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10 Cards in this Set

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  • Back
Aldehydes are easily oxidized to yield carboxylic acids, but ketones are generally inert toward oxidation. The difference is a consequence of?
structure: Aldehydes have a -CHO proton that can be abstracted during oxidation, but ketones do not
Many oxidizing agents, including KMnO4 and hot HNO3, convert aldehydes into?
carboxylic acids

- but CrO3 in aqueous acid is a more common choice in the laboratory. The oxidation occurs rapidly at room temp. and results in good yields
One drawback to this CrO3 oxidation is that?
it takes place under acidic conditions, and sensitive molecules sometimes undergo side rxns
In some cases, the laboratory oxidation of an aldehyde can be carried out using a solution of silver oxide, Ag2O, in aqueous ammonia, the so called?
Tollen's reagent
Aldehydes are oxidized by the Tollens' reagent in high yield without harming?
carbon-carbon double bonds or other acid sensitive functional groups in a molecule
Aldehyde oxidations occur through ________________which are formed by __________________?
- intermediate 1,1-diols or hydrates,

- a reversible nucleophilic addition of water to the carbonyl group
Even though formed to only a small extent at equilibrium, the hydrate in a aldehyde oxidation reacts
like any typical primary or secondary alcohol and is oxidized to a carbonyl compound
Ketones are inert to most oxidizing agents but undergo
a slow clevage rxn when treated with hot alkaline KMnO4.
When Ketones undergo their slow clevage, The C-C bond next to the carbonyl group is ________, and carboxylic acids _________.
- broken

- are produced
The clevage of a ketone is useful primarliy for _______ _______ such as cyclohexanone because ?
- symmetrical ketones

- product mixtures are formed formed from unsymmetical ketones.