CHE 118A Lecture Notes - Lecture 6: Mannose, Hydrolysis, Methylation
Document Summary
Glucose, fructose and mannose produce the same osazone: esterification. Reacts in cyclic form, all the alcohols become esters: ether synthesis. Reacts in cyclic form, all the alcohols become ethers (sn2) H rxn occurs at the anomeric c only. Reverse of acetal formation; reactant could not mutarotate, but following hydroysis, product can undergo ring opening/mutarotation rxn occurs at the anomeric c only. Oh is or/oh up at anomeric c ( eat up), is or/oh down at anomeric c (bow down to lpha) H when attacked, the cho becomes a new chiral center (r/s: kiliani - fischer synthesis. Ch2oh: br2, h2o, fe3+, h2o2 (shortens chain)
