Fall 2022 CHEM215-1

Course Philosophy
In Chem215, you will encounter chemical concepts that have been tested over years of
observation and experiment. The reason there is a “right” and a “wrong” answer to your
chemistry problems is that those answers have stood the test of time and repeated testing.
At one point, however, some scientist made a prediction about something based on an
observation. Over time, that scientist was proven wrong sometimes and proven correct
other times. This is the progression of science.

Learning Objectives
By the end of this course, you will be able to:
• Identify and name important organic functional groups
• Describe the three dimensional structures of the functional groups and relate
structure and physical properties to specific electronic/orbital features
• Predict the acidity/basicity of organic molecules and the product of proton exchanges
based on functional group pKa
• Depict structural dynamics and energetics of organic molecules based on
conformational analysis
• Predict the outcomes, including stereochemistry, of reactions categorized by
functional groups and rationalize these outcomes using a combination of arrow-
pushing mechanisms, electronic and molecular orbital descriptions, and energy
diagrams
o Functional groups explored include hydrocarbons, alkyl halides, alkenes, and
alkynes
• Design short synthetic and retrosynthetic routes for the preparation of small organic
molecules
• Integrate spectroscopic techniques from the laboratory class
• Apply the reasoning and analytical skills you have learned in this course to new
situations, including other courses.

Instructor Information
Prof. Stephanie Knezz (she/her)
Assistant Professor of Instruction
Tech E219 (Just inside the Organic Lab doors)*
*Office hours in D212, just down the hall
stephanie.knezz@northwestern.edu
In person: Office Hours: Monday & Thursday 12-1 pm in D212 (next to the Organic Labs)
On Zoom: Schedule a 15-minute 1:1 appointment that works for you on Calendly:
https://calendly.com/stephanie-knezz/office-hours

Please note that questions about course content are often difficult to answer via email, and
a discussion can go a long way!

Open Door Policy: If I am in my office and the door is open, you are welcome to stop by
and ask questions. If I am not able to meet with you, I will close my door.

Support Staff
Chelsea Watson* & Robin Stark
*primary contact for organic chemistry
chemhelp@u.northwestern.edu

Course Modality
Class sessions for this course will occur in person. Individual students will not be granted permission
to attend remotely except as the result of an Americans with Disabilities Act (ADA) accommodation
as determined by AccessibleNU.

Weekly Schedule*
Day Monday Tuesday Wednesday Thursday Friday

What’s going Lecture in LR5 Lecture in LR5 Lecture in Problem-solving Lab Lecture in
on? @ 10 or M345 @ 10 or M345 LR5 @ 10 or in LR5 @ 10 or LR5 @ 10 or
@ 11 am @ 11 am M345 @ 11 M345 @ 11 am M345 @ 11 am
am

Okay, but Prof. Knezz is Prof. Knezz is Prof. Knezz is We’re solving Prof. Nelson is
what giving an giving an giving an problems in explaining the
specifically? interactive interactive interactive groups or experiment for
lecture lecture lecture taking a quiz next week’s
lab.

And how do I Review the Review the Review the Study for the Look over the
prepare for previous previous previous quiz, and look experiment
that? lecture and lecture and lecture and at the problem details.
read the read the read the set problems.
textbook textbook textbook
material. material. material.

*see end of syllabus for thorough tentative lecture schedule

Course Materials
1. Title: Organic Chemistry, 7th or 6th Edition
Author: Loudon and Parise
Publisher: Macmillan
ISBN: 9781936221349
Approx. price: $180 new, $60 ebook rental

2. (Optional if not purchasing package) Title: Organic Chemistry Study Guide and
Solutions Manual, 7th / 6th Edition
Author: Loudon and Parise
Publisher: Macmillan
ISBN: 9781936221868
Approx. price: $100 new, $45 ebook rental
Recommended:
1. (Optional if not purchasing the custom package)
Title: Organic Chemistry Study Guide and Solutions Manual, 7th / 6th Edition
Author: Loudon and Parise
Publisher: Macmillan
ISBN: 9781936221868
Approx. price: $100 new, $45 ebook rental

2. Molecular Modeling Kit (approx. $20)

Evaluation
Assessment Points

Concept Check 20

Quizzes (Drop one, 20 points each) 40

Midterms* 250

Final 150

Total 460

Please note that Canvas assumes all ungraded assignments will be 100%, which encourages
students to overestimate their final grade. Because of the scaling/dropping policies
described below, the Canvas gradebook will not reflect your final grade accurately.

Exams
Midterm 1: Tuesday, October 4th @ 7 pm
Midterm 2: Tuesday, October 25th @ 7 pm
Midterm 3: Monday, November 21st @ 7 pm
Final Exam: TBD
*At the end of the quarter, the student's exam with the lowest numerical score will be
scaled to 50 points. More guidance on exam policies will be provided via Canvas
Announcements.
Exam absences: Unexcused absences from a quiz or exam will result in a grade of
0. Excused absences must be cleared with Ms. Stark, Ms. Watson, or Prof. Knezz before
the exam. If there is an excused absence for one of the midterms, the other two midterms
will count for 100 points each, and the missed exam score will be the mean of the other two
scores, scaled to 50 points. For absences from the final exam, students will need official
permission from WCAS (http://www.weinberg.northwestern.edu/undergraduate/courses-
registration-grades/incompletes.htmlLinks to an external site.).

Quizzes
There will be three timed quizzes administered via Canvas during the quarter, each
scheduled the week prior to a midterm. These quizzes will be assessed, and the lowest
quiz grade will be dropped. The purpose of the quizzes is to act as a guide for you and me as
to how your learning is progressing, prepare you to answer exam questions, and provide
feedback about your mastery of fundamental material.
Quizzes will be administered in-person but will be accessed via Canvas, using Respondus
Lockdown Browser. See Canvas for technical details about the technology.

Concept Checks
Each lecture, there will be a short 1-point concept check quiz, with some content
questions and a “Muddiest Point” question to assess understanding.
The total number of “concept check” points will be 20 points, but you will have more
than 20 chances to earn those points. Once you reach 20 points, you “max out”, but
this also means that if you miss a quiz or get a question wrong, you will have more
chances to earn your points.

Office Hours
Your lab and lecture TAs will have weekly office hours TechD212 (next to the Organic Labs).
They will be in touch with you to schedule these office hours and a schedule will be posted on
Canvas.

What type of thing can a TA or Professor help you with at an office hour or individual meeting?
1. Clarify topics you read in the book or heard about in lecture
2. Help you get on the right track with homework problems or lab questions
3. Find resources for extra practice problems
Communicating with the Instructors
We are all happy to meet with you and discuss questions about any aspect of the course.
Please be considerate of everyone’s time and consult the syllabus, Canvas postings, and any
other communication from your teaching assistant (TA), the program assistant (Robin
Stark) or Prof. Knezz before asking a question via email.
Prof. Knezz will communicate with you primarily through Canvas, but she promises not to
spam you with a million Canvas notifications. In Canvas, go to Settings > Notification
Preferences and set all to ASAP so that you do not miss any time-sensitive information
about the course.

ASLA Resources
Quarter-Long Study Group Opportunity – Registration Required:
If you would like to study with other students in this class, consider joining a Peer-Guided Study
Group. Participants will meet weekly with about 5 to 8 other students and a peer facilitator, a
student who has already taken and done well in the course. During sessions, students review
concepts, work through practice problems, bring their questions, and work together to develop
answers.
Students register for the full quarter on CAESAR and attendance is expected weekly. Study Group
sessions are listed on CAESAR below course lecture and discussion sections (ex. CHEM 151-SG –
CHEM 151-SG Peer-Guided Study Group: Quantitative Problem Solving in Chemistry). Feel free to
contact Borislava at pgsg@northwestern.edu with any questions. Provided through Academic Support
& Learning Advancement.
Drop-In Peer Tutoring – No Appointment Needed:
Students are welcome to stop by Drop-In Peer Tutoring to get support with a specific question or
issue, or just talk through course materials with others. Covers this course and many introductory
courses in Biology, Chemistry, Economics, Engineering, Math, Physics and Stats. Tutoring takes
place Sundays through Thursdays. Check specific times, courses and locations on the Drop-In
Peer Tutoring website. Feel free to contact Valerie at valerie.wolf@northwestern.edu with any
questions. Provided through Academic Support & Learning Advancement.
New this fall: additional Gen Chem and Calculus tutoring will be available in the Multicultural
Center. See the website for details.

Plagiarism and Academic Integrity

Students in this course are required to comply with the policies found in the booklet, "Academic
Integrity at Northwestern University: A Basic Guide". All papers submitted for credit in this course
must be submitted electronically unless otherwise instructed by the professor. Your written work
may be tested for plagiarized content. For details regarding academic integrity at Northwestern or to
download the guide, visit: https://www.northwestern.edu/provost/policies-procedures/academic-
integrity/index.html
AccessibleNU: Students with Disabilities
Northwestern University is committed to providing the most accessible learning environment as
possible for students with disabilities. Should you anticipate or experience disability-related barriers
in the academic setting, please contact AccessibleNU to move forward with the university’s
established accommodation process (e: accessiblenu@northwestern.edu; p: 847-467-5530). If you
already have established accommodations with AccessibleNU, please let me know as soon as
possible, preferably within the first two weeks of the term, so we can work together to implement
your disability accommodations. Disability information, including academic accommodations, is
confidential under the Family Educational Rights and Privacy Act.

Statement of Inclusivity
This course strives to be an inclusive learning community, respecting those of differing
backgrounds and beliefs. As a community, we aim to be respectful to all students in this
class, regardless of race, ethnicity, socio-economic status, religion, gender identity or sexual
orientation.

Gender Pronouns
This course affirms all gender expressions and gender identities. There will be a survey
administered at the beginning of the quarter asking that you provide the name and
pronouns that you use (which is entirely optional). This information will be given to your
TA in their rosters. Prof. Knezz and your TA welcome you to correct us on your name or
gender pronoun if a mistake is made. If you have concerns, please contact Prof. Knezz in
person or by email, whatever is most comfortable for you.

Support for Wellness and Mental Health

Northwestern University is committed to supporting the wellness of our students. Student Affairs
has multiple resources to support student wellness and mental health. If you are feeling distressed
or overwhelmed, please reach out for help. Students can access confidential resources through the
Counseling and Psychological Services (CAPS), Religious and Spiritual Life (RSL) and the Center for
Awareness, Response and Education (CARE). Additional information on all of the resources
mentioned above can be found here:
https://www.northwestern.edu/counseling/
https://www.northwestern.edu/religious-life/
https://www.northwestern.edu/care/

Class Recordings
This class or portions of this class will be recorded by the instructor for educational purposes. You
will be able to access recordings through the Panopto tab on Canvas. Recordings are typically
accessible within a few hours of class completion Portions of the course that contain images,
questions or commentary/discussion by students will be edited out of any recordings that are saved
beyond the current term.
Unauthorized student recording of classroom or other academic activities (including advising
sessions or office hours) is prohibited. Unauthorized recording is unethical and may also be a
violation of University policy and state law. Students requesting the use of assistive technology as an
accommodation should contact AccessibleNU. Unauthorized use of classroom recordings – including
distributing or posting them – is also prohibited. Under the University’s Copyright Policy, faculty
own the copyright to instructional materials – including those resources created specifically for the
purposes of instruction, such as syllabi, lectures and lecture notes, and presentations. Students
cannot copy, reproduce, display, or distribute these materials. Students who engage in unauthorized
recording, unauthorized use of a recording, or unauthorized distribution of instructional materials
will be referred to the appropriate University office for follow-up.

COVID-19 Classroom Expectations Statement

Students, faculty and staff must comply with University expectations regarding appropriate
classroom behavior, including those outlined below and in the COVID-19 Expectations for Students.
With respect to classroom procedures, this includes:

• Policies regarding masking, social distancing and other public health measures evolve as the
situation changes. Students are responsible for understanding and complying with current
University, state and city requirements.
• In some classes, masking and/or social distancing may be required as a result of an
Americans with Disabilities Act (ADA) accommodation for the instructor or a student in the
class even when not generally required on campus. In such cases, the instructor will notify
the class.

If a student fails to comply with the COVID-19 Expectations for Students or other University
expectations related to COVID-19, the instructor may ask the student to leave the class. The
instructor is asked to report the incident to the Office of Community Standards for additional follow-
up.
.
Tentative Lecture Schedule
Date Lecture Topic (Section in 6th edition / Section in 7th edition) Chapter (6th Chapter (7th
Edition) Edition)

Chemical Bonding and Chemical Structure 1 1

20-Sep 1 · Classical theories of bonding (Lewis structures) (1.2 /1.3)
· Structure of molecules (VSEPR) (1.3/1.6)
· Resonance structures (1.4 / 1.5)

1 1
21-Sep 2 Fundamentals of Molecular Orbitals and Bonding

· Electronic structure (1.6, 1.7 / 1.2, 1.4)

· Molecular & Hybrid Orbitals (1.8, 1.9 / 1.7, 1.8)

2 2
22-Sep 3 Survey of Functional Groups (2.8 / 2.8)

Alkane structure (2.1, 2.2 / 2.1, 2.2) and nomenclature (2.4 /2.4)

2 2
26-Sep 4 Physical properties (2.6 /2.6)

Conformational analysis (2.3 / 2.5)

Cycloalkanes, skeletal structures, substituents (2.5 / 2.3)

· Relative stabilities of cycloalkanes (7.1 /7.1)

27-Sep 5 2 2
Conformations of cyclohexane (chairs) (7.2 /7.2)

· Substituted cyclohexanes (7.3, 7.4 / 7.3,7.4)

· Cyclopentane, cyclobutene, cyclopropane (7.5

/7.5)

28-Sep 6 3 3
Bicyclic and polycyclic compounds (7.6 / 7.6)

Lewis acid/base (3.1 / 3.1)

Electron-pair displacement (3.2 / 3.2) and resonance electron

movement (3.3 /3.3)

29-Sep
QUIZ 1

3-Oct 7 3 3
Quantitative scales and structural trends

· Bronsted-Lowry acids/bases (3.4 / 3.4, 3.6)

· Equilibria and acid-base reactions (3.4 / 3.5)

4-Oct Exam 1 (Problem session Tuesday this week)

5 - Oct 8 3 3
Structural features of acidity (3.5 / 3.7) & Review
6- Oct 9 4 4
Alkene structure (4.1 / 4.1) and nomenclature (4.2 / 4.2), and
properties (4.4 / 4.4)

Alkyne nomenclature (14.2 / 4.2), structure (14.1 /4.1), and

properties (14.3 / 4.4)

10- Oct 10 14 4
Unsaturation number (4.3 / 4.3)

Relative stabilities (4.5 / 4.5)

Alkene addition reactions

· Overall reaction (4.6, 14.4, 5.1 / 4.6,5.1)

11-Oct 11 4/5 4/5

HX addition (4.7 / 4.7,4.9)

· X2 addition (5.2 / 5.2)

H2O addition (5.4 / 5.4-5.7)

· Markovnikov vs anti- Markovnikov

12-Oct 12 5/10 5
Ozonolysis (5.5 / 5.8)

Free radical polymerization (5.6 / 10.3 )

Alkene reactions with peroxides (5.6, 10.1)

Reduction of alkynes (14.6 /10.2)

17-Oct 13 14 10
Acidity of terminal alkynes and acetylenic anions as nucleophiles
(14.7 / 10.6)

Grignards and organometallics / 10.5

Retrosynthetic analysis

18-Oct 14 6 6
Stereochemistry terms and definitions

· Enantiomers, chirality, and symmetry (6.1 / 6.1)

· R, S system (6.2 / 6.2)

19-Oct 15 6 6
Stereochemical relationships between molecules

· Mixtures of enantiomers (6.4 / 6.4)

· Diastereomers (6.6 / 6.6)

· Meso compounds (6.7 / 6.7)

20-Oct
QUIZ 2

24-Oct 16 7 7
Stereochemistry on chair cyclohexane (7.4)·

Stereochemistry of addition reactions (7.8 / 7.8)

25- Oct
Exam 2 (Problem session Tuesday this week)

26-Oct 17 9 9
Synthesis (substitution/elimination reactions)

· Overview of substitution/elimination (9.1 / 9.1), equilibria

(9.2 /9.2), reaction rates (9.3 /9.3)

27-Oct 18 9 9
· SN2 (include stereochemistry/orientation) (9.4 9.4)

Stereochemistry and designation of S 2 (9.4C, 7.8B)

N

· E2 (9.5 /9.5)

31-Oct 17 9 9
SN1/E1 (9.6, 9.6)

· Summary (9.7 /9/7)

1-Nov 18 10 11
Synthesis and reactivity of alcohols

· Alcohols and thiols as acid/base (10.1 / 11.1)

· Dehydration (10.2 / 11.2)

2-Nov 19 10 11
Reaction with HX (10.3 / 11.3)
 · Making good leaving groups (10.4 / 11.4)

Oxidation and reduction reactions

· General oxidation and reduction (10.6 / 11.6)

7-Nov 20 11 12
Oxidation of alcohols (10.7 / 11.7)

Synthesis of ethers/sulfides (11.2 /12.2) and epoxides (11.3 /12.3)

Cleavage of ethers (11.4 / 12.4)

8-Nov 21 11 12
Catch up/ Review

Nucleophilic Substitution Reactions of Epoxides (11.5 / 12.5)

9-Nov 22 11 12
Preparation and oxidative cleavage of glycols (11.6 / 12.6)

Oxidation of ethers and sulfides (11.9 / 12.9)

10-Nov QUIZ 3
14-Nov
Retrosynthetic analysis

Mechanism reviews

15-Nov 26 Intro to benzylic reactivity. 17 17

16-Nov 27 17 17
Benzylic reactions

21- Nov EXAM 3

22-Nov
Catch up and Review

29-Nov – 1-Dec READING WEEK: REVIEW