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2019 Spring Semester

Syllabus for Organic Chemistry 2 (38658), 304-041 Lab, Fall 2019


Mondays in Room AB1 507 between 7.30 - 10.10 pm
Instructor: Virinder Parmar
vparmar@mec.cuny.edu
(718) 270-6453
Office hours: Room, 303C, 1:30-2:30 pm Mondays or by appointment

Course Description: This is a 1 credit course. Laboratory studies will include modern
experimental and research techniques for preparing, purifying and identifying organic
compounds.

Text: Microscale and Miniscale Organic Chemistry Laboratory Experiments, 2nd edition, by
Schoffstall, Gaddis and Druelinger.

Course Objectives: Students will:

 Be capable of proposing reasonable chemical structures for unknown compounds based


on experimental and spectral data.
 Learn to identify the presence or absence of functional groups based on qualitative data.
 Develop skills in the synthesis, isolation and purification of organic compounds.

Grading
Course grades will be given on a percentage basis as outlined in the college catalog. Lab
attendance is mandatory. There are a total of 100 points for this course. The 100 points will be
allocated as follows:

Percent of Final
Assessment Grade

Attendance (10 points) 10 %

Lab Reports* (60 points) 60 %

Final Exam (30 points) 30 %

100%

*Six best Lab Reports (out of 10) shall be taken into account, each Lab Report shall be graded
out of 100 points on the following criteria: Procedure (30 points); Observations, including graphs
if involved (30 points); Calculations/Result (20 points), and Pre/Post Lab Questions (20 points).

Grading Scale (%)


A+ A A- B+ B B-
97-100 93-96.9 90-92.9 87.1-89.9 83-87 80-89.2
C+ C D+ D D- F
77-77.9 70-76.9 67.1-69.9 63-67 60-62.9 0-59.9
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Lab Reports
There will be 10 lab reports, each will be graded out of 100 points (see the lab report format
section above for more details). The lowest scoring lab report may be resubmitted by each student.
Lab reports are due at the beginning of the next class period as a hard-copy. Late reports are subject
to a penalty of -5 with a further -2 points for each additional day they are late. Pre-labs and Post-Labs
are part of the lab report and expected to be submitted as hard copies each time. They are worth 10
points as part of the lab report.

Quizzes
There will be Pre-Lab and/or Post-Lab Questions with each Experiment to form a total of 10
quizzes. While quizzes will cover some basic chemistry concepts, they will mostly consist of questions
related to the upcoming lab, so be sure to prepare your pre/post-lab!

Participation
Each student gets points per day for showing up in the lab and conducts the experiment as
per instructed procedure. Points may be deducted if the student comes unprepared to begin the lab,
is late, behaves in an unsafe manner, or disregards the instructions of the instructor or lab technician.
Students that are more than 15 minutes late will not be allowed to participate in the lab and will be
counted as an unexcused absence.
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Course Policies
Late Work
Lab reports and pre/post-labs are the only assignments that will not be completed in class.
Pre/Post-labs are to be submitted with the corresponding lab report. Lab reports are due at the
beginning of the next lab, if they are late they are subject to a penalty of -5 with a further -2 points for
each additional day they are late. Lab reports will not be accepted after 14 days being overdue.

Make-Up Work
There are no make-ups for quizzes or other in-class work.

Absences and Incomplete Work


Excused absences (as determined by the instructor) may be made-up if there is another lab
section instructor willing to allow the student to participate in their lab. Lab-reports are still due at the
usual time. Unexcused absences cannot be made-up, and four unexcused absences, or four lab-reports
not turned in, will result in the student receiving a grade of WU (Withdraw Unofficially) for the course,
which constitutes a failing grade. Students that are more than 15 minutes late will not be allowed to
participate in the lab and will be counted as an unexcused absence.

Group Work and Academic Integrity


Group work is encouraged, but each student must create original work. Even when working
together, student’s may not copy/paste from one another and must produce their own work. Please
read the CUNY academic integrity policy below. Students found to violate academic integrity will
receive a 0 on the assignment for their first infraction. Further infractions may result in the student
failing to course.

Communication
Your instructor will communicate primarily through email and Blackboard. You should receive
your graded lab reports back the next class after you turned them in. Your instructor will also post all
grades to Blackboard. You should regularly check your MEC email address and Blackboard for
instructions or for your current grades.
Class Conduct
Students are expected to show respect to all other students and instructors in the class.
Students should listen to, and follow instructions from, instructors and lab technicians without
argument. Students should always behave in a safe manner and follow the lab safety protocols.
Students should work neatly and should clean up their workspaces and shared spaces before the end
of class. Students that do not follow proper conduct may lose participation points or be asked to leave
the classroom. Students must wear Laboratory Coat and Safety Glasses all the time while in the
Lab, you may not be allowed to work in the Lab if you do not wear any of these.
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Prerequisites
A passing grade in Organic Chemistry 1 (CHM303 and CHML303) is a prerequisite for this
course. CHM304 is Co-requisite for this course.
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Lab Reports

Lab reports will make up the bulk of your grade in this class. Each report should conform to
the format outlined below unless otherwise instructed for that particular report. Reports should be
handed in at the beginning of the next class period after the lab was completed. Reports may be typed
or handwritten, but should be legible if handwritten, and all graphs and tables should be neatly
arranged. Reports may be mixed handwritten and typed, often the pre/post-lab will be handwritten
while the remainder of the report will be typed.
All numbers in a lab report should be accompanied by units when applicable, any graphs or
charts should have their axes and headers labeled appropriately. Any calculations performed should
be written out entirely. Partial credit is given if a calculation is setup correctly even if the result is
incorrect.

Lab Report Format


A Lab report consists of the following sections in order:
1. Title
A few words that identify the lab the report belongs to.
2. Introduction
The introduction should consist of one-to-three paragraphs providing background and theory
on the lab, as well expectations for results or relationships based on theory.
3. Methods and Observations
The methods should consist of step-by-step instructions for what you will be doing in the lab.
These instructions should be clear and specific, leaving room to fill in information and observations
during the course of the lab. For example:
1. Weigh out 14 g of NaCl (actual 14.21 g)
2. Slowly add the NaCl to 500 mL of boiling water (gas bubbles observed during
addition)
3. Etc.
It is often easiest to do this in your lab notebook by dividing the page in half and putting the
instructions on one side with the relevant observations on the opposite side. See the Example Report
for more details.
4. Data
The data section will contain all the data you collected during the lab. It will include tables,
graphs, calculations of yields, and any other important calculations. There should be no discussion of
the data here, only its presentation.

5. Results
The results section should contain the lab results in a written format. Relevant observations
can be highlighted here (“The condensation ring was observed to remain in the appropriate location
during reflux.”) as well as comparing your results to the expectations (“Our yield of 45 % was lower
than expected.” or “Caffeine had the lowest Rf on the TLC plate, as expected.”).
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6. Discussion
The discussion is possibly the most important part of your lab. Here you will talk about if your
results make sense, why they may or may not make sense, and any sources of error in the lab. For
example, if you have a low yield, here you can explain why that might be. It is less important to get
the correct answer than is it to properly understand the answers you got. That is, even if you didn’t
get the result expected for the lab, if you properly analyze your data and explain it properly, you’ll still
get full credit for it.
7. Pre/Post Lab Questions
There will be several post-lab questions assigned to each lab. These questions are part of the
grade of the lab report, the exact proportion will vary from lab to lab. Students may work together to
solve these problems but must provide and show their original work. Students should show all
calculations and work and include units with all number when applicable.

Lab Reports/Notebook
Your lab reports/notebook should be your record of the entire class. All data and observations
should be recorded in your lab report/notebook. It is also a good idea to have your lab reports in your
lab notebook. You can either write them in your notebook or paste/tape a printout of your typed
report into your notebook in the appropriate place. If a report goes missing, having a copy in your
notebook means there will be no doubt that you completed the report and no penalty will be assessed.
Notebooks should always be written in pen and any mistakes should not be scribbled out, but
rather crossed out with a single line.
Student Support Services

The Medgar Evers Writing Center

The Medgar Evers College Writing Center provides a broad range of tutoring services and computer
assisted instruction to students to improve student writing. In addition, to exceptional student tutors, this
semester we have 12 WAC Fellows (Writing Across the Curriculum) from the CUNY Graduate School.
WAC Fellows are PhD students who also provide tutoring services and provide professional development
workshops for faculty and student tutors. Our tutors serve as writing coaches and are trained to help
students improve their writing skills across all disciplines. The goal of the Writing Center is to mold
students into writers who are able to articulate original ideas both inside and outside of the classroom. If
your professor recommends Writing Tutoring/Coaching or if you think you need to improve your writing
skills, please schedule an appointment with one of our Tutors at 718-804-6953 or click on the link below.
We are open 6 days a week, located on the first floor of the library (in the back corner) in Room Rm. B-
1045A. http://mecwritingcenter.weebly.com/

The Medgar Evers Learning Center

The Medgar Evers College Learning Center has tutors that complement classroom instruction by
offering students a wide range of academic support services including individual and group tutoring for
ATB instruction in Math, Reading and Sentence Structure, CUNY ACT Writing Exam, CUNY
Proficiency Exam workshops, NLN workshops for prospective nurses, to tutorials in many subject areas
including, mathematics, developmental English, logic, biology, chemistry, biochemistry, Spanish all
levels, computer science, Accounting I and II, and other areas depending on need. There is also some
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tutoring in the ASAP, SEEK programs, and Offices of the Differently-Abled, although students in these
programs often use the tutoring services in the Learning Center. Periodically, there is Major tutoring in
Mathematics, Biology, and Chemistry Departments, so check with those departments if these services are
available. If your instructor requires you submit a writing assignment (no matter the Major), you should
go to the Writing Center. The Learning Center is located on the first floor of the library (in the back
corner) in Room Rm. B-1045 and is open 6 days a week. Schedule an appointment with one of our tutors
at 718-270-5138 or send an email request to the Director of the Learning Center, Professor Michael
Chance at michaelc@mec.cuny.edu Additionally, some helpful links may be found at:
https://ares.mec.cuny.edu/academic-affairs/learningcenter/helpful-links/
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Laboratory Schedule: Organic Chemistry (II) Lab CHML 304

Text Book: Microscale and Miniscale Organic Chemistry Laboratory Experiments


by Allen M. Schofstall, Barbara. A. Gaddis, & Melvin L. Druelinger: Second Edition

Lab # Date Topic Readings

Lab 1 05th Sept Check in /Safety

Lab 2 09th Sept Synthesis of Acetanilide from Aniline Page 583

Lab 3 16th Sept Grignard Synthesis: Triphenylmethanol (1) Handout

Lab 4 23rd Sept Grignard Synthesis: Triphenylmethanol (2) Handout

Lab 5 07th Oct Spectroscopy: Worked Problems Handout

Lab 6 16th Oct Synthesis: 1-Bromo-3-chloro-5-iodobenzene: Pgs. 579-585

Step 2: Synthesis of 4-Bromoacetanilide from Acetanilide

Lab 7 21st Oct Synthesis: 1-Bromo-3-chloro-5-iodobenzene: Page 586

Step 3: Synthesis of 4-Bromo-2-chloroacetaniline

Lab 8 28th oct Synthesis of 1-Bromo-3-chloro-5-iodobenzene: Page 587

Step 4: Synthesis of 4-Bromo-2-chloroaniline

Lab 9 04th Nov Synthesis of 1-Bromo-3-chloro-5-iodobenzene: Page 589

Step 5: Synthesis of 4-Bromo-2-chloro-6-iodoaniline

Lab 10 11th Nov Qualitative Analysis of Unknowns (1) Page 574

Functional Group Identification (Aldehydes & Ketones)

Lab 11 18th Nov Qualitative Analysis of Unknowns (2) Page 575

Fnal Gp Ident (Alcohols, Amines & Carboxylic Acids)

Lab 12 25th Nov Chemistry of Phenols Page 486

Synthesis of Acetylsalicylic Acid

Lab 13 02nd Dec FINAL EXAM

Lab 14 09th Dec Laboratory Reports Submission and Check-Out


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You will NOT be allowed in the laboratory if you are more than 15 minutes
late, and also if you do not have a Laboratory Coat and Safety Glasses.
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You will be given your work area by our laboratory technician. Your work area includes fully equipped
drawers, a fume hood, work-bench. Your work area will have access to cold water, hot water, stream, air,
vacuum line. Take some time to familiarize yourself with your work area.

1. Laboratory Safety. You must rigorously follow safety rules. Pay strict attention to our safety video
which will be shown on the first day of class. Important safety rules that MUST be followed at all times
pertain to:

 Eye Protection. (Goggles / Safety Glasses) MUST be worn at all times while working in the
lab.
 Appropriate dress to avoid chemical burns and related incidents
 Working under the hoods when using toxic or irritating chemicals
 Open Flames: DO NOT USE OPEN FLAMES in Organic Labs.
 Handling of volatile Organic Liquids
 Handling Chemicals Appropriately
 Waste Disposal Procedures.

2. Your Laboratory Notebook. During the lab period use your laboratory notebook to record
everything you do including the identity and the amount of each chemical used. Calculate theoretical
yields, % yields, record melting points, and anything that took place that you think might have
impacted your experiment and affect your final results.

3. DO NOT USE SCARPS OF PAPER to record data. Use a black pen and a bound notebook

4. Lab reports: The information you record in your laboratory notebook will be used for preparing your
lab reports. These reports MUST be carefully typed and MUST include the following information.
 Name and Date of the Experiment
 Balanced Equation (for all preparative experiments). Your equation MUST show all
formulas, reaction conditions, and any important side reaction (by-products)
 Reaction Mechanism (if applicable)
 Experimental Procedure
 Results: percent yields, melting point, boiling points, spectra
 Conclusion (discussion).
 Post lab Questions
A Sample Lab Report has been provided here.

5. Glassware:

During your check-in exercise please familiarize yourself with the glassware provided in your drawers.
In addition, locate the following equipment and apparatus:
 Organic Kits: Learn to identify all the pieces (glassware, etc.) provided in these kits
 Variac Transformer
 Heating Mantles
 Hot Plate (with stirrer)
 Pipets (Glass Pipet, Automatic Delivery Pipet, Syringes)
 Thermometers
 Melting Point Apparatus
 Fractional Distillation
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 Liquid Extraction (Separatory Funnels)

6. Review the following techniques

1. Gravity filtration (using fluted filter paper)


2. Suction filtration
3. Simple Distillation Apparatus
4. Reflux Apparatus
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SAMPLE LAB REPORT


Simple Distillation
Sam Groveman
Lab Partner: Fellow Student
01/10/2018

Introduction
According to “A Small Scale Approach to Organic Laboratory Techniques fourth edition” by
Pavia et. al, the distillation theory states that the temperature throughout the distillation of a pure
substance is constant if vapor and liquid are present (724-726). However, the distillation of a liquid
mixture results in a changing (inconstant) temperature and it increases throughout the process
because the composition of the vapor differs continuously in the process of distillation.
For a liquid mixture, the composition of the vapor (which is in equilibrium with the mixture)
is different from the composition of the mixture being heated. In distillation, a mixture of two pure
substances A and B (like methanol-water) will result in the temperature of the liquid mixture increasing
until the boiling point of the mixture is achieved. The first vapor collected during distillation of the
mixture (at the beginning of distillation) does not only consist of a pure substance A (A has a lower
b.p. than B so it evaporates first). The first vapor will contain more of A than in the liquid mixture,
but it will also contain a significant amount of B as well. Therefore, it is never possible to completely
separate a mixture using simple distillation. If substance A contains a small amount of B (less than
10%) or if the two components A and B differ by a large boiling point, then an acceptable separation
can be achieved.

Methods and Observations


See notebook page 1.
Data
See notebook page 2.
Or you can use Excel charts and tables, as shown below:
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mL Temperature
Collected (°C)
1 85
2 86 mL Collected vs. Temperature
3 86 103
101
4 88

Temperature (°C)
99
5 89 97
6 89.5 95
y = 0.954x + 83.76
7 90 93
R² = 0.9924
91
8 91 89
9 92 87
10 93 85
0 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20
11 94
mL Collected
12 95
13 96
14 97
15 99
16 100
17 100
18 101
19 101.2

Results
The data collected show a steady increase from 85°C to 101.2°C with no major jumps. The
relationship appears linear between mL collected and the temperature. Upon reaching 100°C after 16
mL of distillate collected the rate of temperature increase slowed to almost a stop and data collected
was halted.

Conclusion
For the simple distillation, we collected 19 mL of distillate and the temperature was increasing

and constantly changing throughout at a steady rate. This would indicate that the vapor was a mixture

of the two liquids, methanol and water. This means that in simple distillation there is no separation

for the components of the mixture and the methanol and water boiled and evaporated together which

is why temperatures were high and increasing rapidly for the simple distillation. The possible sources

of errors are placing the thermometer too high which can lead to lower boiling point values (the bulb
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of the thermometer should reach the sidearm of the condenser), forgetting to use boiling chips (can

result in loss of product), or the circulation of water was not adequate to condense the vapors (distillate

or yield is less).

Post lab Questions

1) The bulb of the thermometer placed at the head of a distillation apparatus should be
adjacent to the condenser. Explain the effects on the temperature recorded if the thermometer
were placed (a) well below the exit to the condenser and (b) above the exit.
a) If the bulb is below, the temperature recorded would be slightly higher, because what is
going to be measured is the temperature of the vapors which just evaporated, and those tend to have
higher temperatures.
b) If the bulb were above, the temperature recorded would be significantly lower, because at
that point most vapor molecules have already escaped to the condenser.
2) What is the mole fraction of each component if 3.9 g of benzene(C6H6) is dissolved in 4.6
g of toluene(C7H8)?
(3.9 g C6H6) x [(1 mol C6H6)/ (78.11 g)] = 0.050 moles C6H6
(4.6 g C7H8) x [(1 mol C7H8)/ (92.14 g)] = 0.050 moles C7H8
(0.050 mol)/(0.1 mol) = 0.5
The mole fraction of benzene is 0.5.
The mole fraction of toluene is 0.5.
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