Chapter 17.4, Problem 9P

Interpretation Introduction

Interpretation: The reason behind the racemic mixture formed when $\left(R\right)\text{-2-methylpentanal}$ is dissolved in an acidic or basic medium.

Concept introduction: A racemic mixture is formed when $\left(R\right)\text{-2-methylpentanal}$ is dissolved in the acidic or basic medium.  It is because in both acidic and basic medium the enolate anion is formed.  Enolate anion is planar and attacks from both above and below the plane to give a racemic mixture.