2013, Volume 1, Issue 1
A Perkin Reaction: Synthesis of (E)- and (Z)-Phenylcinnamic acids Thusanth Jogarajah, Dr. Lana Mikhaylichenko *
Department of Physical and Environmental Sciences, University of Toronto Scarborough, 1265 Military Trial, Scarborough, ON, M1C 1A4
Received: February 6, 2013; E-mail Thusanth.Jogarajah@mail.utoronto.ca
Abstract – Add text here
The name of this reaction is called the Perkin’s reaction. The reaction was first used by William Perkin to create phenylcinnamic acids (Johnson). It is very similar to the aldol condensation which is followed by elimination. In this reaction E and Z isomers of phenylcinnamic acid are created using benzaldehyde and acetic anhydride. The intermediate product is acetic phenyl acetic anhydride. Benzaldehyde is an aromatic compound that
The reaction involves the use of benzaldehyde with acetic anhydride which gave the phenylacetic acid which would be used with in the farther steps of the reaction to produce the E and Z phenylcinnamic acid. The mechanism for this reaction can be seen in figure 1. Table 1 includes all spectroscopic values for both E and Z isomers of phenylcinnamic acid. The IRs for both E and Z can be seen in figure 2 and 3. The NMR can be seen in figure 4 and 5, while the mass spec can be seen in figure 6. According to the experimental IR spectroscopy for the E isomer of phenylcinnamic acid the peaks of the wavenumber were at 2952, 2518 1672 and 1426 cm-1. The peak at 2952 presents the double bond CH stretch for the alkene carbon. The peak at 2518 presents the carboxylic acid –OH peak. The peak at 1672 could present the carbonyl group. The aromatic ring peaks are around 1600 and 1426-1492. Different values could be seen for the z isomer. The wavenumbers for the IR spectroscopy are 3412, 3247, 1687 and 1552 cm. The value at 3412 presents the carboxylic acid –OH peak. The peak at 3247 presents the –CH that is part of...