The free radical monobromination reaction below will replace one hydrogen with bromine primarily at the benzylic position (next to the benzene ring), resulting in two stereoisomers.

(1) Are the two stereoisomers enantiomeric or diastereomeric?

(2) Will the product mixture be exactly 50:50?

(3) Will the two stereoisomers have identical physical properties (such as solubility, melting point, and boiling point)?

(4) Can the two stereoisomers be separated (at least theoretically) using normal physical separation techniques?

What is a meso compound?

Why does the presence of an internal line of symmetry indicate a meso compound is achiral?

Which of the following molecules is likely a meso compound based on its structure?

How would you design a synthetic route to convert a chiral compound into a meso compound?