NEW YORK UNIVERSITY
Department of Chemistry
Spring 2012
CHEM-UA 228 MAJORS ORGANIC CHEMISTRY LABORATORY II
Instructors:
Office:
Office Hours
Email:
Paramjit Arora
Brown 360
Tuesday 2:30-4 PM
arora@nyu.edu
Adjunct Faculty
*Francesca Gruppi (fragruppi@gmail.com)
Office Hours: W 12-2
Andy Watkins (andy.watkins2@gmail.com)
Section 201
Office Hours: M 1-2
Xiao Zhong (xz389@nyu.edu)
Section 202
Office Hours: Th 9-10
Adjunct Faculty
Matt Miner (mrm530@nyu.edu)
Section 203
Office Hours: Tu 9-10
Danielle Nalband (dmnalband@gmail.com)
Section 204
Office Hours: Tu 1-2
* Major domo for the section.
** You may approach any instructor during their posted office hours in Silver Bldg, Room
1001F.
Stockroom clerks: Patrick Corr and Manuel (Noel) Mendoza
Required Textbook: Experimental Organic Chemistry: A Miniscale and Microscale Approach,
5th Edition, John C. Gilbert, Stephen F. Martin, Cengage Learning, 2011, ISBN 1439049149
(referred to hereafter as G&M)
Required Notebook: Student Lab Notebook, Organic Chemistry, 100 Carbonless Duplicate Sets,
Hayden McNeil, ISBN 978-1-930882-46-1
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TENTATIVE SCHEDULE
Each experiment will have a detailed handout that will be posted online ahead of the experiment
that contains detailed procedures. Most experiments are also written up in the textbook
WEEK DATE
1
2
3
4
Jan 23
Jan 30
Feb 6
Feb 13
EXPERIMENT and GRADERS
PAGES FROM G&M
THEORY
EXPT
1-25
handout
handout
handout
Check-in and Safety
Cycloaddition of fullerene
Fullerene, cont’d
Claisen Rearrangement
Weeks 5-7: MULTISTEP SYNTHESIS OF 4-BROMO-2-CHLOROANILINE
5
Feb 20
Acetanilide (miniscale)
703-712
713
4-Bromoacetanilide (miniscale)
727-728
731
6
Feb 27
4-Bromo-2-Chloroacetanilide (miniscale)
728-729
733
7
Mar 6-9
4-Bromo-2-Chloroaniline (miniscale)
729
734
8
Mar 19
Wittig preparation
601-605
handout
9
Mar 26
Peptidomimetic Synthesis
handout
10
Apr 2
Peptidomimetic Synthesis, cont’d/Aldol
handout
11
Apr 9
Aldol reaction and unknown
617-619
handout
12
Apr 16
Aldol reaction and unknown
617-619
handout
Weeks 10-12: ALDOL REACTION AND UNKNOWN (REPORT IN THE STYLE OF A JOC ARTICLE).
13
Apr 23
Lab Practical Exam
14
Apr 30
Checkout
NOTES:
*Experiments are tied to the lecture. You are responsible for all relevant theory for each
experiment. Relevant theory might/will be part of the questions during the lab experiments.
**Each section in G&M ends with a set of exercises; you would do well to work them. Certain
exercises will be announced for you to address formally in your written report.
***For each experiment, check the Blackboard web site for additional handouts. In case of
conflict, instructions on the handouts supersede those written in the book.
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A.
Course Description
Greetings! This lab course will build on the basic techniques you learned last semester and
introduce you to many reactions. The goal is to test out some of the reactions and concepts you
are learning from Profs. Jones, Canary and Braunschweig.
B.
Contacts and Interactions
Please always add “Orgo Lab” in the subject line of your email to help us promptly answer
your queries, and use the Discussion Board whenever applicable.

Adjunct Faculty: Please contact the adjunct faculty assigned to your lab section for all
inquiries regarding grading, policies, absences, and any other course-related issues. Office
hours during which instructors are available in person or electronically are shown on the first
page. You may approach any instructor during their posted office hours in Silver Bldg,
Room 1001F.

Francesca Gruppi: Dr. Gruppi is in charge of all Blackboard-related issues including
quizzes.

Paramjit Arora: Prof. Arora is the course instructor. He is available during his office hours
or by appointment.

Discussion Board: We have found that the discussion board on blackboard
(‘Communication’ tab followed by clicking ‘discussion board’) provides a useful forum for
discussing general lab related questions. Please use this site to ask your general questions.
Such postings will be answered within a 24-hour period and will be visible to all students.
Remember to monitor announcements on the top page of the Blackboard site as well as the
discussion board.
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C.
Safety
Your and your colleagues’ safety is our highest priority. For the lab to be safe, all of the
occupants must be aware of procedures, policies, and hazards associated with each experiment,
which means they must be prepared.
Safety Goggles: All lab occupants must wear safety goggles (purchase from bookstore) at all
times. If you do NOT have your goggles on, you cannot be in the lab.
Gloves: You will need to wear protective gloves most of the time that you are in the lab. You
may purchase a box of 100 disposable nitrile gloves (enough for you and your locker-mate for
the full semester) from the stockroom or a pair of rubber gloves from the bookstore. We
recommend you purchase both, the nitrile gloves (for everyday lab use) and the rubber gloves
(when needed for strong acids, etc.). Nitrile gloves, while more comfortable to wear, will not
protect you against halogenated solvents such as dichloromethane. Do not wear the gloves
outside of the laboratory as they may have chemicals on them and may lead to contamination.
Lab Coat and Clothing: Protective clothing (i.e., lab coat) is highly recommended. Clothing
that covers your legs and shoulders is a basic requirement for the course. Tights or stockings are
insufficient. Open-toed shoes not allowed. Don’t wear fancy or valuable clothing. You may
discover holes in them from acids or other corrosive chemicals.
Food: No food or drinks are allowed in the laboratory.
Cell Phone: No cell phone use is allowed in the laboratory.
If you are experiencing any physical condition that could affect your ability to function safely in
the lab (i.e., pregnancy, medical conditions, etc.), contact your instructor immediately.
Lockers: Due to safety concerns, please never bring bags and other belongings to the lab. Note
that general lockers are available on the 4th and 7th floors of Silver to store your personal
belongings. The lockers are on a 5-hour timer, i.e. they will open automatically after 5 hours.
The laboratory and teaching staff will NOT be able to open lockers in case you forget your
combination or locker location. You will have to wait for 5 hours when the locker(s) open
automatically. A limited number of non-electronic lockers (for use with personal locks) are
available on the 5th floor of Silver. Personal items left in these lockers for more then 5 hours will
be donated to charities.
D.
Lab Lectures
Key concepts for each experiment will be discussed during your recitation section. There will
also be a lecture during the first 15 minutes of each lab period to discuss logistical issues.
Students must arrive to the lab prepared to do the experiments. The instructor will monitor
preparedness of each student and grade lab note books including having seen the prelab lecture,
completed the prelab assignment, and having entered necessary information in the lab notebook.
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E.
Grading and Requirements
Relationship between lab experiments and the lecture material: We strive to link the material
in the lecture and lab courses as experiments are an integral part of learning organic chemistry.
You will receive a single grade for the combined lecture and lab course. The laboratory portion
contributes to 33% of the overall grade.
Make-ups: It is not possible to offer make-up lab sections because the stockroom needs to
prepare different sets of reagents for each experiment. Thus, there will be no make-up labs.
Your lowest lab score, and one excused absence, will be dropped at the end of the semester. You
are expected to attend each session and perform every experiment. Some experiments run over
multiple weeks, if you miss one week you will not be able to participate in the following weeks.
Any unexcused absence will count as a “zero” toward the final grade. If you miss more than
two experiments, you will be given an “incomplete” for the course because you will not
have had the opportunity to learn sufficient amount of the material presented in this
course.
There are some differences in grading between Orgo I last semester and Orgo II this
semester. We will place increased attention on your preparation and in-lab performance.
E.1 Preparation: It is critical that you arrive to lab fully prepared for each experiment.
Notebook
A laboratory notebook can be purchased from NYU bookstore. Your notebook is a tool to help
you prepare for the experiment and to record your observations during the lab period. Before
you come to the lab, include the following information in your notebook.
Reaction (if appropriate)
Reaction mechanism (if appropriate)
A table of reagents (see sample below)
A brief outline of the procedure: Copy all essential instructions from the textbook and the
handouts into your notebook which will serve as your only source of information in conducting
the experiment. Do NOT copy the whole textbook. A bulleted list will accomplish the job.
View this more like a ‘cooking recipe’ than a novel. You may not bring the textbook OR the
“handouts” posted on blackboard to the lab. At the end of the lab period, please give your
instructor the carbon copies of your notebook pages.
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Table of Reagents and Products
Compound
Reagent
Product
MW
(g/mol)
Theoretical
weight or
volume
Actual weight and
or volumes usedput units next to
value!
For products add
yields
Moles
(reagents
only)
Theoretical
and actual.
Not needed
for products
Equivalents
(theoretical
and actual)
Not needed
for products
3-Sulfolene
118.17
1.5 g
1.51 g
0.0127
(0.0128) mol
1.33 (1.32)
Maleic
anhydride
98.06
0.93 g
0.95 g
0.0095
(0.0097) mol
1
Xylenes
-
1.0 ml
1.3 ml
-
Product A
(based on
100% yield)
Note: Do not put solvents for purification (volumes and amounts) in the table, but mention them
in your observations sections since these values are variable and often less predictable.
E.2 Weekly Lab Quizzes
Quizzes will be given in lab during the first 10 minutes of the period.
E.3 Technique/Safety
You will be assessed qualitatively for your technique in lab during each lab period. Incidents
that reduce the level of safety (yours or that of others) will lower your score.
Your understanding of the experiment and laboratory safety will be evaluated every single lab
period by your adjunct/clinical faculty. Your answers to these questions will be part of your
technique grade. The instructor will evaluate your preparation for the experiment each week.
E.4 Concise Lab Reports (one-two pages would suffice)
- Lab reports are due at the beginning of the lab period one week after finishing the experiment
unless stated otherwise in the handouts. These reports should be short!
- Lab reports have to be submitted as a hard copy to the adjunct/clinical faculty assigned to your
lab section with:
- a concise abstract
- a brief discussion and analysis of the results
- answers to assigned problems and questions
- reports should be typed and given to your instructor a week after the
experiment was run unless advised otherwise.
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-
all Chemdraw drawings MUST use the ACS formatting template (Open
ChemDraw, go to ‘File’, then ‘Open Stationary’ and open ‘ACS Document
1996’) and copy as 100% size into your lab reports.
Weekly Grade Breakdown
In-lab*:
Preparation (quality of lab notebook and general knowledge of the experiment):
2 points
Technique:
2 points
Safety
1 point
Results
1 point
Post-lab:
Analysis and discussion of results (keep to one page or less)
2 points
Post-lab questions (keep to one page or less)
2 points
Total Individual Experiment Grade
10 points
*your instructor will provide a written evaluation of your strengths and weaknesses each weak.
Final Grade Distribution
Pre-lab quizzes:
10% of final grade
Nine experiments :
45% of final grade
‡
Practice writing of JOC Articles:
5% of final grade
†
Aldol unknown + JOC Article style report: 15% of final grade
Lab practical final:
25% of final grade
†
In the Aldol experiment, you will be given two unknown reagents and you will be asked to
identify the reagents and the product. You will write a report similar to an Article in the Journal
of Organic Chemistry (JOC). A sample JOC Article is available on Blackboard. Others can be
located here: http://pubs.acs.org/toc/joceah/current
‡
Scientific Writing Practice
Each week you will practice writing one section of the Article, according the following schedule:
Abstract: Following the Week 3 experiment; due to your instructor during Week 4.
Introduction: Following the Week 4 experiment; due to your instructor during Week 6.
Results and Discussion: Following the Week 6 experiment; due to your instructor during Week
8.
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Experimental: Following the Week 8 experiment; due to your instructor during Week 9.
References: Following the Week 9 experiment; due to your instructor during Week 10.
F.
Academic Honesty
It is expected that all students are aware of their responsibilities not to cheat. No ‘teamwork’
during the exam, writing the reports, or the prelab assignments! Copying anyone else’s work is a
direct violation of NYU’s policies and will be dealt with accordingly.
We expect you to abide by the NYU honor code. Any student who violates the “academic
honesty” clause will be reported to the dean’s office, no exceptions. We will request that a
violation result in a permanent note on your record.
G.
Notes on Recording of Data and Lab Reports
Use the required Lab Notebook which has duplicate pages. You will turn in the copy of your
notes at the end of the lab period. When you arrive at the lab, you should have already initiated
the notebook entry for the day’s experiment. You should have recorded the experiment title, the
date, and your name. You should have entered a table containing a list of compound
names/structures, formula weight, moles required, mass required, and a blank space to write the
actual mass measured. If the experiment involves a reaction, it should be listed (i.e., reactants +
reagents => products). You should have a short list of tasks needed to be done (a bullet list will
suffice). The completeness of your entries will be used as an indicator of your preparedness for
the lab.
When performing an experiment in the laboratory, it is important to record all relevant
procedures and observations, so that some other student would be able to reproduce your work
and understand your results. No one has ever complained that there are too many observations
written in the lab notebook. Make sure your name, the date the data were taken, and the
abbreviated title of the experiment is written on each page. You should write down the
procedure as you do it. Of course it is not necessary to copy the detailed procedure from the
write-up, refer to the write-up and use meaningful abbreviations. Indicate any changes from the
prescribed procedure that may have been necessary, and note any difficulties encountered.
Record your observations and data as you do the experiment. You may also include speculations
about what your observations mean.
Never erase anything written. If you make an error, simply draw a line through the item you
need to correct.
G.
Notes on Writing Lab Reports
Sample Laboratory Report Format
Name:
Experimental Date and Date of Report:
Name of your adjunct/clinical faculty:
Section:
Title of Experiment
8
(Provide a full and informative title of your experiment)
Abstract
Give a concise description of the experiment (what was done?) and the methods used.
Give a summary of the major results (e.g. product yield, reduction potential, absorption and
emission wavelengths). State significant conclusions (e.g. a linear relationship was found
between A and B, molecule X is fluorescent but molecule Y is not).
Results
Calculations: State the limiting reagent here (include weight and moles). Show your
calculations for determining your product yield and indicate clearly the maximum theoretical
yield. It is always appropriate to discuss yield and purity of product from any reaction.
CONCISE Discussion and Interpretation of results
Summarize your findings with your % yield, chromatography, spectra (if provided) and mention
things you might have done differently to improve the experiment if things did not go the way
you planned. If the yield is very poor you could mention the problem/reason if you know
something was mishandled, spilled, you forgot to time something or you overlooked variables
such as temperature. Also describing your observations such as “the gas you saw evolving was
SO2 and leads you to believe the butadiene was formed” is very helpful. Basically summarize all
the possible evidence from your lab period that your experiment worked or failed.
Do not make statements such “the yield was 70% or 80% which is pretty good or close to
100%”- this is your opinion and not a fact. This is a scientific document and you should use
scientific language. Melting points must be compared to literature values. Describe why you
think that your melting points differ from the literature value.
There are many potential topics for discussion. Why was your reaction a different color than
expected? Why was your yield lower than 100%? What was the impact of that last minute
change in procedure necessitated by the shortness of time in the lab? What did you learn from
doing the lab experiment? Did seeing the experiment give you insight into the chemistry of the
reaction that wasn’t obvious from studying just the theory? If you could repeat the experiment,
what would you do to improve your results?
Connect your observations from the procedure with the reaction mechanism (if known) since it
usually provides very useful insights.
Post Lab Questions
Concise, accurate answers are best.
References:
If appropriate. Do not use Web references such as Wikipedia (Wikipedia is NOT a scientific
reference). Use technical books, lab handbooks, or peer-reviewed journals. Do not use MSDS
sheets as source of physical data, only as source of safety information or safety data.
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