Lecture 30 - Oxidation States and Mechanisms

author: J. Michael McBride, Department of Chemistry, Yale University
recorded by: Yale University
published: Aug. 19, 2014,   recorded: May 2011,   views: 1612
released under terms of: Creative Commons Attribution No Derivatives (CC-BY-ND)
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Description

A difficult exam question shows how visible and NMR spectroscopy related to long-term misassignment of the structure for the triphenylmethyl dimer. Evidence from 1970 shows that Friedel-Crafts propylation involves an SN2 mechanism, not a protonated cyclopropane. Assigning oxidation states from -4 to +4 to the carbon atoms of proposed starting material and product allows choosing whether a reagent that is oxidizing or reducing or neither is appropriate. Beyond belonging to the appropriate redox class, the reagent must have an appropriate mechanism. Alcohol oxidations by elemental bromine and by Cr+6 reagents are shown to involve familiar substitution, elimination, and addition mechanisms. Mechanistic understanding allows adjusting conditions to make oxidation selective.

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