Which one of the following undergoes complete inversion of configuration?
A
C6H5CHC6H5Br
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B
C6H5CH2Br
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C
C6H5CH(CH3)Br
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D
C6H5CCH3C6H5Br
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Solution
The correct option is CC6H5CH(CH3)Br In the compound of option B, bromine is attached to a primary carbon atom. The substitution occurs via SN2 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 SN1 and SN2 mechanisms. Hence, complete inversion of configuration is not possible. In case of tertiary carbon atom, (option D) the substitution occurs via SN1 mechanism which cannot result in complete inversion of configuration.