CHEM 321
Organic Chemistry Laboratory Syllabus Fall 2015
Linfield College, McMinnville, Oregon (Also See Course Syllabus)
Required Text and Materials:



Course Website: http://www.linfield.edu/chem/current-courses/chem-321.html
New bound lab notebook with duplicate pages (can be purchased through bookstore or LSUC in the chemistry
department)
Laboratory goggles, long pants, closed toed shoes
NOTE: Disability Statement: Students with disabilities are protected by the Americans with Disabilities Act and Section 504 of the Rehabilitation Act. If you are a
student with a disability and feel you may require academic accommodations please contact Jennifer Gossett, Learning Support Services Coordinator (LSS), as early as
possible to request accommodation for your disability. The timeliness of your request will allow LSS to promptly arrange the details of your support. LSS is located in
Walker Hall, Room 126 (503-883-2562). We also encourage students to communicate with faculty about their accommodations.
Academic Integrity: Please read the section “Academic Integrity” in the college catalog (or at http://www.linfield.edu/academic-affairs/curriculum.html). This class
will adhere to the policy as published in the Linfield College Course Catalog. Work presented with your name on it is assumed to be your own, unless designated
otherwise. Students engaging in cheating, plagiarism, fabrication, or aiding in such activities are subject to disciplinary action.
COURSE OBJECTIVE AND PURPOSE:
Experiments are chosen to offer practical experience with, and enhance the understanding of, topics covered in the lecture portion
of the course. They also introduce students to common methods and procedures used in the organic chemistry laboratory.
On Mondays in class or Tuesdays in discussion there may be a brief outline of the experiment to be performed that week,
depending on its difficulty. Bring your lab notebook with the protocol for the experiment written in your own words and be
prepared to discuss the material for that week’s experiment (see below on keeping a notebook).
Proper preparation of a laboratory notebook, complete with purpose, procedure summary, material toxicity, data tabulation and
writing up of observations and conclusions is an integral component of this course. An equally important focus is on learning how
to write a proper laboratory report.
Grading System: **The total of all lab credit will be normalized to 150 pts of 800 total course pts, except if you fail the lab, you
fail the entire course** Most experiments are worth 20 points apportioned as follows:
Preparation for and Conducting Experiments
Your laboratory instructor and teaching assistant will evaluate the following before and during lab (10 points):

Laboratory notebook and pre-lab questions before you start the experiment. In general (more specific guidelines are given
on the next page), the initial notebook check (including complete pre-lab questions) is worth 5 points. Pre-lab questions for a
given experiment can be found at the end of that week’s experimental handout.

Work habits & Competence at common lab skills - timeliness, safety, overall neatness including care of glassware,
common areas, bench top, etc.); ability to efficiently assemble laboratory each apparatus, effectively use laboratory
equipment, control reaction conditions, and obtain desired results, etc. Your competence at common lab skills is worth 3
points

Laboratory notebook at the conclusion of your experiment for your data / observations. Your data / observations are worth 2
points.
Demonstrating Your Knowledge after Conducting Experiments
Your laboratory instructor and teaching assistant will evaluate what you’ve learned with several types of assignments:
1. Laboratory Reports (Most are normalized to 10 points EACH**):
In general, laboratory report scores are based on use of proper English grammar, clarity and appropriateness of prose,
conciseness, scientific accuracy, and proper formatting.
There are two report formats you will be asked to utilize this semester:
Minor Lab Report – most of your lab reports will use this format (normalized to 10 points each). Each summary should be
concise and filled out electronically using the template provided. This format may be referred to as a “skeleton” report. A minor lab
report should be turned in as a hard copy (with all pre-lab and in-lab notebook pages stapled at the end).
Major Lab Report – 2 lab reports this semester will use this format (normalized to 20 points each).
Scoring of major laboratory reports will focus on 6 main areas: 1) an Introduction section complete with the reaction mechanism (or
reaction), 2) an experimental methods section, 3) a results section, 4) a discussion section, 5) an appendix, and 6) a references
section. See the major lab report guidelines and sample major lab report at the end of this document for guidance. A major lab report
should be turned in as a hard copy (with all pre-lab and in-lab notebook pages stapled at the end) AND electronic copy sent to
ksours@linfield.edu. Name the file with last name, year, experiment (EX: “Sours2015E1”).
If your score on a report falls at or below 60% please make an appointment as soon as possible with the grader. He or she will
discuss with you some ways to improve your writing. You may revise and resubmit up to two lab reports during the semester. If you
choose to revise a report, the revision is due no later than ONE week after the original report was returned to you. No revision will be
accepted after that time. The submission must include the original report and the revision.
** Major laboratory reports will be worth 20 normalized points. Please see schedule of experiments.
2. Quizzes (Normalized to 5 points each):
Quizzes over an experiment will be given the following Tuesday during Discussion. The purpose of the quizzes is to
evaluate what you have learned about the previous experiment’s equipment, techniques, and objectives.
3. Extra Credit (Most likely normalized to a possible 10 points - tentative):
There will be one ongoing opportunity for extra credit during the fall semester – a journal reflecting on topics you’re
learning about in lab. This is an all-or-nothing opportunity: All entries must be complete to receive credit. Journal entry
prompts can be found on the course webpage.
Grading Student Work
Please be respectful about the feedback you receive on lab assignments. The lab instructor will put thought and effort into
feedback, and there are a lot of students in this course. If you have questions about the grade you receive on a lab
assignment, please wait 24 hours after getting it back before approaching the instructor about it. After 24 hours, you may
submit your questions about grades via email (ksours@linfield.edu) and discuss setting up a time to come in and
talk about it in person.
ChemDraw
We will be using this computer program to draw molecular structures and reactions electronically. You can download it to
your personal computer (either PC or Mac), or find it on campus computers. The site to get download information is here,
which you can also access from the Current Course Offerings page of the Department website.
RefME
You can use this online reference generator to help you create accurate references for lab reports. Sign up for free at
https://app.refme.com/i/ (Style: Journal of the American Chemical Society).
LABORATORY NOTEBOOK REQUIREMENTS
The objective of the lab notebook is to encourage you to develop a habit of keeping complete and useful records of your
lab work.
PRE-LAB: Notebooks will be checked when you enter lab for complete pre-lab. All pre-labs must be complete BEFORE you
are allowed to start that day’s experiment. Pre-labs should contain the following eight items:
1. TITLE OF EXPERIMENT (entire title given on handout)
2. SOURCE REFERENCE (where did you find the protocol?) –COMPLETE URL AFTER DOCUMENT DISPLAYS, OR
PROPER BOOK CITATION INCLUDING PAGE NUMBERS – USE AMERICAN CHEMICAL SOCIETY FORMAT
3. PURPOSE STATEMENT: (Objective of experiment to be learned: chemical concepts to be illustrated, type of
reaction, techniques not previously used, etc…)
4. DEFINITIONS: (Define all NEW concepts and techniques to the laboratory – required every week; suggested
terms may be underlined in the experimental handout)
5. BALANCED CHEMICAL REACTION AND REACTION MECHANISM IF APPROPRIATE (omit spectator ions)
6. MATERIAL CHARTS (reactants + products in Table 1, and solvents + potential byproducts to follow –
See PRE-LAB SAMPLE for how to set this up) ; Include citations to footnote references provided
at end of pre-lab pages; Include calculations for finding limiting reagent – see below, and pre-lab
sample
BASIC SETUP FOR DETERMINING LIMITING REAGENT AND CALCULATING THEORETICAL YIELD:
2X
(USED ↓ / THEORY →)
GRAMS
MW
MOLES
“MOLES OF REACTION” THAT
CAN BE RUN
+
Y

TO BE USED**
10.00**
132.0
0.07576
0.07576/2
=0.0379
(LR)
8.65**
173.0
0.050
0.050/1
=0.050
YX2
THEORETICAL
YIELD
11.56
305.0
0.0379*1=0.0379

0.0379
THEOR.
= MOLES USED/STOICH.MOLES*
* limiting reagent = lowest quotient
** once you have completed the experiment you will use the ACTUAL AMOUNTS USED to
determine TRUE theoretical yield for your product
7. NON-ROUTINE EQUIPMENT SETUP; PROCEDURE (condensed but clear protocol)
(left hand side, ¾ of pg width)
APPARATUS DRAWINGS (if needed)
PROTOCOL (Number each step)
(right hand side, ¼ of pg width
DATA
OBSERVATIONS
8. PRE-LAB QUESTIONS (answered completely, after procedure)
9. REFERENCES (for pre-lab sources such as properties of reagents and products, use ACS format)
IN LAB:
Write data and observations AS YOU SEE them. DO NOT wait until the end of lab to try to write
everything down.
LAB CHECK-OUT:
Before you leave the lab:
1. Areas you used must be clean. All equipment must be clean, complete, and in its proper place.
2. A staff member must sign your lab notebook.
The staff member will check your notebook for the following:
1. CONCISE OBSERVATIONS OF WHAT HAPPENED AND DATA
2. ALL MISTAKES STILL LEGIBLE (cross out with only a single line)
3. YOUR SIGNATURE AND DATE
3. Take a picture or write down information from the board to help you study for the quiz and write the report.
Sample PRE-LAB (written into your lab notebook)
FILL OUT TOP, PROVIDING AT LEAST NAME, PARTNER (IF APPLICABLE), DATE, AND LAB SECTION
An E2 Reaction: Dehydrohalogenation of Cyclohexyl Bromide
TITLE:
REFERENCE:
Linfield College Chemistry, CHEM 321, course webpage.
http://www.linfield.edu/assets/files/chem/Courses/CHEM%20321/E2_cyclohexene.pdf (accessed July 2011).
PURPOSE:
The purpose of the “Dehydrohalogenation of Cyclohexyl Bromide” experiment is to learn a typical E2 (elimination,
bimolecular) reaction. A strong base removes a -hydrogen atom as the halide leaving group departs from the -carbon
in an anti-periplanar orientation in the rate determining step. The most stable (most substituted) alkene product is the
result. Other concepts to be practiced are reflux, extraction, distillation, and two chemical tests that can suggest the
presence of unsaturated bonds.
DEFINITIONS:
Dehydrohalogenation: an elimination reaction that results in the loss of H-X from adjacent carbons of the substrate and
the formation of a -bond between those carbons.
Reflux: the boiling of a liquid in an apparatus that condenses the vapor and returns it to the boiling flask. The purpose is
to avoid loss of liquid while maintaining a constant high temperature in the boiling flask.
-hydrogen: a hydrogen atom on the carbon adjacent to a carbon bearing a functional group.
Leaving Group: an atom or group of atoms that departs from a substrate during a substitution or elimination reaction.
-Carbon: the carbon bearing a functional group of interest.
Figure 1: Bimolecular elimination mechanism (E2)
TABLE 1: REACTANT & PRODUCT PROPERTIES AND COMPUTED THEORETICAL YIELD BASED ON ACTUAL AMOUNTS USED1
Reactant(s)/Product(s)
Amount used (g or mL)
MW
Moles used (“moles of
reaction” that can be
run)
Equivalents
Physical properties
(bp/mp, density)
Chemical hazards
(or special notes)
1 cyclohexyl bromide
13.29 g
163.06 g/mol
+ 1 potassium hydroxide
19.5 g
56.11 g/mol
 1 cyclohexene
6.724 g (theoretical)
82.15 g/mol
0.08185 / 1
= 0.08185 mol (LR)
0.3475 / 1
= 0.3475 mol
0.08185 (theoretical)
0.08185 / 0.08185
=1
d: 1.329 g/mL
bp: 163-165°C
0.3475 / 0.08185
= 4.25
1
salt*
d: 0.8098 g/mL
bp 83°C
Severe burns, corrosive
Flammable, irritant
Non-reactant chemicals (solvents, potential byproducts, etc.)2
Substance/Solution
Ethanol
Calcium chloride
Hexane
Bromine
Carbon tetrachloride
Potassium permanganate
Physical Properties
Toxicity/Hazards
MW:46.07g/mol, d:0.794g/ml, bp:78C
flammable liquid, irritant, toxic
MW:110.98g/mol
MW:86.18g/mol, d:0.660g/ml, bp:69C
flammable liquid, irritant
MW:159.82g/mol, d:3.102g/ml, bp:59.5C
highly toxic, oxidizer
MW:153.82g/mol, d:1.594g/ml, bp:76-77C
cancer suspect agent, toxic
MW:158.04g/mol
oxidizer, corrosive
*Note: the density and m.p. for salts are not shown (These data are not relevant to organic chemical experiments)
Procedure:
(Outline)
Observations
1)
2)
3)
4)
5)
6)
7)
8)
9)
10)
11)
12)
13)
14)
weigh 10 gl cyclohexyl bromide into 100ml rb flask
weigh ~20 g KOH into rb flask & add stir bar
add 25 ml 95% EtOH
reflux gently for 45 minutes
allow to cool to RT
pour into sep. funnel containing 50 ml of H2O
wash rb flask 2X w/10 ml of H2O & add to sep. funnel
Shake; discard lower layer
Extract upper layer again with 80 ml H2O
dry organic layer in erlenmeyer over anhydrous CaCl2
(Swirl 10 min)
distill product into pre-weighed receiving flask
Bromine absorption test:
a) Mix 1 ml hexane & 1 drop 2M Br2/CCl4 in each of 3 test tubes
b) Label test tubes +, -, & s
(positive control, negative control and sample, respectively)
c) Add 1 drop of an alkene, an alkane and the product
to the respective test tubes and observe the result
Permanganate test:
a) Mix 1 ml water & 1 drop KMnO4 soln in each of 3 test tubes
b) Label test tubes +, -, & s
(positive control, negative control and sample, respectively)
c) Add 1 drop of an alkene, an alkane and the product
to the respective test tubes and observe the result
Dispose of chemicals properly and clean up
You may want to draw a special setup here.
Answer pre-lab questions here, at end of protocol, clearly marked.
References (at end of pre-lab pages for pre-lab citations, at end of typed reports for citations used in post-lab reports)
__________________________________________________________________
1
2
Sigma Aldrich Webpage. http://www.sigmaaldrich.com/united-states.html (accessed Aug 18, 2015).
Ibid.
LABORATORY REPORT GUIDELINES
All reports are due at the start of lab ONE week after the conclusion of an experiment. All writing must be legible.
For minor (skeleton) laboratory reports, turn in pre-lab and in-lab notebook pages plus a printed copy of your report
worksheet.
For major laboratory reports, turn in pre-lab and in-lab notebook pages plus a printed copy of your 1.5-or-doublespaced typed major report, AND email an electronic copy to ksours@linfield.edu prior to your laboratory period.
Please save your laboratory report with your last name, year and the experiment (EX: “Sours2015Caffeine”). See
sample major lab report below.
All Lab reports (minor skeleton reports and major reports) are written to answer the following five questions:
1.
2.
3.
4.
5.
What were the objectives that this experiment was designed to address?
What was the rationale for the objectives?
Exactly how did you do the experiment?
What did you discover? (i.e. what results did you get?)
How did the results serve the objectives?
Since proper writing is an important component of this course, please ask someone else to proofread your laboratory
report prior to turning it in for a grade. It is best to ask someone who writes well to make sure that your grammar is
correct and your report makes sense. Incorporate suggestions that you think improve the report, but please be a person
of integrity - what you turn in must be your own work. If you are given the opportunity to work with a partner or a
group on a lab assignment, please give credit where credit is due.
The Linfield Writing Center is a great place to go for basic writing help. Also, it is often nice to receive help from
someone who doesn’t know the chemistry concepts – they can’t fill in all the conceptual gaps on their own.
Writing Center Locations and Hours:
T.J. Day 321
Nicholson Library
SUN-THURS 3:30-5:30 PM; 6:30-8:30 PM
SUN-THURS 8:00-10:00 PM
Laboratory Schedule
Dates
Assigned Report
Aug 31-Sept 04
Sept 07 – 11
Sept 14 – 18
Sept 21 – 25
Sept 28 – Oct 02
Oct 05 – 09
Oct 12 – 16
Oct 19 – 23
Oct 26 – 30
Nov 02 – 06
Nov 09 – 13
Nov 16 – 20
Nov 23 – 27
Nov 30 – Dec 04
Dec 07– 11
Laboratory Experiment
Lab Check-In (Must come to assigned section)
Minor (use template)
Minor (use template)
[Workshop] No Report Due
Minor (use template)
Minor (use template)
Minor (use template)
Major Lab Report (typed)
Minor (use template)
Minor (worksheet)
[Workshop] No Report Due
Choose one of 2 options for Experiment 1 on web page
http://www.linfield.edu/chem/
(Click on “Current Course Offerings,” then “CHEM 321/L”)
Isolation of Caffeine Experiment Part One
Isolation of Caffeine Experiment Part Two
Organic Chemistry Nomenclature and Chair Modeling
Resolution of Enantiomers
SN2: Synthesis of 2-ethoxynaphthalene
E2: Dehydrohalogenation of cyclohexyl bromide
E1: Dehydration of cyclohexanol
Oxidation of cyclohexene to adipic acid
SN1: Solvolysis of t-butyl chloride
NMR and IR: Deduce the Structure
No lab this week
Major Lab Report (typed)
Reduction of a ketone to an alcohol
Check out – all students must participate
Typed Major Lab Report Format (5 page maximum, 1.5 or 2.0 spacing)
_______Sample Outline with key requirements to be written in prose (complete sentences)_________
 Title
 Source reference
 Introduction containing:
o experiment objective(s) (what was the purpose of performing the experiment?);
o context (the experiment that was performed as a means through which the purpose could be met – pertinent
concepts and techniques included);
o rationale (why is this objective worthwhile?); and
o Figure 1 (see experimental handouts for more specifics; this will be the reaction mechanism for that week)
 Experimental methods (refer to the sample report below or the last page the first few experiment handouts for
examples of writing a concise experimental protocol)
 Results presenting actual data/observations that support whether the goal was met or not (e.g., mp/bp range, IR
spectra, chemical tests, appearance, percent yield, etc.)
 Discussion containing:
o a reiteration of the objective,
o comments on how these data compare to published values and what conclusions can be drawn,
o % yield or % recovery: plausible reasons for deviations from 100 percent,
o chemistry concepts supporting results/interpretations (including figures when appropriate, such as reactions
for chemical tests), and
o a summary sentence indicating whether or not objectives were met
 References (additional to source reference, and provide appropriate citations throughout the report)
 Appendix containing:
o calculations with work, protocols for chemical tests, and/or additional supporting figures (in general)
Required format:
Times New Roman 11 or 12 point font
1.5 or 2.0 spacing (except for references or text contained in tables, table titles, figure captions, or text in the appendix)
Section headings (except for title, unless you want a heading for this)
______________________________________________________________________________________
Sample MAJOR Lab Report:
An E2 Reaction: Dehydrohalogenation of Cyclohexyl Bromide
Source Reference: Linfield College Chemistry, CHEM 321, course webpage.
http://www.linfield.edu/assets/files/chem/ Courses/CHEM%20321/E2_cyclohexene.pdf (accessed July 2011).
Introduction: The purpose of the “Dehydrohalogenation of Cyclohexyl Bromide” experiment was to learn a typical
E2 (elimination, bimolecular) reaction, a foundational reaction that will continue to be seen throughout the course. In
the rate determining step of this reaction, a strong base removes a -hydrogen atom as the halide leaving group departs
from the -carbon in an anti-periplanar orientation to produce the most stable (most substituted) alkene product
(Figure 1). The product was synthesized by refluxing the appropriate reagents, isolated by a series of water extractions
to remove contaminants, purified by simple distillation, and characterized (identified) by its boiling range, a bromine
absorption test and a permanganate test.
H
H H

K+ OH-
+ K+ Br- + H2O
Br
H and Br are anti-periplanar
Figure 1: E2 Mechanism (in the case that side reactions are discussed in lab, include these as well)
Experimental Methods: Potassium hydroxide (20 g, 0.35 mol) and cyclohexyl bromide (13.35 g, 0.08172 mol) were
refluxed for 45 minutes in ethanol (25 ml, 95 %) with constant stirring. The reaction was cooled to room temperature
and extracted with water (2x 40 ml) to remove water soluble components (KBr, KOH, and ethanol). The organic layer
was dried over anhydrous calcium chloride (10 min) and distilled to purify the cyclohexene product, which was
characterized by its boiling range, a permanganate test and a bromine absorption test (using cyclohexene and hexane as
positive and negative controls, respectively). (See appendix for chemical test procedures.)
Results: The product boiled between 82-84 C. Only 4.217 g of cyclohexene were isolated (62.71 % yield). Note: This
is where you would place the chemical test results tables, first introducing them from within the text.
Discussion: Cyclohexene was formed from cyclohexyl bromide via an E2 reaction as described previously. The
product’s boiling range was accurate and narrow compared to the value provided in the literature (published: 83°C1),
indicating a fairly pure product. A broad range would imply the presence of several types of molecules, and boiling
point elevation would indicate the presence of less volatile impurities, diluting the desired liquid and lowering its vapor
pressure. The product yield may be low due to incomplete conversion of cyclohexyl bromide to cyclohexene. A large
volume of pot residue remained after distillation, which is where unreacted cyclohexyl bromide would have remained
(published BP: 166-167°C1). Other reasons for a low yield may be due evaporation of product, loss of product during
the extractions and incomplete distillation of product.
The presence of unsaturated bonds in the product was supported by two qualitative chemical tests (bromine absorption
and permanganate, Table 1). The product was compared to positive and negative controls (authentic cyclohexene and
authentic hexane, respectively) in each case to help verify the outcome of the test. When 2M bromine/CCl4 solution
was added to hexane, a brown color appeared due to the presence of diatomic bromine (Br2). The brown color
disappeared upon the addition of the product or of authentic cyclohexene, but not when hexane was the only
compound added. Decolorization is due to addition of bromine across the double bond as indicated mechanistically in
Figure 2. Thus, the results suggest an unsaturated bond was present in the product. When either the product or
cyclohexene control was mixed with aqueous permanganate, the color changed from purple to murky brown due to the
change in oxidation state of the Mn (KMnO4 to MnO2) as illustrated in Figure 3, again indicating the presence of
unsaturation.
(Now would be an appropriate time to comment on relevant pre-lab or lab lecture topics.) The results of this
experiment indicate that cyclohexene was successfully formed from cyclohexyl bromide under conditions typical of an
E2 dehydrohalogenation reaction, completing the experiment objectives. The product was synthesized by refluxing the
appropriate reagents, isolated by a series of water extractions to remove contaminants, and purified by distillation. The
product was identified by its characteristic boiling range and two chemical tests for unsaturation.
IR spectra can be inserted as a figure or attached to the lab report. Do not forget that these are figures. Because of
this, you should follow the figure guidelines listed which can be found here:
http://www.linfield.edu/chem/assets/files/Courses/CHEM%20321/Figures%20Guidelines.pdf. In your discussion of the
IR spectra, you should always compare and contrast the product spectrum with those of the starting materials and any
plausible side products (essentially, any potential contaminants). To decide whether contamination from specific
compounds is significant, evaluate the relative intensities of pertinent peaks in the product spectrum along with
intensities of those peaks in the spectra of the starting materials and/or plausible side products.
References (example):
1. Cyclohexene. Sigma Aldrich online catalog
http://www.sigmaaldrich.com/catalog/ProductDetail.do?lang=en&N4=29240|SIAL&N5=SEARCH_CONCAT_P
NO|BRAND_KEY&F=SPEC (accessed July 2011).
2. Continued with numbering
Appendix:
Chemical test procedures should be included here.
Br
Br
Br
+
Br
C
BrC
C
C
Br
alkene
bromonium ion
HOH2O
O
O
O
OH
OH
(Brown)
Mn
Mn
O
O
+ MnO2
O
O-
O-
(Purple)
Figure 3: Oxidation of an Alkene
Calculations:
Theoretical Yield = 6.73 g cyclohexene (calculations will either be shown here or in pre-lab materials)
(See Laboratory Notebook Requirements section for instructions on how to calculate theoretical yield.)
% Yield = (4.22 g cyclohexene/ 6.73 g cyclohexene) x 100 = 62.70% cyclohexene
For ALL lab reports:
Do not include:
Glassware
Equipment
Common laboratory techniques
Solution making procedures
Routine operational details
Do include:
All reagents and solvents (please spell out names)
Solution concentrations
Reaction times and temperatures
Concise isolation and purification method
Chemical amounts used (in parentheses following name, with
mass or volume and computed moles, see experimental above)