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Hydration of Alkenes

Key Concepts

  • Hydration of alkenes is an addition reaction.

  • Water adds across the alkene's double bond.

  • This addition follows Markovnikov's rule.
        (the H+ of H2O goes to the C atom that has the greatest number of H atoms)

  • Used to produce industrial ethanol from ethene.

  • General Equation:
    alkene + water H+
    alkanol

    H+ represents a dilute, strong acid such as dilute sulfuric acid.

Animated Tutorial

Examples

Hydration of ethene (ethylene):
ethene
(ethylene)
+ water H+
ethanol
(ethyl alcohol)
C2H4 + H2O H+
C2H5OH
  H
|
  H
|
 
  C = C  
  |
H
  |
H
 
+ H-O-H H+
  H
|
  H
|
 
H- C - C -OH
  |
H
  |
H
 

Hydration of propene (propylene)

There are two possible products resulting from the addition of water to propene, 1-propanol and 2-propanol.

Markovnikov's Rule predicts that 2-propanol will be the major product, while the other structural isomer, 1-propanol, will be only a minor product of the reaction.

propene
(propylene)
+ water H+
2-propanol
(major product)
+ 1-propanol
(minor product)
C3H6 + H2O H+
H3C - CHOH - CH3
(major product)
+ CH3 - CH2 - CH2OH
(minor product)
  H
|
      H
|
 
  C = C - C -H
  |
H
  |
H
  |
H
 
+ H-O-H H+
  H
|
  OH
|
  H
|
 
H- C - C - C -H
  |
H
  |
H
  |
H
 
+
  H
|
  H
|
  H
|
 
HO- C - C - C -H
  |
H
  |
H
  |
H
 


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