Woodward cis-Hydroxylation Reaction

Chemistry, Medicine
Silver acetate, in combination with iodine, forms the initial reactant package for the Woodward reaction. This reaction, carried to completion, selectively converts an alkene into a cis-diol. The prefix cis- refers to the addition of two atoms (or groups of atoms) to the same side of a molecular double bond. Trans-, when used, refers to addition across the double bond – of one atom or group to one side, one to the other side. The Mechanism The mechanism is illustrated in the image (below) up to the point of hydrolysis. The product of that hydrolysis is pictured in the introductory image. We see, first, the iodine splits, the I atom adding to the double bond. In the next part of the reaction, the silver atom attaches to the iodine, and…
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