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Explain the following behaviours: (i) ...

Explain the following behaviours:
(i) Alcohols are more soluble in water than the hydrocarbons of comparable molecular masses.
(ii) o-nitrophenol is more acidic than o-nitrophenol is more acidic than o-methoxyphenol.

Text Solution

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(i) Alcohols are more soluble in water than the hydrocarbons of comparable molecular masses because alcohols form hydrogen bonds with water.
(ii) The EWG like -`NO_(2)` increases the acidic strength of the phenoxide ion by dispersal of negative change, while EDG like -`OCH_(3)` decreases the acidic strength of phenol by destablising the phenoxide ion by concentrating neative change.
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Knowledge Check

  • Boiling point of p-nitrophenol is more than o-nitrophenol because

    A
    `NO_2` group at p-position behaves differently from that at o-position
    B
    intermolecular hydrogen bonding exists in p-nitrophenol
    C
    intramolecular hydrogen bonding exists in p-nitrophenol
    D
    intermolecular hydrogen bonding exists in o-nitrophenol

  • Which of the following is more acidic than phenol ?

    A
    m-Cresol
    B
    m-Methoxy phenol
    C
    o-Methoxy phenol
    D
    Ethyl alcohol

  • Which concept best explains the fact that o-nitrophenol is more volatile than p-nitrophenol ?

    A
    Resonance
    B
    Steric hindrance
    C
    Hydrogen bonding
    D
    Hyper conjugation

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