The Reaction of Some Sodium Salts of Fatty Acids and Benzoic Acid With α-Bromobenzyl Cyanide

Author

Richard W. Perkins, Utah State University

Date of Award:

5-1953

Document Type:

Thesis

Degree Name:

Master of Science (MS)

Department:

Chemistry and Biochemistry

Department name when degree awarded

Chemistry

Committee Chair(s)

Hanes O. Van Orden

Committee

Hanes O. Van Orden

Abstract

Fife (4) and O'Shaughnessy (12) have made a series of di-esters by allowing the sodium salts of various fatty acids to react with ethyl monochloracetate according to the following equation:

RCO₂Na ≠ ClCH₂CO₂C₂H₅ ---------> RCO₂CH₂CO₂C₂H₅ ≠ 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 .

Checksum

af5498ca0bbf30682905d902e7003773

Recommended Citation

Perkins, Richard W., "The Reaction of Some Sodium Salts of Fatty Acids and Benzoic Acid With α-Bromobenzyl Cyanide" (1953). All Graduate Theses and Dissertations, Spring 1920 to Summer 2023. 7171.
https://digitalcommons.usu.edu/etd/7171