Aldehydes and Ketones - carbonyl compounds carbonyl group - structure, bonding and physical properties
Review of methods of preparation of aldehydes and ketones hydration of alkynes Friedel-Crafts acylation of aromatic compounds
Overview of reactions of carbonyl compounds reduction to alcohols addition of organometallic reagents addition of oxygen, nitrogen, sulfur and phosphorus nucleophiles reduction of carbonyl to methylene (Clemmensen or Wolff-Kishner)
Nucleophilic addition to carbonyls
Synthesis of Alcohols Reduction of Carbonyl Compounds
Synthesis of Alcohols Reduction of Carbonyl Compounds
H 2 /cat., NaBH 4, LiAlH 4 Synthesis of Alcohols Reduction of Carbonyl Compounds
lithium aluminum hydride (LAH)
sodium borohydride
Synthesis of Alcohols Using Organometallic Reagents
Hydration of aldehydes and ketones
An example
Addition of alcohols: hemiacetal and acetal formation
hemiacetal or hemiketal
Addition of alcohols: hemiacetal and acetal formation hemiacetalacetal
Mechanism of acetal formation
An example
Addition of ammonia and amines: imine and enamine formation
Examples
The Wittig Reaction
An example
The mechanism
Mechanism, cont.
Formation of cyanohydrins
Example
Reduction of carbonyls to alkanes Clemmensen reduction Wolff-Kishner reduction Desulfurization of thioketals
Nucleophilic Addition to a,b-Unsaturated Carbonyls
Strong nucleophiles add 1,2 kinetic control Weaker nucleophiles add 1,4 thermodynamic control
Nucleophilic Addition to a,b-Unsaturated Carbonyls