Complete the diagram.

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REACTIONS OF THE CARBONYL GROUP IN ALDEHYDES AND KETONES

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Complete the diagram

Learning Outcomes Understand the reactions of carbonyl compounds with: Fehling’s or Benedict’s solution, Tollen’s reagent and acidified dichromate (VI) ions Lithium tetrahydridoaluminate (lithium aluminium hydride) in dry ether Iodine in the presence of alkali

Oxidation of Aldehydes and Ketones What do you know from Y12? Aldehydes oxidised to carboxylic acids [O] = oxidising agent Acidified potassium dichromate(VI), K2Cr2O7/H+ (dil. sulfuric acid) Ketones CANNOT be oxidised easily (a C-C must be broken)

Distinguishing between aldehydes and ketones Weak oxidising agents (acidified potassium dichromate) can oxidise aldehydes but not ketones. Fehling’s Test: Made from a mixture of two solutions: Fehling’s A (contains Cu2+) and Fehling’s B (contains an alkali and a complexing agent) Aldehyde – when warmed with Fehling’s, a brick red precipitate of copper (I) oxide is produced as the copper (II) oxides the aldehyde to a carboxylic acid and is itself reduced to copper (I) Ketone – no reaction (no C-C bond to break).

Distinguishing between aldehydes and ketones Weak oxidising agents (acidified potassium dichromate) can oxidise aldehydes but not ketones. Silver Mirror Test Tollen’s reagent [Ag(NH3)2]+ is formed when aqueous ammonia is added to an aqueous solution of silver nitrate. Aldehyde – aldehydes are oxidised to carboxylic acids. The Ag+ is reduced to metallic silver. A silver mirror will form: RCHO + [O]  RCOOH ALDEHYDE OXIDISED [Ag(NH3)2]+ + e-  Ag + 2NH3 SILVER REDUCED Ketone – no reaction (no C-C bond to break).

Oxidation Equations Show the oxidation of the following: Propanal Pentanal 3-methylhexanal

Reduction of Aldehydes and Ketones Many reducing agents will reduce both aldehydes and ketones to alcohols. Lithium tetrahydridoaluminate(III), LiAlH4, (lithium aluminium hydride) in AQUEOUS solution Generates nucleophile, H-, the HYDRIDE ION This reduces C=O but not C=C. Why? Repelled by the high e- density in the C=C bond. Attracted to the Cδ+ of the C=O bond. Conditions: Both carbonyl group and LiAlH4 dissolved in dry ether

Mechanism of Reduction: Aldehyde p70

Mechanism of Reduction: Ketone p70

Write the following reduction reactions The reduction of: Propanal Butanone 2-methylpentanal Hexan-3-one 2,3-dimethylhexanal

Exam Questions

Reactions with iodine Triiodomethane reaction Product is CHI3  yellow insoluble solid Carbonyl compound added to alkaline solution of iodine and the mixture warmed and then cooled, a pale yellow precipitate sometimes forms. Positive test for the carbonyl compound containing CH3CO Only found in one aldehyde (ethanal) and all methyl ketones Must be propanone, butanone and pentan-2-one (not pentan-3-one)

Which alcohol would also give a positive test? Oxidation Product Result Butan-2-ol Propan-1-ol 2-methylpropan-1-ol Ethanol Butan-1-ol Propan-2-ol

Which alcohol would also give a positive test? Oxidation Product Result Butan-2-ol CH3COCH2CH3 Positive Propan-1-ol CH3CH2CHO Negative 2-methylpropan-1-ol (CH3)2CHCHO Ethanol CH3CHO Butan-1-ol CH3CH2CH2CHO Propan-2-ol CH3COCH3