Name as Substituent On a molecule with a higher priority functional group, C=O is oxo- and -CHO is formyl. Aldehyde priority is higher than ketone. 3-methyl-4-oxopentanal.

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Presentation transcript:

Name as Substituent On a molecule with a higher priority functional group, C=O is oxo- and -CHO is formyl. Aldehyde priority is higher than ketone. 3-methyl-4-oxopentanal 3-formylbenzoic acid =>

4.5 Isomerism in aldehydes and ketones Aldehydes and ketones are constitutional isomers Aldehydes and ketones can have skeletal and positional isomers if there are enough carbons. Stereoisomers are also possible if there is a ring or C=C in the molecule

4.6 Selected Common aldehydes and ketones Formaldehyde Acetone Vanillin Benzaldehyde Cinnamaldehyde Butanedione

Formaldehyde Gas at room temperature. Formalin is a 40% aqueous solution. trioxane, m.p. 62C formaldehyde, b.p. -21C formalin =>

Industrial Importance Acetone and methyl ethyl ketone are important solvents. Formaldehyde used in polymers like Bakelite. Flavorings and additives like vanilla, cinnamon, artificial butter. =>

Formaldehyde -formalin Acetone – solvent and metabolic product Vanillin - vanilla flavoring Benzaldehyde - almond flavor Cinnamaldehyde - cinnamon Butanedione - butter

4.7 Physical properties Boiling points – page 121 Solubility – water solubility page 123

Boiling Points More polar, so higher boiling point than comparable alkane or ether. Cannot H-bond to each other, so lower boiling point than comparable alcohol. =>

Solubility Good solvent for alcohols. Lone pair of electrons on oxygen of carbonyl can accept a hydrogen bond from O-H or N-H. Acetone and acetaldehyde are miscible in water. =>

4.8 Preparation of Aldehydes and Ketones Oxidation 2 alcohol + Na2Cr2O7  ketone 1 alcohol  aldehyde