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JEE Main · 2022 · 28 Jun 2022 · Shift 1 · Haloalkanes and Haloarenes

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Which one of the following compounds is inactive towards reaction?
  1. (A)(see structure)
  2. (B)(see structure)
  3. (C)(see structure)
    ✓ Correct
  4. (D)(see structure)

Answer: (C)

Solution

In reactions, the rate-determining step is the formation of a carbocation. The bridgehead halide (option C) cannot undergo reaction because the carbocation that would form at the bridgehead position is extremely unstable due to geometric constraints (Bredt's rule). The bridgehead carbon cannot adopt the planar geometry required for a stable carbocation, making this compound inactive towards substitution.

JEE Main · 2022 · 28 Jun 2022 · Shift 1 · Single correct option

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