Key Terms

• acetal, R2C(OR′)2
• acyl group
• 1,2-addition
• 1,4-addition
• aldehyde (RCHO)
• Cannizzaro reaction
• carbinolamine
• conjugate addition
• cyanohydrin
• enamine (R!N–CR═CR₂)
• hemiacetal
• imine (R!C═NR)
• ketal
• ketone (R2CO)
• McLafferty rearrangement
• nucleophilic addition reaction
• phosphorane
• Schiff bases
• Wittig reaction
• Wolff–Kishner reaction
• ylide

Summary of Reactions 19 • Summary of Reactions 19 • Summary of Reactions

• Preparation of aldehydes (Section 19.2)
• Oxidation of primary alcohols (Section 17.7)

• Partial reduction of esters (Section 19.2)

• Preparation of ketones
• Oxidation of secondary alcohols (Section 17.7)

• Diorganocopper reaction with acid chlorides (Section 19.2)

• Oxidation of aldehydes (Section 19.3)

• Nucleophilic addition reactions of aldehydes and ketones
• Addition of hydride to give alcohols: reduction (Section 19.7)

• Addition of Grignard reagents to give alcohols (Section 19.7)

• Addition of HCN to give cyanohydrins (Section 19.6)

• Addition of primary amines to give imines (Section 19.8)

• Addition of secondary amines to give enamines (Section 19.8)

• Wolff–Kishner reaction to give alkanes (Section 19.9)

• Addition of alcohols to give acetals (Section 19.10)

• Addition of phosphorus ylides to give alkenes: Wittig reaction (Section 19.11)

• Conjugate additions to α,β-unsaturated aldehydes and ketones (Section 19.13)
• Conjugate addition of amines

• Conjugate addition of water

• Conjugate addition of alkyl groups by diorganocopper reaction