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Reactions of Aldehydes & Ketones
(Carey, Chap. 17) |
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| 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 hydrolysis 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 ketones 
| "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: Ar>3oR>2oR>1oR>CH3 | ||||||||||||||||||||||||||||