Chemistry 302 Spring 09 Organic Chemistry II Laboratory
Professor:
Dr. Juliet M. Hahn
office:
SCS 305 (office hours will be held either in SCS 305 or in my research lab SCS 312)
phone:
302-857-6537
(lab phone: 302-857-7562)
email: jhahn@desu.edu
office hours: 10- 11 am MWF, 12-1 MW & other times by appointment
textbook:
Modular Laboratory Program in Chemistry, CER (1997), safety glasses,
lab notebook – Your lab notebook should be any notebook which will allow you to pull out
pages such as a spiral notebook or one of those 3 hole binder notebooks. It should have around
100 pages. When your labs are due, you will rip out, staple and hand in the pages to be graded.
At the end of the semester, if you turn in all of your graded lab sheets, you will get extra credit
points.
classroom
T & R 8:00 - 10:50 am SCN 214 (The lab grade is independent of the lecture and recitation.)
Chemistry 302 Organic Chemistry Lab is the second semester of a 2 semester sequence of Organic Chemistry
Lab. The objective of the class is to teach you organic chemistry lab. This includes learning the techniques as
well as the ability to interpret your laboratory results according to the theory. Chemistry is largely an
experimental science and almost all of the material that you learn in chemistry books and lectures is based on
experimental results from the past. Because chemistry is an experimental science, many of the concepts that
you have learned in your past chemistry courses is being constantly modified as a result of recent experimental
results from research labs. Organic Chemistry is also a huge industry with millions of dollars in earnings
mostly in the polymer and pharmaceutical areas. Every organic chemistry industrial process was once
performed on a small scale in an organic chemistry research lab. [Your glassware is slightly different from the
kind of glassware that is used in academic and industrial research labs however the techniques for working with
your glassware kit would be very similar to the techniques that would be used in research labs.] At the end of
the course, I expect you to have learned some of the commonly used techniques in organic chemistry. I also
expect you to understand the theory behind the experiments and to be able to interpret experimental results. At
the end of this class you should be able to go into an organic research or industrial lab and with a little
introduction to the different glassware used in the research lab, be able to carry out organic chemistry
experiments with a little supervision.
The most important factor in your success in this course is preparation. No matter how smart you are or how
adept you are in the lab, coming into lab unprepared is going to result in your wasting time, bumbling your way
through the experiments, being a danger to yourself and your classmates not to mention almost certainly
lowering your grade by a letter grade. The major reason that people get bad grades in lab is: (1) not turning
in the lab notebook on time or not turning in the lab notebook at all (2) coming to class with the prelab portion
incomplete (3) turning in the lab notebook with large portions missing or without answering the question. If
you listen to my prelab talk, you will notice that I will also give you all the information which should be in the
theory, conclusion & question portions of the lab notebook. Of course if you aren’t taking notes, you won’t
remember what I said in answer to the question or for theory and conclusion.
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Grading: There are 10 labs during the semester. You will get to drop one (and only one) lab grade. You
may drop one lab which you missed with no excuse or your lowest grade lab. (This leaves 9 lab grades.)
1x15 pts safety quiz ………………………………………………………………………. 15 pts
9 x 15 pts each lab notebook …………………………………………………………… 135 pts
Extra credit …………………………………………………………………………turn in all graded lab reports
at the end of the semester
___________________________________________________________________________________
Total # points ……………………………………………………………………………… 150 pts
Your grades will be based on percentage of 150 pts. [135 / 150 = 90%, etc.]
[90% & above A, 80% & above B, 70% & above C, 60% & above D]
notebook consists of: a)
prelab (notebook parts 1,4,5)……………………………………. 2 pts
(already graded during lab – If the prelab is still missing when you turn in the lab
notebook, you will lose another 2 pts, you can lose a maximum of 4 pts for not having a
prelab)
b)
theory (notebook part 2) …………………………………………. 1 pt
c)
figure of apparatus used (notebook part 3) ……………………… 1/2 pt
d)
observation (notebook part 6)………………………………….
1/2 pt
e)
data (notebook part 7) ………………………………………… 1/2 pts
f)
calculation (notebook part 8) ……………………….................... 1/2 pts
g)
conclusion (notebook part 9)…………………………………….. 2 pts
h)
answer to question ………………………………………………… 2 pt
i)
product points ………………………………………………………2pts*
j)
sign out at the end of lab ……………………………………….. 2 pts*
(There will be a sign out sheet which you should sign at the end of lab. You will
sign and give the time that you finished the lab.)
k)
attendance at 9am ………………………………………………
2 pts*
lateness to lab points - I will take attendance at 9am by roll call. If you are not there
at 9am but you come in and complete the lab and sign out, you will lose 2 points. This
is a penalty for missing 1/3 of the class and for missing all of the safety information
which is given out at the beginning of lab.
Total notebook points per each lab …………………………………… 15 pts
By showing up to lab and performing the experiment and having the prelab done, you will get 8 points of 15
points or 53 % of your lab grade points. By just showing up and doing the experiment and not even having the
prelab done, you get 6 points of 15 points or 40 % of your lab grade points. Clearly if you turn in no lab
notebook all semester long you will get a D or F on the class.
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Exlanation of notebook points:
2 pts prelab (checked during lab, checked again after you turn in your notebook) [* Prelab consists of: (a)
the title, (b) table of constant and (c) the procedure part of your lab notebook]
Due at the beginning of lab period or whenever I come around to check your prelab.
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(prelab consists of: table of constants & procedure in own words in lab notebook) [1 point for each of the
above 2 categories] I will come around look at your prelab in your notebook,sign your notebook during the
first few minutes of lab & input your prelab score in my gradebook. After the time that I come around to check
your prelab, you will get no points for the prelab. If your prelab is still missing when you turn in your final
notebook, you will lose another 2 points …. so you can lose 4 points for never having the prelab done.
2 pt product points
Due at the end of the lab period during which the experiment was performed. You have to show me the
product in order to get the product points. I may also ask you to turn in your product to a common
product vial at the end of lab.
(product grade: If a lab has no product, you automatically get this point. If you have a product, you will get
this point. Your product grade does not depend on amount of yield or purity of product.)
2 pt answer to question
The answer should be given after the conclusion in the lab notebook. (The question will be posted on the
chalkboard during the lab.) The answer to the question is not the same as the conclusion.
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demerit technique points –
technique points: You can lose up to a total of 2 points for technique from your lab notebook grade. (This is
the same as losing 13% of your lab notebook grade. If you lose these points at every lab, you will get no
more than 86 % of your lab notebook grade.) Possible reasons for losing technique points are:
(1) not having safety glasses on 100% of the time that you are in the lab as soon as one person starts doing
experimental chemistry in the lab until not one person is still doing experimental chemistry in the lab. (In
addition to losing those 2 points, you may also go blind by spilling concentrated sulfuric acid on yourself or
your lab neighbor may make you go blind by splashing concentrated sulfuric acid on you.)
(2) If you do anything which is a danger to yourself or to anyone in the lab, you will lose the 2 points. For
example if the lab book and I point out that you should not go near the open container of ether with your lighted
bunsen burner and you do go near the ether with your lighted Bunsen burner, you will lose 2 points for
technique. (You will also probably set yourself and the open container of ether on fire as well.)
(3) Not following Dr. Hahn’s directions is also grounds for losing technique points. (see above – setting self
on fire)
(4) Not cleaning up your chemical spills is also grounds for losing technique points. (For instance if I tell
you to clamp the sidearm flask before attaching the Buchner funnel and you do not, you will lose the 2 points
for technique and will probably also break $$ of glassware. If you spill 10 grams of solid NaOH and do not
clean it up, someone else may come along and possibly injure themselves on your spilled NaOH. If you spill
100 mL of ether and don’t do anything about it, someone else may come along and not knowing what the liquid
is may start a serious fire. If it is a significant spill, you should notify me about your spill and I will tell you
how to take care of the spill. If it is a small spill of an inert chemical like the spice clove, you may just dump
the spill into the garbage pail without notifying me. Etc.)
***************
There will be no makeup prelab or lab notebook without a documented excused absence. Without a
valid excuse, you will receive a zero on missed* prelab, product & lab notebook grade. If you have a
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valid excuse (at my discretion), I will replace the missed lab grade with an average of your other labs prorated
for the difficulty of the missing lab. Alternatively if you have a valid excuse, you may do a makeup lab on
3/10 T or 3/12 R and 4/21 T or 4/23 R. Excused absences will be allowed only under clearly documented (i.e.
written doctor's excuse, written obituary, etc.)
Please provide me a hard copy of your documentation for my files. Examples of valid excuses include:
medical grounds, death in the immediate family and documented weather related transportation problems and
university business. Examples that are not valid excuses include: personal problems, going away for the
weekend, intramural sports, etc. (*If you come to the lab at 10:50 am, you will not be allowed to do the lab –
this would be a missed lab. If you come to the lab at 9:50 am, you will be able to do the lab only until
10:50am.) (You get to drop ****one and only one**** lowest grade lab – this may be an unexcused absence
which has turned into a zero.)
Deadline: Your completed lab notebook are due one week after the completion of the lab by 8 am
Tuesday for the Tuesday section lab and 8 am Thursday for the Thursday section lab . There will be a
48 hour grace period during which you will lose no points for late labs. (T lab grace period ends on R at
8 am, R lab grace period ends on M at 9am) (Please note that each class voted on these deadlines so you
really have no excuse for not being able to meet these deadlines.) You may turn in your lab notebook pages
by putting it into the locked box on Dr. Hahn’s office door so that I can get your notebook before I walk over to
class (SCS 305) or by turning it in directly to Dr. Hahn during the organic chemistry lab or lecture. The
graded notebook pages will be returned either during the organic chemistry lecture or during lab. (If
you are not taking the organic chemistry lecture this semester, please make some other arrangement with me.
You should talk to me about this.) Your product will be graded as yes you had a product or no you did not
have product when you show your product to me at the end of the class period in which you made the product.
If you are late in turning in your lab notebook pages, you will lose 1 point for every 24 hour period after
the time that the notebook is due. (example: If your notebook is due 2/3 T at 8:00 am, if you turn in
your notebook on 2/5 R at 8:00 am. it would still be within the 48 hour grace period so you would lose
no points. You will lose the first 1 points by 8:30 am on 2/5R. Any time after 8:00 am on 2/6, you lose
another 1 points for every 1 business days that you are late. If you turn in a perfect lab on by 2/26 R at
8:30 am (about 3 weeks late), the notebook is worth zero points. You would only get the 6 or 8 points for
attendance to lab and the prelab for that experiment. If you do this for every experiment, you will get a
D or F in the class.
Lab notebooks (please note the sample notebook posted in the lab) should be kept in a spiral notebook (some
notebook where you can rip out the pages) and should be written in ink as a permanent record of your
experiments. Number your lab notebook pages consecutively starting from page 1. (* parts are the prelab &
must be done before class)
Only the professor may use red ink in your lab notebook. (To make it easier for me to spot my signature and
grade assignments in the notebook.) You should bring your lab notebook to every lab period. The notebooks
should be organized as shown in the following list for each experiment. Neatness in terms of handwriting
doesn't count (as long as I can read your writing) but neatness in terms of organization does. (Please write
only on one side of the notebook paper.)
Organize your notebook to follow the numbering given below. ( i.e #1 should come before #2 etc., You can
leave lots of blank pages for things you expect to fill in later but you need to have the notebook contents in the
order given. If you mess up the order in which you write your lab notebook, you may lose points. I am
grading some 35 student’s x 10 pages of crappy handwriting x 10 labs this semester or around 3500 pages of
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crappy handwriting. Please do not make it hard for me to grade your lab notebook pages by hiding your
answers from me.)
Start each section in the list below with the word underlined so that the professor can
easily find each part of your lab notebook write-up. Remember to include units for data and calculations.
(You have to admit 100 mL and 100 L are quite different and if you just write 100 in your notebook, if this is a
new experiment that no one in the world has done before you, whomever tries to repeat your experiment from
your notebook could make a big, possibly dangerous mistake.) When I come around to check your prelab,
I will also sign and date your notebook. Please write only on one side of your lab notebook so that your
notebook is easier to grade. (Please do not write my lecture notes and include those together with the
lab notebook. You should have another notebook for the lab lecture notes. I do give the answers to
questions in my lab lecture but you need to put the answer after the question to get credit for correctly
answering the question. Having the answer somewhere in your lab notebook because you copied down
my lecture notes into your lab notebook pages will earn you no points.)
*1.
Title of Experiment and Expt. # - date started experiment (prelab)
2.
Theory - In a few sentences explain the theoretical purpose of the week's experiment. If you are doing
a reaction, write down the balanced reaction. Most of what needs to be in this section will be discussed in the
short mini-lecture before that week's lab. NOTE: This should not be the procedure - example [This week
we are doing the Friedel Crafts Reaction followed by recrystallization and spectral identification is not a good
theory.] [This week we are doing the following Friedel Crafts Reaction (show structural formula for the
equation). The reaction goes to the o,p products because the substituent is an electron donating group and one
may get multiple substitution products. This is a good theory. ] (at least 2 sentences for full credit)
3.
Sketch of Apparatus - Draw any experimental setup which you are using in the lab. i.e. Most of these
diagrams are given in your lab textbook. However you will notice that most of your actual lab setup are not the
same as the figures in you book. If there are changes in the glassware that you use, you should draw the
actual glassware which you yourself used. Your drawing does not need to be a work or art and you don't get
any extra points for a beautiful drawing. You may xerox the figure from your book if you find that easier. If
you just freehand draw your apparatus, it should not take you that much time. If you did not use the setup
shown in your lab book and you xerox and submit that incorrect drawing, then you may lose points. (You do
not need to draw equipment like spectroscopy equipment, balances, and melting point apparatus. You need to
draw equipment like figure 3.a on page 51 without the thermometor.)
*4.
Physical Constants -. These can be found in your lab book in table format as “Reagents and
Properties”. The cautions may be highlighted as “Cautions” separately from the reagents and properties table.
(Can also be found in the Handbook of Chemistry and Physics or in the Aldrich catalog.) Give the table of
physical properties and list the hazards associated with the chemicals. The idea is for you to come to lab
knowing what the hazards are for all of the chemicals that you are handling in the lab before you walk into lab.
Also this information can be used by a trained chemist to predict how a reaction will go before stepping into the
lab and starting any experiments. (in table form) (prelab)
*5.
Procedure - Briefly write down what you will be doing in the lab in your own words so that you can do
the experiment by following your lab notebook. Please do not copy your book word for word. (use half the
page for procedure, leave the other side of the same page for observations or changes in procedure). You
do not get extra points for having an unusually long procedure section because this is not a handwriting practice
class. Your procedure section should however not be two lines that say something like "...set up simple
distillation. Do simple distillation...." You should try to write this so that your notebook procedure will make
your doing the lab easier. If you do this correctly, the few minutes that it takes to write this will save you an
hour of bumbling around in the lab. (prelab)
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6.
Observation - Write down everything that happens during the lab. There is no lab in which you will
have no observations. [examples of observations: reaction warmed up slowly as acid added; reaction only
started after violent stirring with glass rod; product formed clear- needlelike crystals as cooled] (same lab
notebook page as the page for the procedure and opposite to the procedure that corresponds to your
observation so that you don’t have to repeatedly write your procedure again to explain when your
observation occurred.)
7.
Data - This consists of things like weight of reactant used, weight of your product after the end of your
observation, temperature and volume chart . You should report the amounts of things which you actually used
and not the amounts given in your lab book. When you give weights or volumes, you should also give the
units. Yes I know that your lab book gives these numbers but when you actually weigh out or measure out
your chemicals, you should list the actual accurate amounts of what you yourself used.
8.
Calculation - This consists of theoretical yield, % yield and any other calculations. Don't just give me
the final number, show your work. You may lose points if you just give me only the final numbers. Note that
if you show me your calculations, even if you get the final wrong number, you will get the majority of the
points if you set up your calculations correctly.
9.
Conclusion. - In a sentence or two, explain what you learned by doing the lab. Something like " ...in
the distillation experiment, I learned that fractional distillation gives better results in separating two liquids than
simple distillation or although I expected the fractional distillation to give better results my results did not agree
with the expected... or in this experiment I learned how to do a Diels Alder reaction for cyclopentadiene using
microscale glassware. My experiment resulted in a good yield of 72%...." Other things that could be included
in your conclusion is why your experiment did not give you a good yield and how you should redo the
experiment if you want to improve your yield. etc. example: “… I got bad results because I spilled most of the
product and had only half the yield…. or…. I would have gotten better yield if I had heated my reaction at a
lower temperature. I believe most of my product decomposed because I could see the charring in the reaction
pot....or I believe I got reaction but then distilled at too high a temperature so that I lost most of my product as it
evaporated away….”) (at least 2 sentences for full credit)
Your notebook is supposed to be a permanent document of everything which occurred in the lab. Please do
not white out mistakes. You should neatly cross out your mistakes and write down your corrections besides
the mistakes. If a large section of the notebook is in error, just put a large cross mark on the page, but you
should not cut out or rip out the page.
You should complete 1,4, and 5 before coming to the lab (title & date, table of constants and procedure).
This is the prelab portion of your lab notebook grade. Your lab notebooks will be checked at the beginning of
each class for completion of 1,4 and 5 after the prelab lecture. During lab you should write down everything
that happens during your experiment so that if anything goes wrong you can retrace your steps and figure out
what you did wrong. (In research labs keeping a complete set of lab notebooks is almost as important as
actually doing the experiment. If you make a Nobel prize winning discovery but cannot repeat your
experiment, your experiment is going to be considered worthless. Also lab notebooks can be used to back up
dates for patent claims. i. e. If both lab A and lab B made the same discovery at the same time but lab A cannot
back up their date of the discovery with documentation, then lab B is going to get credited with the discovery.)
Your notebooks will be signed and dated by Dr. Hahn while the prelab is checked during each lab period.
(Signing and dating lab notebooks is common practice in industrial labs to document research. Also this
ensures that if I forget to input your prelab grade into my gradebook, there is backup evidence that you actually
did the prelab.)
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You will rip out your lab notebook pages for each experiment and turn in your lab notebook pages each
week at the deadline given. Please note that if all you do for each lab is do nothing but come to lab and
perform the experiment and turn in nothing, you will probably get either a D or F for the class. If you
hold all of your lab notebook pages until the end of the semester and then turn in your lab notebook
pages, you will also get either a D or F for the class because you will only get 6 or 8 out of 15 points for
each lab because your lab notebook becomes worth nothing after about 3 weeks. This is not a good idea
anyway because there is nothing worse than trying to write up 100 pages of lab notebook (all 10 labs) the week
that you are studying for the final exams anyway. You writing up 100 pages of a lab notebook is only a little
better than me grading 3500 pages of everybody’s lab notebook pages the week that I am calculating your final
grades and making up your final exams. (I simply cannot grade all of your late lab notebooks the week of
finals.)
Schedule of Experiments: The following is the schedule of experiments for this semester. You need to come
to lab with the lab text and lab notebook every time you come to lab. You should come to lab the day of the
experiment having read the experiment and prepared to do the lab.
date
experiment
1/13T, 1/15R ……………… introduction & discussion of syllabus
1/19M …………………… MLK Holiday
1/20T, 1/22R ……………… check in, safety quiz & safety contract
1/27T, 1/29R ……………… Reducing Benzil using Sodium Borohydride, (micro) (Synt 715, p. 22-23)
2/3T, 2/5R ………………… Williamson Ether Synthesis Phenacetin, (micro) (Synth 726, p. 99-101, fig3a)
2/10T, 2/12R …………… Diels Alder, Anthracene & Maleic Anhydride, (micro) (Synth 717, p. 50-52)
2/17T, 2/19R……………… Spectroscopy Lab Part I (IR,UV-Vis Dr. Hahn’s handout)
2/23M …………………… midterm grade due
2/24T, 2/26R …………… Spectroscopy Lab Part II (NMR, Dr. Hahn’s handout)
3/3T, 3/5R ……………… Nitrating Methyl Benzoate (Reac 716, p 37-39, part 3B)
3/10T, 3/12R……………
makeup lab day Lab makeup will be allowed only with an excuse acceptable to
Dr. Hahn. You must bring the documentation for the excused lab prior to doing the experiment. You must
request that you be allowed to do a lab makeup in writing the week of 3/3 T, 3/5 R so that the lab makeup can
be prepared for you. (Otherwise you will come to lab and the chemicals and equipment for the experiment will
not be out so that you will not be able to do the experiment.)
3/16M to 3/20F ………… Spring Break
3/24T, 3/26R …………… Friedel Crafts Acylation, 4-Methoxyacetophenone (Synth 723, p. 85-88)
3/31T, 4/2R ……………… trans-9-(2-phenylethenyl) anthracene, Wittig, (micro) (Synt 721, p. 75-76)
4/7T, 4/9R………………… Preparing Isopentyl Acetate, Fisher Esterification (Synt 713, p. 12-13)
4/10F to 4/13M ………….. Easter Break
4/14T, 4/16R……………
Amide Synthesis of Phenacetin(micro), (Synt 726, p. 105-106)
4/21T, 4/23R ……………… makeup lab day Lab makeup will be allowed only with an excuse acceptable to
Dr. Hahn. You must bring the documentation for the excused lab prior to doing the experiment. You must
request that you be allowed to do a lab makeup in writing the week of 4/14 T, 4/16 R so that the lab makeup
can be prepared for you. (Otherwise you will come to lab and the chemicals and equipment for the experiment
will not be out so that you will not be able to do the experiment.)
4/28T, 4/30R ……………… check out
4/30R Last day classes; 5/1F Reading Day; 5/11M grades due to registrar
*** Please note: All page numbers given above covers the portions of the procedures which will be carried
out in the lab. For your reading prior to coming to the lab, you should read the introductory sections as well as
the procedure. The page number for the introduction is given in the table of contents in the lab book. ***
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