CHEM 12A—Trego

Formal Lab Report Guidelines The formal lab report should be similar to the format used in the chemical literature. Your report should have the following components/sections in the order shown below:

• A Cover Page with the following information: o Title o Names of Authors o Name of Institution where the work was performed o Date of Submission

• Abstract • Introduction • Results and Discussion • Experimental Section • References (sources cited) • Supporting Documents (attachments) • Responses to assigned questions (separate page attached at the end of the report)

Title, Authors, etc. Example:

The Isomerization of (-)-Borneol to (-)-Isoborenol by an Oxidation-Reduction Scheme

William E. Trego Chemistry, Physics and Astronomy Department, Laney College, Oakland, CA

Submitted: February 12, 2014

Abstract—In 4-5 sentences (no more than a paragraph), describe the experiment and results. Keep procedural detail to a minimum—this is not the place to report significant quantities of data—but should report the major findings of the experiment. Example: The isomerization of borenol to isoborenol was achieved in moderate overall yield by the oxidation of borenol to camphor and subsequent reduction to isoborneol. The sodium borohydride reduction of camphor proceeded with a moderately high diastereoselectivity. Introduction—Here is where you justify your work and provide pertinent background information. In a research paper, you would attempt to convince the reader that your research is novel and significant. You might describe how the product of your work is biologically or clinically important, or discuss how the product is expected to exhibit interesting physical/chemical properties. The product may have been particularly challenging to synthesize—so you might use the introduction to review past attempts to make the product, and speculate on why the synthesis of this product posed such a challenge. If you are reporting a new reaction, you will want to review similar reactions that already exist in the literature. If you are communicating new physical properties of an interesting molecule, you will want to convince your reader that this data is previously unreported. Results/Discussion—If your work involved synthesizing a product, you should show the reaction scheme employed. You are strongly encouraged to use an organic chemistry drawing program.† You should discus the reactions used, yield(s) obtained and report any difficulties encountered. If you are reporting on a particular chemical reaction, you should propose a mechanism for the reaction. You should discuss how you verified the

†ChemSketch is a free for download drawing program available on the following site:

formation of the desired product through spectroscopy. Be specific—identify peaks observed in the various spectra. Correlate these signals to functional groups, protons, or carbon atoms in the product. You do not need to interpret every peak in each spectrum (especially for the infrared spectra). Again, you should not provide actual experimental procedure detail in this section—just report the results and provide commentary on your work. Experimental Section—For a synthetic organic chemistry research paper, the experimental section is generally organized by the compounds synthesized. The synthesis of each compound receives an entry in the experimental section. The title of each procedure is the IUPAC name for the compound synthesized. If the research was centered on making measurements or carrying out a new spectral technique, you would describe the procedure employed. The melting point, chromatographic and spectral data are reported at the end of each entry for each compound. Chemical shifts, multiplicity and integral values (as number of hydrogen atoms) are reported for 1H NMR spectra. For 13C spectra, only the chemical shifts are reported. FTIR spectral data should be reported for all the diagnostic bands (in other words, bands >1500 cm-1 that can readily correlated to functional groups in the product). (1S,2S,4S)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ol (-)-Camphor (0.100 g, 0.648 mmol) was dissolved in 5 mL of anhydrous methanol at room temperature. NaBH4 (0.100 g, 2.64 mmol) was added slowly in four portions. The resulting mixture was heated to boiling, and then stirred for 2 minutes. After cooling to room temperature, 5 mL of ice water were added which resulted in the precipitation of a white solid. The solid was collected by vacuum filtration, dissolved in 5 mL of CH2Cl2 and dried over anhydrous Na2SO4. The supernatant was decanted from the Na2SO4, which was rinsed with an additional 2 mL of CH2Cl2. The combined solutions were concentrated on the rotary evaporator until a constant mass was attained. 75 mg (0.49 mmol, 74%) of a white solid were collected, mp = 212°C. 1H NMR (300 MHz, CDCl3) δ 3.6 (t, 1H), 1.75 (m, 3H), 1.5 (q, 1H), 1.10 (s, 3H), 0.81 (m, 3H), 0.80 (s, 3H), 0.75 (s, 3H) 13C NMR (100 MHz, CDCl3) δ 80, 50, 47, 45, 41, 37, 34, 20, 21, 15 FTIR (thin film) ν (cm-1) 3320, 2980, 2960, 2910, 2860 References You will want to cite outside resources in the introduction and results sections of your report. These resources might include your textbooks and papers in the chemical literature. While Wikipedia is generally a useful resource, it should not be cited as a reference in your report—it does not conform to the editorial/peer review standards that other resources meet. But…you might consider the references cited on the Wikipedia page. When citing a reference in your report, use a superscript number at the end of the sentence (outside the punctuation) that refers to a citation in the reference section. The entries in the reference section should conform to the style shown below. Book Citation: 1Pavia, D.; Lampman, G.M.; Kriz, G.S. Introduction to Organic Laboratory Technique: A Microscale Approach, 3rd ed. Saunders:Philadelphia,, 1999; pp. 268-269. Journal Citation: 2Paquette, L.A.; Trego, W.E. Chem. Commun., 1996, 419-420 Supporting Documents: Attach any spectra recorded, chromatograms, and the copies from your lab notebook. Questions: Attach the responses to assigned questions on a separate page at the end of the report.

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