Fundamentals of Organic ChemistryChemistryGeneral Organic Chemistry
Which of the following reactions will yield a racemic mixture of enantiomers? (I) (II) (III)
Options
- ABoth (II) and (III)
- B(III) only
- C(II) only
- D(I) only
Correct answer
A. Both (II) and (III)
Step-by-step solution
Let us analyze each reaction to determine the stereochemistry of the products: Reaction (I): Methyl propanoate ( CH ₃ CH ₂ COOCH ₃ ) reacts with an excess of methyllithium ( CH ₃ Li ) to first form butan-2-one, which further reacts with another equivalent of CH ₃ Li to yield 2-methylbutan-2-ol. CH ₃ CH ₂ COOCH ₃ CH ₃ Li CH ₃ CH ₂ C ( OH )( CH ₃)₂ The central carbon in 2-methylbutan-2-ol is attached to two identical methyl groups. Therefore, the molecule is achiral and cannot form a racemic mixture. Reaction (II): P