Question

What would happen if you attempted to separate a racemic mixture of (±)-Ibuprofen with a mixture of (±)-α-methylbenzylamine? Would it be possible to perform the resolution of (±)-Ibuprofen with (±)-α-methylbenzylamine? Explain.

Answer 1

The resolution of a racemic mixture of (±)-Ibuprofen with (±)-α-methylbenzylamine would not be possible as it wouldn't create diastereomers with distinguishable properties amenable to separation. The utilization of an enantioselective approach or reaction with a pure enantiomer would be necessary for successful resolution.

Step-by-step explanation:

The resolution of a racemic mixture of (±)-Ibuprofen using (±)-α-methylbenzylamine would not be successful as both are racemic mixtures. The process of racemate resolution is generally based on transforming a racemic substrate into diastereomers by reacting it with a single-enantiomer compound. These diastereomers are separable due to their differing physical and chemical properties.

However, when you attempt to separate racemic Ibuprofen with another racemic reagent like (±)-α-methylbenzylamine, you don't form diastereomers with unique properties, and thus, the two cannot be separated based on those differences. A better approach would be using enantioselective enzymatic resolution or reacting with an enantiomerically pure reagent like L-tartaric acid. These methods rely on the principle that biological systems or chemical reactions can discriminate between enantiomers, leading to a successful separation.