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Organic Chemistry

Chapter 22-23. Organic Chemistry. Organic Chemistry. Study of carbon-based compounds Carbon has 4 valence electrons Carbon always forms 4 covalent bonds N (3), O (2), H (1) Carbon compounds form chains and/or rings. Hydrocarbons. Molecule or compound composed of carbon and hydrogen only

shaeleigh-aguirre
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Organic Chemistry

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  1. Chapter 22-23 Organic Chemistry

  2. Organic Chemistry • Study of carbon-based compounds • Carbon has 4 valence electrons • Carbon always forms 4 covalent bonds • N (3), O (2), H (1) • Carbon compounds form chains and/or rings

  3. Hydrocarbons • Molecule or compound composed of carbon and hydrogen only • Three Main Types • Alkanes, Alkenes, Alkynes

  4. Alkanes • All single C─C bonds H H H │ │ │ H─ C─ C─ C─ H │ │ │ H H H H H H H │ │ │ │ H─ C─ C─ C─ C─ H │ │ │ │ H H H H H H H H H │ │ │ │ │ H ─ C─ C─ C─ C─ C─ H │ │ │ │ │ H H H H H C3H8 C4H10 C5H12 General Formula CnH2n+2

  5. Alkenes • At least one double C=C bond H H H │ │ │ H─ C─ C= C─ H │ H H H H H │ │ │ │ H─ C─ C─ C= C─ H │ │ H H H H H H H │ │ │ │ │ H ─ C─ C─ C─ C= C─ H │ │ │ H H H C3H6 C4H8 C5H10 General Formula CnH2n

  6. Alkynes • At least one triple C≡C bonds H │ H─ C─ C≡ C─ H │ H H H │ │ H─ C─ C─ C≡ C─ H │ │ H H H H H │ │ │ H ─ C─ C─ C─ C≡ C─ H │ │ │ H H H C3H4 C4H6 C5H8 General Formula CnH2n-2

  7. Homologous Series • Group of compounds with similar structure and function • Table Q • Members increase by one carbon and two hydrogens

  8. H │ H─ C─ H │ H H H │ │ H─ C─ C─ H │ │ H H H H H │ │ │ H─ C─ C─ C─ H │ │ │ H H H H H H H │ │ │ │ H─ C─ C─ C─ C─ H │ │ │ │ H H H H CH4 C2H6 C3H8 C4H10 H H H H H │ │ │ │ │ H ─ C─ C─ C─ C─ C─ H │ │ │ │ │ H H H H H H H H H H H │ │ │ │ │ │ H ─ C─ C─ C─ C─ C─ C─ H │ │ │ │ │ │ H H H H H H C5H12 C6H14 Alkane Homologous Series

  9. H H │ │ H─ C= C─ H H H H │ │ │ H─ C─ C= C─ H │ H H H H H │ │ │ │ H─ C─ C─ C= C─ H │ │ H H C2H4 C3H6 C4H8 H H H H H │ │ │ │ │ H ─ C─ C─ C─ C= C─ H │ │ │ H H H H H H H H H │ │ │ │ │ │ H ─ C─ C─ C─ C─ C= C─ H │ │ │ │ H H H H C5H10 C6H12 Alkene Homologous Series

  10. H─ C≡ C─ H H │ H─ C─ C≡ C─ H │ H H H │ │ H─ C─ C─ C≡ C─ H │ │ H H C2H2 C3H4 C4H6 H H H │ │ │ H ─ C─ C─ C─ C≡ C─ H │ │ │ H H H H H H H │ │ │ │ H ─ C─ C─ C─ C─ C≡ C─ H │ │ │ │ H H H H C5H8 C6H10 Alkyne Homologous Series

  11. Saturated vs. Unsaturated • Saturated Hydrocarbons • Contain only single Carbon to Carbon bonds (Alkanes) • Unsaturated Hydrocarbons • Contains at least one multiple (double, triple) Carbon to Carbon bond • Alkenes and Alkynes

  12. Naming Simple Hydrocarbons • Name is based on two parts • Number of carbons in longest continuous chain (Table P) • Type of bonds between carbons • Single –ane • Double –ene • Triple –yne

  13. Examples H H H H │ │ │ │ H─ C─ C─ C─ C─ H │ │ │ │ H H H H • Butane • Pentane H H H H H │ │ │ │ │ H ─ C─ C─ C─ C─ C─ H │ │ │ │ │ H H H H H

  14. Alkenes and Alkynes • Name includes location of multiple bond • Carbons numbered to give multiple bond the lowest possible number • 1-butyne 2-butyne H H │ │ H─ C─ C─ C≡ C─ H │ │ H H H H │ │ H─ C─ C≡ C ─ C─ H │ │ H H

  15. Chemical Formula • Shows only number of each type of element • C2H6 • C6H12O6

  16. Structural Formula • Shows how each atom is bonded to each other H H H H H │ │ │ │ │ H ─ C─ C─ C─ C─ C─ H │ │ │ │ │ H H H H H H H │ │ H─ C─ C─ C≡ C─ H │ │ H H

  17. Condensed Structural Formula • Shows who is bonded to who, without the actual bonds H H H │ │ │ H─ C─ C─ C─ H │ │ │ H H H H H H │ │ │ H─ C─ C= C─ H │ H

  18. Branched Hydrocarbons • Alkyl Group • Hydrocarbon branch • Branch name ends with -yl • Location of branch is indicated by number • Number carbons to give lowest possible number • Multiple bond still takes priority in numbering

  19. Examples H H CH3 H H │ │ │ │ │ H ─ C─ C─ C─ C─ C─ H │ │ │ │ │ H H H H H • 3-Methyl Pentane • 2-Methyl 1-Butene H │ H─ C─ H │ H CH2 H │ │ │ H─ C─ C= C─ H │ H

  20. Isomers • Two or more compounds with the same chemical formulas, but different structural formulas and properties • Different Names

  21. Isomer Example C5H12 H H H H H │ │ │ │ │ H ─ C─ C─ C─ C─ C─ H │ │ │ │ │ H H H H H H H CH3 H │ │ │ │ H─ C─ C─ C─ C─ H │ │ │ │ H H H H Pentane Methyl Butane H CH3 H │ │ │ H─ C─ C─ C─ H │ │ │ H CH3 H Dimethyl Propane

  22. Functional Groups • Specific arrangement of atoms that give compounds a unique property • Table R • Examples • Hydroxyl Group, -OH O • Carbonyl Group, ─ C ─ ǁ

  23. Halogen attached to a carbon Prefix indicates which halogen Table R # for which carbon halogen is attached Multiple bonds still take priority in numbering Halides

  24. Halides H H Cl H │ │ │ │ H─ C─ C─ C─ C─ H │ │ │ │ H H H H Br H H │ │ │ H─ C─ C= C─ H │ H 2-Chlorobutane 3-Bromopropene CH3CH2CHClCH3 CH2BrCHCH2

  25. Hydroxyl group (-OH) attached to a carbon # for which alcohol group is attached Name ends in –ol Multiple bonds still take priority in numbering Alcohol

  26. Alcohol H H H H │ │ │ │ HO─ C─ C─ C─ C─ H │ │ │ │ H H H H H H H H H H │ │ │ │ │ │ H ─ C─ C─ C─ C─ C─ C─ H │ │ │ │ │ │ H H H OH H H 3-Hexanol 1-Butanol CH3CH2CH2CH2OH CH3CH2CH2CHOHCH2CH3

  27. Carbonyl group at end of chain Name ends with –al Condensed structural formula ends with -CHO Aldehyde O ǁ ─ C ─ H

  28. Aldehyde H H H H O │ │ │ │ ǁ H ─ C─ C─ C─ C─ C─ H │ │ │ │ H H H H H H O │ │ ǁ H─ C─ C─ C─ H │ │ H H Propanal Pentanal CH3CH2CHO CH3CH2CH2CH2CHO

  29. Ketones • Carbonyl group not on end of chain • Number indicates which carbon the oxygen is attached to • Name ends with –one • Condensed structural formula has -CO- in it O ǁ ─ C ─

  30. Ketones H O H H H │ ǁ │ │ │ H ─ C─ C─ C─ C─ C─ H │ │ │ │ H H H H H O H │ ǁ │ H─ C─ C─ C─ H │ │ H H Propanone 2-Pentanone CH3COCH3 CH3COCH2CH2CH3

  31. Amine • Nitrogen attached to a carbon • Number indicates which carbon the nitrogen is attached to • Name ends in –amine • Multiple bonds still take priority in numbering

  32. Amine H H H H │ │ │ │ H2N─ C─ C─ C─ C─ H │ │ │ │ H H H H H H H H H H │ │ │ │ │ │ H ─ C─ C─ C─ C─ C─ C─ H │ │ │ │ │ │ H H H NH2 H H 3-Hexanamine 1-Butanamine CH3CH2CH2CH2NH2 CH3CH2CH2CHNH2CH2CH3

  33. Amide • Carbonyl group with an amine group attached to it • Must be on an end • Name ends in -amide O H ǁ ǀ ─ C ─ N ─ H

  34. Amide H H H H O │ │ │ │ ǁ H ─ C─ C─ C─ C─ C─ NH2 │ │ │ │ H H H H H H O │ │ ǁ H─ C─ C─ C─ NH2 │ │ H H Propanamide Pentanamide CH3CH2CONH2 CH3CH2CH2CH2CONH2

  35. Organic Acid O ǁ ─ C ─ O ─ H • Carbonyl group with a hydroxyl group attached to it • Must be on an end • Name ends in –oic acid • Condensed structural formula ends with -COOH • Hydroxyl H is the acidic H

  36. Organic Acid H H H O │ │ │ ǁ H ─ C─ C─ C─ C─ OH │ │ │ H H H H O │ ǁ H ─ C─ C─ OH │ H Ethanoic Acid Butanoic Acid CH3COOH CH3CH2CH2COOH

  37. Ether • Single oxygen between 2 carbon chains • Name each carbon chain H H H H │ │ │ │ H─ C─ C─O ─ C─ C─ H │ │ │ │ H H H H H H H H H H │ │ │ │ │ │ H ─ C─ C─ C─ C─ O─ C─ C─ H │ │ │ │ │ │ H H H H H H Diethyl Ether Butyl Ethyl Ether CH3CH2OCH2CH3 CH3CH2CH2CH2OCH2CH3

  38. O ǁ ─ C ─ O ─ Ester • Carbonyl group with single oxygen between carbon chains • Name in two parts • 1st – Branch off oxygen as alkyl group • 2nd – Chain containing Carbonyl group • Ending in –oate

  39. Ester H O H │ ǁ │ H ─ C─ O ─ C─ C─ H │ │ H H H H H O H H │ │ │ ǁ │ │ H ─ C─ C─ C─ C─ O─ C─ C─ H │ │ │ │ │ H H H H H Methyl Ethanoate Ethyl Butanoate CH3COOCH3 CH3CH2CH2COOCH2CH3

  40. Organic Reactions • Saponification • Fermentation • Combustion • Addition • Substitution • Polymerization (2 types) • Esterification

  41. Organic Reactions • Saponification • Production of Soap • Fermentation • Production of ethanol and CO2 from sugar • C6H12O6 2C2H5OH + 2CO2

  42. Combustion • Complete Combustion of a Hydrocarbon • CxHy + O2 CO2 + H2O • Example: • C3H8 + 5O2 3CO2 + 4H2O

  43. Addition • Addition of a halogen onto an alkene or alkyne Br Br │ │ H─ C≡ C─ H + Br─Br  H─ C= C─ H Br Br Br Br │ │ │ │ H─ C= C─ H + Cl─Cl  H─ C─ C─ H │ │ Cl Cl

  44. Substitution • Substitution of one halogen in place of a hydrogen on an alkane H H H H │ │ │ │ H─ C─ C─ H + Cl─Cl  H─ C─ C─ H + H ─ Cl │ ││ │ H H H Cl H H Br H │ │ │ │ H─ C─ C─ H + Br─Br  H─ C─ C─ H + H ─ Br │ ││ │ H Cl H Cl

  45. Polymerization • Connecting of smaller pieces into a long repeating chain • Plastics, starches, nylon • Two types: • Addition • Condensation -(C2H4)n-

  46. Addition Polymerization • Double or triple bonds break to connect pieces together H H H H H H H H │ │ │ │ │ │ │ │ C═C + C═C  ─ C─C─C─ C ─ │ │ │ │ │ │ │ │ H H H H H H H H n

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