Williamson Ether Synthesis (Guaifenesin)

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Last updated 12:52 AM on 6/10/26
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10 Terms

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Guaifenesin

An expectorant synthesized by Williamson ether synthesis.

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Starting materials for guaifenesin synthesis

Guaiacol and 3-chloro-1,2-propanediol.

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Role of NaOH in guaifenesin synthesis

Converts guaiacol into a stronger nucleophile (phenoxide ion).

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Reaction mechanism for guaifenesin synthesis

SN2 substitution.

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Phenoxide ion

Strong nucleophile formed from guaiacol.

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Guaiacol

Weak nucleophile before deprotonation.

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How is glycerol formed

Through hydrolysis side reactions of the chlorohydrin.

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Is glycerol polar or nonpolar

Polar.

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Where is glycerol removed

In the aqueous layer during extraction.

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Why is guaifenesin isolated from cough tablets

To compare synthetic and isolated samples