Question

Which describes the best stereochemical aspects of the following reaction?

• A. Inversion of configuration occurs at the carbon undergoing substitution.
• B. Retention of configuration occurs at the carbon undergoing substitution.
• C. Racemization (loss of configuration) occurs at the carbon undergoing substitution.
• D. The carbon undergoing subtraction is not stereogenic.

Answer 1

The correct option is C Racemization (loss of configuration) occurs at the carbon undergoing substitution.

(Refer to Image)

Mechanism:-

Here $H^{+}$ from $HBr$ attacks $-OH$ from reactant to form a stable carbocation with planar $s{p}^2$ structure. So, when $B{r}^{⊝}$ attacks both configurations are possible so, Racemization occurs.