Chemistry 24 – Organic Chemistry II Laboratory – Fall 2014
Section 1359
Instructor Information
Meeting Time - Thursday 12:45 pm – 5:50 pm, SCI 305
Texts
Deborah Schwyter Ph.D.
Modern Projects and Experiments in Organic
Chemistry, (MPE) Mohrig et al. SMC Custom Packet
office: SCI 282
office hours: MW 10:20 – 11:30 am
M-Th by email
by appointment
telephone: 1. 310. 434.4066
e-mail: schwyter_deborah@smc.edu
Prerequisites
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Two semesters General Chemistry
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Two semesters of Organic chemistry
(Chem. 22 may be taken concurrently)
Week
Thursday’s
Date
1
September 4
2
September
11
Techniques in Organic Chemistry (TOC)
Mohrig et al. 4th edition
http://bcs.whfreeman.com/mohrig4e/default.asp#t_923302
Accessories:
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a non-graphing calculator
lab goggles
a lab coat –blue, flame resistant
a box of nitrile gloves
bound and gridded lab notebook
a locker card from the bookstore
Lab
Orientation and Safety
Pre-lab Lecture for Lab 1
Lab 1 – 18 M
Phase - Transfer Catalysis: Synthesis of Butyl Benzoate
Procedure: Loose-leaf Mohrig Lab Manual, miniscale procedure starting on page
28. Note that we are doing the actual miniscale lab, as opposed to the one that
is microscale, but labeled as miniscale. We will use diethyl ether instead of
methylene chloride as the extraction solvent.
Background: In loose-leaf pages before experimental procedure. The use of
crown ethers as phase-transfer catalysts in SN reactions is on page 511 of the
7th edition of Bruice.
Techniques book: Background and Safety Information in Chapters 1-4; Essay on
Intermolecular Forces starting on page 99 Sections 7.1 (reflux), 11.2-11.4, 11.6
(extraction), 20.4, 20.5 (IR). Chapters 12 (drying), 21 & 22 (NMR).
Lab 2 – 4.1 M
HOCl oxidation of 4-t-butylcyclohexanol (Save product for Lab 6!)
3
September
18
Procedure: This is the oxidation of the alcohol, 4-t-butylcyclohexanol, to the
ketone, 4-t-butylcyclohexanone. The procedure starts on page 62 in the looseleaf Mohrig pages.
Background: In loose-leaf pages, starting on page 57. To get an idea of how this
was done in the old days, using a chromium (VI) compound as the oxidizing
agent: http://www.youtube.com/watch?v=ToSmwYgbvI0
Techniques book: Sections 11.4, 11.6 (extraction), 20.6 (IR ATR for solid
samples); Chapters 12 (drying organic liquids), 17 (TLC).
Lab 3 - 28.1 m
Synthesis of benzoylamino acids
4
September
25
Procedure: Loose-leaf Mohrig Lab Manual, microscale procedure starting on page
38.
Background: In loose-leaf pages before experimental procedure.
5
6
October 2
October 9
Techniques book: Sections 15.5, 15.7 (recrystallization); 21.9 (NMR splitting),
and sections on NMR and H-bonding, proton exchange and chemical exchange
that start on page 356.
EXAM I (Lab 1 -3)
Finish Lab 1-3 Analysis of products Labs 1-3
NMR Lecture (exchange, chemical equivalency)
Lab 4: Experiment - 12.1m
Synthesis and Identification of an Ester (C5-C6 isomers)
(We will do the experiment labeled “optional” —with unknown alcohol.)
Procedure: Loose-leaf Mohrig Lab Manual, microscale procedure using an
unknown alcohol. The procedure starts near the bottom of page 7 (next to where
it says MICROSCALE PROCEDURE). You will need to incorporate the microscale
procedure for the preparation of isopentyl acetate that starts on page 5, but you
will use an unknown alcohol instead of isopentyl alcohol. Each pair of students
will be given an unknown primary or secondary alcohol with the formula C 5H12O
or C6H14O.
Background: In loose-leaf pages before experimental procedure, starting on
page 1.
Techniques book: Sections 7.1 (reflux), 11.4 (extraction), 13.1-13.3B (bp
determination and distillation); Review chapter 21, especially 21.9 (coupling) and
21.12 (second-order spectra, diastereotopic H), and chapter 22 (C
NMR)Techniques: 4 (p 197).
Lab 5 Experiment - 15.1/15.2 M
Grignard synthesis of 1,1-diphenylethanol
Procedure: Miniscale versions of both 15.1 and 15.2
7
October 16
Background: In loose-leaf pages.
Techniques book: Sections 7.2 (anhydrous reactions), 7.3 (adding reagents),
11.4 (extraction).
Lab 6 Project - 4.2 M
Reduction of 4-t-butylcyclohexanone (product from Lab 2)
NMR Lecture: Splitting Trees, Karplus Relationship,
Calculation of chemical shifts
8
October 23
Procedure: This is the reduction of the ketone that you prepared in Lab 2, 4-tbutylcyclohexanone, to the alcohol, 4-t-butylcyclohexanol. The procedure starts
at the top of page after the page where "4.2" is in a gray box. We will do the
miniscale version, scaling down if necessary to accommodate the amount of
ketone that you made in the previous lab.
Background: Loose-leaf pages for reaction background. The mechanism in the
lab text attaches a boron group to the oxygen in the tetrahedral intermediate:
you don't need to do this when writing your mechanism for the lab report.
9
October 30
Techniques book: NMR (chapter 21), especially calculating the ratio of products
from NMR (pages 352-4), splitting trees (pages 344-351), and determining J
values from spectra (NMR Lecture - Spin Spin Splitting II)
EXAM II (Labs 4 -6)
Lab 7 Project 11.1M
Aldol Dehydration (With known aldehyde & unknown ketone)
Procedure: Miniscale version of project 11.1
Background: In loose-leaf pages.
Techniques book: Review recrystallization (Chapter 15), especially selecting a
recrystallizing solvent (section 15.3)
Lab 8 Experiment - 22m
Di-Alkylation of 1,4-dimethoxybenzene
Procedure: Microscale procedure in loose-leaf pages.
10
November 6
Background: Loose-leaf pages for the reaction. The background on the reaction
is in the section or chapter of the lecture text on electrophilic addition reactions
of substituted benzenes. If you haven’t gotten that far in lecture yet, you can
probably figure out what’s going on by using a combination of carbocation
stability and reactions of alcohols with strong acids.
Techniques book: You should be familiar with the ones used by now, but they
include vacuum filtration (chapter 10), recrystallization (chapter 15), microscale
extraction using a centrufuge tube (chapter 11), drying an organic solution to
remove water (chapter 12), evaporation of a solvent (chapter 12), and proton
NMR (chapter 21).
11
November 13
Lab 9 - Handout
Synthesis of Para Red –See handout for background and techniques.
Lab 10 Online - Text and Handout
Qualitative Analysis of Unknowns
12
November 20
Each student will be given two unknowns: one general unknown and one
carbohydrate. Each student will work independently. The general unknown is an
organic compound that contains one or more functional groups. The
carbohydrate is a monosaccharide or disaccharide.
The general unknown will be purified and then identified based on physical
properties, solubility tests, melting or boiling point, IR spectrum, chemical tests
for functional groups and sub-groups, and NMR.
The carbohydrate unknown will be identified based on melting point, polarimetry
data, and a chemical test for reducing sugars.
13
November 27
Thanksgiving Holiday
14
December 4
15
December 11
Lab 10 Finish
Locker Check-out
16
December 18
EXAM III (Labs 7 -10) 12:45 pm – 2:00 pm
Lab 10 continued
Qualitative Analysis of Unknowns
Final Letter Grade Breakdown:
Summary of Graded Work:
3 Exams
80 pts./ Exam
Lab Reports (1-9)
8 pts./ Report
Lab 10 Report
18 pts./ Report
Notebook Entries 1-10) 4 pts./ Lab
Total
240 pts.
72 pts.
18 pts.
40 pts.
370 pts.
A = 90 -100%
B = 78-89.9 %
C = 63 – 77.9%
D = 50 – 62.9%
F < 49.9%
There will be no accommodations for make-up exams.
There will be point deductions for late lab reports.
Student Learning Objectives
As assessed by: questions on exams and/or observation of laboratory
performance and/or evaluation of notebook data and lab reports.
1-The student will follow a logical process based on well-established scientific principles and demonstrate
the ability to use the appropriate problem-solving techniques to solve a scientific problem such as the
determination of the structure of a compound based on spectroscopy (IR, NMR, MS) and/or chemical
evidence, or the prediction of a compound’s chemical and/or physical behavior based on the behaviors of
similar compounds.
2-When conducting a laboratory experiment, the student will follow written procedures commonly used in
the organic lab (such as thin-layer chromatography, recrystallization and reflux) accurately and safely.
The student will maintain an accurate and organized lab notebook. When completing a lab report the
student will apply the scientific method correctly by being able to state a hypothesis, take careful
measurements, estimate uncertainties and draw appropriate conclusions based on gathered data and
scientific principles.
3-The student will explain observable phenomena using appropriate scientific theories, such as explaining
the likely meaning of a lower-than-expected melting point, correlating the color and visible spectrum of a
molecule, or other observations made during lab experiments.
Please Note:
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For Labs 1 – 10, An Experiment Report Worksheet + copies of any relevant
spectra + copies of your completed lab notebook entry + vial (one vial / group)
containing your organic product (not relevant for Exp. 10) will be due 1 week after
the completion of the lab experiment.
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Guidelines for each of the Experiment Reports will be found at the eCompanion site.
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The Experiment Reports are graded according to the quality and accuracy of responses to
the guidelines as well as the quality of the experimental results.
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Lab Notebook entries will be graded for format, completion, clarity, lab preparedness, lab
skill, and participation. Get the instructors signature in the lab notebook at the end of every lab
period.
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While conducting a lab experiment, each student is required to wear googles, wear closed
toe shoes, and wear long pants or skirt.
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Excessive Absences (> 1 unexcused absence) may result in the student being dropped
from the roster and/ or a deduction in the final, overall grade.
For Success:
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Attend all class meetings – for extenuating circumstances, contact instructor as soon as
possible.
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Behave respectfully with everyone in the campus community. Students who fail to adhere
to the student code of conduct will be reported to and handled by the Campus Disciplinarian
and the Campus Ombudsperson.
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Work on exams and lab reports with integrity. All incidents of academic dishonesty will be
reported to and handled by the Campus Disciplinarian. The academic code of conduct outlines
behavior that is considered academically deceptive or fraudulent.
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Note that eating, drinking (water included), gum chewing, and smoking are not permitted
in any classroom or lab throughout the Science Building!
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Maintain a sincere interest in learning!
Important Dates:
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Withdrawal by Web Deadline:
Last Day to Withdraw to Receive a Refund: September 14, 2014
Last Day to Withdraw to Avoid a "W": September 14, 2014
Last Day to Withdraw to Guarantee a "W": November 23, 2014
 After Sunday, Nov. 23, 2014 and before the final exam is administered – Late
withdrawals are handled by Admissions and Records and require documentation of extenuating
circumstances.
General Information on Lab Notebooks
Your lab notebook is like a diary of your experiments. Good Experimental work consists of preliminary planning, carrying out the
experiment, keeping a record of the observations and results, and finally evaluating and reporting the results. It is importa nt to keep a
good notebook, as you will include copies of the relevant pages in your lab reports and will refer to it when taking the lab quizzes.
The notebook must be bound (no spiral bound or loose-leaf notebooks allowed). The most useful types have pages with a grid or lines.
You my wish to use a notebook with carbonless copying—each page is doubled so that a copy of your work is made, with one page
perforated for easy removal. Only pages designed for removal should be torn out. Always write in ink in your notebook so that the data
cannot be altered. Water insoluble ink is highly recommended. If you make a mistake, put a neat line through the error and record the
correct information. This allows referral back to the data if it turns out to be useful later. Make a brief note about why you made the
change. Removal of pages from notebooks or altering of data with whiteout is viewed as fraud in the context of laboratory research.
Organize your notebook. Write your name on the front cover and inside the cover. If page numbers are not already present, number all
pages in the notebook before writing anything else in them. Leave the first few pages blank for a Table of Contents. Enter experiment
titles and page numbers in this table as you do each experiment. Start each experiment on a new page, leaving a few blank pages at the
end of the previous experiment if you still have work to do on it. Avoid running experiments together in your notebook. As long as they are
properly labeled, you may mix pre-lab lecture notes with experiments in your notebook, or you may wish to take the lecture notes at the
end of the notebook in a separate section. If you have unused pages once your work is completed, write in large print “This page
intentionally left blank” so it is clear that no data has been omitted or removed deliberately.
Organize yourself by doing the preliminary write up for each experiment. Plan your work before you come to lab so that you can utilize the
lab period most efficiently; for example, using "dead time" while your reaction is heating for other procedures. Each experiment will be
recorded in your notebook in labeled sections as noted below. This work in your notebook will constitute an informal “report” of the
experiment.
The originality of the notebook content is vital to the integrity of you as a scientist. (See lab policy above for explanation of plagiarism.) All
sources used for pictures, diagrams, or physical data should be properly referenced. You may not photocopy material from the lab text
into your notebook, with the exception of apparatus diagrams (no captions) and spectral reference tables. Any plagiarism issues in
your notebook will be treated as dishonest academic conduct. Do not copy material from other students. You may work with your
partner on your notebook, but you should develop your own unique notebook style. Small portions of text may be cited from legitimate
resources, as long as a proper citation is used.
Step-by-Step Guide to Notebook Format
Before you come to lab each week, read the lab textbook pages found in your syllabus AND any Techniques (gray pages at the back of
your lab text) listed before the procedure section of the experiment. Note from the syllabus whether we will be following the miniscale or
the microscale procedures. Each numbered step below represents a discrete section in your notebook. Please label each section clearly
(section heading is shown in bold below) and include the appropriate content within each section. If a section is not relevant to an
experiment, you may omit that section; otherwise, each section below must be included in each notebook submitted.
Before coming to lab:
1. Write the title of the experiment on a new right-hand page of your notebook. Give a simple reference (e.g. Mohrig MPE, p. 59). Enter
the title and notebook page number for the experiment in your table of contents.
2. The purpose of your experiment should be summarized in a few sentences. Although the purpose is short it is still important, as all
scientific experiments are designed to answer a specific question or questions. You must determine what that question is and phrase it as
a concise, passive-voice statement. You should also give the name of the methods (techniques) used to accomplish the purpose.
“Caffeine will be isolated from tea by extraction …” is much better than “We will learn how to get caffeine… " or “I will isolate caffeine … ".
3. Make a table of the names and structures with appropriate physical data of every compounds used, prepared and isolated. Include
the molecular weight, boiling and/or melting point for each reactant and product; include densities for pure organic liquids, and
concentrations for solutions. These values are referred to as literature values or theoretical values. Information on using physical data
handbooks appears on pages 34-38. (Technique 4) of TOC. You need to include data for solvents and reagents as well, not just the
reactants and products. This information can also be found on the web; for example, Material Safety Data Sheets (MSDS) provide a
wealth of information that includes physical properties and safe handling of the substance. Sigmaaldrich.com also is a great source of
information. The Aldrich catalog and CRC index will be available at all times in the laboratory. Other useful links can be found on Dr.
Anderson’s homepage.
4. For lab experiments that involve the preparation of a substance (a synthesis), include a balanced structure-equation for the reaction
to be performed. If a series of reactions is used to prepare a substance, include all of them. Reactions that produce multiple products or
by-products can be problematic: in some cases, an unbalanced equation with major and minor products should be written with the reaction
stoichiometry clearly explained.
5. Write your procedure. A useful method is to first draw a vertical line in your notebook to divide the page into two columns, making the
line about two-thirds of the way from the left hand edge of the paper. Use the wider column on the left to write a detailed list of the steps
you will follow in the laboratory in your own words. This can be in complete sentences, written as a list of instructions, or whatever works
best for you. Remember that a picture is worth a thousand words when trying to describe lab set-ups. You should write your procedure so
that you do not have to look at your textbook while performing the experiment. The blank right hand column will be used during the lab to
write procedural changes, observations and data. Before beginning the experiment, you may want to write down blank lines on which to
record certain numerical data.
6. Prepare a table for your results section now so that you know exactly what is required during the laboratory. In many cases, organic
labs do not involve recording an extensive amount of numerical data; this can often lead to a difficulty in finding the one or two important
numbers that constitute the final result. When a result table is clearly separated from other parts of the experiment, you will know what
values to record and share with your partner before you leave lab each week.
During Lab:
1. Write the date on which you are performing the experiment and the name(s) of your lab partners at the top of the right hand column of
your procedure section. (If you finish the lab at a later date, make sure that you write in that date next to the appropriate part of the
procedure.)
2. Use the right hand column of your procedure section to record all data and observations that you are asked to record or that you think
might be important. Also use this space to note any changes or additions to the procedure. Try to record the data as close as possible to
the corresponding part of the procedure. If you are not sure whether or not to write down a given observation or piece of data, remember
that another student in the class should be able to repeat the procedure exactly as you performed it by referring only to your notebook. To
avoid deductions, write this information only in your notebook, rather than on your hand, paper towels or the lab bench. Each person is
expected to have a complete set of data in his/her notebook; this way you won't be out of luck if your lab partner suddenly drops or
“flakes”.
If you change any step in the procedure, or if steps are omitted, you must note those changes by describing those changes in the
procedure and data sections. Leave yourself enough space when writing the original procedure so that changes can be easily noted.
Some examples of data and observations are reagent amounts used, even if you use the amount in the lab book; time and temperature of
heating, cooling, or reaction; changes in color or temperature during reaction; general appearance observed during a reaction; actual
(experimental) boiling points during distillations; approximate amounts of solvents or drying agents used; amount of product obtained or
isolated (both crude and purified, when appropriate); physical characterization of the substance produced or isolated (appearance, melting
or boiling point reported as ranges, any chemical tests or spectrometric data); the look on your partner's face when informed that you just
dropped the reaction on the floor, etc.
3. More extensive data that won't fit neatly in the right column of the procedure section should be recorded below the procedure section.
This may include spectral printouts, chromatograms, or other tabular numeric data. Outside pieces of paper that are included in your
notebook should be attached with tape, staples, or glue-stick. Remember to include spectra on both the original page and on submitted
copied pages.
4. Before you leave the lab, make sure that you obtain the instructor’s signature on your notebook. This is done at the end of the last
procedure instruction that you competed that day. At this time, you may wish to ask the instructor to check your notebook for content.
After the Lab Period:
1. Perform any necessary calculations, including calculation of theoretical and percent yields for synthesis experiments, R f values for thin
layer chromatography, and percent composition of a mixture from gas chromatography. Show your work in this section. In addition, make
sure that you show the final result(s) in this calculations section, as well as in the results section, which should be completed once you
have all your final results available.
2. When appropriate, provide spectral analysis of the information obtained from spectra and chromatographs. This section should include
the meaning of the spectrum or chromatogram, and a summary table when appropriate. It may be clearer to include the spectral analysis
on or near the actual spectra copy found in your notebook.
3. To complete the results section for your experiment, fill in the required values and, write a simple sentence that describes whether or
not you achieved the goal(s) set forth in your purpose. For example, "Cyclopentene was obtained in 86% yield from cyclopentanol using
the procedures described …”
4. Write the conclusion section. This is the most important part of your notebook. Whether or not your experiment worked as planned,
you must justify the result statement you just wrote by summarizing and clarifying the physical, chemical, and instrumental data you
obtained. (How do you know that the experiment worked? Is it the product you expected? Why are you sure?) For example, “The product
contained a carbon-carbon double bond based on the infrared spectrum; in addition, a positive bromine test was obtained, verifying this
conclusion. The infrared spectrum further indicated the absence of the cyclopentanol starting material, as there was no O-H stretch in the
IR spectrum. Furthermore, the boiling point observed was within 5˚ of the theoretical value of…"
Also in this section, make comments about how effectively you were able to follow the planned procedure. You must explain how mistakes
made affected the outcome, and why deliberate procedural modifications were made during the lab and their effect your result. If you failed
to obtain product or only got a miserable yield, try to explain why. Indicate any procedural modifications that could help future
experimenters. Remember to write this section from the point-of-view of the experiment (passive voice), not the experimenter. It is not
appropriate to write, "I learned to perform extractions and had a wonderful and fulfilling experience." Use the report form questions as a
suggestion for some possible topics to address in your conclusion. NOTE: Separate your various conclusions into paragraphs for ease in
reading.
5. Look over the questions from the lab texts. It is a good idea (but not required) to answer them in your notebook.
Student Profile - Chem 24 Fall 2014
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Name (please print) :
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For Pre-Baccalaureate Students:
What is your major area of study?
Where and when did you study General Chemistry?
Where and when did you study Organic Chemistry?
Do you intend to transfer to a 4-year college? Where and when?
What are your career goals?

For Post- Baccalaureate Students:
In what field/s and from what institution/s do you hold degrees?
Where and when did you study General Chemistry?
Where and when did you study Organic Chemistry?
Do you intend to transfer to a professional program?
What are your career goals?
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For All Students:
Please sign below to indicate that you have read and understood the policies of the class as stated in the
“Syllabus and Schedule.”