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Carbonyl Compounds

Carbonyl Compounds. Vladimíra Kvasnicová. Carbonyl functional group: C=O. carbonyl- = oxo- group polar , planar, 2 nonbonded pairs of electrons (:O:) it is found in aldehydes and ketones ALDEHYDES: terminal carbon; -CHO -al in addition to a parent chain: -carbaldehyde

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Carbonyl Compounds

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  1. Carbonyl Compounds Vladimíra Kvasnicová

  2. Carbonyl functional group: C=O • carbonyl- = oxo- group • polar, planar, 2 nonbonded pairs of electrons (:O:) • it is found in aldehydes and ketones • ALDEHYDES: terminal carbon; -CHO -al • in addition to a parent chain: -carbaldehyde • prefix:formyl- (1,2,3-propane tricarbaldehyde) • KETONES: middle carbon; -CO- - one • prefix:oxo- or keto-

  3. Carbonyl compounds • names: systematic or common (trivial) • aldehydes: substitution principle or name derived from common name of a corresponding acid • ketones: substitution principle / radical function principle or common names • properties: • formation of H-bonds with water  solubility of low MW carbonyl compounds in water (C1-C4) • sharp and irritant odour ( MW) – toxic comp., alergy;or pleasant smell ( MW)

  4. Carbonyl compounds • important aldehydes: • methanal = formaldehyde • ethanal = acetaldehyde • 2,3-dihydroxypropanal = glyceraldehyde • benzaldehyde (bitter almond odour, little toxic) • important ketones: • propanone = dimethyl ketone = acetone • 1,3-dihydroxypropanone = dihydroxyacetone ketones are more narcotic than aldehydes

  5. Carbonyl compounds Aromatic ketones • with phenyl group: phenones (-ophenone) • with naphtyl group: naphtones (-naphtone) • root of acyl name (= rest of a carboxylic acid)+ the suffix • acetophenone = methyl phenyl ketone • benzophenone = diphenyl ketone • 2-acetonaphtone = methyl 2-naphtyl ketone

  6. Carbonyl compounds - REACTIONS • oxidation • prim. alcohol  aldehyde  carboxylic acid • sec. alcohol  ketone  no more oxidized Tollens´ reagent: Ag(NH3)2+  Ag Benedict´s or Fehling´s solution: Cu2+(l)  Cu2O (s) • reduction • aldehyde  primary alcohol • ketone  secondary alcohol

  7. Carbonyl compounds - REACTIONS • addition reactions • addition of waterhydrate is formed (it exists only in aqueous solution)e.g. formalin • addition of alcoholshemiacetal or hemiketal is formed (see saccharides)= unstable compounds; but cyclic products are stableIf 2nd alcohol reacts  acetals or ketals (e.g. disaccharides)reversible reaction: hydrolysis • addition of nitrogen compoundsimine is formed (it is important in biochemistry)

  8. Carbonyl compounds - REACTIONS • reactions of alpha carbon atom (= 2nd C) • the carbon is somewhat acidic • keto-enol tautomers (constitutional isomers)aldehydes and ketones exist in an equilibrium mixture of the keto and enol forms • aldol condensation= reaction between two molecules of carbonyl compounds -hydroxyaldehyde („aldol“) is formed

  9. cyclohexanol cyclohexane carbaldehyde cyclohexanone dicyclohexyl ether diphenyl ether phenol -naphtol benzyl alcohol phenyl propyl ether ethyl methyl ketone propanal methyl phenyl ether methyl phenyl ketone 2-methylcyclopentanone 1-hydroxybutanone benzaldehyde EXERCISE

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