Chapter 1: Alcohols and Ethers

1.3 Synthesis of Alcohol from Alkenes

For organic synthesis purposes, alkenes are the common starting materials to produce alcohols. In the sections of “Reactions of Alkenes” in Book I, several methods have been discussed for the synthesis of alcohols from alkenes, including the acid-catalyzed hydration of alkene (section 10.3 in Book I), oxymercuration–demercuration of Alkenes and hydroboration–oxidation of Alkenes (section 10.6 in Book I). These methods are summarized and compared in the following table.

Synthesis of alcohols from alkenes

Acid-catalyzed hydration of alkene

General reaction:

Example:

Notes:

  • Follow Markovnikov rule
  • Rearrangement might occur because the carbon cation intermediate involved
Oxymercuration–Demercuration of Alkenes

General reaction:

Example:

 

Notes:

  • Follow Markovnikov rule
  • No Rearrangement
Hydroboration–Oxidation of Alkenes

General reaction:

Example:

Notes:

  • Follow anti-Markovnikov rule
  • Syn-addition

Table 1.2 Synthesis of alcohols from alkenes summary

 

 

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