CHEM 202L - Organic Chemistry II Laboratory – Spring 2023

w Organic Laboratory Manager: Dr. Farrell Kersey (Email: [email protected])

w Lab Teaching Assistant (please fill in below during your first lab meeting):

TA NAME TA EMAIL

1. COURSE DESCRIPTION
Pre-requisite: To enroll in CHEM 202L you must either be enrolled in 202D lecture in the same semester or have
received credit for the lecture in a previous semester. CHEM 202 laboratory is worth 0.25 credits.
The purpose of CHEM 202 laboratory is to build upon students’ experiences in CHEM 201L with the basic
understanding of separation & purification techniques and spectral analysis. Students will be introduced to synthetic
methods, qualitative analysis, and applications of organic chemistry in the fields of green chemistry and molecular
biology.
The lab course has been designed to complement the lecture but may not necessarily correspond topic-by-topic
as the semester progresses. Different lecturers teach at different paces, so it is difficult to align lecture and lab. As
such, your experimental handouts, literature references, Sakai resources, and TA presentations will provide you with
adequate background to conduct each experiment and write thoughtful post-laboratory write-ups.
Lab meetings will begin the week of January 30th and will meet every week unless shown otherwise in the lab
schedule.
Before the first lab you will be responsible for reviewing 1) the CHEM 202 lab syllabus & experiment schedule, 2)
reading the Lab 1 experiment handout, and 3) completing the written pre-lab assignment from the Lab 1 handout. See
the lab handout on the Sakai lab site and/or Labflow site for details.

2. COURSE POLICIES
2.1 Supplies (notebook, safety glasses, and a facemask are mandatory)

§ 1) Carbonless-copy lab notebook & 2) Safety glasses/goggles. These items can be purchased at the Bryan Center
bookstore or by ordering through Duke Graduate Chemistry Council (https://graduate-chemistry-
council.square.site/). For notebooks, you may use one from a previous semester; if you run out of pages you will
need to purchase a new one. You can also purchase your lab notebook from an online site like Amazon.

§ 3) Labflow account: The Labflow website will be used for uploading pre-lab and post-lab assignments and reports,
and for subsequent grading by your TA. Additionally, you will complete pre-lab quizzes during the week of each
experiment. At present, the cost for access to Labflow is $46 for one semester. You will receive instructions on
signing up for Labflow prior to your first lab meeting.

§ There is not a required textbook for lab, but some reading assignments with references within Loudon text
are included in the experiment handouts. Additional resources for lab can be found under the Resources folder
on Sakai. These include documents on writing post-lab reports, IR & NMR spectral analysis, and a copy of
Laboratory Techniques in Organic Chemistry, 3rd ed. (J. R. Mohrig)

CHEM 202 Laboratory – Spring 2023 | Duke University 1

2.2 Lab Safety
**All students will be required to always wear a face mask and gloves in the lab**
You and your lab mates must maintain a safe learning environment while in the laboratory. Your TA will review
proper safety procedures in the event of a chemical spill or exposure, fires, or other emergencies that may occur.
Learn the location of the eyewash stations, safety shower, fire extinguishers, and both laboratory-exit routes.
§ If you arrive at lab without a proper face mask, you can obtain one from the lab manager (1225 FFSC).
§ If you sustain an injury or if there is an accident, no matter how seemingly minor, you must report it to
your TA.
§ Food and drink are NOT permitted in lab. This includes sealed water bottles & drink containers. These items
must be kept outside of the lab or disposed of to prevent contamination.

2.3 Proper Lab Attire

§ Safety glasses, face masks and gloves are to be always worn in the laboratory. Additionally, shoes that cover
the entire foot, shirts that cover the torso, chest and back, with sleeves past the shoulder (no tank tops!),
and pants or shorts at or below the knee are required.

§ NO SKIRTS, LEGGINGS, TIGHTS, or similar attire are allowed in lab. If you arrive without the proper
attire, you may not be allowed to participate in lab. There are NO makeup labs under these circumstances.

§ Disposable foot coverings and lab coats may be available under certain circumstances. Please see the lab
manager (1225 FFSC) if you arrive to lab without the proper attire. Points will be deducted from your
preparedness score if you need to use these.

2.4 Attendance Policies

Lab attendance is mandatory, and you must arrive on time. If you arrive so late that you will not be able to
contribute sufficiently, you will not be allowed to participate in lab. Points will be deducted from your preparedness
grade (see below) for tardiness. Due to the nature of the course, there will be no opportunities for make-up
labs.
§ One excused absence is allowed from an in-person lab meeting. If you miss a lab for an excusable reason
(e.g., illness, family emergency, religious observation, etc.), complete and send the applicable electronic form
to the lab manager ([email protected]). The Additional Comments section of the form MUST contain
your course (CHEM 202), lab section number, TA name, and name of the lab from which you are
requesting excusal.

§ Failure to submit a completed excuse form to the Lab Manager within 48 hours of the lab’s normal meeting
time may result in a grade of zero for that assignment.

§ In the event of an excused absence, you will still be responsible for completing the post-lab report for the
missed lab experiment. You may obtain any data needed to complete this from your lab partner. If necessary,
contact your lab TA to help facilitate this process.

§ Varsity Athletics: If you are involved in varsity athletics, you must provide the lab manager with a schedule
of events and the Department of Athletics Notification Letter at the BEGINNING of the semester. If you will
miss a lab due to a university-sanctioned event, you must contact the lab manager at least two weeks in
advance.

§ An unexcused absence will result in a grade of zero for that lab.

§ If you experience more than one excused absence from lab, please contact the lab manager as soon as possible
to discuss options.

CHEM 202 Laboratory Spring 2023 | Duke University 2

 2.5 Academic Accommodations
The Student Disability Access Office (SDAO) is available to ensure that students can engage with their courses
and related assignments. Students should contact the Student Disability Access Office to request or update
accommodations under these circumstances. For CHEM 202L, accommodations typically involve deadline
extensions for lab reports and/or online assignments. Accommodations are usually limited to deadline
extensions of 24- to 48-hours and should only be used in the event of unpredictable health events. To
accommodate students who have extended time on quizzes, the time limit for all online quizzes will be three
hours for all students (this is much more time than you’ll need).

2.6 Academic Honesty & Integrity (READ CAREFULLY!)

This course will be conducted according to the Duke Community Standard. Reference information on academic
integrity and the Duke Community Standard can be found at www.integrity.duke.edu. While students will work
together in groups to complete experiments, students will be responsible for completing all other work on
an individual basis.

§ ALL work in the lab notebook must be completed by the student, and everything should be in the student’s
own words. Each student must complete all subsequent data analysis individually.

§ ALL written & online work (pre-labs, quizzes, post-lab reports, etc.) must be completed individually:
answers to questions should not be shared with other students. Students may discuss general theories about
the background of the experiment, but all submitted answers should be in each student’s own words and
formatting.

§ Any collaboration between students when completing graded assignments (quizzes, reports, etc.) for this
lab course is strictly forbidden. This is considered a serious offense and will result in a grade of zero. Treat
every lab assignment/quiz as you would an exam.

2.7 Important dates

§ Last day to turn in assignments for the term: Friday, April 21 (not more than two weeks late)
§ Last day to report grade mistakes posted on Sakai: Thursday, April 30

3. ASSIGNMENTS AND GRADING

Items that will constitute your lab grade are given on the following page. Grades will be maintained on the Labflow
& lab Sakai sites.

Item No. Points each Total

Post-Lab Reports 5 70 350
Labflow Lab Quizzes 5 18 80
Labflow Safety Quiz 1 20 20
Performance & Preparedness 2 15 30
Cleanliness Czar Duties 1 10 10
End-of-Semester Survey 1 10 10
Course Total 500

w Post-lab Reports: Your full lab reports will consist of your 1) pre-lab assignment, 2) in-lab notebook pages, 3)
handout worksheets, 4) analyzed spectra (when applicable), and 5) typed discussion. Your pre-lab assignments
(Item 1) will be due before the start of each lab meeting and must be uploaded to Labflow. Each Post-lab report

CHEM 202 Laboratory Spring 2023 | Duke University 3

 (Items 2 – 5) must be uploaded to Labflow by 11 PM EST ONE WEEK after your lab meeting. Review
Section 4 of this syllabus for guidelines and each lab document for specific post-lab report instructions. The late
penalty for post-lab reports is 10% per day late. Reports will not be accepted after a period of 10 days.

w Lab & Safety Quizzes: Quizzes will be completed on Labflow and will cover material related to the experiment
to be performed during the week of lab. They may include questions on safety, reactions, mechanisms, techniques,
pre-lab readings, spectroscopy, and calculations of limiting reagents and percent yield, etc. Quizzes will open
Mondays at 12 PM EST and close Fridays at 11 PM EST unless otherwise specified.
w Performance: This is based on your overall performance in lab, including the following: following lab safety
protocols, wearing goggles, gloves, and face masks, familiarization with the experiment, working efficiently
during lab, and keeping your hood and glassware clean.
w Preparedness: To earn full credit for preparedness you must arrive to lab ON TIME, prepared with your face
mask, goggles, notebook, and appropriate lab attire, and, as a result of sufficient preparation, conduct yourself
in an organized and efficient manner.
w Cleanliness Duties: You will be designated as the Cleanliness Czar at least once during the semester. This
responsibility includes maintaining the cleanliness of the balances and balance area, as well as cleaning up
glassware, chemicals, and equipment left out at the end of the experiment. The czar will also be responsible for
organizing and wiping down the common chemical hood and maintaining the IR instruments.

! In addition to Cleanliness Czar duties, you will also be responsible for cleaning and disinfecting your
hood and your workspace before leaving the lab. This will the responsibility of every group.
w Lab End-of-Semester Survey: A link for this will be sent out at the end of the semester. This is not related to
any survey that is part of the lecture portion of the course.

4. LAB REPORTING
4.1 General Guidelines
w Your graded labs will consist of three parts: (1) a written Pre-Lab assignment, (2) In-lab Notebook Pages,
and (3) the Post-Lab Report (worksheets, typed discussion, and analyzed spectra).
w The items above must be submitted on Labflow one week after the experiment by 11 PM, unless indicated
otherwise. Some items will have boxes for entering data directly on Labflow, primarily for handout worksheet
entries. Instructions for uploading documents can be found on the Labflow website. Your name, section
number, and TA name must be clearly marked on the front to receive full credit.
w Check your grades on the Labflow regularly to make sure that all items have been graded correctly. It is
the student’s responsibility to report discrepancies to the TA as soon as they are recognized and before the “last
day to report mistakes” (see section 2.8).

4.1.1. Pre-lab Work

Before each lab you should:

1. Read through the experiment handout and read/view supplementary materials posted on the Labflow
site and/or lab Sakai page.

2. Familiarize yourself with the equipment, glassware, and techniques that will be utilized in the
experiment by referring to the assigned pages in the Mohrig textbook available on reserve at the Perkins
library circulation desk or on the Sakai lab page under Resources. These items can also be searched for online.

3. Complete the pre-lab assignment in your lab notebook (see next page: Pre-lab Notebook Guidelines).

CHEM 202 Laboratory Spring 2023 | Duke University 4

 Pre-lab Notebook Guidelines
The following items must be in the notebook before lab. Your Pre-lab assignment must be written by hand
unless accommodations have been approved.

w Table of Contents entry – Enter the title and page number of each experiment in the table of contents.

w Name, course and section number, title, and date – A full title should go on the first page of the experiment
and an abbreviated title on the top of every page thereafter. Your name and the date must appear on every
page.

w Objective – This is the purpose for performing the experiment. DO NOT copy this directly from the handout.
These are good guidelines, but you should write in your own words the reason(s) for conducting the
experiment and what you hope to learn. Include the reaction (show structures!) and mechanisms (if known)
for synthetic experiments. All structures should be drawn neatly, with clear bonds between each atom.

w Table of Reagents and Products – A table of reagents used and of product(s) synthesized in this experiment,
and the relevant physical constants. The relevant information will vary depending on the exact experiment.
When a technique is central to an experiment include the chemicals being isolated or analyzed. Be sure to
reference values found in the literature.

w Separation Scheme (when required) – A flowchart detailing how you will purify/isolate the product of interest.
See Appendix 1 for a general example of a separation scheme.

w Procedure – For each lab experiment you will write an abbreviated version of the procedural steps as part of
the pre-lab assignment. This will help you in be prepared and familiar with the experiment and help you work
more efficiently in the lab. For all procedures written there must be sufficient information included that
someone not familiar with the experiment could repeat it without referring to the handout.

w Your pre-lab work will be graded by your TA for organization, legibility, effort, and completeness.

4.1.2. In-lab Notebook Guidelines

The goal when writing in your lab notebook should be to write clearly and with sufficient organization and detail
such that someone unfamiliar with the subject would be able to repeat your experiment exactly, using only your
notebook. The following general guidelines should be followed:
w Write your procedural steps on the LEFT side of the page (left of the dividing line). Measurements, observations,
and procedural changes will be recorded on the RIGHT side of the page.

w Write directly into your notebook, NOT on a separate sheet of paper. To encourage formation of good habits
your TA will sign your notebook pages before you leave lab each day. All procedural information and
observations must be recorded before having your TA sign your notebook pages.

w Write in pen only, NOT pencil. Do not erase or use whiteout. Make corrections by drawing a single line
through the mistake.

w Write neatly and leave plenty of space! Avoid jumbling data collected in lab on the page, making it
difficult for your TA or others to decipher. If someone is to repeat your work, they must be able to read it
and follow your organization.

The following items will be written in the notebook during lab:

Procedural Changes and Observations –The following should be included:

w Include all changes or additions you made to the procedure described in the handout.

CHEM 202 Laboratory Spring 2023 | Duke University 5

 w Exact measurements and data; exact reagent amounts and concentrations should be included in the Table of
Reagents and Products.
w Problems encountered and steps taken to correct them

w Physical data such as appearance, temperature, etc.

w Amount of time required for addition of reagent or reflux, etc.

w Observations must be written directly in the notebook as you are conducting the experiment, not after the
lab is complete. Failure to comply will result in a loss of all points associated with the observations.

4.1.3. Post-Lab Report Guidelines

These items will be written in the POST-LAB REPORT during or after lab. You may choose to work through
some of the items below first in your notebook then transfer some of the information to the post-lab report.
However, you are only required to include information through the observations section in your notebook. The
items are given on the next page.

w Mechanisms and separation schemes – Graded for accuracy on the post-lab report. Based on what you learn
during your pre-lab discussion, performing the experiment, asking questions, reading Loudon, etc., revise your
original mechanism and separation scheme for the post-lab report.

w Calculations – Use of dimensional analysis and units will be required. You will be graded on the correct use of
significant figures, but 2-3 figures are typically sufficient. See Appendix 2 for details on the calculations that
will most commonly be encountered.

w Results – The post-lab report worksheets will have places for you to include important results and to tabulate
spectral information; this must be filled in for every lab report. Some of these items will be entered directly
into the Labflow prompts.

w Spectroscopy – Include copies of all analyzed spectra. Indicate peak assignments and functionalities directly
on the spectra as directed in the lab handout.

In addition to the items below, you must read and follow the instructions within the document under
“Resources” on Sakai entitled Writing Post-lab Report Discussions. This will be your main resource on
properly writing and formatting lab report discussions.

w Discussion – Typed, 11- or 12-point font, 1-inch margins, double-spaced, 2-page limit. This section allows the
TA to see if you understood the important concepts of the experiment. Think about the results obtained and
attempt to analyze them according to the statements/questions at the end of each lab document and include
the following:
w Summarize your findings. Use your results as evidence to tell a story that culminates in your major
conclusions. Be sure to evaluate your confidence in the results. Important note: any organic chemist can tell
you that following a written, published procedure is no guarantee that you will get the product you set out
to make. Therefore, treat all products (isolated or synthesized) as unknowns. Prove to the reader the
identity of the product(s).
w Do your data agree with the accepted (literature) values? Always be sure to include the literature
value and reference the source. Note: even though you have tabulated this information in the Table of
Results, it is still necessary to discuss its relevance.

CHEM 202 Laboratory Spring 2023 | Duke University 6

 w If applicable, include spectral analysis results. Identify absorbances (IR) and resonances (NMR) that
give specific information about the structure of the product, and that suggest whether you have re-isolated
the starting material.
w Discuss how your results could have been improved. Be specific; DO NOT state “human error.” Focus
on issues specific to the experiment (e.g., impurities present, by-product formation, moisture-sensitive
starting materials, solubility problems, etc.)
w What would you do differently if you were to repeat the experiment? Are there any additional experiments
that could have made the results more definitive?
w References – You must properly cite all resources used when writing your report. Most references are
related to citing physical properties found in literature or from websites. Instructions on formatting references
can be found on Sakai in the document mentioned above.

5. GRADING OF LAB REPORTS & FINAL COURSE GRADES

§ Your TA is expected to grade your lab reports within one week after receiving them. If your TA has not
returned your graded work after one week from when it was due, please email them directly.
§ If your TA has still not returned your graded work after 10 days from time of submission, please contact
the lab manager directly.
§ Regrades will only be considered for up to ONE WEEK after a lab report has been returned.
§ Grading mistakes may be corrected up until the last day to report grading mistakes (see Section 2.8).
§ The Lab manager retains the right to regrade all parts of a lab report submitted for regrade.

Final letter grades will be awarded according to the table below. +/- grades are not awarded for this course (see
Section 3 for more information). Final lab grades may be calculated by normalizing each section’s average to match
the class average, but this is only done when there are statistically significant grading differences among TA’s. If
your final lab score is within 5 points of the next higher letter grade, your grade will be bumped to the higher
letter grade.

Minimum Final Score (%) Final Letter Grade

Class Average (CA) A
CA – 10% B
CA – 20% C
CA – 30% D
55 F

CHEM 202 Laboratory Spring 2023 | Duke University 7

APPENDIX 1. SEPARATION SCHEMES

Generic Example of a Separation Scheme

Mixture at end of a reaction (e.g. product + byproducts + unreacted starting materials +solvent
+ other impurities) or beginning of isolation experiment (all ingredients in a tablet of
ibuprofen)

An OPERATION that results in some

kind of separation. Examples:
extraction (aqeous/organic layers)
filtration (solid/filrate), distillation
(forerun and main fraction), etc.

Product + some impurities (make sure Some of the impurities

(again, specify)
you specify what the impurities are!)

Another operation
resulting in further
purification.

Pure product impurities (specify)

A separation scheme may have only one "Y" (e.g. a single distillation) or several "Y's" e.g. a basic wash
followed by a neutral wash followed by a distillation. It is essential that you know why each operation is
performed and what impurities are removed.

Example of a Separation Scheme for a Recrystallization Step

benzoic acid + impurities Blue text corresponds to individual chemical

components

1. Dissolve in hot H2O Green text corresponds to the operation

steps (in order) used for the recrystallization.
2. Cool to room
This is one exception where all the steps are
temperature listed together. In most cases there will be
3. Vacuum filtration several separate operation steps.

solid Red text corresponds to the separated

phases. When separating two liquid phases,
the designations “organic layer” and
Impurities + H2O pure benzoic acid “aqueous layer” are used.

CHEM 202 Laboratory Spring 2023 | Duke University 8

APPENDIX 2. COMMON CALCULATIONS REQUIRED IN ORGANIC CHEMISTRY

Many of the techniques in CHEM 201L involve purification and isolation of substances, and you will often be
required to calculate the amount of material isolated during an experiment. These calculations include percent yield,
percent recovery & percent mass. Percent yield refers to the actual amount of a pure compound obtained compared
to the expected theoretical amount (calculated based on limiting reagent). This can be determined using either moles
or mass. Percent recovery refers to the percent of purified compound recovered following a purification step relative
to the crude material (e.g., mass of pure benzoic acid / mass of crude benzoic acid), while percent mass refers to the
percent of isolated compound present in a sample containing many compounds (e.g., mass of essential oil / mass of
cloves). Equations for these calculations are given below and are described within the experimental handouts when
necessary.

Percent Yield = [(actual amount of pure compound) / (theoretical amount of compound)] x 100%

Percent Recovery = [(mass of pure recovered compound) / (mass of crude compound)] x 100%

Percent Mass = [(mass of isolated material) / (mass of starting material)] x 100%

Significant Figures. You will be responsible for reporting an appropriate number of significant figures for all
values reported in your Post-lab Reports. Generally, 2-3 figures are recommended. Calculation of significant
figures is also a function of the glassware and equipment you use in lab to measure substances. The significant figures
associated with glassware/equipment are given in the table below.

Equipment No. of Sig Figs after Decimal

Graduated glassware (graduated cylinders, etc) ONE sig fig
Volumetric glassware (volumetric flasks, burets) TWO sig figs
Rulers (for thin-layer chromatography) ONE sig fig + ONE estimated fig
Balances (organic labs) THREE sig figs

APPENDIX 3. ADDITIONAL RESOURCES

Lab syllabus: This document contains most of the course reference information you need regarding safety,
attendance policies, notebook keeping, etc. Refer to it frequently; it has been prepared with students’ needs in
mind.

Lab teaching assistant: Your TA is your primary resource for questions regarding lab, notebook keeping, etc.
They will provide you with contact information (section 1.2).

Lab director: Dr. Kersey is available to address concerns regarding your teaching assistant, lab grades, or
answer questions about lab after you have consulted your TA. If you withdraw from CHEM 202L during the
academic term, please contact Dr. Kersey so that your status in the course can be updated.

Tutoring: Peer tutoring is available as a free resource through the Peer Tutoring Office (684-8832). Private
tutoring is a fee service offered by graduate students in the Chemistry Department:
http://chem.duke.edu/undergraduate/tutors

Academic Skills Instructional Program (ASIP): provides additional help developing appropriate study
habits, time management or exam taking strategies: http://duke.edu/arc/academic_skills

CHEM 202 Laboratory Spring 2023 | Duke University 9

Behavior and Community Standards

All students must adhere to the Duke Community Standard (DCS): Duke University is a community dedicated
to scholarship, leadership, and service and to the principles of honesty, fairness, and accountability. Citizens of
this community commit to reflect upon these principles in all academic and non-academic endeavors, and to
protect and promote a culture of integrity.

To uphold the Duke Community Standard, students affirm their commitment to uphold the values of the Duke
University community by signing a pledge that states:

• I will not lie, cheat, or steal in my academic endeavors.

• I will conduct myself honorably in all my endeavors.
• I will act if the Standard is compromised.
Regardless of course delivery format, it is the responsibility of all students to understand and follow Duke
policies regarding academic integrity, including doing one's own work, following proper citation of sources,
and adhering to guidance around group work projects. Ignoring these requirements is a violation of the Duke
Community Standard. If you have any questions about how to follow these requirements, please contact Jeanna
McCullers, Director of the Office of Student Conduct.

Resources for Coping with Stress & Mental Health Concerns

If your mental health concerns or stressful events negatively affect your daily emotional state, academic
performance, or ability to participate in your daily activities, many resources are available to you, including the
ones listed below. Duke encourages all students to access these resources, particularly as we navigate the
transition and emotions associated with this time.

! DukeReach. Provides comprehensive outreach services to identify and support students in managing all
aspects of wellbeing. If you have concerns about a student's behavior or health visit the website for
resources and assistance. http://studentaffairs.duke.edu/dukereach

! Counseling and Psychological Services (CAPS). CAPS services include individual, group, and couples
counseling services, health coaching, psychiatric services, and workshops and discussions. (919) 660-
1000; http://studentaffairs.duke.edu/caps

! Blue Devils Care. A convenient and cost-effective way for Duke students to receive 24/7 mental health
support through TalkNow. bluedevilscare.duke.edu

Managing daily stress and self-care are also important to well-being. Duke offers several resources for students
to both seek assistance on coursework and improve overall wellness, some of which are listed below. Please
visit https://studentaffairs.duke.edu/duwell/holistic-wellness to learn more about

! The Academic Resource Center: (919) 684-5917, [email protected], or arc.duke.edu

! DuWell: (919) 681-8421, [email protected], or https://studentaffairs.duke.edu/duwell
! WellTrack: https://app.welltrack.com/

CHEM 202 Laboratory Spring 2023 | Duke University 10