Question

Consider the chlorination of sec-butylbenzene. If the compound is chlorinated on the extreme carbons, it results in a total of 4 stereoisomers due to chiral carbon in both resulting compounds. When chlorination occurs on the 2nd or 3rd carbon, there is still a chiral carbon in both resulting compounds. What is the total number of stereoisomers, considering racemization?

a.6 stereoisomers
b.8 stereoisomers
c.10 stereoisomers
d.12 stereoisomers

Answer 1

The total number of stereoisomers, considering racemization, is 8.

Step-by-step explanation:

The total number of stereoisomers, considering racemization, can be calculated using the formula 2 to the power of n, where n is the number of chiral centers. In the case of chlorination of sec-butylbenzene, there are two chiral carbons, so the total number of stereoisomers is 2 to the power of 2, which equals 4. However, racemization occurs when chlorination occurs on the 2nd or 3rd carbon, resulting in mirror image pairs being formed. This doubles the number of stereoisomers. Therefore, the total number of stereoisomers, considering racemization, is 4 multiplied by 2, which equals 8.