dihydF10 - Evaluating Mechanisms of Two Dihydroxylation...

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Evaluating Mechanisms of Two Dihydroxylation Reactions
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Objective To use TLC to determine the products formed in 2 dihydroxylation reactions. Determine which mechanism is consistent with products formed. Practice “arrow pushing” to show the flow of electrons in a mechanism.
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The Dihydroxylation Reaction A type of addition reaction where an OH group is added to each carbon of a double bond. The pi bond is lost as the sigma bonds to OH are made. The product of the reaction is called a diol, short for di alcohol C C + 2 OH C HO C OH
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What is a Mechanism? The mechanism describes the course of the reaction by breaking it down into a sequence of bond making and breaking steps. The bond making and breaking steps are illustrated by arrows moving electrons
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How do we study mechanisms? We will perform 2 dihydroxylation reactions and analyze the reaction products by TLC. In this case we can test our proposed mechanisms since each addition reaction mechanism proposed makes specific products.
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When cycloalkenes undergo addition different products are possible: OH OH OH OH Syn Addition Anti Addition OH OH + OH OH Mixed Addition OH OH + OH OH + Cis diol has hydroxyl groups
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This note was uploaded on 05/15/2011 for the course CHM 241 taught by Professor Jennifermorris during the Winter '09 term at Grand Valley State University.

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dihydF10 - Evaluating Mechanisms of Two Dihydroxylation...

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