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Name as Substituent

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.

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Name as Substituent

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  1. 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 =>

  2. 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

  3. 4.6 Selected Common aldehydes and ketones • Formaldehyde • Acetone • Vanillin • Benzaldehyde • Cinnamaldehyde • Butanedione

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

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

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

  7. 4.7 Physical properties • Boiling points – page 121 • Solubility – water solubility page 123

  8. => 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.

  9. 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. =>

  10. 4.8 Preparation of Aldehydes and Ketones • Oxidation • 2 alcohol + Na2Cr2O7  ketone • 1 alcohol  aldehyde

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