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CHEM 2203 FA 2014

Lab Report Instructions for E1 Elimination Experiment



General Information
Your report MUST be typed and should NOT be submitted on laboratory notebook pages.
Much of the information and data from your lab notebook will be transferred to your report, but
you will not submit any lab notebook pages with or as part of your report. Copies of your lab
notebook pages should have been submitted when you left lab on the day of the experiment
The lab report is due at the beginning of the lab period on the week following the completion
of the experiment. For this experiment, the due dates will be during the week of October 21.

Specific Information for the E1 Elimination Experiment
Your report will consist of the following sections. Use the headers listed below to designate each
section, except for the Title.

Title: The title of the experiment, the experiment number, and the date that the experiment was
performed in lab. This information is identical to that required in your pre-lab write-up. The title
should be complete and accurate.

Objective: List the goals, or the purpose, of the experiment. This information is identical to that
required in your pre-lab write-up.

Experimental Procedure: You do NOT need to copy the experimental details that were
included in your pre-lab write-up. It is sufficient to include a reference to the source of the
procedure, as well as any modifications that were posted on Blackboard. If necessary, these
statements should be followed by a list of any additional modifications to the
experimental procedure (list in bulleted, complete sentences). It is very important that you
document any changes to the procedure in your lab notebook at the time of the experiment, and
include them in your report. This section may help to explain unexpected results, for instance.

Reaction Scheme: A balanced chemical reaction consistent with the experiment being
conducted, including reactants, products, solvent(s), and reaction temperature. This scheme is
identical to that required in your pre-lab write-up and should immediately precede the Data and
Results Table (see below). The reaction scheme may be hand-written, but please be as neat
and clear as possible.

Below is a sample Reaction Scheme for this lab report. As this experiment marks your first
chemical reaction, this scheme serves to set expectations. You may use it directly in your report.




Data and Results: Organized in three parts as shown below.


Data and Results Table
Lab Report: E1 Elimination

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Give original data and calculated values in an organized tabular format, essentially, an updated
version of the Reaction Table from your pre-lab.
Include appropriate units and pay attention to significant figures.
Data may differ slightly from that reported in your pre-lab write-up. You must report and use
the actual values in your calculations. In this way, your final results and conclusions match
what you actually did in the experiment, not what you intended to do in your pre-lab.
The amount of product included in the table should represent the calculated theoretical
yield based on the reaction stoichiometry.

This report should contain two tables, one for the reaction details, and one for the GC results.
Below is a sample Data and Results Table 1 for this lab report. As this experiment marks
your first chemical reaction, this scheme serves to set expectations. You may use it directly in
your report.

Data and Results Table 1

2-butanol
sulfuric
acid
trans-2-butene, cis-2-butene, 1-butene
Mol. Formula C
4
H
10
O H
2
SO
4
?
Amount (mg) ?*
Amount (L) ? ?
mmoles ? ? ?*
Molar Mass ? ?
Concentration** 18 M
Density (g/mL) ?
Boiling Point (C) 98*** ~290*** ?
*Theoretical yield of butenes, regardless of product ratio.
**Needed in this case because one of the reactants, H
2
SO
4
, is a solution. For most
experiments, concentration will not be included in the Data Table.
***www.sigmaaldrich.com

For Data and Results Table 2, prepare a table that contains the following gas chromatography
peak data and calculations (recall the Fractional Distillation lab report table):
1. Retention Time (min)
2. Peak Area (mm
2
)
3. Peak Identity

Observations
Data includes all relevant observations, such as heat evolved, initial color and color changes,
precipitate formation, etc. Observations should be listed in bulleted, complete sentences.

Calculations
For any calculated values, show your work. This part does not have to be typed, and you may
prefer to leave space in your document and enter the calculations by hand. Please be as neat
as possible.

Note the distinction between yield and % yield. A yield is simply an amount of product (how
much was formed?) and is also referred to as an actual or experimental yield. For example, the
yield of the reaction was 152 mg. A % yield relates how much of a product is produced (actual
Lab Report: E1 Elimination

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or experimental yield) compared to the theoretical maximum that could have been formed
(theoretical yield). See pages 42-43 in the lab textbook.
Because the products are gases, you will not determine a yield or a % yield for this
reaction (but you will do so for future experiments).

1) Theoretical yield of butene products (reported in the Data and Results Table above, show
calculation here). The product ratio is irrelevant in this calculation because all three products
have the same molar mass. No matter the ratio, the theoretical yield of butene products (the
sum of the weights of all products) is constant.

Include the following calculations for ALL GC peak data reported in Data and Results
Table 2.
2) Gas chromatography retention time, in minutes (min) Calculate for each peak from the
distance between the zero point line and the top of the peak. Use the markings on the chart
recorder and a ruler to measure these values. Each bold vertical line on the chart paper
corresponds to 1 min (chart speed = 1 cm/min).

3) Gas chromatography peak area, in mm
2
Estimate by the triangle method. If the peak is
treated as a triangle, then determining the area of the triangle approximates the area of the
peak. The area of the peak triangle is calculated by multiplying the height of the peak (in
mm) times its width at half height (in mm). Use the markings on the chart recorder and a
ruler to measure these values.

Notes on GC calculated values:
There is not baseline resolution of the peaks (they overlap to some extent), and this
introduces some additional error into the peak area calculation. Nevertheless, this method still
provides a reasonable estimate for our purposes.
If the peaks are very small in your GC trace, just do your best with the peak area calculations.
Include your gas chromatogram (from the chart recorder), or a copy of your gas
chromatogram, with your lab report.

Questions: Answer the following questions. Be as complete as possible, and always explain
your reasoning.
1. Write a mechanism for the E1 elimination reaction of 2-butanol with sulfuric acid. Be as
complete as possible and show electron flow for all steps. You should clearly indicate the
mechanistic pathways that lead to each of the products formed in the reaction (there is no
need to duplicate common steps, but at some point the pathways diverge).

Do NOT simply copy the book mechanism without any critical review. It may not be complete
in terms of showing ALL electron flow (proton transfers, in particular, are often assumed and
not drawn out fully). You are responsible for writing complete reaction mechanisms that
are inspired by the rules and guidelines set forth in both the lab AND lecture courses.


2. 1-Butanol also undergoes an acid-catalyzed dehydration reaction.
a) Draw the product or products of this reaction.
b) The reaction likely does NOT occur via an E1 elimination process. What type of
mechanism operates in this case?
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c) Explain why the acid-catalyzed dehydration reaction of 1-butanol does NOT proceed via an
E1 mechanism.

3. Refer to your product GC data and calculations
a) What are the relative peak areas (convert to a ratio) of the GC peaks observed for your
products?
b) Are the relative peak areas consistent with your expectations of the product distribution for
the dehydration of 2-butanol? Why or why not?

4. Provide a detailed explanation for the expected (and hopefully, experimentally observed)
product distribution.

Works Cited: Full references for the experimental procedure(s) in the appropriate format.

Remember to include your gas chromatogram, or a copy of it, with your report.

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