MDCAT Chemistry MCQ #538

In the presence of a strong base, which reaction of benzaldehyde involves the formation of a resonance-stabilized intermediate?

MDCAT Chemistry MCQ #538

  1. Question 1

    Q1. In the presence of a strong base, which reaction of benzaldehyde involves the formation of a resonance-stabilized intermediate?

    • A) Nucleophilic addition of hydroxide ion to produce a hemiacetal
    • B) Electrophilic aromatic substitution with acetyl chloride
    • C) Base-catalyzed elimination to produce an alkene
    • D) Reductive amination with ammonia

    Answer: Nucleophilic addition of hydroxide ion to produce a hemiacetal

    Explanation: Nucleophilic addition of hydroxide ion forms a resonance-stabilized intermediate. It fails because electrophilic aromatic substitution involves the formation of a sigma complex.