Bryan Luu

Discussion
The preparation of ethyl acetoacetate ethylene ketal from ethyl acetoacetate as a first step
was essential because it allowed specific addition of the following Grignard reagent. The ketone
of ethyl acetoacetate had to be protected for Grignard addition to the ester. A Dean-Stark trap
was used to extract water, another product, from the reaction in order to keep equilibrium
unbalanced, and therefore, the reaction moving forward. At completion of ketal protecting group
addition, two equivalents of phenyl magnesium bromide were added to ethyl acetoacetate
ethylene ketal reducing the ester to an alcohol and adding two phenyls. After addition of phenyl,
dilute aqueous HCl was added to remove ethylene glycol protecting group resulting in 1,1-
Diphenyl-1-hydroxy-3-butanone. Additional concentrated HCl was added to protonate and
remove the hydroxyl group, forming a double bond at carbon 1.
The termination of reaction 1, preparation of ethyl acetoacetate ethylene ketal, yielded
78% product. The principal cause of yield reduction was due to systematic error of the
incomplete extraction of water during the reaction. For complete yield, enough water must be
removed to keep the reaction going until completion. However, this would require longer reflux
time, extending pass the procedural constraints of time. The percent yield dropped even further
in week 2 resulting in 50.4%. It should be noted that a small amount of sample was used for
NMR and IR reading after each stage. Though miniscule, such an amount will contribute
slightly to the reduction in yield. The percent yield of week 3 was maintained in a similar range
at 55.6%. Other loss of product was from careless handling of flasks during transportation from
one work area to the next. After reviewing experimental documentation, an error was discovered
which produced an erred final theoretical and percent yield. At the start of week 4, an incorrect
starting mass of reactant, 0.64g, was used which in turn, led to incorrect scaling of reagents. An
incorrect theoretical yield of 0.59g. Actual theoretical yield should have been based on 0.30g
which would have resulted in a theoretical yield of 27.8g. Product mass at the end of week 4
was 0.42g, a higher yield than should be expected. A likely cause for this high value may be the
neglect of completely drying the round bottom flask after removing it from the rotary evaporator
before weighing.
Conclusion
Despite seemingly error prone procedural technique, end product,1,1-diphenyl-1-buten-3-
one, was formed and purified with a final yield of 0.14g. Success of production of desired
product allowed students to practice and observe commonly used multistep synthesis techniques.
The experiment demonstrated utility of protecting groups in forcing desired addition of Grignard
reagents. In the absence of careless error, the above procedure is a reliable method of
synthesizing 1,1-Diphenyl-1-hydroxy-3-butanone.