Haloalkanes and HaloareneshardNUMERICAL

The bromination of trans-2-butene with in yields a set of stereoisomeric products. What is the totalHaloalkanes and Haloarenes Chemistry Question

Question

The bromination of trans-2-butene with $Br_2$ in $CCl_4$ yields a set of stereoisomeric products. What is the total number of stereoisomers obtained in this reaction?

Answer: 1

💡 Solution & Explanation

The addition of halogens like $Br_2$ to an alkene proceeds via a cyclic halonium ion intermediate, resulting strictly in anti-addition. When anti-addition occurs on a symmetric trans-alkene (like trans-2-butene), the spatial arrangement leads to the formation of a meso compound. Specifically, meso-2,3-dibromobutane is formed. Because the meso compound contains an internal plane of symmetry, it is achiral and exists as a single stereoisomer. Therefore, the total number of stereoisomers obtained is 1.

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