Q57 / 160 · JIPMER 2013 · Chemistry

The correct order of increasing acidic strength is

  • A
    phenol $ \lt $ ethanol $ \lt $ chloroacetic acid $ \lt $ acetic acid
  • B
    ethanol $ \lt $ phenol $ \lt $ chloroacetic acid $ \lt $ acetic acid
  • Correct answer
    C
    ethanol $ \lt $ phenol $ \lt $ acetic acid $ \lt $ chloroacetic acid
  • D
    chloroacetic acid $ \lt $ acetic acid $ \lt $ phenol $ \lt $ ethanol

Solution

Due to - I effect of Cl , chloroacetic acid is a stronger acid than acetic acid. Further dur to stablisation of phenoxide ion by resonance and no such stabilisation in case of ethoxide ion, phenol is a stronger acid than ethanol. Hence, overall acid strength increases in the order; ethanol $ \lt $ phenol $ \lt $ acetic acid $ \lt $ chloroacetic acid.

Hence, the correct answer is option: 'C'.

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