Indirect hydration methods hydroboration-oxidation

Like alkenes (Sections 7.4 and 7.5), alkynes can be hydrated by either of two methods. Direct addition of water catalyzed by mercury(II) ion yields the Markovnikov product, and indirect addition of water by a hydroboration/ oxidation sequence yields the non-Markovnikov product. 

Alcohols can be prepared by hydration of alkenes. Because the direct hydration of alkenes with aqueous acid is generally a poor reaction in the laboratory, two indirect methods are commonly used. Hydroboration/oxidation yields the product of syn, non-Markovnikov hydration (Section 7.5), whereas... 

Our previous method for alcohol synthesis, hydration of aikenes, necessarily produced the more substituted alcohol. So now we have complementary synthetic methods for producing hoth possible alcohols from a given alkene (Fig. 9.69). Direct hydration gives the more substituted product (Markovnikov addition) and the indirect hydroboration/oxidation method gives the less substituted alcohol (anti-Markovnikov addition). Be sure to add these reactions to your file-card collection of synthetically useful reactions. 

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