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JEE Advanced levelSingle correct optionDifficulty 3 of 3o1054

When is dissolved in 50% aqueous ethanol it gives both and . The most direct inference is that

  1. Awater attacks the bromide by and ethanol attacks by
  2. Bbackside attack by ethanol is faster than by water, giving a retention product
  3. Cthe rate-determining ionisation gives a carbocation that is captured by either water or ethanol of the solvent
  4. Dthe substrate first eliminates and then adds the solvent

Answer: C

A tertiary substrate cannot be attacked from the back, and both products come from the same intermediate. Ionisation is rate determining, giving , which is trapped competitively by (giving alcohol) and (giving ether after loss of a proton). The product ratio reflects solvent composition and capture selectivity, not the ionisation rate.
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