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JEE Main levelSingle correct optionDifficulty 2 of 3o3195

Cyclohexyl methyl ether is best prepared by the Williamson method from

  1. Asodium cyclohexoxide and
  2. Bsodium methoxide and bromocyclohexane
  3. Ccyclohexanol and methanol heated with conc.
  4. Dsodium methoxide and cyclohexyl tosylate

Answer: A

The Williamson reaction is SN2, which works best at a methyl or primary carbon. Secondary bromocyclohexane or its tosylate with the strongly basic methoxide mainly gives cyclohexene by E2. Acid-catalysed condensation of two different alcohols gives a mixture of ethers. Hence the alkoxide of the secondary alcohol is alkylated with methyl iodide.
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