Grignard Reaction: Carbon–Carbon Bond Formation by Carbonyl Addition

Master the Grignard reaction mechanism: nucleophilic addition to carbonyls, alkoxide formation, and acidic workup. Includes stereochemistry notes, scope, and common reasons it fails.

• Nucleophile: RMgX (carbanion-like carbon)
• Electrophile: Aldehyde/ketone (carbonyl carbon)
• Outcome: New C–C bond → alcohol after workup
• Workup: H3O+ (acidic) to protonate alkoxide
• Scope shortcut: Formaldehyde → 1° alcohol; aldehyde → 2°; ketone → 3°
• Exam type: Predict the major product
• Exam type: Synthesis / retrosynthesis
• Exam type: Failure modes / distractors