Welcome to Organic Chemistry Laboratory
Instructor: Dr. Matthew Evans
Course: Chemistry 70A, Organic Chemistry Laboratory
Contact:
Office: 1405
E-Mail: mevans@shastacollege.edu
Phone: (530) 242-2316
Office Hours:
M 9-10, W 9-11, and F 9-11 in Room 1405
Laboratory Schedule:
Th 1-4 in Room 1404
Course Description: Theory and application of organic chemistry laboratory techniques.
Corequisites: Students must be concurrently enrolled in, or have completed CHEM 70
with a grade of C or higher
Prerequisites: A grade of C or higher in CHEM 1B
Course Homepage: http://www.mattdevans.com/sc/courses/chem70a/contactinfo.html
Laboratory Manual: Introduction to Organic Laboratory Techniques, A Small Scale
Approach, 2010, Pavia, et al., 3rd ed., Thompson Brookes/Cole. Unfortunately, the 2nd
edition will not be acceptable for this course, too many changes occurred between the 2nd
and 3rd editions! Sorry...
Additional Materials Required: Instructor-approved safety goggles (not glasses),
hard-bound laboratory notebook, latex or nitrile gloves, and optionally, a laboratory coat
Enrollment Information:
• The number of students I can add is based on available lab space. I can only allow
24 students to be enrolled in the lab (and maybe a few more)!
o I can only add people once I know how many people show up for the first
two laboratories, but not sooner than this!
o If you do not show up for the first lab, I will drop you! (unless you have
contacted me ahead of the first lab meeting)
Lab Meetings: Please be on time to lab! I need you in lab on time to hear the pre-lab
discussion of the experiment and safety issues that may need to be discussed. Habitually
tardy people will incur penalties to be determined by the instructor!
For Students with Special Needs:
If you feel that you will need academic accommodations in this class due to limits imposed by a
disability then contact the Disability Resource Center (225-3973) to make the necessary arrangements. It is
the student’s responsibility to provide documentation that verifies the disability and the type of limitations that
may result. The Disability Resource Center has been delegated the authority to, 1) evaluate that
documentation and determine if it is sufficient to justify accommodations, 2) determine which
accommodations are appropriate, 3) facilitate the provision of approved accommodations.
Matt Evans
Page 1 of 10
Shasta College
Chemistry 70A
Organic Chemistry Laboratory
Grade Breakdown:
Laboratory Reports/Handouts
Laboratory Notebook Check (2)
Discretionary
Laboratory Final Exam
Grading Scale:
A
900 – 1000 pts
B
800 – 899 pts
C
700 – 799 pts
D
600 – 699 pts
F
< 600 pts
700
50
50
200
pts
pts
pts
pts
Fall 2014
Lab notebooks will be checked
at the 8th week (25 pts) and the
final week of classes (25 pts).
It may become necessary to adjust these
grading ranges (so-called “curving”). The
ranges may become larger but never smaller!
Laboratory Notebooks:
• Everyone must have and maintain their own lab notebook, even if we work in
pairs!
• A sample notebook can be provided by the instructor for reference
o Your laboratory textbook has great information on laboratory notebooks, check it
out!
• I will check your laboratory notebooks at the 8th and final weeks of classes
• I will be looking for a title, reaction schemes, complete procedure (procedure has
to be reproducible), and data and observations for each experiment performed
• Results, calculations, and conclusions do not need to be in the lab notebook (but
you may put summaries in the notebook if you wish), but they must be present in any
lab reports that you submit, more on that below...
Laboratory Reports:
• There will be occasional, formal laboratory reports due one week after the completion of
a laboratory experiment
o Some experiments may take several laboratory periods!
o Multiple experiments may at times be combined into 1 report
o Late lab write-ups will incur stiff penalties!
• The format of the laboratory report should be in the same style and format as the
sample report included in this first day handout
Laboratory Worksheets:
! For the majority of experiments, there will be a worksheet due one week from the
completion of the experiment
! The handouts can be printed out from the course homepage if you should happen to
lose it
! Late worksheets (and reports) will incur stiff penalties at the instructor’s discretion
Yield / Purity:
• Always report the percent yield and/or recovery of any product synthesized or isolated
in the laboratory
o This should be reported on both the sample vial and in your laboratory report
• Please turn in your product vial at the completion of each experiment
• Please attach to your lab report (or handout) plots, graphs, and gas chromatograph
traces, etc. if appropriate to the worksheets or reports that you submit
Matt Evans
Page 2 of 10
Shasta College
Chemistry 70A
Organic Chemistry Laboratory
Fall 2014
Laboratory Safety:
• Laboratory safety goggles must be worn at all times in lab!
• For those of you who insist on wearing expensive clothes to lab, I recommend
either purchasing or borrowing a lab coat (we have a few loaners available)
• Redding is a hot place but please try to avoid wearing open-toed shoes and clothes
that expose a lot of skin. This lab generally has more accidents when compared to
general chemistry laboratories.
Glassware Policy:
• Organic glassware is extremely expensive, please do not break it!
o Discretionary points may be taken away for breaking the glassware
• Be especially careful with mercury thermometers, mercury is toxic and requires
time-consuming clean up. Oh yes, you will most certainly lose points for breaking a
mercury thermometer...
Laboratory Participation:
• Please show up to lab, you will receive a zero for missed experiments!
• Please be on time to lab, I will be penalizing people who miss the pre-lab discussion
o If you are more than 10 minutes late to lab, I reserve the right to dismiss
you from the laboratory for that day
Laboratory Final Exam:
• The lab final will be a random laboratory experiment at the instructor’s discretion
o You will have only your laboratory notebook as reference, make sure that
your procedures are completely reproducible!
o If you need a copy of the procedure from the textbook, the “price” is 15% of
your final laboratory exam score
• You will NOT work in pairs on the lab final no matter which experiment I choose;
make sure that you thoroughly understand the experiments and techniques
o Please do not discuss your final exam with anyone but the instructor
o Please ask the instructor for permission to use online tools
Academic Honesty: Verified cases of cheating will result in a zero for that assignment.
Laboratory Experiments: (The most up-to-date experiment schedule will be published
to the course homepage)
For sure: Solubility of organic compounds
For sure: Melting point determination
For sure: Extraction
For sure: Re-crystallization of organic compounds
For sure: Distillation (simple, fractional, and steam)
For sure: Gas, thin-layer, and column chromatography
Possibly: Synthesis of fragrant esters by simple Fischer esterification
Possibly: Substitution and elimination reactions
Possibly: Reactivity of alkyl halides
Long-shot: Molecular modeling
Matt Evans
Page 3 of 10
Shasta College
Chemistry 70A
Organic Chemistry Laboratory
Reduction of Fluorenone to Fluorenol by
Sodium Borohydride
Evans, Matt; Lab, Partner (if there is one!)
Submitted January 12, 2012
Introduction
Fall 2014
Please list the
principal author first!
(If working in pairs)
Please double-space your reports!
Reduction reactions are an integral part of organic chemistry synthesis. The two
most common reducing agents used in reactions are lithium aluminum hydride (LiAlH4)
and sodium borohydride (NaBH4). Lithium aluminum hydride is an
extremely potent reducing agent and will reduce all carbonyl-containing
Give at
compounds with relative ease. However, lithium aluminum hydride is an
least one
extremely hazardous reagent to work with, the reagent is known to react
interesting
violently with water. Sodium borohydride, in contrast to lithium aluminum
tidbit about
hydride, is a much safer reagent for reduction of carbonyl-containing
the
compounds. Sodium borohydride was developed by Schlesinger and Brown
molecules
and is used as a mild reducing agent for reduction of aldehydes and ketones
you are
into corresponding alcohols.[1]
about to
In this experiment, [2, pg. 36] we have successfully reduced
synthesize!
fluorenone to fluorenol using sodium borohydride (see Figure 1). Since both
products and reactants contain fluorophores, we are able to monitor the
reaction progress using thin layer chromatography visualized by ultraviolet radiation. We
determined the purity of the final product by melting point and infrared spectroscopy.
Feel free to “hand-draw”
your reaction schemes!
Figure 1. Reaction scheme for the reduction of fluroenone into fluorenol using sodium
borohydride.
Experimental Procedure
Reduction of Fluorenone
To reduce fluorenone, 0.405 g of fluorenone was added to a 25mL Erlenmeyer flask along with 8.0 mL of methanol and a magnetic
stirbar. The mixture was magnetically stirred until the fluorenone was
completely dissolved. Next, 0.040 g of sodium borohydride was
measured and quickly transferred to the reaction mixture with
constant stirring. The reaction was allowed to stir for approximately
3 minutes at which point we began the final workup.
Matt Evans
Page 4 of 10
You don’t
need to draw a
reflux
apparatus as
long as you
provide a
reference!
Shasta College
Chemistry 70A
Organic Chemistry Laboratory
Fall 2014
Reaction Progress Monitoring
A TLC plate was prepared prior to the addition of sodium borohydride. The plate
was spotted with the reaction mixture contents before any sodium borohydride was added
to the reaction vessel. After the addition of borohydride, the plate was spotted with the
reaction mixture contents at 15, 30, 60, and 120-second intervals.
The TLC plate was developed using dichloromethane and visualized by ultraviolet
radiation.
Isolation of Fluorenol
The reaction mixture was transferred to another 25-mL flask and 2.0 mL of water
was added to the new flask. The reaction contents were heated to near boiling for two
minutes. The flask was then allowed to cool to room temperature to crystallize the
fluorenol product. The crystals were finally isolated by cold vacuum filtration. The
crystals were characterized by yield, melting point determination, and infrared
spectroscopy.
Results
Yield, Melting Point and Appearance
Data tables allow the reader to quickly find data.
They are easy to make in Word (ask if you don’t know
how) and they are very simple in format, see below!
Table 1. Data for the reduction of fluorenone into fluorenol.
Product
Yield (g)
Yield (%)
Experimental
Melting Point (°C)
Fluorenol
3.721
48
150-154
†
Literature Melting
Point (°C)
Appearance
153-154†
White solid
[2, pg. 42]
TLC and IR Data Summary
I should note that the data and
references are completely fictional!
We monitored the reaction progress by TLC. We found that the
reaction proceeded quickly with only fluorenone observed at the 0
second mark and only fluorenol observed at the 120 second mark (see
Figure 2 below).
The infrared spectrum (see Figure 3) showed no carbonyl
absorption at 1700 cm-1, which indicated that fluorenone was completely
reacted. Additionally, a clearly visible –OH stretch at 3289 cm-1,
indicative of the alcohol-containing product.
Discussion and Conclusion
We have successfully reduced fluorenone to fluorenol by a
reduction reaction using sodium borohydride. Our evidence in
support of this conclusion is the close similarity of our experimental
Matt Evans
Page 5 of 10
Please attach your
spectra, TLC,
chromatograms to
the report!
The discussion and
conclusion should
contain the
“bottom-line”!
Shasta College
Chemistry 70A
Organic Chemistry Laboratory
Fall 2014
melting point determination compared with literature (0.9772 % difference), our infrared
spectrum showed no trace of fluorenone in the final product, and the thin-layer
chromatography analysis showed the final solution mixture was free of starting materials.
Our yield was 48%, we note that our “recovery” from the crystallization step was not as
successful as it could have been. We suggest removing the ethanol solvent from the final
solution mixture and experimenting with better solvent systems for recrystallization.
Figure 2. TLC analysis of reaction progress.
References
[1] “Sodium Borohydride.” Wikipedia. Accessed July 6, 2012.
<http://en.wikipedia.org/wiki/Sodium_borohydride>
[2] Pavia, D. L., Lampman, et al. Introduction to Organic Laboratory Techniques, A Small
Scale Approach. 2nd ed. Belmont, CA: Brookes/Cole, 2005.
Matt Evans
Page 6 of 10
Shasta College
Chemistry 70A
Organic Chemistry Laboratory
Fall 2014
Figure 3. Infrared spectrum of the fluorenol product.
Matt Evans
Page 7 of 10
Shasta College
Chemistry 70A
Organic Chemistry Laboratory
Fall 2014
Course Objectives:
Upon successful completion, the student will be able to:
1. Utilize laboratory safety methods regarding laboratory equipment and chemicals.
2. Determine melting points of chemicals.
3. Prepare, isolate, and purify acetylsalicylic acid using crystallization and vacuum
filtration.
4. Re-crystallize a pure substance from an impure substance.
5. Extract organic compounds from a natural products..
6. Distill mixtures of substances.
7. Ferment a substance and separate its products.
8. Fractional distill mixtures.
9. Perform chemical identification procedures.
10. Separate substances using column chromatography.
11. Isolate oils using steam distillation.
12. Synthesize several different chemicals, separate them, and purify them, realizing
sufficient product purity and identification.
13. Determine boiling points of liquids
14. Demonstrate how to use proper procedures in compiling a laboratory report.
15. Demonstrate how to use reference sources for laboratory data.
16. Prepare and use flow diagrams for complicated procedures.
Course Content:
1. Purification of Organic Compounds
2. Determination of Melting Point of Organic Compounds
3. Determination of Boiling Point of Organic Compounds
4. Isolation of Organic Compounds from Natural products
5. Thin Layer Chromatography
6. Column Chromatography Gas
7. Simple Distillation
8. Fractional Distillation
9. Isolation of Essential oils
10. Fermentation
11. Synthesis of Alkenes
12. Chiral Reactions
13. Synthesis of Alkyl Halides
14. Nucleophilic Substitution Reactions
15. Competing Nucleophile in Nucleophilic substitutions
16. Synthesis of 4-methylcyclohexane
17. Lab Reactions of Functional Groups
Student Learning Outcome(s):
1. Interpret, analyze and/or apply accurately collected lab data to solve a chemical problem.
Matt Evans
Page 8 of 10
Shasta College
Chemistry 70A
Organic Chemistry Laboratory
Fall 2014
CHEMISTRY LABORATORY SAFETY RULES
1. Perform no unauthorized experiments.
2. No lab experiments should be performed without your instructor present.
3. All students are required to have a pair of ANSI-approved safety goggles, which must be worn in the lab when anyone is
working with chemicals and/or heat.
4. Contact lens wearers; it is recommended that you avoid wearing contacts, if possible, when working with chemicals.
5. Wear appropriate clothing, avoiding bulky or loose items and open-toed shoes. Long hair should be restrained.
6. Gloves are recommended when working with particularly hazardous chemicals.
7. MSDS (materials safety data sheets) on all chemicals in stock are available; you have the right to request to see them.
Your instructor will show how to use them.
8. Please do not eat or drink in the lab. Also, be sure to wash hands after lab periods before touching any food (or your
eyes).
9. Notify your instructor if you are pregnant; you may be asked to take additional precautions.
10. Laboratory desks and hoods should always be cleaned after use; also, be sure to wipe up spills and remove clutter as
you work.
11. Dispose of chemical wastes as directed by your instructor each lab period. Many chemicals may not be flushed down
the sink or put in ordinary trash containers.
12. Do not taste chemicals. If checking chemicals for odors, use the wafting technique. (See instructor for method.)
13. Never heat or cool a closed system (one that is not vented to the surrounding atmosphere).
14. If caustic chemicals (e.g., strong acid and bases) are spilled on the body, wash liberally with water. If spill is over a
large portion of the body, use safety shower and remove clothing quickly. For chemicals in eyes, use the eyewash and rinse
continually for 15 minutes.
15. In case of any accident in the lab (spills, fires, explosions, etc.), yell “help” first to get assistance, then be sure to call
the instructor. (Seek professional medical help for serious injuries.)
16. When heating a test tube, be sure the open end is not aimed in anyone’s direction.
17. Never pour water into a strong acid or base, but add the acid or base to the water.
18. It is your responsibility to act in a safe manner while in the chemistry laboratory.
19. Never use open flames in the lab when using volatile organic solvents. (Hot plates are fine.)
20. Never use force to place a stopper, cover, etc., on a glass container. When inserting glass tubing into holed stoppers,
use lubricant and hand protection. In case of laceration, first priority is to curtail bleeding.
If you are not sure about any of the safety procedures or safety issues, ask your instructor immediately.
“I have read and agree to abide by these safety guidelines.”
Signature:
Date:
________________________________________
________________________________
Print Name (legibly please!):
Instructor:
________________________________________
________________________________
Matt Evans
Page 9 of 10
Shasta College
Chemistry 70A
Organic Chemistry Laboratory
Fall 2014
(This page was intentionally left blank.)
Matt Evans
Page 10 of 10
Shasta College