Report

We have provided a sample report for you to plagiarize (as appropriate) as you prepare your own report. However, unlike previous reports, this one is incomplete. You will need to figure out how to write your own Abstract, and how to report IR and NMR data in the Experimental section.

The appendix How to Write Lab Reports describes what is expected in the Abstract and Experimental sections. A relevant example of a complete abstract can be found in the sample report from Experiment 3 (pay attention to how short it is and what it contains).

Note that all of the chemical shifts in the Results & Discussion section are listed as XX ppm. The GC retention times in the Experimental are also listed as XX. You must fill in the correct values from your own data.

Important - staple your GC, IR, and NMR data to your lab report.

Sample Report

Synthesis of Isopentyl Acetate from Isopentyl Alcohol

H. Belafonte

Wed lab, Box 60109

Abstract
[Insert abstract here. Note: an abstract is required for every report]

Results and Discussion
Isopentyl acetate was prepared by refluxing isopentyl alcohol with excess acetic acid and sulfuric acid. The acetate was obtained by distillation in 72% yield, bp 140-143 ^oC (lit. 142 ^oC [1]). GC analysis of the acetate revealed only traces of the starting alcohol (Figure 1).

The acetate's structure was confirmed using IR and ¹H NMR spectra. The IR spectrum (Figure 2) shows a strong absorption at XX cm^-1 consistent with a C=O stretching vibration. The NMR spectrum of the acetate (Figure 3) contains all of the signals expected for this compound. A singlet at XX ppm is assigned to the acetyl methyl group, while a doublet at XX ppm is assigned to the two isopentyl methyl groups. A 7 line pattern at XX ppm is assigned to the methine group (9 lines are expected), and a triplet at XX and a quartet at XX ppm are assigned to the OCH₂ and CHCH₂ methylene groups, respectively.

Experimental
 
Preparation of isopentyl acetate. Isopentyl alcohol (4.6 mL, 42 mmol), acetic acid (4.8 mL, 126 mmol), and concentrated sulfuric acid (1 mL, 18 mmol) were refluxed for 60 minutes. The solution was diluted with water (50 mL) and extracted with ether (40 mL). The ether layer was washed with saturated aq. NaHCO₃ (2 x 40 mL), dried with MgSO₄, and distilled to give isopentyl acetate: 3.9 g (72% from isopentyl alcohol), bp 140-143 ^oC (lit. 142 ^oC [1]); [insert IR & NMR data here; instructions for citing spectroscopic data are provided in the Formatting your Experimental Section portion of the How to Write Lab Reports appendix]; GC (120 ^oC, right-hand column): isopentyl acetate (XX min), isopentyl alcohol (XX min).

References
1. Yeast, R.C. ed. "Esther's Ester Handbook, 11th Ed.", Fruity Publishing, Boca Raton, 1984.

E-factor
Insert list and mass of consumed materials, product, and e-yield here.

Figures
[staple GC data, IR spectrum, and NMR spectrum; label each one as a numbered figure (see above) and give the figure an appropriate title; see appendix for additional instructions]

Post-report questions
(Because this section does not involve our sample report, feel free to copy-and-paste material from the Journal of Organic Chemistry electronically into your report.)

Please locate a published article in the Journal of Organic Chemistry (anything published 1980 or later will do) that includes 1) an Experimental section, and 2) an experiment in that section that describes the proton NMR data for at least one compound. (Try not to pick a structure that is too complicated.)

Cite the article so that I know which one you are looking at. Reproduce the NMR data from the Experimental section in your report. Then do the following: 1) Draw a skeletal formula for the molecule whose spectrum is being reported (if it is helpful, draw individual hydrogens in the formula). 2) Label/number the hydrogens in this formula so that each group of NMR equivalent hydrogens are assigned the same label. 3) How many different signals or patterns were observed in the NMR spectrum and at what chemical shifts? 4) Does the number of distinct hydrogens in the formula match the number of signals or patterns in the spectrum? If not, why not?

Notice: I am not asking you to assign the spectrum. Also, I am not asking for any other data - splittings, integrations - about these patterns.