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
page 2 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
page 3 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? Lab Report: E1 Elimination
page 4 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.