Suppose that you carried out the following synthesis of octyl salicylate:
cat. H2SO4
salicylic acid + 1-octanol (large excess-------------> 1-octyl salicylate + H2O
The structures of salicylic acid and 1-octanol can readily be found.
1-Octyl salicylate is the octyl ester of salicylic acid (you can look up
the way esters are named and how this implies their structure). Now for
the question. This reaction is an equilibrium reaction, so it is expected
that not all of the starting materials will be consumed. Explain how you
would go about isolating 1-octyl salicylate from the reaction mixture in
as pure a form as possible. Assume you need to make use of the physical
properties of the compounds present, including their solubility in various
solvents, acid-base reactivity (and solubility after acid-base reaction),
and boiling point/melting point. You can use water, diethyl ether (a
solvent that is immiscible with water and also serves as a good solvent
for neutral organic compounds), 5% aqueous NaOH, 5% aqueous NaHCO3, and 5%
aqueous HCl. Note that most neutral organic compounds of 6 carbons or
greater are not soluble in water unless they are significantly polar.
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Craig B. Fryhle, Ph.D. Office 206-535-8314 FAX 206-536-5055
Associate Professor Email fryhle@u.washington.edu
Department of Chemistry URL http://rainier.chem.plu.edu/fryhle.html
Pacific Lutheran University
Tacoma, Washington 98447 ^ ^ ^ ^ ^ ^
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