Alcohols from Alkenes through Oxymercuration-Demercuration Markovnikov Addition

6 Alcohols from Alkenes through Oxymercuration-Demercuration Markovnikov Addition  

A useful laboratory procedure for synthesizing alcohols from alkenes that avoids rearrangement is a two-step method called oxymercuratioii-demercuration. 

Mercury compounds are extremely hazardous. Before you carry out a reaction involving mercury or its compounds, you should familiarize yourself with current procedures for its use and containment. There are no satisfactory methods for disposal of mercury. 

Both steps can be carried out in the same vessel, and both reactions take place very rapidly at room temperature or below. The first step—oxymercuration—usually goes to completion within a period of 20 s to 10 min. The second step—demercuration—normally requires less than an hour. The overall reaction gives alcohols in very high yields, usually 

The oxymercuration-demercuration of 3,3-dimethyl-l-butene is a striking example illustrating this feature. It is in direct contrast to the hydration of 3,3-dimethyl-l-butene we studied previously (Section 8.5B). 

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ALCOHOLS FROM ALKENES THROUGH OXYMERCURATION-DEMERCURATION MARKOVNIKOV ADDITION... 

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