1-chloroapocamphane is a bridgehead halide. W | vedclass

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(D) $1$-chloroapocamphane is a bridgehead halide where the chlorine atom is attached to the bridgehead carbon of a bicyclic system. According to Bredt

Vedclass · Accepted Answer

Does not react

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(D) $1$-chloroapocamphane is a bridgehead halide where the chlorine atom is attached to the bridgehead carbon of a bicyclic system. According to Bredt's rule,the formation of a carbocation at the bridgehead position is highly unstable because the resulting carbocation cannot achieve the required planar $sp^2$ hybridization due to the rigid bicyclic structure. Furthermore,an $S_N2$ mechanism is impossible because the backside of the bridgehead carbon is sterically shielded by the bicyclic framework,preventing the nucleophile from attacking. Therefore,bridgehead halides like $1$-chloroapocamphane are extremely unreactive toward both $S_N1$ and $S_N2$ reactions with $AgNO_3$.

$1$-chloroapocamphane is a bridgehead halide. Which of the following statements about its reactivity toward $AgNO_3$ is true?

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