Laboratory Reference Manual, Chemistry 201/202
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Experiment 3   Synthesis of Salicylic Acid from Oil of Wintergreen (Methyl Salicylate)

OVERVIEW | BACKGROUND | PROCEDURE | NOTES | REPORT

Report

All experiments in Chem 201/202 must be described by a lab report. The lab report must be turned in as a separate document that follows the technical writing conventions used by organic chemists (the appendix How to Write Lab Reports provides complete instructions for preparing a technically sound lab report). Neatly handwritten reports are appreciated, but typed reports are also accepted.

Because some of the writing conventions used in organic chemistry will seem strange (the passive voice, the repetition of some information, but not all, etc.), we have provided several sample reports for you to study and learn from. Assuming your experiment went according to plan, you can prepare your reports by plagiarizing our samples, but you are permitted to copy only the material that accurately describes your work.

You will need to think carefully about each word, each number, and each symbol, in the sample report to make sure that these items accurately reflect your work. Do not trust (or copy) any numerical values that appear in the sample report. Do not trust (or copy) any of the literature references. "Plagiarize" does not mean "stop thinking".

To make this a genuine learning experience, you must write your report "from scratch". If you can, neatly write your report by hand, but if typing is easier, go ahead. If you choose to type, do not copy-and-paste directly from this web page to your word processor. Do not prepare an electronic file and share it with classmates. Etc. Etc. The standard operating procedures of Reed College (and scientific) ethics apply. You might enjoy reading a short essay that we have posted on the Honor Principle.

Sample Report

Synthesis of Salicylic Acid from Methyl Salicylate

C. Diver

Tues Lab, Box 007

Abstract
Salicylic acid was obtained from methyl salicylate in 78% yield. The product was identified by its melting point.

Results and Discussion
Salicylic acid was obtained in 78% yield by refluxing methyl salicylate with aqueous NaOH. Recrystallization of the acid gave white needles, m.p. 157-158.5 oC (lit. 159 oC [1]).

Experimental
Preparation of salicylic acid. Methyl salicylate (4 mL, 31 mmol) and 2 M aq. NaOH (10 mL, 20 mmol) were refluxed for 30 min. The solution was acidified with 6 M aq. H2SO4 (~25 mL) and filtered. The crude product was recrystallized from boiling ethanol and dried for three weeks to give green crystals of salicylic acid: 3.33 g (78% from methyl salicylate), m.p. 157-158.5 oC (lit. 159 oC [1]).

References
1. Kaplan, R., ed. "Bob's Big Book of Chemicals", 1st Ed., XYZ Press, New York, 1984.

E-factor
This experiment used the following materials: methyl salicylate (3 g), NaOH (3 g), sulfuric acid (4 g), ethanol (40 g); total consumables (50 g). The product (3.33 g) does not count as waste; total disposables (46.7 g). E-factor = 14.

Post-report questions
(Because this section does not involve copying phrases from the sample report, feel free to 1) type this section and 2) copy material from the Journal electronically.)

Please attach the title and abstract from a recently published article in the Journal of Organic Chemistry to your report (electronic copy-and-paste is perfectly acceptable here). The journal is available online through the Reed library's web site. Any article of any length will do so long as the title and abstract mention the synthesis of an organic molecule (the word "synthesis" will probably appear in the article's title).

Cite the article so that I know which one you are looking at. Then provide brief answers to the following questions: 1) To what extent do the title and abstract comply with the standards set out by the Journal of Organic Chemistry's guidelines? (see How to Write Lab Reports for a short version of these guidelines), 2) In what ways does the information in the abstract supplement/extend the information found in the title? 3) In what way(s) does the information in the body of the article supplement/extend the information found in the abstract? Just pay attention to information that relates to the synthesis. Don't bother with other parts of the article.


OVERVIEW | BACKGROUND | PROCEDURE | NOTES | REPORT

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