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JEE Advanced levelSingle correct optionDifficulty 3 of 3ap142

A compound CHO does not evolve hydrogen with sodium. When treated with one equivalent of at room temperature it gives methanol and a tertiary alkyl iodide. The compound is

  1. A1-methoxy-2-methylpropane
  2. B2-methoxybutane
  3. C2-methoxy-2-methylpropane
  4. D2-ethoxypropane

Answer: C

No reaction with Na means there is no , so the compound is an ether. A tertiary iodide is formed with the alcohol part being methanol, so the ether cleaves by SN1 at the tertiary carbon, i.e. tert-butyl methyl ether (CHO). The other isomers would give or secondary/primary products by SN2.
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