Enediol Rearrangement In base,the position of the C=O can shift Chemists use acidic or neutral solutions of sugars to preserve their identity. Step I:Remove Step 2: Step 3: Step 4:Reprotonate on CI the a proton Reprotonate Deprotonate onO the O on C2 H H H OH OH +OH H,O TOH H20 H-C- OH +-OH H-C-OH OH OH+ C=0 HO H HO H HO- 一H →HO H HO 一H H OH H -OH H- OH H OH H OH H一OH H OH H一OH H OH H -OH CH,OH CHOH CH,OH CH2OH CH2OH D-glucose enolate enediol enolate D-fructose => Chapter 23 14Chapter 23 14 Enediol Rearrangement In base, the position of the C=O can shift. Chemists use acidic or neutral solutions of sugars to preserve their identity. =>