Oxidation of Alcohols with Pyridinium Chlorochromate: Primary and secondary alcohols are smoothly oxidized by pyridinium chlorochromate (PCC) in CH2Cl2 to form aldehydes and ketones, respectively. The PCC oxidation of primary alcohols to give aldehydes is a very useful reaction, since aldehydes are difficult to prepare and are easily over-oxidized to the carboxylic acid.
Oxidation of Alcohols with "Jones Reagent": Primary and secondary alcohols are oxidized by CrO3/H2SO4 (Jones Reagent) to form carboxylic acids and ketones, respectively; sodium dichromate in acetic acid (Na2Cr2O7) can also be used.
Ozonolysis of Alkenes: Simple alkenes are oxidized by O3 to form an intermediate ozonide, which undergoes dissolving metal reduction with Zn/H3O+ to produce aldehydes and ketones.
Oxidation of Alkenes: Simple alkenes are oxidized by MnO4- to produce aldehydes and ketones. Terminal alkenes yield CO2, while alkene carbons bearing one hydrogen form the corresponding carboxylic acid.
Hydration of Alkynes: Acid-catalyzed hydration of alkynes in the presence of Hg+2 yields an intermediate enol, which rapidly equilibrates with the corresponding carbonyl compound. The regiochemistry of the reaction is "Markovnikov"; that is, hydroxide anion will bond to the most stable potential carbocation center of the alkyne.
Hydroboration of an Alkyne, with Oxidative Work-up: Reaction of an alkyne with BH3 results in the syn-addition of the boron and a hydrogen across the triple bond. Rearrangements do not occur and the hydrogen will bond to the carbon of the alkyne which would form the most stable carbocation center (overall anti-Markovnikov's addition). The driving force for the regiochemistry may actually be more steric than electronic, but viewing the reaction as a concerted, but polar transition state, easily rationalizes the observed product distribution. On oxidative work-up, the borane is converted to the enol, which rapidly equilibrates with the corresponding carbonyl compound.
Friedel-Crafts Acylation: Arenes react with acid halides and acid anhydrides in the presence of AlCl3 to form aryl ketones. This is an example of electrophilic aromatic substitution, and the reaction does not proceed well on rings which are strongly deactivated.
Reactions that Yield Aldehydes & Ketones