H3C- ~ OH H H :ÖH H3C-C-H H Aco Dess-Martin periodinane provides a means to oxidize a primary alcohol to an aldehyde, while avoiding the use of toxic Cr(VI) compounds. The mechanism involves a reaction similar to the E2 elimination, whereby a C=O double bond is formed with a reduced iodine compound as the leaving group. The reaction occurs in a nonaqueous solvent, CH₂Cl₂, so that the aldehyde product can be recovered. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions →XT -OAC ACO OAc H₂C -OAC Aco O CH3 OAc OAC
H3C- ~ OH H H :ÖH H3C-C-H H Aco Dess-Martin periodinane provides a means to oxidize a primary alcohol to an aldehyde, while avoiding the use of toxic Cr(VI) compounds. The mechanism involves a reaction similar to the E2 elimination, whereby a C=O double bond is formed with a reduced iodine compound as the leaving group. The reaction occurs in a nonaqueous solvent, CH₂Cl₂, so that the aldehyde product can be recovered. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions →XT -OAC ACO OAc H₂C -OAC Aco O CH3 OAc OAC
Chapter22: Carbonyl Alpha-substitution Reactions
Section22.SE: Something Extra
Problem 31MP: The Favorskii reaction involves treatment of an -bromo ketone with base to yield a ring-contracted...
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