Date of Award:
Master of Science (MS)
Chemistry and Biochemistry
Hanes O. Van Orden
Fife and O'Shaughnessy have made a serices of di-esters by allowing the sodium salts of various fatty acids to react with ethyl monochloracetate according to the following equation:
RCO2 Na + ClCH2 CO2 C2 H5 -----------> RCO2CH2CO2 C2 H5 + NaCL
The mechanism of the reaction appears to be ionic and to involve the attack of an RCO2- ion on the carbon atom to which the chlorine atom is attached. As the RCO2- approaches this carbon atom the chlorine atom moves away and leaves as a chloride ion. This reaction appears to be similar to the Williamson synthesis of ethers:
RONa + R'X --------------> ROR' + NaX
Perkins, Richard W., "The Reaction of Some Sodium Salts of Fatty Acids and Benzoic Acid With a-Bromobenzyl Cyanide" (1953). All Graduate Theses and Dissertations. 7171.
Copyright for this work is retained by the student. If you have any questions regarding the inclusion of this work in the Digital Commons, please email us at .