Synthesis Review

Oxidation
2 alcohol + Na2Cr2O7 ketone 1 alcohol + [O] aldehyde

Oxidation of Aldehydes
Easily oxidized to carboxylic acids.

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Chapter 18 2

Tollens Test
Add ammonia solution to AgNO3 solution until precipitate dissolves. Aldehyde reaction forms a silver mirror.
O R C H + 2
+ Ag(NH3)2

_ + 3 OH

O H2O 2 Ag + R C O

_ + 4

+ NH3)2

_ + 3 OH

O H2O 2 Ag + R C O

_ + 4 NH3 + 2 H2O

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Reduction Reagents
Sodium borohydride, NaBH4,dissolved in ethanol. Lithium aluminum hydride, LiAlH4, much stronger, dissolved in dry ether (ethoxyethane).

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Addition of HCN
HCN is highly toxic. Use NaCN or KCN in base to add cyanide, then protonate to add H. Reactivity formaldehyde > aldehydes > ketones >> bulky ketones.
O CH3CH2 C HO CH3 + HCN CH3CH2 C CH3
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CN

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Carbonyl Compounds

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The mechanism for the addition of HCN to propanone

In the first stage, there is a nucleophilic attack by the cyanide ion on the slightly positive carbon atom.

The negative ion formed then picks up a hydrogen ion from somewhere for example, from a hydrogen cyanide molecule.

Triiodomethane reaction
Is a test for the existence of CH3-CO group in a molecule Reagent aqueous NaOH and iodine Condition : warm Product: iodofrom, CH3I Observation: yellow crystals of CH3I insoluble in water
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The reaction
Ethanal, CH3CHO All methyl ketones

Uses of aldehydes and ketones

Propanone: solvent, nail polish remover Methly ethyl ketone : paint stripper Benzaldehyde: almond extract (-) Carvone: spearmint flavour (+) Carvone: seed flavouring Vanillin: vanilla flavouring
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