address: orgochem@mcmaster.ca. Within a few days of submitting
your MSAF, check your gradebook on Avenue to see that your MSAF has been acknowledged.
Academic Accommodation of Students with Disabilities
Students with disabilities who require academic accommodation must contact Student Accessibility
Services (SAS) at 905-525-9140 ext. 28652 or sas@mcmaster.ca to make arrangements with a Program
Coordinator. For further information, consult McMaster University’s Academic Accommodation of
Students with Disabilities policy.
Academic Accommodation for Religious, Indigenous Or Spiritual Observances (Riso)
Students requiring academic accommodation based on religious, indigenous or spiritual observances
should follow the procedures set out in the RISO policy. Students should submit their request to their
Faculty Office normally within 10 working days of the beginning of term in which they anticipate a need
for accommodation or to the Registrar's Office prior to their examinations. Students should also contact
their instructors as soon as possible to make alternative arrangements for classes, assignments, and tests.
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Courses with An On-Line Element
In this course we will be using Avenue to Learn (A2L), Crowdmark, and Microsoft Teams. Students should
be aware that, when they access the electronic components of a course using these elements, private
information such as first and last names, usernames for the McMaster e-mail accounts, and program
affiliation may become apparent to all other students in the same course. The available information is
dependent on the technology used. Continuation in a course that uses on-line elements will be deemed
consent to this disclosure. If you have any questions or concerns about such disclosure, please discuss this
with the course instructor.
All submitted work is subject to normal verification that standards of academic integrity have been
upheld (e.g., on-line search, other software, etc.).
Academic Integrity
You are expected to exhibit honesty and use ethical behaviour in all aspects of the learning process.
Academic credentials you earn are rooted in principles of honesty and academic integrity.
It is your responsibility to understand what constitutes academic dishonesty.
Academic dishonesty is to knowingly act or fail to act in a way that results or could result in unearned
academic credit or advantage. This behaviour can result in serious consequences, e.g. the grade of zero
on an assignment, loss of credit with a notation on the transcript (notation reads: “Grade of F assigned for
academic dishonesty”), and/or suspension or expulsion from the university. For information on the
various types of academic dishonesty please refer to the Academic Integrity Policy, located at
https://secretariat.mcmaster.ca/university-policies-procedures- guidelines/
The following illustrates only three forms of academic dishonesty:
•
Plagiarism (e.g., the submission of academic work that has been, entirely or in part, copied from or
written by another person without proper acknowledgement, or, for which previous credit has
been obtained)
•
Improper collaboration on group or individual work (e.g., preparation of solutions within a group
for individual assessments, submission of questions or use of solutions from an online tutor
website)
•
Aid or abet another student’s academic dishonesty (e.g., sharing your solutions with another
student)
Page 15 of 18
•
Fail to take reasonable precautions to protect academic work such as assignments, projects,
laboratory reports or examination from being used by other students (e.g., electronic distribution
of assessment solutions)
•
Copying or using unauthorized aids (e.g., cheat sheets, cell phones) in tests, examinations or
laboratory reports
•
Impersonate another student either in person or electronically for the purpose of academic
assessment (e.g., submission of another student’s answers during student response sessions,
writing of another student’s examination)
Authenticity / Plagiarism Detection
Some courses may use a web-based service (Turnitin.com) to reveal authenticity and ownership of
student submitted work. For courses using such software, students will be expected to submit their work
electronically either directly to Turnitin.com or via an online learning platform (e.g. A2L, etc.) using
plagiarism detection (a service supported by Turnitin.com) so it can be checked for academic dishonesty.
Students who do not wish their work to be submitted through the plagiarism detection software must
inform the Instructor before the assignment is due. No penalty will be assigned to a student who does not
submit work to the plagiarism detection software. All submitted work is subject to normal verification
that standards of academic integrity have been upheld (e.g., on-line search, other software, etc.). For
more details about McMaster’s use of Turnitin.com please go to the McMaster Office of Academic
Integrity’s webpage.
Conduct Expectations
As a McMaster student, you have the right to experience, and the responsibility to demonstrate,
respectful and dignified interactions within all our living, learning and working communities. These
expectations are described in the Code of Student Rights & Responsibilities (the “Code”). All students
share the responsibility of maintaining a positive environment for the academic and personal growth of
all McMaster community members, whether in person or online.
It is essential that students be mindful of their interactions online, as the Code remains in effect in virtual
learning environments. The Code applies to any interactions that adversely affect, disrupt, or interfere
with reasonable participation in University activities. Student disruptions or behaviours that interfere with
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university functions on online platforms (e.g. use of Avenue 2 Learn, WebEx or Zoom for delivery), will be
taken very seriously and will be investigated. Outcomes may include restriction or removal of the involved
students’ access to these platforms.
Discrimination Policy
McMaster University is concerned with ensuring an environment that is free of all adverse discrimination.
If there is a problem that cannot be resolved by discussion among the persons concerned, individuals are
reminded that they should contact their Department Chair, or Human Rights and Equity Services, as soon
as possible. Issues involving teaching assistants should also be brought to the attention of the course
coordinator. For further information, consult McMaster University’s Policy on Discrimination and
Harassment: Prevention and Response.
Copyright and Recording
Students are advised that lectures, demonstrations, performances, and any other course material
provided by an instructor include copyright protected works. The Copyright Act and copyright law protect
every original literary, dramatic, musical and artistic work, including lectures by University instructors.
The recording of lectures, tutorials, or other methods of instruction may occur during a course. Recording
may be done by either the instructor for the purpose of authorized distribution, or by a student for the
purpose of personal study. Students should be aware that their voice and/or image may be recorded by
others during the class. Please speak with the instructor if this is a concern for you.
Research Ethics -N/A
Extreme Circumstances
The University reserves the right to change the dates and deadlines for any or all courses in extreme
circumstances (e.g., severe weather, labour disruptions, etc.). Changes will be communicated through
regular McMaster communication channels, such as McMaster Daily News, A2L and/or McMaster email.
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Modifications to The Course
The instructor and university reserve the right to modify elements of the course during the semester. The
university may change the dates and deadlines for any or all courses in extreme circumstances. If either
type of modification becomes necessary, reasonable notice and communication with students will be
given with explanation and the opportunity to comment on changes. It is the responsibility of the student
to check their McMaster email and the course website weekly during the semester and to note any
changes.
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