Chemistry 317 Laboratory Reports

I. Quantitation by NMR and Hydroboration-Oxidation of an Alkene

This is a single report - NOT TWO. In addition to this report make sure to complete your lab notebook conclusions. The report needs to be typed and double spaced. Please obey all of the rules of English grammar.  Try to be concise and exact.  Use ChemDraw or a similar program to draw the structures of all organic molecules. When you submit this report, please include your spectra.  After the reports have been graded and returned to you, please place your spectra back in your spectral notebook. 

IMPORTANT! - Your reports must be written independently. You may help one another with discussions, structure drawing, etc., but do not plagiarize in any form. Your report is to be written in clear and coherent English! Do not use the first person in your reports (e.g., I; my; we; our; etc.)! Do not write in the command form for any part of your report (e.g. of command form; "Avoid contact with this chemical."; "Do not inhale the fumes."; etc.)! Write in the past tense! EXAMPLE - "After steam distillation the layers were separated. The organic layer was washed twice with water and then dried with magnesium sulfate."

The following link (Silvestri et al., Journal of Organic Chemistry, 1999, 64, 6597-6602) will take you to a paper that describes a body of work that we did some time ago. Please use this paper as a model for constructing your own reports. Please follow the format we employed there. The order of parts for the paper is:

• Title
• Author list
• Abstract (summary not to exceed one paragraph)
• Introduction
• Discussion
• Experimental
• Summary
• References

Make sure that your report includes the following information.

Quantitation by NMR

• Draw the structures of the three components of the mixture on your NMR, and show with arrows, which peaks correspond to which parts of the molecules.
• Show your conversion of the NMR integration values into integration/H values.
• Show how you use your integration/H values to determine the percentage of each isomer.
• What was the relative percentage of each molecule present in your quantiation mixture.

Hydroboration-Oxidation of an Alkene

• Show the balanced chemical equations for the reaction of BH3 and styrene to the alkyl borane intermediate, and its conversion to the 2-phenylethanol product.
• Write the mechanism for the two reactions indicated above.
• Draw the structures of styrene, the Markovnikov product and the anti-Markovnikov product.
• On your spectrum, draw the structures of the three possible products and show where the peaks should appear for each (use an arrow as you did in quantitation).
• Use the integration for the methyl doublet of the Markovnikov product and the methylene triplet from the benzylic position of the anti-Markovnikov product, to determine the relative percentages of each isomer.  If Styrene appears in your spectrum, you must use the three double bond hydrogens to calculate its percentage.
• From the website, download the proton NMR spectra for styrene and each of the two products.  It is usually easier to search by molecular formula.  Your products are sometimes referred to as phenethyl alcohol and alpha-methylbenzyl alcohol.
• Show your calculation of isomer distribution and the percent yield for your product formation.
• After consulting the MSDS website (http://hazard.com/msds/index.php), report briefly on the hazards of styrene and your phenethyl alcohol and alpha-methylbenzyl alcohol products.