When (S)-2-butanol is treated with tosyl chloride and pyridine, followed by exposure to bromide, (R)-2-bromobutane is formed.
A substance may undergo inversion of configuration during nucleophilic substitution when the leaving group is bulky such that attack must occcur at the reverse side.
Hence, when (S)-2-butanol is treated with tosyl chloride and pyridine, followed by exposure to bromide, (R)-2-bromobutane is formed.
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