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In the nucleophilic substitution reaction R−Br + Cl− (DMF)→ R−Cl + Br−, which substrate will show complete inversion of configuration?

1. C6H5CHClCH2Br
2. C6H5CH2Br
3. C6H5CHCH3Br
4. C6H5CH2CH2Br

Correct answer: C6H5CHCH3Br

Solution

The substrate C6H5CHCH3Br has a chiral center that allows for complete inversion of configuration during the nucleophilic substitution reaction. The presence of the bulky groups on either side of the chiral center facilitates this inversion, making it the only option that exhibits this behavior.

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