Download 0A-INTRODUCTION TO ORGANIC II LAB Fall2021

Florida International University – Biscayne Bay
Campus
Organic Chemistry Lab II
CHM 2211L
Welcome to your second semester of Organic Chemistry Lab! This lab is the
second half of a two-semester sequence consisting of CHM 2210L and CHM
2211L, each of which must be taken in conjunction with the corresponding lecture
course. To be enrolled in this course, you must have completed the General
Chemistry lecture and laboratory course sequence, as well as the Organic Chemistry
I lecture and lab, and passed all of these courses with a ‘C’ or better. Although a
great deal of the theory you will encounter in this laboratory will be new, we assume
that you have a good grasp of the principles learned in the Organic I lab. For
example, the names/functions of the laboratory equipment, the proper way to set up
and carry out particular experiments (e.g. distillation, extraction, recrystallization,
etc.), and basic organic reactions (e.g. oxidation, elimination, substitution, etc.)
are expected to be prior knowledge and thoroughly understood.
This course will cover the same breadth of topics as the ones offered at
the Modesto Maidique Campus and will include all of the essential concepts that
should be covered in any Organic Chemistry II Laboratory class. However, the
individual experiments, and the approach that we will take are somewhat different
from those used at the other campus. For the students who have completed the
Organic I lab in the fall semester at the Biscayne Bay Campus, some of the materials
covered will be familiar. For any students who have not taken Organic I lab on this
campus, let us explain some of the changes you can expect and the reasons why we
have decided to make those changes.
This semester we will continue operating on FIU Canvas that will allow
students to see their grades and view additional material via the Internet.
Also, in designing the new experiments, we have decided to use natural
products (i.e., compounds that are found in living systems) whenever possible as the
starting materials for most reactions/investigations or as unknowns. In particular, we
will use compounds that are found in the foods and flavorings that you encounter in
everyday life. Because you may have studied the chemistry of these substances
during your Mini-Project based experiment last semester, at least the compounds
we have chosen will not seem completely unfamiliar. More importantly, the reason
for incorporating these new chemicals is that these natural compounds are fairly safe
to use, and we can study almost all of the common functional groups using the
appropriate natural products. The same chemistry that can be performed on a
chemical extracted from the peel of an orange, can also be accomplished with a
highly toxic synthetic compound. Thus, we will minimize the inherent risks of
working with organic molecules (and since many of the compounds that we will
use have pleasant scents, the laboratory environment will be more fragrantly
pleasing than usual). This does not mean that the course was unsafe the way it was
previously taught nor the way it is currently taught at Modesto Maidique Campus.
When proper safety precautions are followed (which we will encounter later), even
compounds that are much more dangerous than any of you would encounter in a
teaching laboratory can be handled without fear. [Note: If you watch TV, or read
advertisements, you may have the impression that “If it is natural, it is good.” You
need only think of the toxicity of snake venom to see that this is nonsense. However,
you will not be working with any highly toxic natural substances.] Since the goal of
the lab is to teach particular reactions and investigate how certain functional groups
behave, anything we can do to make the lab safer without compromising the rigor of
the course, is advantageous to the students, the staff, and the environment.
Another significant development in this course relates to the scale of reactions.
We shall carry out reactions on a variety of scales, ranging from the classical macroscale (using 5 g or more of reagents and 25 mL or more of solvent) to micro-scale
reactions (involving less than 1 g of reagents and a few mL of solvents). Although
conducting macro-scale reactions are important (in that you must learn how to work
with relatively large quantities of material, especially if you continue to study Organic
Chemistry in the future), we have introduced the small-scale experiments for several
reasons. Firstly, there is the issue of safety. By reducing the scale, we have limited
the amount of potentially hazardous materials that you will encounter. Secondly,
small-scale reactions usually can be carried out more rapidly than traditional macroscale experiments, which will certainly reduce, and hopefully eliminate, the
likelihood of experiments taking longer than the allotted class period. In the past,
students have complained that they had to rush too much in order to finish
experiments within the three-hour session. Thus, in an effort to work quickly, there
was not enough time devoted to truly thinking about the purpose of the experiments
and the point of the lab was often lost. Furthermore, another more troubling
consequence of haste was that when students were forced to hurry, they often made
the kinds of mistakes that ruined their results and forced them to start over. The new,
smaller scale allows for faster experiments, which will provide students with more
time to focus on completing the experiments correctly, obtaining proper results, and
fully understanding the objectives of each lab.
Along with the change in scale, we have changed how you will analyze results.
We will analyze products using a variety of modern devices such as infrared,
ultra violet/visible, nuclear magnetic resonance (NMR) spectroscopy and/or gas
chromatography, along with the more traditional methods of melting point, boiling
point, and Thin Layer Chromatography (TLC)/Column Chromatography. These
devices are not only more conventional (i.e. more likely to be used in research labs
as principle investigative tools), but they also allow for very accurate, and very quick
analysis of data. These devices generate graphs and charts that allow for the easy
comparison of experimental results with known standards. Often, a single peak on
a graph will immediately let you know if your goals have been achieved. In the
process, you will learn how these machines run and gain some experience running
them yourselves; skills that may help some of you in your major or beyond.
One of the changes is the way in which you will analyze your unknowns.
This year, we will have the unique opportunity to use a benchtop 1H-NMR and 13CNMR spectrometer to analyze your products and unknowns. In addition, we can also
use the 1H-NMR and
13
C-NMR predictor software, an effective and theoretical
spectra model, combined with powerful and user-friendly software. We will also use
the modeling tool IQmol along with experimental methods, as a legitimate and
practical means for exploring chemistry.
We hope this discussion of our teaching philosophy and the changes we have
made give you more insight into this course and what we hope to accomplish. We
will be most grateful for your feedback. We will not be offended by constructive
criticism. When we teach this course, our primary goal is to serve our students to the
best of our ability. We cannot achieve this goal without input from students.
The remainder of this introduction covers basic safety information,
attendance, grading procedures, and grading scale and penalties all of which should
seem familiar to anyone who has taken any of the Chemistry labs at FIU. We hope
that this semester proves to be both educational and enjoyable for all parties
involved. Good luck!
BASIC SAFETY INFORMATION
Working with chemicals
Even though we have made every effort to make this course as safe as possible,
it is vital that you do not treat chemicals lightly. When working with chemicals, it
is always best to assume that they are potentially hazardous. Do not get chemicals
on your skin. You should wear gloves, if it is necessary. If you spill any chemicals
on yourself, tell your TA immediately. Never smell chemicals directly (if you must
test for odor, use your hand to waft the fumes toward your nose) and never taste
chemicals. When you have finished working in the laboratory, wash your hands
thoroughly.
Dress Code
Every student can make his or her lab experience safer simple by wearing
the appropriate clothing. Wear safety goggles AT ALL TIMES in case of chemical
splash. Eye glasses does not substitute for safety goggles. If eyeglasses are worn,
safety glasses must be worn over the eye glasses. Make sure your goggles are
covering your eyes, rather than dangling from your neck, or pushed up onto your
forehead. Wear long pants (no leggings) and lab coats or long-sleeved shirts to
ensure your skin is covered. Wear only closed-toed shoes that cover the entire foot
and tie back long hair. Wear gloves whenever you are in doubt as to what you
are working with, or when directed to do so. Any violation of this dress code, for
any reason (and we really mean it), will result in automatic dismissal from the
lab (and a possible zero if you cannot attend another lab section). This is one
rule that we will not waiver on. We have had an impeccable safety record in this
laboratory in the past and intend to keep it that way. This is your one and only
warning, so heed to it well!
Spills and Clean-up
Clean up spills promptly and alert your TA whenever an accident occurs,
especially when a thermometer breaks (thermometers require special tools to capture
spilled mercury and suppress mercury vapors). Dispose of organic waste in
appropriate containers. NEVER dump organic liquids down the sink. Organic waste
will be separated into halogenated (i.e. organic compounds containing the halogens:
F, Cl, Br, or I) and non-halogenated waste, and disposed of in special receptacles.
Furthermore, after washing your glassware with soap and water, rinse the glassware
with acetone to remove any traces of water residue. Many of the reactions we will be
doing will not work properly if water is present
ATTENDANCE
NOTE: An absence counts as a zero.
ATTENDANCE IN THE LABORATORY IS MANDATORY! Attend every
lab and be there on time. Owing to the complexity of the experiments, the shortage of
personnel to teach the lab, make-ups will be allowed under VALID RESTRICTED
CONDITIONS with proper documentation during the same week of that experiment.
Only ONE make up occurrence is allowed per semester. A missed lab will count as a
ZERO, and THREE missed labs during the semester will result in AUTOMATIC
FAILURE. If you cannot attend the particular lab section you’re enrolled in, let your
TA know in advance so that you can attend another section (space permitting) to avoid
missing the lab and the subsequent zero. When you come to lab each week, make sure
you adhere to the aforementioned dress code and have the pre-lab section of your
notebook complete (the pre-lab will be covered when we discuss lab notebook).
Remember, this lab is scheduled for three hours, and although many experiments will
take less than three hours, plan on being here the whole time (or even a bit longer) just
in case. As we mentioned already, we are doing our best to ensure that the experiments
can be completed in the allotted time; however, we cannot guarantee that there will not
be slight overruns. Additionally, if you make a serious mistake, then it might take you
extra time to finish.
GRADING PROCEDURES
Lab Notebook
Students are required to record all data in a bound carbon-copy laboratory
notebook. Writing on scrap paper or any other paper besides the carbon-copy
laboratory notebook during the laboratory period is NOT allowed. Preparation for
laboratory work is demonstrated by notes recorded in the laboratory notebook prior to
performing the experiment.
Everything recorded in the laboratory notebook should be recorded with a blue
or black pen. No pencils should be used. If there is a mistake, simply cross out the
mistake and continue. White-out is not allowed.
Every laboratory experiment will culminate in a written lab report, similar to the
reports in General Chemistry. A pre-lab section of the lab report must be completed
before coming to class. Failure to do so will result in not being able to do the
experiment and a zero.
Lab reports
Every laboratory experiment will culminate in a written lab report, similar to
the reports in Organic Chemistry I. Every experiment is worth 15 points unless stated
otherwise, with the final project worth 90 points, which include 30 points each for
the formal lab report, the oral presentation and another 30 points are awarded
on the basis of the instructors’ evaluation of your lab performance (taking into
consideration work habits, tardiness, etc.). Lab reports are to be written in special
laboratory notebooks that have carbon copy included and must be written in pen. Lab
reports are to be collected at the beginning of the NEXT lab session in order to allow
students more time to effectively analyze data.
The format of the pre-lab and point distribution is as follows:
Heading and
Purpose (0.5 point):
One to two sentences to sum up the main idea of the
experiment. Usually the title of the experiment will give
you a good idea. Writing the proper heading for your lab
report is required. Elements of a proper heading includes
your name, lab partner’s name (if applicable), experiment
name and number, date, etc.
Introduction (1 point): The summary of the experiment IN YOUR OWN
WORDS. This is
where you’ll discuss the theory of the
experiment, include relevant equations and reactions, and
address the intended goals of each experiment. It is
important that the introduction is comprehensive.
Table of Physical Constants
(1 point):
Owing to the fact that there are so many organic
compounds, it is a good idea to know beforehand what you
are working with. a) Name of chemical b) Structure, c)
Formula, d) Solubility in various solvents, e) Density, f)
Molecular mass, g) Melting/boiling point are important
pieces of information and required for the Table of Physical
Constants.
Not all of the chemicals included in an
experiment warrant listing in this section, but the main
solvents/reagents should be covered (here you are free to
use your own judgment, but remember, being more
inclusive can only help you when you work in the
laboratory). The data for the table can be found in the CRC:
Handbook of Chemistry and Physics (any modern edition
is fine) or one of several websites. This must be in a table
format.
Safety Guidelines
(0.5 points):
In this section, you will identify and list the special
precautions that need to be taken while working with
chemicals listed in the table of physical constants for each
experiment. You will also list special precautions
pertaining to particular lab techniques and procedures for
each experiment.
Procedures (2 points): Organize this section as your plan for running the
experiment.
However you format this section is fine
because it is for your personal use. Paragraph form,
abbreviations, bullets, outlines, flowcharts, etc. are all
acceptable. Your procedures should be detailed enough so
that you could conduct the experiment properly just by
following your own procedures without the aid of your lab
manual.
******* This concludes the pre-lab section of your report
*******
You should write these five sections before coming to the class. Your TA
will check your notebook to be sure you have completed them. If you have not
completed your pre-lab, you will lose 5 points off your grade and will not be allowed
to complete the experiment. We are not doing this because we want to be strict, but
we know that students who have completed the pre-lab prior to class have a better
understanding of the goals, work faster, work safer, and produce better results. Thus,
this rule is for your own good, and that of your colleagues. If you are not adequately
prepared, the TA will have to spend a disproportionate amount of time helping you
and will not be able to spend enough time with the other students.
The format of the post-lab and point distribution is as follows:
Observations (1 point):
You must write down any changes you made to your
basic procedure when you carried out the experiment. You
should also make a note of your observations: color
changes, phase changes, temperature changes, etc. The best
way to do this is to write these observations next to the
appropriate step in the procedures section. These
observations should be made as you go along. Be sure to be
as detailed as possible. By doing this, you’ll be reminded
when and where specific events occurred at the appropriate
time during the experiment. This step is vital if you carry
out research projects in the future. BE SURE TO WRITE
DIRECTLY INTO YOUR LAB NOTEBOOK.
Results (7 points):
This is really the heart of your report. This section is
commonly divided into two parts.
The first is the Data section of the results. In this section,
you will include all of your quantified data (showing all of
your work), calculations, charts, spectra, graphs, tables,
etc. You will also include all of your qualitative data. This
includes your judgement of a result based on your
observations (negative and positive results). This section
should be organized, labeled properly and in table format.
The second part is the Discussion section of the results.
Whereas in the Data section you explain your results with
numbers, here you explain and analyze your results in
words. In this section, you should explain your results and
discuss what it means. Did the results turn out as
expected? Do the results make sense? For unknowns, a
conclusion of what the unknowns may be should be
discussed and based on results. Explanation and analysis
should be detailed and based on the knowledge you know
and concepts and goals of the experiment. Data should be
compared with literature value if applicable and
discussed. If there are multiple parts of the experiment, be
sure to explain all parts. Note what went right, what went
wrong, things you would like to change, and your overall
understanding of the experiment. The length is up to you
but be comprehensive.
Conclusion,
Post Lab Questions,
References (2 points):
One to two sentences to wrap up the experiment. Very
briefly state your important data/finding and address
whether the objectives of the experiment were met or not.
Answer any end-of-experiment questions.
This semester post lab questions includes the analysis of
theoretical IRs. Be sure cite properly all references used.
Minimum of two sources should be cited for each
experiment.
Quality of Writing and
Organization (impacts
points from all sections):
Scientific
writing
uses
passive
third
person
statements, be sure to use the proper style. Pages in report
must be sequential and no page numbers should be missing.
If you make a mistake, cross the section but include the
page. Data should be in table format with headings and
units. Handwriting must be legible and check for
misspelling.
Quizzes
A short quiz, before the start of each lab, will be given every week. The quiz will
be based on the material to be covered that day. The quizzes will total 5 % of your
final grade. In each experiment, you will find a series of questions pertaining to what
is expected in the lab that day (e.g. procedures, theory, safety etc.) from which we
will select a couple of questions to make the quiz. Possible quiz questions can be
found on Canvas.
GRADING SCALE AND PENALTIES
By now everyone has taken Organic I and knows the difference between a
good, comprehensive report and one that is unacceptable. We need to stress that
effort counts for a lot. Organize your reports so that they are neat and easy to follow.
Poor reports that are not up to the standards of a course at this level will be
heavily penalized. Handing in all of your assignments on time is critical for a good
grade. Tardy reports will not be tolerated; it’s unfair to the students who completed
their assignments on time and inconvenient for the TA. Late reports will be
penalized 1 POINT PER DAY that the report is late and reports more than
one week late will result in an automatic zero, unless previous arrangements with
the TA have been made.
This semester your lab reports will be graded as follows:
Entry
TOTAL
5
Report
submissio
n
15
5
10
15
5
10
15
Study of Aldehydes and Ketones
5
10
15
Study of Carboxylic Acids and
5
10
15
See
syllabus
for
specifics
---
See
syllabus
for
specifics
---
90
Synthesis of Aspirin from Wintergreen
Oil (Part I and II)
Introduction to Solubility Examination
and Study of Hydrocarbons
Study of Alcohols, Phenols, and
Pre-lab
20
Ethers
Esters
Study of Two Unknown Compounds
(Formal Report, Presentation, and Work
Performed)
Quizzes
10 points
each
Final Grade is distributed as follows:
a) Lab reports with all the data and work done
……………………………….
55%
b) Quizzes
………………………………………………………………………..
5%
c) Oral power point presentation on project, Formal report on project, and
work
in the lab during the project
…………………………………………………...
40%
The grading policies are strict, and the grading scale is tough, so earn every point you
can!
The following grading scale will be used:
95-100
90-94
88-89
A
84-87
A- 80-83
B + 77-79
B
BC+
70-76
65-69
< 64
C
D
F