32.4k views
5 votes
Which of the following is the best method to make racemic mixture of (+)and (-)-2,3-dibromobutane?

A. photochemical bromination of 2-bromobutane
B. addition of HBr to racemic 3-bromo-2- butene
C. addition of Br 2 to cis-2-butene
D. addition of Br 2 to trans-2-butene

User Khadisha
by
8.2k points

1 Answer

5 votes

Final answer:

The best method to produce a racemic mixture of (+) and (-)-2,3-dibromobutane is by the addition of Br2 to cis-2-butene, allowing for anti-addition and equal formation of both enantiomers.

Step-by-step explanation:

The best method to make a racemic mixture of (+) and (-)-2,3-dibromobutane would be option C: addition of Br2 to cis-2-butene. This method allows for an anti-addition of bromine across the double bond, leading to a mixture of both enantiomers, or a racemic mixture. This process is stereoselective and will generate both stereoisomers equally due to the planar nature of the sp2-hybridized carbon atoms in the double bond of cis-2-butene.

Options A, B, and D do not produce a racemic mixture. Photochemical bromination may not be selective, and addition of HBr to a racemic alkene would not necessarily lead to a racemic product due to potential regioselectivity, while addition of Br2 to trans-2-butene would lead to a meso compound, which is not optically active.

User Jzepeda
by
8.2k points