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JEE Main levelSingle correct optionDifficulty 2 of 3ap238

Lucas reagent is added to the alcohol shown at room temperature. Assume that the rate is governed by carbocation formation. What is observed?

  1. ANo turbidity even after several hours, because it is a primary alcohol.
  2. BTurbidity appears only after about 5 minutes.
  3. CTurbidity appears immediately, because the benzylic cation is resonance stabilised.
  4. DTurbidity appears only on heating above 373 K.

Answer: C

The alcohol is benzyl alcohol. Although it is primary, loss of water gives the benzyl cation, delocalised over the ring, so chloride formation is fast. Benzyl chloride separates at once, in the same way as with a tertiary alcohol.
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