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JEE Main · 2004 · 24 Apr 2004 · Offline · Alcohols Phenols and Ethers

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Among the following compound which can be dehydrated very easily is
  1. (A)(see structure)
  2. (B)(see structure)
  3. (C)(see structure)
    ✓ Correct
  4. (D)(see structure)

Answer: (C)

Solution

Dehydration of an alcohol runs through a carbocation, so it comes easiest for the alcohol giving the most stable cation, which puts tertiary ahead of secondary ahead of primary. The tertiary alcohol among the choices, with its hydroxyl on a carbon joined to three other carbons, loses water most readily to form a stable tertiary carbocation and then an alkene, so it is the one dehydrated most easily.

JEE Main · 2004 · 24 Apr 2004 · Offline · Single correct option

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