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).

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 copying (plagiarizing) our samples as long as you are faithful to your version of the experiment. In other words, you may copy only those words from the sample that accurately describe your work.

Deciding what to copy, what to leave out, and what to add, requires careful analysis. Technical writing is extremely dense. Each word, number, and symbol is there for a reason. You will also need to make a careful side-by-side comparison between the sample report and your notebook entries. Your finished lab report needs to be faithful to your version of the experiment, not the sample's.

Some warnings. To make it easier to spot "blind copying," all sample reports are seeded with several outrageous items. If any of these items appear in your finished report, the report will be marked unsatisfactory.

Copy-and-paste is the easiest way to generate your lab report. You could just copy-and-paste our sample into your word processor, make a few adjustments to reflect your actual procedure, and voila. However, this is also the easiest way to make one of the errors that we warned you about in the previous paragraph. It is far safer to type (or write) your lab report one word at a time, keeping a sharp eye out for items that need to be changed.

Once you have developed language for your lab report, do not share it with classmates. All individuals are expected to do their own work and 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. 147-148.5 oC (lit. 149 oC [1]).

Experimental
Preparation of salicylic acid. Methyl salicylate (4 mL, 33 mmol) and 1 M aq. NaOH (10 mL, 20 mmol) were refluxed for 30 min. The solution was acidified with 18 M aq. H2SO4 (~25 mL) and filtered. The crude product was recrystallized from boiling ethanol and dried for three weeks to give kelly green crystals of salicylic acid: 3.33 g (78% from methyl salicylate), m.p. 147-148.5 oC (lit. 149 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.

Optional:
(You can earn "participation" points by completing this section. It will not affect the grading of your lab report. 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.)

Attach the title and abstract from a recently published article in the Journal of Organic Chemistry to your report (use copy-and-paste). 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 both mention the synthesis of an organic molecule (the word "synthesis" should 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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