Reactions of Aldehydes & Ketones
(Carey, Chap. 17)

Reaction Product Notes
Hydrate formation
Equilibrium; K usually < 1
Hemiacetal formation
Equilibrium; K usually < 1,
   except for 5-6 memb cyclic
Acetal formation
Reverse reaction, acetal
C=O "protecting" group
Thioacetal formation
Thioacetal hydrogenolysis
Y = H or R", imine
Y = OH, oxime
Y = NH2 or NHR", hydrazone
2,4-DNP diagnostic for alde. or
   ketone - get orange ppt
Amine synthesis
"Wolff-Kishner reduction"
Decomposition of hydrazone

Cyanohydrin formation
Equilibrium; K > 1 only
   with alde. or cyclic ketone

Cyanohydrin hydrolysis
Carboxylic acid synthesis
Alcohol synthesis
Prep of 1o or 2o alcohols
NaBH4 selective for alde. or
"Wittig reaction"
Synthesis of alkenes
R'' and/or R''' can be H
Ag+/HO- ("Tollen's reagent") -
selective for aldehydes;
diagnostic - get silver mirror
"Baeyer-Villiger oxidation"
Cation rearrangement
Migratory aptitudes: