Organic Chemistry Aldehydes And Ketones - Oxidation

Front 1

Aldehydes are easily oxidized to yield carboxylic acids, but ketones are generally inert toward oxidation. The difference is a consequence of?

Back 1

structure: Aldehydes have a -CHO proton that can be abstracted during oxidation, but ketones do not

Front 2

Many oxidizing agents, including KMnO4 and hot HNO3, convert aldehydes into?

Back 2

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

Front 3

One drawback to this CrO3 oxidation is that?

Back 3

it takes place under acidic conditions, and sensitive molecules sometimes undergo side rxns

Front 4

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?

Back 4

Tollen's reagent

Front 5

Aldehydes are oxidized by the Tollens' reagent in high yield without harming?

Back 5

carbon-carbon double bonds or other acid sensitive functional groups in a molecule

Front 6

Aldehyde oxidations occur through ________________which are formed by __________________?

Back 6

- intermediate 1,1-diols or hydrates,

- a reversible nucleophilic addition of water to the carbonyl group

Front 7

Even though formed to only a small extent at equilibrium, the hydrate in a aldehyde oxidation reacts

Back 7

like any typical primary or secondary alcohol and is oxidized to a carbonyl compound

Front 8

Ketones are inert to most oxidizing agents but undergo

Back 8

a slow clevage rxn when treated with hot alkaline KMnO4.

Front 9

When Ketones undergo their slow clevage, The C-C bond next to the carbonyl group is ________, and carboxylic acids _________.

Back 9

- broken

- are produced

Front 10

The clevage of a ketone is useful primarliy for _______ _______ such as cyclohexanone because ?

Back 10

- symmetrical ketones

- product mixtures are formed formed from unsymmetical ketones.