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JEE Advanced levelOne or more correct optionsDifficulty 3 of 3ap143

Select the Williamson syntheses that give the stated ether as the major product.

  1. Asodium 2-methylpropan-2-oxide iodomethane 2-methoxy-2-methylpropane
  2. Bsodium phenoxide bromoethane ethoxybenzene
  3. Csodium methoxide 2-bromo-2-methylpropane 2-methoxy-2-methylpropane
  4. Dsodium ethoxide bromobenzene ethoxybenzene

Answer: A, B

Both successful routes combine a (aryl or tertiary) alkoxide with an unhindered primary/methyl halide for SN2. The tertiary bromide with methoxide undergoes E2 to 2-methylpropene, and an unactivated aryl halide does not undergo nucleophilic substitution with ethoxide.
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