Formal lab report assignment: (30 pt)

This formal lab report is due on Friday, Dec 1 by 1pm, in your GSI’s mail box on the 3rd floor of Latimer
by the elevators. It should be typed (12 pt font, double spaced) and should be a total of 3–5 pages in
length (including figures). You must use the program ChemDraw for your figures. It will be graded on
content, organization, grammar and style and so it is important that your writing is coherent and well-
organized. This formal lab report is a separate assignment from the notebook pages, and may not be
used as your dropped lab score.

The formal lab report should include the following:

Introduction [5 pt]
• Introduce the synthesis of methyl diantilis in general (why it’s important, etc). In this introduction,
include at least two reference to a peer-reviewed journal article. Indicate the references using
superscripted numbers which correspond to a numbered list of properly formatted citations at the
end of the report.
• Draw a reaction scheme for the specific reactions that you carried out.
• Describe this reaction scheme in 2-3 sentences.

Results, Discussion, and Conclusions [10 pt]

• Write a summary of your results.
• Write a cohesive discussion regarding the experimental details for the reaction that you carried
out. Your discussion should include:
o An analysis of all NMR spectra of your group
o A rational arrow-pushing mechanism for both reactions
o A discussion of your yields with all four alcohols
o Discuss the composition of each product. In this discussion, include information gained
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from TLC as well as H NMR and C NMR. Include the purity calculations and a
qualitative comparison of your group’s products with the products from other groups in
your lab section.
o Describe the experimental factors that you believe had the biggest effect in causing any
variability between different groups in your laboratory section.
• Write a concise conclusion that summarizes the results of your experiment.

Experimental [6 pt]
• Write a concise description of the steps that were taken to carry out this reaction in the lab. This
should be written in the third person passive tense, and should constitute an overview of the
procedure without including all of the details. (See the example on page 202 in the Pedersen lab
text)
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• Report the H NMR and C NMR data for your intermediate and products. (The format for this is
described in section 8.1.6, page 168 of the Pedersen lab text, and is also demonstrated in the
examples on page 202.)

References [2 pt]
• Your references should be formatted according to the American Chemical Society style:
• § Author 1 Last Name, First and Middle Initials; Author 2 Last Name, First and Middle Initials; etc.
Journal Abbreviation, Year, Volume, start page–end page.
• Example: § Robak, M. T.; Trincado, M.; Ellman, J. A. J. Am. Chem. Soc. 2007, 129, 15110-
15111.

Supporting Information: [7 pt] Attach copies of each NMR spectrum, annotated as described below.

Make sure you include all of the following spectra with your report:
• Ethyl vanillin (available on bcourses)
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• All H and C NMR spectra for your group
• Identify any peaks that correspond to known impurities (for example, if there is diethyl ether in
your sample, write Et2O next to each of the corresponding peaks). If there are no impurities in
 your crude sample, circle areas of the spectrum where you would expect the starting materials to
appear if they were present.
• For any impurities that you can identify, use the integral values to calculate the molar ratio of
each impurity to the desired product. Show your work for this in Part II of the discussion section. If
your sample had no impurities visible by NMR or TLC, state this in your discussion section.
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Use MNova to process each H NMR and C NMR spectra:
• calibrate the TMS peak to zero ppm
• Peak pick all relevant peaks in the spectrum
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• For H NMR spectra:
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o integrate the relevant peaks in each H NMR spectrum
§ adjust the integrals to match the number of hydrogen atoms in the molecule
associated with each peak.
• print out the spectrum (10 ppm to -0.5 ppm range)
• print out any expanded regions required to see all of the peaks or coupling.
• draw the structure on the printout
• label each hydrogen or carbon on the structure with a letter, taking care to indicate symmetry with
the labels
• assign the resonances by writing the corresponding letter(s) near them