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COMEDK2023Evening ShiftChemistryAlcohols Phenols and EthersActual

Choose the correct order of increasing acidic strength of the following compounds.

Options

  1. ACH ₃ CH ₂ OH < CCl ₃ CH ₂ OH < CF ₃ CH ₂ OH
  2. BCCl ₃ CH ₂ OH < CF ₃ CH ₂ OH < CH ₃ CH ₂ OH
  3. CCH ₃ CH ₂ OH < CF ₃ CH ₂ OH < CCl ₃ CH ₂ OH
  4. DCF ₃ CH ₂ OH < CCl ₃ CH ₂ OH < CH ₃ CH ₂ OH

Correct answer

A. CH ₃ CH ₂ OH < CCl ₃ CH ₂ OH < CF ₃ CH ₂ OH

Step-by-step solution

The acidic strength of alcohols depends on the stability of the conjugate base (alkoxide ion) formed after the loss of a proton. The stability of the alkoxide ion is increased by the presence of electron-withdrawing groups (EWG) through the inductive effect (-I effect). The compounds are CH ₃ CH ₂ OH , CCl ₃ CH ₂ OH , and CF ₃ CH ₂ OH . In CH ₃ CH ₂ OH , the ethyl group is electron-donating (+I effect), which destabilizes the alkoxide ion, making it the least acidic. In CCl ₃ CH ₂ OH and CF ₃ CH ₂ OH , the halogen

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