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NEET levelSingle correct optionDifficulty 1 of 3o1005

Alcohols react with concentrated HBr much faster than with alone because

  1. AHBr supplies a stronger nucleophile than
  2. Bthe acid makes the carbon atom of the C-O bond more electron rich
  3. CHBr converts the alcohol into an alkoxide ion, which is a better nucleophile
  4. Dprotonation of the group gives , so the leaving group becomes neutral water instead of

Answer: D

is a poor leaving group (conjugate acid pKa about 15.7). Protonation by HBr converts it into (conjugate acid , pKa about -1.7), a neutral and much better leaving group. Bromide then displaces water.
Practice Organic Reaction Mechanisms I: Nucleophiles and Carbonyl Addition More on Electrophiles, nucleophiles, nucleophilicity and leaving groups

More questions on Electrophiles, nucleophiles, nucleophilicity and leaving groups