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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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Related AUS-e-TUTE Topics

Fermentation

Summary of Nomenclature

Naming Straight Chain Alkanes

Naming Branched Chain Alkanes

Naming Simple Alkenes

Naming Simple Alkynes

Naming Structural Isomers of Alkanes

Naming Structural Isomers of Alkenes

Naming Alkanols

Naming Haloalkanes

Functional Groups

Combustion of Hydrocarbons

Halogenation of Hydrocarbons

Hydrohalogenation of Hydrocarbons

Oxidation of Alkanols

Dehydration of Alkanols (alcohols)

Preparation and Naming of Esters (Esterification)

Substitution Reactions of Haloalkanes (alkyl halides)

Preparation and Naming of Polymers (Polymerization)

Properties and Uses of Alkanes

Properties and Uses of Ethene (ethylene)

Properties and Uses of Polythene (polyethylene)

 
 

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