In a nucleophilic substitution reaction: $\mathrm{R}-\mathrm{Br}+\mathrm{Cl}^{-}…

In a nucleophilic substitution reaction: $\mathrm{R}-\mathrm{Br}+\mathrm{Cl}^{-} \stackrel{\mathrm{DMF}}{ightarrow} \mathrm{R}-\mathrm{Cl}+\mathrm{Br}^{-}$, which one of the following undergoes complete inversion of configuration?
  1. \(\mathrm{C}_6 \mathrm{H}_5 \mathrm{CH}_2 \mathrm{Br}\)
  2. \(\mathrm{C}_6 \mathrm{H}_5 \mathrm{CH}\left(\mathrm{CH}_3ight) \mathrm{Br}\)
  3. \(\mathrm{C}_6 \mathrm{H}_5 \mathrm{CHC}_6 \mathrm{H}_5 \mathrm{Br}\)
  4. \(\mathrm{C}_6 \mathrm{H}_5 \mathrm{CCH}_3 \mathrm{C}_6 \mathrm{H}_5 \mathrm{Br}\)

Solution

\(\mathrm{C}_6 \mathrm{H}_5 \mathrm{CHBrCH}_3\) Being an optically active secondary alkyl bromide undergoes \(S_N 2\) nucleophilic substitution reaction. Hence it undergoes complete inversion of configuration.

Asked in: JEE-TOPICTESTS-CHEMISTRY

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