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Dehydration of 2-methylcyclohexanol Lab, Lab Reports of Chemistry

Lane CollegeChemistry

Full Report Guidelines by Stephen Corlett at laney college

Typology: Lab Reports

2020/2021

Uploaded on 05/11/2021

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ORGANIC CHEMISTRY LANEY COLLEGE
CHEM 12B INSTRUCTOR: STEPHEN CORLETT
Version 201 80215
Dehydration of 2-methylcyclohexanol – Full Report Guidelines
Reading: Experiment 24A (microscale version) and unsaturation tests (p. 214) in Pavia (5th edition); review
Techniques listed under Required Reading. See also Klein, secs. 7.12 and 12.9
Introduction
Heating an alcohol with acid results in the formation of alkenes along with the loss of water (hence, this is
referred to as a dehydration reaction). In our experiment, we will substitute 2-methylcyclohexanol for the 4-
methylcyclohexanol prescribed in Pavia. Our substrate can potentially lead to three unique alkene products.
The product(s) will be removed from the reaction mixture using continuous azeotropic distillation. The organic
product will be separated from the water that co-distills with it, and then dried over anhydrous sodium sulfate.
The product mixture will be analyzed by infrared spectroscopy, gas chromatography-mass spectrometry (GC-
MS), and we will perform the unsaturation tests described in Pavia.
Prelab
Include the usual Name, Date, Purpose, and Outline. The Chemical Equation should depict all three of the
products that can formed from 2-methylcyclohexanol. The prelab write-up must include a detailed Reagent
Table. Be sure to calculate the total theoretical yield of the alkene products (note that all three products have
the same MW). Additionally, you should find and list the boiling points for the three isomeric alkenes that can
be formed. Include a sketch of the reaction apparatus as part of the procedural summary.
Procedure
The experiment is described in Pavia 24A—follow the procedure given except substitute 2-methylcyclohexanol
for the substrate. Our Hickman stills are equipped with the side ports. Will also perform the unsaturation tests
described on page 214. Carefully note the results of the unsaturation tests in your notebook.
To Complete the Experiment – Formal Report (see below)
Items that you need from this experiment to complete the report:
1. FT-IR spectrum
2. GC/MS chromatogram with integrated peaks and the percent report.
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CHEM 12B INSTRUCTOR: STEPHEN CORLETT

Dehydration of 2-methylcyclohexanol – Full Report Guidelines

Reading : Experiment 24A (microscale version) and unsaturation tests (p. 214) in Pavia (5th^ edition); review Techniques listed under Required Reading. See also Klein, secs. 7.12 and 12. Introduction Heating an alcohol with acid results in the formation of alkenes along with the loss of water (hence, this is referred to as a dehydration reaction). In our experiment, we will substitute 2 - methylcyclohexanol for the 4 - methylcyclohexanol prescribed in Pavia. Our substrate can potentially lead to three unique alkene products. The product(s) will be removed from the reaction mixture using continuous azeotropic distillation. The organic product will be separated from the water that co-distills with it, and then dried over anhydrous sodium sulfate. The product mixture will be analyzed by infrared spectroscopy, gas chromatography-mass spectrometry (GC- MS), and we will perform the unsaturation tests described in Pavia. Prelab Include the usual Name , Date , Purpose , and Outline. The Chemical Equation should depict all three of the products that can formed from 2-methylcyclohexanol. The prelab write-up must include a detailed Reagent Table. Be sure to calculate the total theoretical yield of the alkene products (note that all three products have the same MW). Additionally, you should find and list the boiling points for the three isomeric alkenes that can be formed. Include a sketch of the reaction apparatus as part of the procedural summary. Procedure The experiment is described in Pavia 24A—follow the procedure given except substitute 2 - methylcyclohexanol for the substrate. Our Hickman stills are equipped with the side ports. Will also perform the unsaturation tests described on page 214. Carefully note the results of the unsaturation tests in your notebook. To Complete the Experiment – Formal Report (see below) Items that you need from this experiment to complete the report:

  1. FT-IR spectrum
  2. GC/MS chromatogram with integrated peaks and the percent report.

CHEM 12B INSTRUCTOR: STEPHEN CORLETT

This experiment requires a full write-up, typed report, double-spaced and single-sided. It will involve the following items (excerpts from the Lab Report Guidelines and Notes ): The Cover Page has the Title, Author, and Affiliation (only) Title The title should be descriptive, but not too long (and is the same as used in your notebook) – it should be the same as the title given on the experimental handout. Authors Put your full name first, then any names of partners second (or third). Affiliation Indicate where you performed the experiment (e.g., Department of Organic Chemistry, Hauser Laboratory, University of Colorado, Boulder, Colorado, or in your case, Department of Chemistry, Organic Laboratory, Laney College, Oakland, CA). (New page) Abstract Probably the hardest part to write, the abstract is a concise statement that tells the purpose of the experiment, the essential elements of the procedure, and the results. The abstract is only one paragraph in length (and approximately five sentences). Consider writing this part last! (A good reference for this is the The ACS Style Guide. Effective Communication of Scientific Information. Editor(s): Anne M. Coghill, Lorrin R. Garson. 2006 American Chemical Society) See also the provided excerpt from this guide. Introduction and Background Provide the background for the experiment that was performed. Discuss and show all aspects of the relevant chemical reactions – the expected products, side-products and maybe even another example from the literature (your textbook, or another book suggested by the instructor). This experiment is somewhat challenging in this regard, since our standard textbook for the course suggests that a relatively small number of products (3) should be produced from this particular elimination reaction. Upon closer analysis of the chromatogram (thanks to the GC/MS), we have observed more products, so you will need to do a little bit of research to find out how to rationalize the products that were formed. You should summarize the expected mechanism for the dehydration that was performed and under the conditions that were used. Your introduction, however should describe the expected formation of the three most likely alkenes – ones that might be presented in Klein. Other items to discuss are the experimental conditions that are normally used for the type of experiment you performed and potential methods to identify your product.

CHEM 12B INSTRUCTOR: STEPHEN CORLETT

followed by the major product, 1-methylcyclohexene; at a much longer retention time, one product that was found in small concentration was 2-methylcyclohexanone (a clue to the formation of one of the products above). References Provide all references to the experiment and the procedure used, including any modifications, and the information used in your introduction, using the correct bibliographic format for each type of reference. (see the MLA standards at: https://owl.english.purdue.edu/owl/resource/747/06/ if you are unsure) Usually, your source will be your laboratory textbook, however give the full correct citation. Since, you will likely do some investigation into the mechanism of the dehydration (to explain the large number of products), be sure to cite any internet sources of information. Final order of assembly:

  1. Cover Page
  2. Abstract
  3. Introduction/Background 4 Chemical Equation
  4. Procedure
  5. References
  6. Laboratory notebook pages Rough Draft of items 1-6 are due a week after the lab is finished. Final version due TBD