1. ORGANIC CHEMISTRY

2. The chemistry of carbon compounds
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, ethane, propane, butane…
Methane: CH4
Ethane C2H6
Propane C3H8
Butane C4H10
All have the formula:

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

9. Methane, ethane, propane, butane…
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

10. Lewis diagrams H H H H C H H C C H H H H H H H H H H H H C C C H H C C
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

12. Here’s a hint– it’s not the formula!
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 H C H H

13. These are structural isomers
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 H C H
Methylpropane H

14. The longest chain has branches
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?

16. What is the longest chain?

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

18. Lewis diagrams 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
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. 3-ethyl-4,5-dimethyloctane
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 butene

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

51. Chirality—”handedness”OH H H H H H C C C C H H C H H H H H Cl H H C C C OH H H Cl
There really is a difference—these are mirror-image molecules.

52. Chirality—”handedness”OH H H H H H C C C C H H C H H H H H Cl H H C C C OH H H Cl
Any time you find four different groups attached to one (chiral) carbon there are two optical isomers (L and D) of the molecule

53. Geometric Isomers Alkenes may have both a cis- and a trans- isomer
Cis-2-butene (two methyl groups are on the same side)
Trans-2-butene (two methyl groups are on opposite sides)

54. Reactions You will be responsible for: Oxidation Addition
Esterification and
Polymerization
reactions

55. Oxidation Combustion: CxHyOz + O2CO2 + H2O
More gentle oxidations: (use MnO4-, CrO4-2 and others)
Primary alcoholsaldehydesacids
Secondary alcoholsketones

56. Addition X
YX + Y
YX can be H2O, HCl, Hl, HF, HBr , F2, H2, Br2, Cl2, H2SO4, HNO3 and others

57. Sometimes you get a mixture of products
Addition
HCl + Cl
2-chloroheptane AND Cl
3-chloroheptane
Sometimes you get a mixture of products

58. Sometimes you don’t X HX + X HX +
Markovnikov’s Rule: When adding HX, the H joins the carbon with more H to start with.

59. Esterification
An acid and an alcohol make an ester by dehydration synthesis. O
+ HO OH O O
+ H2O

60. Esterification Propanic acid and ethanol form ethyl propanoate O + HO
The acid keeps the carbonyl, so it takes the –oate ending

61. Polymerization
There are two ways to form polymers (repeating chains of monomers)
Addition
B) Dehydration

62. Polymerization
There are two ways to form polymers (repeating chains of monomers)
Addition—a p bond forms a s bond to the
next monomer
B) Dehydration—a dehydration synthesis
occurs to the next monomer

63. Polymerization
There are two ways to form polymers (repeating chains of monomers)
Addition—a p bond forms a s bond to the
next monomer —requires a double bond
B) Dehydration—a dehydration synthesis
occurs to the next monomer —requires
hydroxyl groups at each end of monomer

64. Addition polymerization+

65. Dehydration polymerizationHO
OH + HO OH O O O O O O O
+ H2O
(can be double acids, amino acids, alternating monomers, etc.)