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Why primary alcohols are more acidic tha...

Why primary alcohols are more acidic than secondary alcohols?

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The structure of a primary alcohol and secondary alcohols
`underset(1^@-"alcohol")(CH_3 rarr underset(H)underset(|)overset(H)overset(|)C rarr O-H)" "underset(2^@-"alcohol")(H_3C rarr underset(H)underset(|)overset(CH_3)overset(|)C rarr> O-H)`
We know that acidic nature of compounds is based upon the removal of hydrogen ion i.e. `H^(+)`. The easier the release of `H^(+)` ion, the more will be acidic strength. As we have seen in the structure above, there are two alkyl group in `2^@`-alcohol which are electron releasing in nature. So due to electron releasing effect i.e. + .I effect, the electron density will be more on oxygen atom in `2^@`-alcohols as compare to `1^@`-alcohol. Large electron density on oxygen atom will hold hydrogen atom strongly and hence removal of `H^(+)` ion difficult in `2^@` alcohols. Hence `2^@` alcohols are less acidic than `1^@`-alcohols.
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Knowledge Check

  • Phenols are more acidic than alcohols because

    A
    phenoxide ion is stabalised by resonance
    B
    phenoxide ion does not show resonance
    C
    alcohols do not show any acidic property
    D
    phenols are soluble in polar solvents
  • Phenols are more acidic than alcohols because

    A
    Phenols are more soluble in polar solvent
    B
    Phenoxide ion is stablised by resonance
    C
    Alcohols do not hydrogen atoms at all
    D
    None of these
  • Carboxylic acids are more acidic than phenols and alcohols because of

    A
    intermolecular hydrogen bonding
    B
    formation of dimers
    C
    highly acidic hydrogen
    D
    resonance stabilization of their conjugate bases
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