CHE 327 Study Guide - Quiz Guide: Saponification, Hydrophile, Acid Dissociation Constant

• School: Stony Brook University
• Department: Chemistry
• Course: CHE 327
• Professor: Rong Chen

Document Summary

Esters are the least electrophilic and hydrolyze slowly when neutral. Bases (cid:272)a(cid:374) irreversi(cid:271)ly a(cid:272)(cid:272)elerate hydrolysis rate through (cid:862)sapo(cid:374)ifi(cid:272)atio(cid:374)(cid:863) Base must be reasonably stronger than product carboxylate. Oh and alkoxides (ro-) are stronger bases than carboxylates. Base-promoted ester hydrolysis is thermodynamically favored, but kinetically unfavored. Activation energy is lower subsequent to starting, but still high. Hydrolysis reaction is run at bp for solute which is close to bp for solvent. Trimyristin is triglyceride with parent alcohol, glycerol, and three ester functional groups. 3 moles of oh required per mole of trimyristin. 3 moles of myristic acid yielded from mole of trimyristin mmol koh = mmol trimyristin x (3 mmol koh / 1 mmol trimyristin) Theoretical yield = mol l. r used x (3 mol product / 1 mol l. r) x mw of product. If k > (cid:1005) (cid:894) g < (cid:1004)(cid:895), the(cid:374) produ(cid:272)t favored ther(cid:373)ody(cid:374)a(cid:373)i(cid:272)ally. If k < (cid:1005) (cid:894) g > (cid:1004)(cid:895), the(cid:374) rea(cid:272)ta(cid:374)ts favored.