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JEE Advanced levelOne or more correct optionsDifficulty 3 of 3o3054

The chloromethyl methyl ether reacts with water. Choose the correct statement(s).

  1. AThe carbocation intermediate is stabilised by donation of an oxygen lone pair.
  2. BThe final organic products are methanol and methanal.
  3. CThe rate is almost independent of the polarity of the solvent.
  4. DIt reacts faster than under the same conditions.

Answer: A, B, D

Ionisation gives , stabilised by the oxygen lone pair (1 true). Water addition gives a hemiacetal that collapses to and (2 true). Because ionisation has a charge-separated transition state, a polar solvent accelerates it markedly (3 false). The resonance-stabilised cation makes it far more reactive than a primary alkyl chloride (4 true).
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