Benzocaine

In chemistry class we were asked a concept question on why the addiction of p-aminobenzoic aid and 95% ethanol in the presence of an acid catalyst prefers to form benzocaine instead of poly(4-aminobenzamide).  I made two mechanisms about the Fischer esterification process going on but not sure if its correct.

References:

(1) Callam, Christopher; Paul, Noel M.: Synthesis of Aspirin. Organic Chemistry Lab- Chemistry 255; McGraw-Hill: New York, 2009; pp 109-129.

(2) Chemical Book Online Catalog. http://www.chemicalbook.com/ChemicalProductProperty_EN_CB1217951.htm

Homework

Due tomorrow:

ASL Expressive Test self evaluation.

Chem 255 Lab report on the synthesis of Benzocaine, as well as prelab for QuASI Day 3 lab experiment (a part of the REEL experiments).

Outline of questions for tomorrow bible study, focusing on Romans 8:1-14.

Sounds like its going to be a very long night. I do need a reference on how the addition of to improve the reaction of p-aminobenzoic acid and ethanol to result in a higher yield of Benzocaine. Seriously, who makes a lab report due on a Wednesday….its unheard of. RAWR