Nucleophilic Addition Reactions
Start with the big picture
The reaction begins when a nucleophile donates an electron pair to the carbonyl carbon and the C=O π bond shifts to oxygen, forming a tetrahedral alkoxide. Protonation then gives an addition product. Aldehydes generally react more readily than ketones because they have less steric hindrance and weaker electron donation from alkyl groups. Acid catalysis can increase carbonyl electrophilicity, while base catalysis can strengthen the nucleophile. The lesson distinguishes strong nucleophiles, which commonly give effectively irreversible additions, from weaker neutral nucleophiles that may add reversibly. Examples include reductions, carbon–carbon bond formation, cyanohydrin formation, and reactions with alcohols or amines. Because the carbonyl is planar, attack on either face can produce a racemic mixture unless chiral control is introduced.
What you'll learn
- Describe the steps from nucleophilic attack to protonation of the alkoxide intermediate.
- Compare aldehyde and ketone reactivity using steric and electronic effects.
- Explain how acid and base catalysis influence nucleophilic addition.
- Recognize major product classes formed by common nucleophiles.
- Relate carbonyl planarity to stereochemical outcomes.
Continue your study
Work through the complete notes and reinforce the topic with the study tools available in the full lesson.