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Preparation of ethers by acid - catalyse...

Preparation of ethers by acid - catalysed dehydration of secondary and tertiary alcohols is not a suitable method. Give reason.

Text Solution

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Acid catalysed dehydration of `1^(@)` alcohols to ethers occurs by `S_(N)2` reaction involving nucleophilic attack by the alcohol molecule on the protonated alcohol molecule.

Under these conditions, `2^(@)` and `3^(@)` alcohols, however give alkenes rather than ethers. The reason is that due to steric hindrace, nucleophilic attack by the alcohol molecule on the protonated alcohol molecule does not occur. Instead protonated `2^(@)` and `3^(@)` alcohols lose a water molecule to form stable `2^(@)` and `3^(@)` carbocations. These carbocations prefer to lose a proton to form alkenes rather than undergoing nucleophilic attack by alcohol molecule to form ethers.
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Knowledge Check

  • The major product in the acid catalysed dehydration of 2-pentanol is :

    A
    4-pentene
    B
    3-pentene
    C
    2-pentene
    D
    1-pentene
  • Intermediate product formed in the acid catalysed dehydration of n-propyl alcohol is:

    A
    `CH_3 - CH_2 - CH_3`
    B
    `CH_3 - CH - CH_2^+`
    C
    `CH_3 - CH^+ - CH_3`
    D
    `CH_3 - CH_2 - CH_2`
  • Primary , secondary and tertiary alcohols can be distinguished by employing :

    A
    Oxidation
    B
    Victor Meyer's test
    C
    Lucas test
    D
    All of these
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