1. AP Notes Chapter 10
Organic Chemistry

2. Alkanes and Cycloalkanes
Hydrocarbons
Alkanes and Cycloalkanes

4. Alkanes: hydrocarbons containing only carbon-carbon single bonds
the first two alkanes are methane and ethane

5. Hydrocarbon: a compound composed of only carbon and hydrogen

6. Alkanes
the first 10 alkanes with unbranched chains
Generic Alkane Formula: CnH2n+2

7. Constitutional Isomerism
Constitutional isomers: compounds that have the same molecular formula but different structural formulas (connected differently)

8. Constitutional Isomerism

9. Map of Organic Isomerization

10. Nomenclature

11. IUPAC Names
The IUPAC name of an alkane with an unbranched chain of carbon atoms consists of two parts:
(1) a prefix: the number of carbon atoms in the chain
(2) the suffix -ane: shows that the compound is a saturated hydrocarbon

12. IUPAC Names
Alkyl group: a substituent group derived from an alkane by removal of a hydrogen atom
commonly represented by the symbol R-
named by dropping the -ane from the name of the parent alkane and adding the suffix -yl

14. IUPAC Names
1. The name for an alkane with an unbranched chain of carbon atoms consists of a prefix showing the number of carbon atoms and the ending -ane

15. IUPAC Names
2. For branched-chain alkanes, longest chain of carbon atoms is the parent chain and its name is the root name

16. IUPAC Names
3. Name and number each substituent on the parent chain; use a hyphen to connect the number to the name

17. Nomenclature Example

18. IUPAC Names
4. If there is one substituent, number the parent chain from the end that gives the substituent the lower number

19. IUPAC Names
5. If the same substituent occurs more than once,
number the parent chain from the end that gives the lower number to the substituent encountered first

20. IUPAC Names
5. If the same substituent occurs more than once,
indicate the number of times the substituent occurs by a prefix di-, tri-, tetra-, penta-, hexa-, and so on

21. use a comma to separate position numbers
IUPAC Names
5. If the same substituent occurs more than once,
use a comma to separate position numbers

23. list them in alphabetical order
IUPAC Names
6. If there are two or more different substituents
list them in alphabetical order

24. IUPAC Names
6. If there are two or more different substituents
number the chain from the end that gives the lower number to the substituent encountered first

25. IUPAC Names
6. If there are two or more different substituents
if there are different substituents in equivalent positions on opposite ends of the parent chain, give the substituent of lower alphabetical order the lower number

27. IUPAC Names
7. Do not include the prefixes di-, tri-, tetra-, and so on, or the hyphenated prefixes sec- and tert- in alphabetizing;
alphabetize the names of substituents first, and then insert these prefixes

28. Nomenclature Example

29. Cycloalkanes
Cyclic hydrocarbon: a hydrocarbon that contains carbon atoms joined to form a ring

30. Cycloalkanes

31. Cycloalkanes Nomenclature
to name a cycloalkane, prefix the name of the corresponding open-chain alkane with cyclo-, and name each substituent on the ring
if there is only one substituent on the ring, there is no need to give it a location number

32. Alkenes and Alkynes
Alkene: a hydrocarbon that contains one or more carbon-carbon double bonds
ethylene is the simplest alkene

33. Alkenes and Alkynes
Alkyne: a hydrocarbon that contains one or more carbon-carbon triple bonds
acetylene is the simplest alkyne

34. Alkenes Cis-trans isomerism
because of restricted rotation about a carbon-carbon double bond, an alkene with two different groups on each carbon of the double bond shows cis-trans isomerism

35. Alkenes - IUPAC Names To name an alkene
use the ending -ene to show the presence of the C=C
branched-chain alkenes are named in a manner similar to alkanes; substituted groups are located and named

36. Alkenes - IUPAC Names
Examples

37. Alkenes - IUPAC Names
Examples

38. Alkenes - IUPAC Names
Examples

39. Benzene and its Derivatives

40. Aromatic Compounds
Aromatic compound: a hydrocarbon that contains one or more benzene-like rings
arene: a term used to describe aromatic compounds
Ar-: a symbol for an aromatic group derived by removing an -H from an arene

41. Kekulé structure for benzene (1872)

42. The electrons of Benzene are Delocalized
sp2 hybridized

43. Nomenclature Example

44. Functional Groups and Reactions of Organic Compounds

45. Alkanes
They burn!
Hydrocarbon and Oxygen yields Carbon Dioxide and Water

46. Reactions of Alkenes: ADDITION REACTIONS
Alkenes are unsaturated — more bonds can form to the C atoms
Molecules such as Br2, H2, HCl, HBr, and H2O add to the double bond

47. An Addition Reaction
Fat placed in Br2 vapor

48. An Addition Reaction
The fat in bacon is partially unsaturated. The fat adds Br2 to the C=C bonds.

49. An Addition Reaction Saturated Fats
Fats can be “hydrogenated” with H2.
Saturated Fats
Peanut butter has partially hydrogenated vegetable oil.

50. Reactions of Aromatics
Substitutions — not additions — are typical. + C H 3 l A
AlCl3 is a catalyst. Catalysts typically used in aromatic substitutions.

51. Functional Groups
See CD-ROM Screens 10.5 & 10.6

52. Alcohols Butanol Methanol Characterized by –OH group [R-OH
Name: add – ol to name of hydrocarbon
Methanol
Butanol

53. Structures of Alcohols
C3H5OH: how many structural isomers?
Add -ol to name of 3-C hydrocarbon. Indicate position of OH with number.

54. Alcohol Properties Alcohols are a derivative of water
Many alcohols dissolve in water
Methanol dissolves in water.
Butanol is NOT soluble in water.

55. “Sterno” Alcohols burn in air
A mixture of ethanol + calcium acetate = STERNO

56. GLYCOLS Alcohols with Two OH Groups
Ethylene glycol
Propylene glycol

57. Alcohol Reactions Screen 11.6
Substitution
Elimination

58. Sugars: Related to Alcohols
Sugars are carbohydrates, compounds with the formula Cx(H2O)y. O H C 2 1 3 4 5 a - D g l u c o s e b p n h i f r m

59. Amines Alcohols are derivatives of H2O
(R–OH) and amines are derivatives of NH3.
Trimethylamine
Dimethylamine
Methylamine

60. Amines generally have terrible odors!
Pyridine
Cadaverine

61. Amines, like NH3, are bases2 C 6 H 5 N ( a q ) + S O 4 3 - A n i l e u m o

62. Amines
Many natural products and drugs (such as nicotine and cocaine) are bases.
Nicotine

63. Structures of Aldehydes
Odors from aldehydes and ketones
Cinnamaldehyde

64. carbonyl group

65. H H
methanal
FORMALDEHYDE

66. CH3CH2 H
propanal

67. R H
an ALDEHYDE

68. CH3
CH3
dimethylketone
propanone
ACETONE

69. CH3
CH2CH2CH3
2-pentanone

70. CH3CH2
CH2CH3
3-pentanone

71. R R’
a KETONE

72. Carboxylic acid group with acidic H+
Carboxylic Acids
Acetic acid
Benzoic acid
Carboxylic acid group with acidic H+
All are WEAK acids
Acids are found in many natural substances: bread, fruits, milk, wine

73. Formic acid, HCO2H, gives the sting to ants.
Carboxylic Acids

74. OH H
methanoic acid
FORMIC ACID

75. OH
CH3
ethanoic acid
ACETIC ACID

76. OH
CH2CH2CH3
butanoic acid
BUTYRIC ACID

77. OH R
a CARBOXYLIC ACID

78. an AMINO ACID

79. Acids + Alcohols --> ESTERS
Esters have generally pleasant odors

80. Acids + Alcohols --> ESTERS3 2 A c e t i a d E h n o l y

81. Acids + Alcohols --> ESTERS— H + ' 2 a r b o x y l i c d A h E s t e

82. Aspirin,
acetylsalicylic acid,
Acid and Ester

83. Fats with C=C bonds are usually LIQUDS
Fats and Oils
Fats with C=C bonds are usually LIQUDS
Oleic acid: a monounsaturated fatty acid
C=C Bond

84. Fats and Oils Saturated fats are more common in animals.
Fats with saturated acids (no C=C bonds) are SOLIDS.
Saturated fats are more common in animals.

85. Trans Fatty Acids
Acid
and
Alkene
C=C Bond

86. Trans Fatty Acids Oleic acid is a mono–unsaturated cis-fatty acid
Trans fatty acids have deleterious health effects.
Trans fatty acids raise plasma LDL cholesterol and lower HDL levels.

87. Acids + Amines --> AMIDES
N-methylacetamide

88. Acids + Amines --> AMIDES
Acetoaminophen
Tylenol, Datril, Momentum, ...

89. Polymers
Giant molecules made by joining many small molecules called monomers
Average production is 150 kg per person annually in the U.S.

90. Polymer Classifications
Thermoplastics (polyethylene) soften and flow when heated
Thermosetting plastics — soft initially but set to solid when heated. Cannot be resoftened.

91. Polymer Classifications
Other classification: plastics, fibers, elastomers, coatings, adhesives

92. Polymer Preparation
Addition polymers — directly adding monomer units together
Condensation polymers — combining monomer units and splitting out a small water (water)

93. Polyethylene: Addition Polymer
A polymer with a molar mass of a million has about 36,000 units.

94. Mechanism of Addition Polymerization
Initiation
Addition
Propagation
Termination
Addition Polymerization

95. Types of Polyethylene Cross-linked PE, CLPE
Linear, high density PE (HDPE)
Cross-linked PE, CLPE
Branched, low density PE, LDPE

96. Types of Polyethylene
Table 11.12: others are PVC, acrylonitrile, polypropylene, polymethyl methacrylate

97. Polystyrene
Polystyrene is nonpolar material and dissolves in organic solvents.
PS foam is mostly air, and when it dissolves it collapses to a much smaller volume.

98. Condensation PolymersH O C 2 + n t e r p h a l i c d y g o P ( E T ) , s

99. Polyesters, PET Jackets made from recycled PET soda bottles
Soda bottles, mylar film.

101. Polyesters: Mechanism
Reaction of Diacid and Diol

102. Polyamides: Nylon
Nylon Rope Trick

103. Polyamides: Nylon Each monomer has 6 C atoms in its chain.
A polyamide link forms on elmination of HCl
Result = nylon 66
Proteins are polyamides

105. Polymer Recycling Symbols
LDPE = Low density PE = g/cm3
HDPE = High density PE =
PP = Polypropylene = 0.90
V = PVC (Vinyl chloride) =