NEET levelSingle correct optionDifficulty 1 of 3o3011
(CHX3)X3C−OH reacts with concentrated HCl readily by SN1, but does not react with NaCl in water. The role of the acid is to
Aconvert the substrate into a primary carbocation
Breduce the concentration of chloride ion
Cconvert the poor leaving group OHX− into the good leaving group HX2O by protonation
Dmake the oxygen atom a stronger nucleophile
Answer: C
Hydroxide is a strong base and a very poor leaving group. Protonation gives (CHX3)X3C−OHX2X+, which loses neutral water easily to give the tertiary carbocation that is then captured by chloride.