1. Tardigrade
  2. Question
  3. Chemistry
  4. In a nucleophilic substitution reaction: R - Br + Cl- xrightarrowDMF R - Cl + Br- which one of the following undergoes complete inversion of configuration?

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Q. In a nucleophilic substitution reaction:
$R - Br + Cl^{-} \xrightarrow{DMF} R - Cl + Br^{-}$
which one of the following undergoes complete inversion of configuration?

Haloalkanes and Haloarenes

Solution:

In the compound of option B, bromine is attached to a primary carbon atom. The substitution occurs via $SN _{2}$ mechanism which involves the inversion of configuration. In the remaining compounds the bromine is attached to a secondary or tertiary carbon atom. In case of secondary carbon atom (options A and C), the substitution occurs via a combination of $S N _{1}$ and $S N _{2}$ mechanisms. Hence, complete inversion of configuration is not possible. In case of tertiary carbon atom, (option D) the substitution occurs via $SN _{1}$ mechanism which cannot result in complete inversion of configuration.