Chapter 33 – The aldehydes and the ketones Section A – Structures of the aldehydes and the ketones The aldehydes The aldehydes are a homologous series with the functional group: __________, this means that they all contain a carbonyl group (________), where at least one of the atoms attached to the carbon of the carbonyl group is a ________________. Methanal Ethanal Propanal Butanal Benzaldehyde St.Dominic’s College Use: Chemistry notes Page 1 Chapter 33 – The aldehydes and the ketones The ketones The ketones are a homologous series with the functional group: __________, this means that they all contain a carbonyl group (________), and each group attached to the carbon of the carbonyl group is an alkyl group. Propanone Butanone Use: Section B – Physical Properties Melting and boiling points Aldehydes and Ketones have _____________ melting and boiling points than their corresponding alkanes. This is due to the presence of the carbonyl group (___________) which is highly polar, and allows the formation of _______________ ____________ intermolecular forces between the molecules. However they cannot form intermolecular hydrogen bonds as the alcohols can, so they have ___________ melting and boiling points than their corresponding alcohols. Solubility in water The lower members of the aldehydes and ketones are _____________ in water. The presence of the polar _______ bond allows them to dissolve with water efficiently (Hydrogen bonding can occur) The higher members of the aldehydes and ketones are ____________ soluble in water. This is because in these the non polar alkyl chain gets longer and its effect becomes more significant. Section C – Formation of aldehydes and Ketones from alcohols In the previous chapter we studied the formation of aldehydes by the ____________ of __________ alcohols, using acidified ___________ dichromate. The formation of ketones is achieved by the ____________ of __________ alcohols, using acidified ___________ dichromate. Aldehydes can be produced by the ________________ of their corresponding carboxylic acids using hydrogen gas and a hot nickel catalyst. St.Dominic’s College Chemistry notes Page 2 Chapter 33 – The aldehydes and the ketones Section D – Chemical reactions of the aldehydes and ketones Oxidation reactions Aldehydes can be oxidised to form their corresponding carboxylic acids by reaction with acidified sodium dichromate solution Example Ethanal Ethanoic acid ***Ketones cannot take part in this kind of reaction! Reduction reactions Aldehydes can be reduced to their corresponding primary alcohols by reaction with hydrogen gas passed over a hot Nickel catalyst. Ethanal Ethanol Ketones can be reduced to their corresponding secondary alcohols by reaction with hydrogen gas passed over a hot Nickel catalyst. Propanone St.Dominic’s College Propan – 2- ol Chemistry notes Page 3 Chapter 33 – The aldehydes and the ketones Section E – Mandatory experiment: To study the following reactions… Part 1 :Reaction of Ethanal with acidified potassium permanganate solution 1. Some _______________________potassium permanganate solution is placed in a test-tube. 2. Some Ethanal is added 3. The test tube is warmed in a hot beaker of water Result: The potassium permanganate changes colour from _____________ to _________________, Explanation: The Ethanal reacts with the acidified potassium permanganate and is oxidised to _______________ acid. As this occurs the Mn(7) ions which are _____________ in colour and are reduced to Mn (2) ions which are __________________. Half reaction equations: Part 2: Reaction of Ethanal with Fehling’s solution 1. Some Fehling’s solution is placed in a test-tube. 2. Some Ethanal is added 3. The test tube is warmed in a hot beaker of water Result: The Fehling’s solution changes colour from _____________ to _________________, Explanation: The Ethanal reacts with the Fehling’s solution and is oxidised to _______________ acid. As this occurs the Cu+2 ions from the Fehling’s solution which are _____________ in colour are reduced to Cu +1 ions which are __________________ in colour. Half reaction equations: Part 3: Reaction of Ethanal with ammonical silver nitrate solution – The ___________mirror test. 1. Some Tollens reagent is placed in a test-tube( This is made from mixing silver nitrate, dilute _____________ hydroxide and dilute ___________ solution together) 2. Some Ethanal is added 3. The test tube is warmed in a hot beaker of water Result: A silver ___________ is formed inside the test-tube. Explanation: The Ethanal reacts with Tollens reagent and is oxidised to _______________ acid. As this occurs the Ag+ ions from the Tollens reagent which are _____________ are reduced to Ag which are a shiny silver colour. Half reaction equations: Note that none of these reactions would occur with ketones and so these tests can be used to distinguish between an aldehyde and a ketone St.Dominic’s College Chemistry notes Page 4 Chapter 33 – The aldehydes and the ketones Check your learning of Organic Chemistry - The Aldehydes and the ketones Green = I can do this already Orange = I’m not sure – have to revise this Red = I don’t know this yet – have to start learning it Do you know about… Structure of aldehydes Aldehydes: structure and names up to C-4. Geometry of carbon atoms. Presence of carbonyl group Physical properties of the alcohols [physical state and explanation of boiling points of the members of the family compared to corresponding alkanes, and each other} Solubility (qualitative only) in water and explanation and in nonpolar solvents Uses of aldehydes Benzaldehyde in almond kernels Reactions of aldehydes Oxidation of alcohols using Na2Cr2O7 to (i) aldehydes and (ii) acids(equations required). Reduction of carbonyl compounds using H2/Ni catalyst. (equations required). Mandatory experiment – reactions of aldehydes with acidified potassium permanganate, Fehlings solution and Tollens reagent Structure of ketones Ketones: structure and names up to C-4. Geometry of carbon atoms. Presence of carbonyl group Physical properties of the ketones [physical state and explanation of boiling points of the members of the family compared to corresponding alkanes, and each other} Solubility (qualitative only) in water and explanation and in nonpolar solvents Uses of ketones Propanone in nail varnish remover Reactions of ketones Oxidation of secondary alcohols using Na2Cr2O7 to ketones. REACTION CAN GO NO FURTHER!! Reduction of carbonyl compounds using H2/Ni catalyst. (equations required). The three tests to distinguish ketones from alcohols – reagents used and results obtained St.Dominic’s College Chemistry notes Green Orange Red Page 5