Orgo 2 Lab Exam 2: Fischer Esterification

Gen rx.

carboxylic acid + alcohol + H+ cat. > ester +H20

carbonyl comes from acid

ester part comes from alcohol

mechanism

..

improving yield/ shifting equilibrium to product

-eliminating one product (H20) from product

-excess of one reactant

-heating reaction

Why reflux? What is temp of reaction during reflux?

don't want reagents to evaporate

temp is ~bp of acetic acid (118), the bp of the solvent because the solvent recondenses

isolating and purifying the product

-extraction using NaHCO3: neutralizes organic layer (top): separates ester from acids, know reactions

-extraction using NaCl: strong ionic solution extracts anything left in product

-add anhy. NaSO4 to dry

-filtering pasteur pipette: removes solid impurities

IR of an ester

~2950: C-H stretch

~1740: C=O

~1230: C-O