Aldehydes and Ketones - carbonyl compounds carbonyl group - structure, bonding and physical properties.

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Presentation transcript:

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