Chapter 19: Aldehyde ands Ketones (Reagents + Reactions)

1.)RMgBR 2.)H3O+

Grignard Reaction

H30+

Hydrolysis of acetals mines, or enamines, generates a carbonyl group

[H+], RNH2 (-H2O)

Imine formation (primary amine or ammonia is used to begin with)

RCO3H (starting compound is an aldehyde)

Baeyer- Villiger oxidation converts aldehyde to carboxylic acid

RCO3H (starting compound is a ketone)

Baeyer-Villiger oxidation Converts a ketone into an ester

[H+], HOCH2CH2OH -H20

Cyclic Acetal formation

Raney nickel

Desulfurization: Converts a thioacetal (or cyclic thioacetal) to an alkane

[H+] R2NH, (-H2O)

Enamine formation (secondary amine starting compound)

HWE reaction (Horner-Wadsworth- Emmons)

A HWE reagent functions like a stabilized witting reagent. It will react with an aldehyde of ketone to give the (E) alkene as the major product

[H+], NH2OH (-H2O)

Oxime formation

1.) LiAH4 2.)H30+

Reduction of aldehyde/ketone to alcohol

H2C=PPh3

Wittig Reaction

NaOH, H20 Heat

Wolff-Kishner reduction reduces hydrazone to alkane

HCN, KCN

cyanohydrin formation

[H+}, HSCH2CH2SH, (-H2O)

cyclic thioacetal formation

[H+], NH2NH2 (-H2O)

hydrazone formation

[H+], 2 ROH (-H2O)

Acetal formation