ENADE Química Practice Questions - ENADE Química - Exame Nacional De Desempenho Dos Estudantes Exam

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In a nucleophilic aliphatic substitution reaction, (2R)-2-bromobutane is treated with sodium cyanide (NaCN) in dimethyl sulfoxide (DMSO) at room temperature. What is the primary IUPAC product and the stereochemical outcome of this transformation?

(2R)-2-methylbutanenitrile via retention of configuration (2S)-2-bromobutane via carbocation racemization (2S)-2-methylbutanenitrile via complete inversion of configuration A 50:50 racemic mixture of (2R)- and (2S)-2-methylbutanenitrile

Correct Answer:

(2S)-2-methylbutanenitrile via complete inversion of configuration

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