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Alcohol, Phenol and Ether Test - 12

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Alcohol, Phenol and Ether Test - 12
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  • Question 1
    1 / -0

    Ethers is more volatile than isomeric alcohols (having the same molecular formula). This is due to

    Solution

    Alcohols have stronger intermolecular interactions as compared to ethers because of extensive H-bonding in alcohols. Hence, alcohols have higher boiling points (are less volatile) than ethers.

     

  • Question 2
    1 / -0

    Which of the following ethers is cleaved even by hydrogen chloride at room temperature?

    Solution

    Di-tert-butyl ether is readily cleaved by HCl due to the formation of stable tert-butyl carbocation (SN1 mechanism) to give tert-butyl chloride and tert-butyl alcohol.

     

  • Question 3
    1 / -0

    The compound tert-butyl methyl ether on heating with one mole of HI in anhydrous ether gives

    Solution

    Low polarity of anhydrous HI does not favour SN1 but favours SN2 mechanism. As a result, I- attacks the less hindered methyl group.

    But in this case, the reaction involves protonation of oxygen which is followed by SN1 substitution, due to the formation of the stable tert-butyl carbocation intermediate.

    The products of the reaction will be:
    CH3OH + (CH3)3Cl

     

  • Question 4
    1 / -0

    Which of the following phenols has the lowest solubility in water?

    Solution

    Due to chelation, o-nitrophenol has the lowest solubility.

     

  • Question 5
    1 / -0

    Which of the following has the highest dipole moment?

    Solution

    Among isomeric nitrophenols, p-nitrophenol has the maximum dipole moment. This is due to strong electron-donating resonance effect (i.e. +R–effect) of the OH group on one side and powerful electron-withdrawing resonance effect (i.e. -R-effect) of the –NO2 group on the other side of the molecule. As a result, magnitude of +ve and –ve charges is high and the distance of charge separation is the longest, and hence, it has the highest dipole moment.

     

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