The Perkin Reaction - The Perkin Reaction Synthesis of...

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The Perkin Reaction Synthesis of a-Phenylcinnamic Acid Michael Lester, Raymond Oldham, Audrey Paulzak QZ-238
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Introduction The Perkin reaction is a condensation reaction similar to the aldol condensation reaction, except that it is between an aromatic aldehydes and an acid anhydride. Also, the Perkin reaction requires a mild base, usually KOH or a tertiary amine, to de-protonate the acid anhydride. For the purposes of this particular experiment, phenylacetic acid is the aromatic aldehyde and acetic anhydride is the acid. The molecule produce will be a mixed anhydride, because there are two distinct reactants. This molecule then reacts with the provided base, triethylamine, to form an intermediate. The reactive anion intermediate is attracted to the hydrogen on benzaldehyde, reacts, and then the acetate ion is removed from solution. The final product is formed with both Z and E isomers, but due to steric strain, the E isomer is more prolific. Table of Reagents Compound Melting Point (ºC) Boiling Point (ºC) Density (g/ mL) Molecular Weight (g/mol) Phenylacetic Acid 77 265 136.14 Acetic anhydride 138-140 1.082
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The Perkin Reaction - The Perkin Reaction Synthesis of...

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