CHEM 233 – Elementary Organic Chemistry Lab I

Syllabus Fall 2019

Instructor: Dr. David Kell Office Hours: Mon 2-3, Thu 10:30-11:30
Email: [email protected] 367 J Noyes Laboratory

Course Lecture Times & Locations:

Section (CRN) Time Day Location

Lecture: AL1 (36313) 9:00-9:50 AM R 100 Noyes Laboratory

Lecture: AL2 (36315) 3:00-3:50 PM R 100 Gregory Hall

Prerequisite: CHEM 232 (previous credit or concurrent registration)

Required Materials:

Lab Manual: Organic Chemistry Laboratory Manual eText available at

http://go.illinois.edu/chem233etext. You must purchase this.

Lab Notebook: Self-Copying Student Laboratory Notebook (ISBN: 978-0-7380-9252-2). Any lab
notebook with self-copying pages such as your gen chem lab notebook will do; this
version includes Spectroscopy tables you will use throughout the course.

Lab Goggles: UVEX Stealth OTG safety goggles, available at Illini Union Bookstore.
Safety glasses and previously used green goggles are not acceptable.

Lab Coat: Must cover arms to wrists and legs to knees, available at the Illini Union
Bookstore. The fire-proof coat is not required. Lab aprons are unacceptable.

Lab Attire: You must wear appropriate lab attire under your lab coat. A good rule of thumb
is that no skin should be visible below the neck. Pants or sweatpants must
cover openings at the tops of your shoes or boots and remain there. They may
not be tucked into your boots. Leggings, tights and skinny jeans are
examples of tight fitting leg wear that are unacceptable.

Suggested Materials:

Calculator: A non-programmable scientific calculator is recommended for use in lab and on

exams. Programmable calculators (TI-80 and above or similar) are not
permitted on the Exam or the Laboratory Practical. Other electronic devices,
including phones, are not permitted in lab or during exams.

Text: Zubrick, J.W. The Organic Chem Lab Survival Manual: A Student’s Guide to
Techniques, 7 ed.; Wiley: New York, 2008. (ISBN: 0-470-12932-8)

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Course Overview

Chem 233 is a laboratory course that utilizes recorded video webcasts as the primary source of
information and uses the lecture periods as optional problem solving sessions. The video
webcasts (located in each week’s folder on Compass) and lecture periods focus on the theory
and concepts behind the techniques and reactions used in each experiment, while the
laboratory sessions focus on the physical application of techniques and reactions.

Associated with each laboratory experiment is a Pre-lab Quiz, a Laboratory Notebook

submission, and a Post-lab Quiz. At the end of the course you are evaluated by a Laboratory
Practical experiment and an Exam. The exam focuses on material from the webcasts and
lecture. This course assumes students possess fundamental knowledge of general chemistry.

Course Objectives

CHEM 233 is a technical course designed to provide you with an opportunity to learn about the
properties, syntheses, separation, purification, and identification of organic compounds. By
watching recorded video webcasts, you will learn the theory and detailed background behind
spectroscopic and experimental techniques that will be applied in the laboratory portion of the
course. During the in-person lecture periods, you will work problems and ask questions related
to what was discussed in the recorded lectures. In lab, you will conduct experiments designed to
introduce you to these spectroscopic and experimental techniques. Additionally, this course will
provide you with the opportunity to learn how to properly keep records of your scientific research
in a laboratory notebook, a valuable skill that is required in many scientific disciplines. You are
expected to carefully and efficiently perform the assigned experiments in the lab, but you are
also expected to understand the principles behind these experiments.

By the end of this course, you will be able to…

 …explain the theory behind standard organic chemistry laboratory techniques and
instruments.
 …predict the outcome of an experiment using knowledge of the theory behind the
experiment.
 …execute basic organic chemistry laboratory procedures safely and efficiently.
 …record relevant scientific data and observations in a laboratory notebook.
 …perform arithmetic calculations using recorded scientific data.
 …draw conclusions and justify those conclusions using spectroscopic data or recorded
laboratory data.

You will prepare for and practice achieving these objectives by…

 …watching and taking notes on the pre-recorded webcast video(s) for each week’s
topic(s).
 …participating in (optional) problem-solving sessions during lecture periods.
 …preparing for lab by completing your Pre-lab Notebook and online Pre-lab Quiz.
 …attending every lab on time.
 …being safe in the lab.
 …taking graded online Post-lab Quizzes.
 …asking for help when needed.

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You will be assessed on how you have achieved these objectives using…

 …the aforementioned online quizzes.

 …submitted Laboratory Notebook pages.
 …Lab Cleanliness grades.
 …a Laboratory Practical.
 …an End-of-semester Exam.

Course Communication

Rather than emailing questions about the lecture or labs to the instructor or a TA, you are
strongly encouraged to attend office hours. These times are set aside especially for you, so visit
us! Students may attend any office hours, not just those of their own TA. A schedule of TA office
hours will be posted on the CHEM 233 Compass website under “Syllabus and Course Logistics
Documents” within the first week of class. There may be time at the end of most lab periods to
get help from your TA as well. The instructor will hold regular office hours as listed in this
syllabus as well as by request. Make an appointment to discuss any personal matters.

When you e-mail your TA or the instructor, please include your name and lab section in your
email. We will attempt to respond to your e-mails in a timely manner, but we have
responsibilities outside of the course that may prevent us from doing so,and ask you to be
patient after sending e-mail. You should use your “[email protected]” address with a descriptive
subject line beginning with “CHEM 233” to avoid your email being filtered as junk mail.

Make an appointment to discuss any personal matters - be sure to include some possible days
& times you can meet in your message.

Getting Started in Chem 233

1) Before the first lecture Week 1…

a) Read the course syllabus.. Acquire the Laboratory Manual eText, a laboratory
notebook, appropriate lab goggles, and a lab coat.
b) Read the “Laboratory Safety” chapter in the Laboratory Manual eText, Watch the
assigned video webcasts in the “Week 1A – Getting Started” folder. Read the course
syllabus, Both the syllabus and webcasts can be found on the Compass course website
https://compass2g.illinois.edu/webapps/login/
c) Complete the “Getting Started” online quiz located on the Compass2g course
website. This quiz is worth 50 points and covers course policy and lab safety as detailed
in the previously mentioned resources. The quiz opens one week in advance and
closes at 11:00 AM on Monday 9/02, the week of Check-in. The Getting Started quiz
will be graded immediately upon completion and may be attempted an unlimited number
of times. Not all questions on the Getting Started quiz will be explicitly addressed in the
video webcasts, syllabus, or laboratory manual. Safe conduct in the lab must be based
foremost on good judgment regarding risks and questionable situations, and this quiz will
aim to illustrate this need. If you see no score in your Gradebook, no attempt was
submitted.

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 d) Review the material in the “Week 1B – Fundamental Concepts” folder on the CHEM 233
Compass2g website. To prepare, print and fill in the Week 1 Worksheet if you wish.
2) Check-in Week 2…
a) Check-in is in your assigned lab and time, 255, 256, 257 or 262 Noyes at 8 AM or 1 PM
*Due to the holiday, Monday sections will have to check in Week 3, Mon. 9/09, 1
PM
b) Be sure to wear appropriate lab attire, lab goggles, and a lab coat.
3) Before your first “dry” lab (worksheet packets on spectroscopy) Week 3 (1/28–31)…
a) Complete the Mass/IR Spec Pre-lab Quiz before Monday 11 AM of that week.
b) Check the chart in the Dry Lab folder on Compass for your time and location.
4) Before your first “wet” laboratory session Week 6 (2/18-21)…
a) Complete the Pre-lab Quiz by Mon.11 AM and the Pre-lab portion of your lab notebook.
b) Be sure to wear appropriate lab attire, lab goggles, and a lab coat to your assigned lab
and time, in 255, 256, 257 or 262 Noyes

Online Video Webcasts and In-Class “Lecture” Periods

Webcast videos located on the course Compass 2g page are the primary method of content
communication in this course. It is assumed that you watch the webcast videos prior to the
optional lecture and corresponding laboratory period. You are strongly encouraged to take
notes while watching the videos as you would for any lecture. You may find such notes useful
when taking the online quizzes and when preparing for the Laboratory Practical and the Exam.

Attendance at lectures is optional. Lectures will not duplicate the video webcasts. Instead
they will briefly review the webcast material, and then be used to work practice problems related
to topics discussed in the videos. You should print the worksheets located on the course
website associated with a given week’s lecture topic if you attend lecture. By practicing in the
lecture periods, you will be better prepared for the Post-lab Quizzes and the Exam.

Laboratory Check-in is Mandatory

Lab Check-in will introduce you to your TA, the lab space you will work in [255, 256, 257 or 262
Noyes], contents of your assigned equipment drawers, and discuss safety information directly
relevant to your laboratory workspace. Failing to attend Laboratory Check-in results in a zero
grade and the absence also counts toward a failing grade for 3 missed labs. Lab Check-in
cannot be made up. If you know that you will miss Laboratory Check-in due to a University-
sanctioned event, you must give prior notice to the instructor to make other arrangements.

Preparing for Lab

Having watched the online video webcast(s) for an experiment and taken thorough notes, you
must read any supplementary online material before each lecture. Starting with the week 6 ,
also read the pertinent information in the Laboratory Manual e-Text for the “wet lab” experiment.
For success in this course, you should be an active participant when thinking about the course
material and always ask yourself “how and why?” Every step in an Experimental procedure is
necessary. At each step, you should be able to explain why that particular step is being
performed.

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Once you have established a firm foundation of what the experiment entails, you must complete
the online Pre-lab Quiz and the Pre-lab Notebook portion for Wet Labs. Failing to complete
either the Pre-lab Quiz on time, or the Pre-lab Notebook (for wet labs) prior to your lab
section will disqualify you from performing the experiment and will result in a score of
zero for that experiment.

The Pre-lab Quiz, worth 5 points, is a short quiz designed to be answered easily if you have
watched the video webcast(s) and completed your Pre-lab notebook materials. The Pre-lab quiz
for an experiment will open at 11:00 AM on Monday the week before an experiment is
performed and will be due at 11:00 AM on the Monday the week the experiment is performed
for all laboratory sections. Pre-lab Quizzes are not graded until after the due date and no
feedback will be shown until after the due date. You will have 60 minutes to complete each
Prelab Quiz, and the quiz may be taken twice. The second attempt is to accommodate any
technical issues experienced during the first attempt, such as losing internet connectivity. You
are responsible for ensuring you have a stable internet connection. Extra attempts will not be
given under any circumstances. The last submitted attempt is the score that will be kept. If
you completed one attempt, and then began a second attempt only to accidentally
submit early, lose connectivity, or experience any other issue, the second attempt will
still be the score accepted. You will see either a checkmark or a score in your Gradebook
upon submitting a quiz attempt. If you do not see either a checkmark or a score, no attempt
was submitted. You are responsible for checking that your quiz was successfully
submitted. You can view your Quiz submissions after their due dates by going to your
Gradebook, clicking on the desired Quiz, and then click on the score. `.

Detailed guidelines on preparing and keeping a Laboratory Notebook, along with an Example
Pre-lab Notebook entry, can be found in the Laboratory Manual.

ChemNet Tutorials

These optional, interactive tutorials are available online for some Experiments. Completing
these tutorials is suggested, as they will support your understanding of the experiments and
make laboratory work easier by demonstrating the techniques and experimental set-ups you will
encounter. You may access these tutorials via Compass 2g under ”Supplemental Lab
Preparation Materials.”

Performing an Experiment

There are 11 laboratory sessions. Each laboratory session is assigned one experiment and, as
this is a technical performance-based course, each experiment is mandatory. Make-up
experiments for religious obligations, university-sanctioned events, or similar conflicts may be
possible if the instructor is notified well in advance. Due to their sudden nature, make-up
experiments are generally not granted for absences due to illnesses or other unexpected
scenarios. The lowest experiment score during the semester will be dropped, so a single missed
experiment will not detrimentally affect your grade. As this is a course with a large enrollment,
opportunities for a make-up experiment are few even with advance notice and must be
scheduled during one of the existing lab times that same week: Tue-Thu 8-12, or Mon-Thu 1-5.
Per department policy, missing 3 or more laboratory sessions for any reason will result
in an automatic failing grade. At that point you will not be allowed to complete the course.

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Each TA will give a brief lecture immediately at the start of the laboratory session; therefore, you
must arrive to your lab sessions on time. The TA’s pre-lab lectures are critical to your safe and
successful performance of each experiment. Arriving late means you will miss this important
information. TAs will deduct 10 points from the experiment grade of any student arriving
during the TA pre-lab lecture. Students that miss the TA pre-lab lecture entirely, or arrive
more than 15 minutes late, whichever comes first, will be denied entry and will receive a
score of zero for the experiment.

Dry Labs

As shown in the course schedule at the end of this syllabus, the first three experiments are
listed as “dry” labs, which are 2 hours long, and will not be in your assigned laboratory room.
Instead, you will perform the dry labs in classrooms that will be assigned to you. A listing of
room assignments and times based on your TA will be located on the Compass2g course
website in the “Dry Lab Instructions” folder. Due to room availabilities, start times are typically 8
AM and 3 PM. You are responsible for checking this document and arriving to your
assigned room on time. These dry labs consist of spectroscopy worksheet packets that will
be provided to you. There are Pre-lab Quizzes for the dry labs, but there are no Pre-lab
Notebooks to write up and you do not need to bring your notebooks to the Dry Labs, although
you may find the spectroscopic tables on the covers of your notebook helpful.

Wet Labs

All other laboratories are “wet” experiments that will be performed in your assigned laboratory
room [255, 256, 257 or 262 Noyes] starting week 6. Information and procedures for each
experiment are found in your Laboratory Manual e-text. Only groups of 1 or 2 are allowed. If
your partner is absent or drops, you may pair up with another unpaired person.

At the beginning of each lab session, your TA will check to see that you have completed the
Pre-lab materials (Pre-lab Quiz & Pre-lab Notebook). Students who have not completed the
Pre-lab materials will not be allowed to participate in the laboratory session and will
receive a score of zero for the experiment.

Only items required to complete the day’s lab are allowed into the laboratory space. No food or
drink is allowed; do not bring in water bottles; do not use cell phones, tablets, laptops, or other
unauthorized electronic devices in the laboratory. No coats, backpacks, purses, etc. are
allowed. It is suggested that students do not bring expensive items with them at all. Leave all
items not required for the lab in the lockers located in the north corridor of the 2nd floor of Noyes
Laboratory. Please check that your locker is carefully closed and secured. The university and its
employees are not responsible for items left in lockers.

No work may be performed in the hallway outside the lab rooms. Complaints were lodged of
students blocking passage so this practice has been banned by the Safety Officer.

Safety is the top priority in this course. Details on what is and is not acceptable lab attire are
found in the Laboratory Manual. (See the “Laboratory Attire” section, paying particular attention
to #6. Note that tights and hosiery made of synthetic fabrics should not be worn.) You must
wear laboratory goggles and a lab coat in the laboratory at all times. You must wear
appropriate lab attire under your lab coat. A good rule of thumb is that no skin should be visible
below the neck. Due to safety concerns, there is a zero tolerance policy for students who are
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not appropriately dressed for lab. Such students will not be allowed to complete the
experiment and will receive a score of zero for the experiment.

At the discretion of your TA, your experimental grade may be reduced for unsafe or
irresponsible conduct in the lab. Penalties will be enforced for tardiness, improper use of
personal protective equipment, unsafe technique, improper disposal of waste, failure to clean
lab space, or any other behavior or activity that your TA determines to be unsafe, disruptive, or
reckless. Each observed infraction will reduce your notebook page grade by 10 points, up to a
maximum deduction of 20 points per lab session. If you commit more than two infractions in
one lab session, your TA will dismiss you from the lab and you will receive a score of
zero for the experiment.

You will have only the allotted time of 3 hours and 50 minutes in lab to finish each experiment.
This includes clean-up. Most experiments will require the majority of the scheduled lab period,
so it is important that you come to lab prepared to perform the experiment and that you work
efficiently. There should be no instances when you are “doing nothing” in lab. Prepare for what
is going to be done next. Each new technique will be described to you in detail before you
employ it in lab for the first time. Thereafter, you will be expected to be able to use each
technique without any further detailed directions. TAs have the authority to instruct you to begin
cleaning, even if you have not yet completed the lab, to ensure you leave the lab on time.

Students with health or physical conditions that warrant additional precautions (respiratory
ailments, pregnancy, etc.) should contact the instructor immediately to discuss their
circumstances. Student safety in the laboratory is our top priority.

Post-Lab Responsibilities

Lab Cleanliness Points

Part of ensuring a safe environment includes keeping the laboratory clean and organized. At the
end of each wet lab period, your TA will grade the cleanliness and organization of the
community areas in your lab, such as the weighing balances, waste areas, and sinks, as a
section out of 5 points. Every student in a lab section will receive the same Lab Cleanliness
Grade on their Lab Report for that week. For example, this means if the area around the
weighing balances is messy at the end of lab, everyone is penalized even if you did not
personally make the mess. Remind each other that it is everyone’s responsibility to leave the
lab in good condition. A rubric for how Lab Cleanliness points are assigned is located on the
course Compass2g website under “Syllabus and Course Logistics Documents.”

Notebook Page Submission

At the end of each lab session, you will remove the perforated white notebook pages used that
day and submit them to your TA before leaving the lab; you will keep the other copy of your
notebook pages in your lab notebook. Your notebook pages will be graded for completeness
and correctness including an accurate account of the procedure as you actually performed it,
with all relevant data and observations, calculations, and conclusions well organized and clearly
labeled. Pre-lab portions of the notebook cannot be altered once you enter the laboratory. Be
sure to report your actual procedure, data, and observations honestly. Inconsistencies are

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cause for suspicion of academic misconduct and may incur deductions. Experimental work
submitted after the end of your 3 hour and 50 minute lab period will not be graded.

Post-lab Quiz

After every experiment, there is a Post-lab Quiz, worth 20 points, designed to test your
understanding of the theoretical and applied aspects of the experiment. These quizzes will
cover material from both the video webcasts and the experiment itself. Post-lab Quizzes will
be made available at 5:00 PM the Thursday of the week an experiment is performed and
will close at 11:00 AM the following Monday. Post-lab Quizzes may be taken with the
assistance of notes, but not other people. Post-lab Quizzes are not graded until after the due
date and no feedback will be shown until after the due date. You will have 60 minutes to
complete each Post-lab Quiz. Each quiz may be taken twice, if desired. The second attempt is
to accommodate any technical issues experienced during the first attempt, such as losing
internet connectivity. You are responsible for ensuring you have a stable internet connection.
Extra attempts will not be given under any circumstances. The last submitted attempt is the
score that will be kept. If you completed one attempt, and then began a second attempt
only to accidentally submit early, lose connectivity, or experience any other issue, the
second attempt will still be the score accepted. You will see either a checkmark or a score in
your Gradebook upon submitting a quiz. You can view your quiz submissions after their due
dates by going to your Gradebook, clicking on the desired quiz, and then clicking on the score.
The lowest Post-lab Quiz score is dropped at the end of the course.

Academic integrity

All University of Illinois academic integrity policies are strictly enforced. All students at the
University of Illinois agree to be bound by the Student Code regardless of whether they
have actually read it. See http://admin.illinois.edu/policy/code/ for further information.
Students found guilty of academic misconduct on any assignment will, at minimum, be given a
zero for the assignment and have the full value of that assignment deducted from their
final course grade. Actions up to and including a failing grade for the course are options
available to the instructor. Any academic misconduct will be reported to your college in writing.

Plagiarism on any assignment will not be tolerated. NEVER transcribe,

copy, or paraphrase statements (verbal or written) or materials from a
classmate, a past student’s lab report, or any other source. To avoid the
appearance of academic misconduct, never share your notebook or your
responses to any assignment with any other person.

Examinations

There will be one examination date, time and locations to be determined by the Registrar.
The Examination may contain multiple choice questions, free response questions, spectroscopy
problems, mechanism questions, and/or mathematical calculation problems.

Students with a Letter of Academic Accommodation who wish to utilize their

accommodations for the exam must provide a copy to the instructor and formally submit a
request to the instructor within the first 2 weeks of the semester.

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Students with a University-sanctioned conflict who wish to petition for a Conflict Exam must
provide documentation for the conflict and formally submit a request to the instructor. A form
and instructions will be posted on Compass a few weeks before the exam.
You must bring a photo ID to the exam. Please arrive to your exam location at least 15 minutes
before the scheduled exam time to check in. Students arriving late to the exam will forfeit the
lost time. No other materials (including but not limited to music playing devices, headphones,
cell phones, textbooks, course notes, etc.) are permitted. Per Chemistry Department policy, any
talking during an Exam, including asking a neighbor to borrow materials, will be considered
cheating. If you require something, raise your hand and ask the proctoring TA.

A Laboratory Practical will be held the last full week during your normal laboratory period. The
experimental procedure is in the Lab Manual e-Text. The late penalty is 25 points and you will
have to complete the experiment on your own in the time remaining.

Grading

This is a tentative grading rubric and is subject to change. The scores represent
totals after appropriate lowest scores have been dropped.

Points Earned Grade

Getting Started Quiz 50
Lab Check-in 40 985 – 1015 A+
Lab Notebook Pages (10x40pts) 400 945 – 984 A
Pre-lab Quizzes (10x5pts) 50 905 – 944 A-
Post-lab Quizzes (10x20pts) 200 880 – 904 B+
Exam 175 835 – 879 B
Lab Practical 100 805 – 834 B-
Total points 1015 775 – 804 C+
735 – 774 C
705 – 734 C-
675 – 704 D+
635 – 674 D
605 – 634 D-
0 – 594 F

Course totals will be rounded to the nearest whole number. The instructor may choose to
standardize the Laboratory Notebook Pages scores only for each lab section independently if
and only if significant differences in grading are observed between TAs. This works both ways:
Section grades that are above the normal range will be reduced while Section grades that are
below the normal range will be increased to lie within the normal range.

Your TA is the instructor of record for all grading related to the laboratory experiments
(Laboratory Notebook and Laboratory Cleanliness points). Questions about lab report point
deductions must be addressed to your TA.

This is an experiential course; you must attend lab to gain that experience. Per
department policy, missing 3 or more laboratory sessions for any reason will result in a
failing grade.

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Drop Date

The deadline for undergraduates to withdraw from this course without a grade of W is Friday,
October 19 (https://registrar.illinois.edu/academic-calendars/fall-2019-academic-calendar/).
Fall 2019 Schedule
Please look carefully at the following schedule for the correct order of lectures and
laboratory experiments.

Laboratory Activity
Week # Dates Thursday Lecture Topic
(Experiment # - Name)

Introduction, Fundamentals,
1 8/26-29 No Lab (only Lecture)
Intro to Spectroscopy

Lab Check-In
2 9/03-05 Mass and IR Spec
255/256/257/262 Noyes

Mass Spec and IR (dry lab) 1

3 9/09-12 H NMR Part 1
See chart on Compass for location

NMR Part 1 (dry lab) 1

4 9/16-19 H NMR Part 2 and 13C NMR
See chart on Compass for location

NMR Part 2 (dry lab)

5 9/23-26 Thin Layer Chromatography
See chart on Compass for location

9/30- 1 – TLC of Analgesics Absolute Configuration

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10/03 255/256/257/262 Noyes Determination

2 – Absolute Configuration Melting Point and

7 10/07-10
Determination Recrystallization

Mechanism Determination of
8 10/14-17 3 – Recrystallization
Bromination of an Alkene

9 10/21-24 4 – Bromination of an Alkene Acid-Base Extraction

Nucleophilic Substitution
10 10/28-31 5 – Acid Base Extraction
Reactions

6 – Unimolecular Nucleophilic
11 11/04-07 Elimination Reactions
Substitution

12 11/11-14 7 – Unimolecular Elimination Aldol Condensations

13 11/18-21 8 – Aldol Condensation Lab Practical

Thanksgiving Break

Laboratory Practical
14 12/02-05 Exam Review
and Lab Check-Out

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 Exam: Date, Time & Locations TBD
Details will be posted later in the semester, closer to the exam date

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