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ORGANIC CHEMISTRY

ORGANIC CHEMISTRY. ORGANI C—C HEMISTRY. The chemistry of carbon compounds. Hydrocarbons. Hydrocarbons. … are the simplest organic molecules … containing only hydrogen and carbon. The names of the hydrocarbons are used in the naming system of the other organic compounds.

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ORGANIC CHEMISTRY

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  1. ORGANIC CHEMISTRY

  2. ORGANIC—CHEMISTRY The chemistry of carbon compounds

  3. Hydrocarbons

  4. Hydrocarbons • … are the simplest organic molecules • … containing only hydrogen and carbon. The names of the hydrocarbons are used in the naming system of the other organic compounds.

  5. Methane, ethane, propane, butane…

  6. Methane, ethane, propane, butane… • Repeat it with me: Methane, ethane, propane, butane… Methane, ethane, propane, butane…

  7. Methane: CH4 Ethane C2H6 Propane C3H8 Butane C4H10 All have the formula: Methane, ethane, propane, butane…

  8. Methane: CH4 Ethane C2H6 Propane C3H8 Butane C4H10 All have the formula: CxH2x+2 Methane, ethane, propane, butane…

  9. Methane: CH4 Ethane C2H6 Propane C3H8 Butane C4H10 All have the formula: Pentane: C5H12 Hexane C6H14 Heptane C7H16 Octane C8H18 (and so on…) CxH2x+2 Methane, ethane, propane, butane…

  10. Lewis diagrams H H H H C H H C C H H H H Methane, ethane, propane, butane… H H H H H H H H C C C H H C C C C H H H H H H H H

  11. What is the difference? H H H H H C C C C H H H H H H H H H C C C H H H C H H H

  12. What is the difference? H H H H C4H10 H C C C C H Here’s a hint– it’s not the formula! H H H H H H H C4H10 H C C C H H H C H H H

  13. These are structural isomers H H H H Butane H C C C C H Different chemical and physical properties H H H H H H H H C C C H H H C H H Methylpropane H

  14. Substituted alkanes • Still have CxH2x+2 • No rings or double bonds • But!—not a single chain. • The longest chain has branches

  15. What is the longest chain? H C H H H C H H H H H H H H C C C C C H H C C H H H H C C C H H C H H H H C H H C H H H H

  16. What is the longest chain? H C H H H C H H H H H H H H C C C C C H H C C H H H H C C C H H C H H H H C H H C H H H H

  17. Now is a very good time… • …to shift to the carbon skeleton diagrams.

  18. Lewis diagrams Propane Butane H H H H H H H H C C C H H C C C C H H H H H H H H

  19. Carbon skeleton diagrams Propane Butane The bars represent the C-C bonds. H are not shown

  20. Carbon skeleton diagrams Propane Butane 2 2 4 3 1 3 1 Count your carbons carefully!

  21. What molecule is shown?

  22. What molecule is shown? Hexane Pentane Butane Heptane

  23. Naming substituted alkanes

  24. Naming substituted alkanes 3-methylhexane 2-methylhexane Heptane 3-methylhexane (again!)

  25. Rules: • Find the longest chain, name it • Branches are named by their length, using a –yl ending to show they are attached • Methyl, ethyl, propyl, butyl… • Show where the branches come from using carbon numbers before the branch name • Start from the end to minimize the numbers • Multiple branches use di, tri, tetra,…prefixes • Alphabetize the branches

  26. For example

  27. For example Longest chain=8 carbons, octane

  28. Or… Longest chain=8 carbons, octane

  29. For example 2 methyl groups, on the 4th and 5th carbons

  30. For example Ethyl group, on the 3rd carbon (not the 6th!-number from the end that minimizes the total)

  31. For example Which gives us: 3-ethyl-4,5-dimethyloctane

  32. Name these molecules 1) 2) 3) 4)

  33. Functional groups: • Double bonds (-C=C-) • Make alkenes • End in –ene • CxH2x • 1-butene 2-butene

  34. Functional groups: • Triple bonds (-C≡C-) • Make alkynes • End in –yne • CxH2x-2 • 1-butyne 2-butyne

  35. Name these molecules 1) 2) 3) 4)

  36. Functional groups: • Hydroxyl groups (-O-H) • Make alcohols • End in –ol • CxH2x+1OH • 1-butanol 2-butanol OH OH

  37. Functional groups: • Terminal carbonyls (-CHO) • Make aldehydes • End in –al • CxH2xO • butanal propanal O O

  38. Functional groups: • Internal carbonyls (-C=O) • Make ketones • End in –one • CxH2xO • 2-pentanone 3-pentanone O O

  39. Name these molecules O 1) 2) 3) 4) HO O OH

  40. Functional groups: • Ether linkages (-C-O-C-) • Make ethers • End in “ether” • CxH2x+2O • ethylmethyl ether ethylpropyl ether O O

  41. Functional groups: • Ester linkages (-C-O-C=O) • Make esters • End in “-oate” • CxH2xO2 • ethylmethanoate propylethanoate O O O O

  42. Functional groups: • Carboxyl groups (-COOH) • Make organic acids • End in “-oic acid” • CxH2xO2 • ethanoic acid propanoic acid O O HO OH

  43. Functional groups: • Amino groups (-C-NH2) • Make amines • End in “-amine” • CxH2x+1NH2 • 2-pentamine 1-butamine NH2 NH2

  44. Functional groups: • Halides ( -X where X=Cl, F, Br, I) • Make organic halides • Named as a branched alkane • CxH2x+1X • 2-chloropentane 1,1-dibromobutane Br Cl Br

  45. Functional groups: • Rings • Make cycloalkanes • Named with prefix “cyclo-” • CxH2x • cyclopentane methylcyclobutane

  46. Functional groups: • The benzene ring Make substituted benzene or phenylalkanes Named as “–benzene” or a branch “phenyl-” • C6H6—has 3 double bonds! • benzene

  47. Methylbenzene Hydroxybenzene Aminobenzene Benzoic acid NH2 OH COOH Usually called: (Once known as: toluene phenol aniline carbolic acid)

  48. Ortho-, meta-, para. Meta-dichlorobenzene Cl Cl Cl Cl Cl Ortho-dichlorobenzene Cl Para-dichlorobenzene

  49. Draw and name all of the isomers of C5H10

  50. Chirality—”handedness” Draw a Lewis diagram of 2-chloro-2-butanol

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