Ch 19 Aldehydes and Ketones Flashcards
Preparation of aldehydes: Oxidation of primary alcohols
PCC/ CH2Cl2
Primary alcohol –> Aldehyde
Preparation of aldehydes: partial reduction of esters
1) DIBAH, toluene/ 2) H2SO4
Ester –> Aldehyde + Alcohol
Preparation of ketones: Oxidation of secondary alcohols
PCC, or CrO3
secondary alcohol –> Ketone
Preparation of ketones: diorganocopper reaction with acid chlorides
R’2CuLi, ether
Acid chloride –> ketone
Oxidation of Aldehydes
CrO3,H2SO4
Aldehyde –> Carboxylic acid
Nucleophilic addition reactions of aldehydes and ketones: Addition of hydride to give alcohols: reduction
1) NaBH4, ethanol / 2) H2SO4
Ketone –> alcohol
Nucleophilic addition reactions of aldehydes and ketones: Addition of grignard reagents to give alcohols
1) R’‘MgX, ether / 2) H2SO4
Ketone – > alcohol
Nucleophilic addition reactions of aldehydes and ketones: Addition of secondary amines to give imines
R’‘NH2
Ketone – > dbl bnd NR’’ + H2O
Nucleophilic addition reactions of aldehydes and ketones:Wolff-Kishner reaction to give alkanes
HNR’2
Ketone – > alkene w/ C binded NR’2 + H2O
Nucleophilic addition reactions of aldehydes and ketones: Addition of alcohols to give acetals
H2NNH2, KOH
Ketone – > alkane + N2 + H2O
Nucleophilic addition reactions of aldehydes and ketones: Addition of alcohols to give acetals
Ketone + 2R’‘OH – acid catalyst – > Acetal + H2O
Nucleophilic addition reactions of aldehydes and ketones: Formation of phosphorus ylide
3(Ph)P + R”-CH2-Br – > 3(Ph)p-CH2-R” + Br- – BuLi, THF– > 3(Ph)p-CH-R”
Nucleophilic addition reactions of aldehydes and ketones: addition of phosphorus ylides to give alkenes: Wittig Reaction
THF
Ketone + (C6H5)3P–CHR” – > alkene + (C6H5)3P=O
Conjugate additions to alpha,beta-unsaturated aldehydes and ketones: Conjugate additions of amines
R’NH2
Ketone/ alkene – > ketone/ alkane w/ C bonded NHR’
Conjugate additions to alpha,beta-unsaturated aldehydes and ketones:conjugate addition of water
H2O
Ketone/ alkene – > Ketone/ alkane/ Alcohol
