Carbonyl Compounds

1 Aldehydes

1.1 Prep.

1.1.1 Primary alcohol + ox. agent --> aldehyde + water

1.1.1.1 Ethanol + [O] -> ethanal

1.1.2 Products should be distilled as they form

1.1.2.1 Oxidation under reflux gives carboxylic acid

1.1.2.1.1 Ethanal + [O] -> ethanoic acid

1.2 Reduction:

1.2.1 NaBH4 or LiAlH4

1.2.2 Al + red. agent --> primary alcohol

1.2.2.1 Ethanal + 2[H] -> ethanol

1.2.3 Can be thought of as nucleophilicaddition

1.3 Nucleophilic addition:

1.3.1 HCN: Sn1 mechanism (formation of carbocation)

1.4 Tests:

1.4.1 2,4- DNPH

1.4.1.1 Positive, pulpy orange ppt

1.4.1.2 -hydrazine to -hydrazone

1.4.2 Felhing's:

1.4.2.1 From blue to brick red on warming

1.4.2.1.1 Cu(2+) to Cu(+) ions

1.4.2.2 Positive

1.4.3 Tollens':

1.4.3.1 Positive

1.4.3.2 Silver mirror formed on warming

1.4.3.2.1 Carboxylate ion formed as organic product

2 Ketones

2.1 Prep.

2.1.1 Secondary alcohol + ox. agent --> ketone + water

2.2 Reduction:

2.2.1 Ketone + 2[H] -> secondary alcohol

2.2.1.1 Propanone + 2[H] -> propan-2-ol

2.3 Nucleophilic addition:

2.3.1 Sn1 addition of HCN

2.4 Tests:

2.4.1 2,4- DNPH

2.4.1.1 Positive, pulpy orange ppt

2.4.1.2 -hydrazine to -hydrazone

2.4.2 Tollens':

2.4.2.1 Negative

2.4.2.2 No change

2.4.3 Fehling's

2.4.3.1 Negative

2.4.3.2 No change

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Carbonyl Compounds

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	Created by Fangirl.Ana about 5 years ago