Question:
C6H5-CH2-Cl can be converted to C6H5-CH2-OH by boiling with aqueous alkali. However C6H5-Cl cannot be converted to C6H5-OH by this method. Explain.
Answer:
This is because C6H5-CH2-OH is more stable than C6H5-CH2-Cl, due to the factor of resonance stabilisation in C6H5-CH2-OH which extends upto -OH in C6H5-CH2-OH, and is only limited within the benzene ring in C6H5-CH2-Cl. So it is easy to hydrolyse C6H5-CH2-Cl by boiling in aqueous alkali which produces C6H5-CH2-OH. However, C6H5-CH2-OH cannot be converted to C6H5-CH2-Cl as it is more stable, and moreover alkali cannot hydrolyse a hydroxide at all.
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