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Oxidation and Reduction of Carbonyl Compounds

The document summarizes various reactions and properties of carbonyl compounds such as aldehydes and ketones. It discusses common oxidation and reduction reactions that convert alcohols to carbonyls and vice versa. It also describes tests to identify carbonyl groups, including the Tollens test using silver mirrors, addition of hydrogen cyanide, and the triiodomethane reaction test. Finally, it lists some common uses of important aldehydes and ketones as solvents, flavors, and fragrances.

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Amna Yousaf
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9 views10 pages

Oxidation and Reduction of Carbonyl Compounds

The document summarizes various reactions and properties of carbonyl compounds such as aldehydes and ketones. It discusses common oxidation and reduction reactions that convert alcohols to carbonyls and vice versa. It also describes tests to identify carbonyl groups, including the Tollens test using silver mirrors, addition of hydrogen cyanide, and the triiodomethane reaction test. Finally, it lists some common uses of important aldehydes and ketones as solvents, flavors, and fragrances.

Uploaded by

Amna Yousaf
Copyright
© Attribution Non-Commercial (BY-NC)
We take content rights seriously. If you suspect this is your content, claim it here.
Available Formats
Download as PPTX, PDF, TXT or read online on Scribd

Synthesis Review

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

Oxidation of Aldehydes
Easily oxidized to carboxylic acids.

=>
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

=>
3

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

=>
4

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
5

CN

=>

Carbonyl Compounds

=>
6

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
8

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
10

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