Organic Chemistry I: Compounds

1
Chapter 25

• Organic Chemistry I Compounds

2
Chapter Goals

• Saturated Hydrocarbons
• Alkanes and Cycloalkanes
• Naming Saturated Hydrocarbons
• Unsaturated Hydrocarbons
• Alkenes
• Alkynes
• Aromatic Hydrocarbons
• Benzene
• Other Aromatic Hydrocarbons
• Hydrocarbons A Summary

3
Chapter Goals

• Functional Groups
• Organic Halides
• Alcohols and Phenols
• Ethers
• Aldehydes and Ketones
• Amines
• Carboxylic Acids
• Some Derivatives of Carboxylic Acids
• Summary of Functional Groups

4
Chapter Goals

• Fundamental Classes of
• Organic Reactions
• Substitution Reactions
• Addition Reactions
• Elimination Reactions
• Polymerization Reactions

5
Saturated Hydrocarbons

• Hydrocarbons are chemical compounds that contain
  only C and H atoms.
• Saturated hydrocarbons contain only single or
  sigma (?) bonds.
• There are no double or triple bonds in these
  compounds.
• The primary source of hydrocarbons is petroleum
  and natural gas.

6
Alkanes and Cycloalkanes

• The simplest saturated hydrocarbons are called
  alkanes.
• Methane, CH4, is the simplest alkane.
• The alkanes form a homologous series.
• Each member of the series differs by a specific
  number and kind of atoms.

7
Alkanes and Cycloalkanes

• The alkanes differ from each other by a CH2 or
  methylene group.
• All alkanes have this general formula.
• CnH2n2
• For example ethane, C2H6 , and propane, C3H8 ,
  are the next two family members.

8
Alkanes and Cycloalkanes

• Isomers are chemical compounds that have the same
  molecular formulas but different structures.
• Two alkanes have the molecular formula C4H10.
• They are a specific type of isomer called
  structural isomers.

9
Alkanes and Cycloalkanes

• Three alkanes have the formula C5H12.
• There are three structural isomers of pentane.

10
Alkanes and Cycloalkanes

• Three alkanes have the formula C5H12.
• There are three structural isomers of pentane.

11
Alkanes and Cycloalkanes

• Three alkanes have the formula C5H12.
• There are three structural isomers of pentane.

12
Alkanes and Cycloalkanes

• There are five isomeric hexanes, C6H14.
• You draw them!

13
Alkanes and Cycloalkanes

• There are five isomeric hexanes, C6H14.

14
Alkanes and Cycloalkanes

• There are five isomeric hexanes, C6H14.

15
Alkanes and Cycloalkanes

• There are five isomeric hexanes, C6H14.

16
Alkanes and Cycloalkanes

• There are five isomeric hexanes, C6H14.

17
Alkanes and Cycloalkanes

• The number of structural isomers increases
  rapidly with increasing numbers of carbon atoms.
• The boiling points of the alkanes increase with
  molecular weight.

18
Alkanes and Cycloalkanes

• Cyclic saturated hydrocarbons are called
  cycloalkanes.
• They have the general formula CnH2n.
• Some examples are

19
Alkanes and Cycloalkanes

• Cyclic saturated hydrocarbons are called
  cycloalkanes.
• They have the general formula CnH2n.
• Some examples are

20
Alkanes and Cycloalkanes

• Cyclic saturated hydrocarbons are called
  cycloalkanes.
• They have the general formula CnH2n.
• Some examples are

21
Naming Saturated Hydrocarbons

• The International Union of Pure and Applied
  Chemistry (IUPAC) names for the first 12
  "straight-chain" or "normal" alkanes are given in
  this table.

Number of carbon atoms in chain Name
1 Methane
2 Ethane
3 Propane
4 Butane
5 Pentane
6 Hexane
22
Naming Saturated Hydrocarbons
Number of carbon atoms in chain Name
7 Heptane
8 Octane
9 Nonane
10 Decane
11 Unidecane
12 Dodecane
23
Naming Saturated Hydrocarbons

• Other organic compounds are named as derivatives
  of the alkanes.
• Branched-chain alkanes are named by the following
  rules.
• Choose the longest continuous chain of carbon
  atoms which gives the basic name or stem.

24
Naming Saturated Hydrocarbons

• Number each carbon atom in the basic chain,
  starting at the end that gives the lowest number
  to the first group attached to the main chain
  (substituent).
• For each substituent on the chain, we indicate
  the position in the chain (by an Arabic numeric
  prefix) and the kind of substituent (by its
  name).
• The position of a substituent on the chain is
  indicated by the lowest number possible.
• The number precedes the name of the substituent.

25
Naming Saturated Hydrocarbons

• When there are two or more substituents of a
  given kind, use prefixes to indicate the number
  of substituents.
• di 2, tri 3, tetra 4, penta 5, hexa 6,
  hepta 7, octa 8, and so on.
• The combined substituent numbers and names serve
  as a prefix for the basic hydrocarbon name.
• Separate numbers from numbers by commas and
  numbers from words by hyphens.
• Words are "run together".

26
Naming Saturated Hydrocarbons

• Alkyl groups (represented by the symbol R) are
  common substituents.
• Alkyl groups are fragments of alkanes in which
  one H atom has been removed for the connection to
  the main chain.
• Alkyl groups have the general formula CnH2n1.
• In alkyl groups the -ane suffix in the name of
  the parent alkane is replaced by -yl.
• A one carbon group is named methyl.
• A two carbon group is named ethyl.
• A three carbon group is named propyl.

27
Unsaturated Hydrocarbons

• The three classes of unsaturated hydrocarbons
  are
• alkenes and cycloalkenes, CnH2n
• alkynes and cycloalkynes, CnH2n-2
• aromatic hydrocarbons

28
Alkenes

• The simplest alkenes contain one CC bond per
  molecule.
• The general formula for simple alkenes is CnH2n.
• The first two alkenes are
• ethene, C2H4

29
Alkenes

• The simplest alkenes contain one CC bond per
  molecule.
• The general formula for simple alkenes is CnH2n.
• The first two alkenes are
• and propene, C3H6

30
Alkenes

• Each doubly bonded C atom is sp2 hybridized.
• The sp2 hybrid consists of
• two s bonds (single bonds) and
• one s and one p bond (double bond)

31
Alkenes

• The systematic naming system for alkenes uses the
  same stems as alkanes.
• In the IUPAC system, the -ane suffix for alkanes
  is changed to -ene.
• Common names for the alkenes have the same stem
  but use the suffix -ylene is used.
• In chains of four or more C atoms, a numerical
  prefix shows the position of the lowest-numbered
  doubly bonded C atom.
• Always choose the longest chain that contains the
  CC bond.

32
Alkenes

• Polyenes contain two or more double bonds per
  molecule.
• Indicate the number of double bonds with
  suffixes
• -adiene for two double bonds.
• -atriene for three double bonds, etc.
• The positions of the substituents are indicated
  as for alkanes.
• The position of the CC bond(s) is/are given the
  lowest number(s) possible.

33
Alkenes
34
Alkenes
35
Alkenes
36
Cycloalkenes

• Cycloalkenes have the general formula CnH2n-2.
• Examples are
• cyclopentene

37
Cycloalkenes

• cyclohexene

38
Cycloalkenes

• cycloheptene

39
Alkynes

• Alkynes contain C?C bonds.
• The simplest alkyne is C2H2, ethyne, or
  acetylene.
• Alkynes with only one C ? C bond have the formula
  CnH2n-2.
• Each carbon atom in a C ? C bond is sp
  hybridized.
• Each sp hybrid contains two ? bonds and two ?
  bonds.
• The carbon atom will have one single bond and one
  triple bond.

40
Alkynes

• Alkynes are named like the alkenes except that
  the suffix -yne is used with the characteristic
  stem
• The alkyne stem is derived from the name of the
  alkane with the same number of carbon atoms.

41
Alkynes

• Acetylene is an important industrial chemical.
• It is prepared by the reaction of calcium carbide
  with water.

42
Alkynes

• Acetylene burns in a highly exothermic reaction
• The combustion produces temperatures of about
  3000C.
• Acetylene is used in cutting torches for welding.

• Alkynes are very reactive
• The two p bonds are sights of special reactivity.
• Addition reactions, such as hydrogenation, are
  common.

43
Hydrocarbons A Summary
Carbon Atom Hybridization C uses C forms Example
sp3 tetrahedral 4 sp3 hybrids 4 ? bonds CH4
sp2 trigonal planar 3 sp2 hybrids 1p orbital 3 ? bonds 1 ? bond C2H4
sp linear 2 sp hybrids 2 p orbitals 2 ? bonds 2 ? bonds C2H2
44
Aromatic Hydrocarbons

• Historically, aromatic was used to describe
  pleasant smelling substances.
• Now it refers to benzene, C6H6, and derivatives
  of benzene.
• Other compounds that have similar chemical
  properties to benzene are also called aromatic.

45
Benzene

• The structure of benzene, C6H6, is

46
Other Aromatic Hydrocarbons

• Coal tar is the common source of benzene and many
  other aromatic compounds.
• Some aromatic hydrocarbons that contain fused
  rings are
• napthalene

47
Other Aromatic Hydrocarbons

• phenanthrene

48
Other Aromatic Hydrocarbons

• Many aromatic hydrocarbons contain alkyl groups
  attached to benzene rings (as well as to other
  aromatic rings).
• The positions of the substituents on benzene
  rings are indicated by the prefixes
• ortho- (o-) for substituents on adjacent C atoms
• meta- (m-) for substituents on C atoms 1 and 3
• para- (p-) for substituents on C atoms 1 and 4

49
Other Aromatic Hydrocarbons
50
Functional Groups

• Functional groups are groups of atoms that
  represent potential reaction sites.
• Compounds that contain a given functional group
  usually undergo similar reactions.
• Functional groups influence physical properties
  as well.

51
Organic Halides

• A halogen atom may replace almost any hydrogen
  atom in a hydrocarbon.
• The functional group is the halide (-X) group.
• Examples include
• chloroform, CHCl3

52
Organic Halides

• 1,2-dichloroethane, ClCH2CH2Cl

53
Organic Halides

• para-dichlorobenzene

54
Alcohols and Phenols

• The functional group in alcohols and phenols is
  the hydroxyl (-OH) group.
• Alcohols and phenols can be considered
  derivatives of hydrocarbons in which one or more
  H atoms have been replaced by -OH groups.
• Phenols are derivatives of benzene in which one H
  has been replaced by replaced by -OH group.

55
Alcohols and Phenols

• Ethyl alcohol (ethanol), C2H5OH, is the most
  familiar alcohol.

56
Alcohols and Phenols

• Phenol, C6H5OH, is the most familiar phenol.

57
Alcohols and Phenols

• Alcohols are considered neutral compounds because
  they are only very slightly acidic.
• Alcohols can behave as acids but only in the
  presence of very strong bases.
• Phenols are weakly acidic.
• Ka ? 1.0 x 10-10 for phenol
• Although phenols are very weakly acidic, they are
  also very corrosive.

58
Alcohols and Phenols

• Alcohols can be classified into three classes
• Primary (1) alcohols like ethanol have the -OH
  group attached to a C atom that has one bond to
  another C atom.

59
Alcohols and Phenols

• Secondary(2) alcohols have the OH group
  attached to a C atom that has bonds to 2 other C
  atoms.
• For example,2-propanol

60
Alcohols and Phenols

• Tertiary (3) alcohols have the OH group
  attached to a C atom that is bonded to 3 other C
  atoms.
• For example, 2-methyl-2-propanol

61
Alcohols and Phenols

• The stem for the parent hydrocarbon plus an -ol
  suffix is the systematic name for an alcohol.
• A numeric prefix indicates the position of the
  -OH group in alcohols with three or more C atoms.
  
• Common names are the name of the appropriate
  alkyl group plus alcohol.

62
Alcohols and Phenols

• Alcohols are named using the stem for the parent
  hydrocarbon plus an -ol suffix in the systematic
  nomenclature.
• A numeric prefix indicates the position of the
  -OH group in alcohols with three or more C atoms.
  
• Common alcohol names are the name of the
  appropriate alkyl group plus the word alcohol.

63
Alcohols and Phenols

• There are several isomeric monohydric acyclic
  (contains no rings) alcohols that contain more
  than three C atoms.
• There are four isomeric four-carbon alcohols.

64
Alcohols and Phenols
65
Alcohols and Phenols

• There are eight isomeric five-carbon alcohols.
• You do it!

66
Alcohols and Phenols

• Polyhydric alcohols contain more than one -OH
  group per molecule.

67
Alcohols and Phenols

• Phenols are usually called by their common
  (trivial) names.

68
Alcohols and Phenols

• Phenols are usually called by their common
  (trivial) names.

69
Alcohols and Phenols

• Phenols are usually called by their common
  (trivial) names.

70
Alcohols and Phenols

• Phenols are usually called by their common
  (trivial) names.

71
Alcohols and Phenols

• Because the -OH group is quite polar, the
  properties of alcohols depend upon the number of
  -OH groups per molecule and the size of the
  organic group.
• The boiling points of monohydric alcohols
  increase with increasing molecular weight.
• The solubility of monohydric alcohols in water
  decrease with increasing molecular weight.
• Polyhydric alcohols are more soluble in water
  because of the two or more polar groups (-OH).

72
Ethers

• Ethers may be thought of as derivatives of water
  in which both H atoms have been replaced by alkyl
  or aryl groups.

73
Ethers

• Ethers may be thought of as derivatives of water
  in which both H atoms have been replaced by alkyl
  or aryl groups.

74
Ethers

• Ethers may be thought of as derivatives of water
  in which both H atoms have been replaced by alkyl
  or aryl groups.

75
Ethers

• Ethers are not very polar and not very reactive.
  
• They are excellent solvents.
• Common names are used for most ethers.

76
Aldehydes and Ketones

• The functional group in aldehydes and ketones is
  the carbonyl group.

77
Aldehydes and Ketones

• Except for formaldehyde, aldehydes have one H
  atom and one organic group bonded to a carbonyl
  group.

78
Aldehydes and Ketones

• Ketones have two organic groups bonded to a
  carbonyl group.

79
Aldehydes and Ketones

• Common names for aldehydes are derived from the
  name of the acid with the same number of C atoms.
  
• IUPAC names are derived from the parent
  hydrocarbon name by replacing -e with -al.

80
Aldehydes and Ketones

• Common names for aldehydes are derived from the
  name of the acid with the same number of C atoms.
  
• IUPAC names are derived from the parent
  hydrocarbon name by replacing -e with -al.

81
Aldehydes and Ketones

• Common names for aldehydes are derived from the
  name of the acid with the same number of C atoms.
  
• IUPAC names are derived from the parent
  hydrocarbon name by replacing -e with -al.

82
Aldehydes and Ketones

• The IUPAC name for a ketone is the characteristic
  stem for the parent hydrocarbon plus the suffix
  -one.
• A numeric prefix indicates the position of the
  carbonyl group in a chain or on a ring.

83
Aldehydes and Ketones

• The IUPAC name for a ketone is the characteristic
  stem for the parent hydrocarbon plus the suffix
  -one.
• A numeric prefix indicates the position of the
  carbonyl group in a chain or on a ring.

84
Aldehydes and Ketones

• The IUPAC name for a ketone is the characteristic
  stem for the parent hydrocarbon plus the suffix
  -one.
• A numeric prefix indicates the position of the
  carbonyl group in a chain or on a ring.

85
Aldehydes and Ketones

• Many aldehydes and ketones occur in nature.

86
Amines

• Amines are derivatives of ammonia in which one or
  more H atoms have been replaced by organic groups
  (aliphatic or aromatic or a mixture of both).
• There are three classes of amines.

87
Amines

• Amines are derivatives of ammonia in which one or
  more H atoms have been replaced by organic groups
  (aliphatic or aromatic or a mixture of both).
• There are three classes of amines.

88
Amines

• Amines are derivatives of ammonia in which one or
  more H atoms have been replaced by organic groups
  (aliphatic or aromatic or a mixture of both).
• There are three classes of amines.

89
Amines

• Amines are derivatives of ammonia in which one or
  more H atoms have been replaced by organic groups
  (aliphatic or aromatic or a mixture of both).
• There are three classes of amines.

90
Amines

• Aniline is the simplest aromatic amine. It is
  much less basic than NH3.
• Aniline is a very important industrial chemical.

91
Amines

• Heterocylic amines have one or more N atoms in a
  ring structure.
• Many are important in living systems.

92
Amines

• Heterocylic amines have one or more N atoms in a
  ring structure.
• Many are important in living systems.

93
Amines

• Heterocylic amines have one or more N atoms in a
  ring structure.
• Many are important in living systems.

94
Carboxylic Acids

• Carboxylic acids contain the carboxyl functional
  group.

• The general formula for carboxylic acids is
• R represents an alkyl or an aryl group

95
Carboxylic Acids

• IUPAC names for a carboxylic acid are derived
  from the name of the parent hydrocarbon.
• The final -e is dropped from the name of the
  parent hydrocarbon
• The suffix -oic is added followed by the word
  acid.
• Many organic acids are called by their common
  (trivial) names which are derived from Greek or
  Latin.

96
Carboxylic Acids
97
Carboxylic Acids

• Positions of substituents on carboxylic acid
  chains are indicated by numeric prefixes as in
  other compounds
• Begin the counting scheme from the carboxyl group
  carbon atom.
• They are also often indicated by lower case Greek
  letters.
• ? 1st C atom
• ? 2nd C atom
• ? 3rd C atom, etc.

98
Carboxylic Acids
99
Carboxylic Acids
100
Carboxylic Acids
101
Carboxylic Acids

• Dicarboxylic acids contain two carboxyl groups
  per molecule.

102
Nomenclature of Carboxylic Acids

• Dicarboxylic acids contain two carboxyl groups
  per molecule.

103
Nomenclature of Carboxylic Acids

• Dicarboxylic acids contain two carboxyl groups
  per molecule.

104
Carboxylic Acids

• Aromatic acids are usually called by their common
  names.
• Sometimes, they are named as derivatives of
  benzoic acid which is considered to be the
  "parent" aromatic acid.

105
Carboxylic Acids
106
Carboxylic Acids
107
Carboxylic Acids

• Acid strengths of simple carboxylic acids vary
  little with chain length.
• However, substituents on a carbon atom in the
  chain can cause large variations in acid
  strengths .

108
Carboxylic Acids
109
Carboxylic Acids
110
Carboxylic Acids

• The -OH group in the carboxyl group of carboxylic
  acids, is displaced in many of their reactions.
  
• The non -OH portion of a carboxylic acid is
  called an acyl group.

111
Some Derivatives of Carboxylic Acids

• Four important classes of compounds contain acyl
  groups
• They are all considered to be derivatives of
  carboxylic acids.
• In these structures R's may represent either
  alkyl or aryl groups.

112
Some Derivatives of Carboxylic Acids
113
Some Derivatives of Carboxylic Acids
114
Some Derivatives of Carboxylic Acids

• Acid anhydrides are related to their parent acids
  as follows
• The word anhydride means without water.

115
Some Derivatives of Carboxylic Acids

• Acyl halides are much more reactive, and more
  volatile, than their parent acids.
• They react with water to form their parent acids
  and a hydrohalic acid.

116
Some Derivatives of Carboxylic Acids

• Acyl halides are prepared by reacting their
  parent acids with PCl3, PCl5, or SOCl2.
• The more volatile acid halide is then distilled
  out of the reaction mixture.

117
Some Derivatives of Carboxylic Acids

• Esters are prepared by heating a carboxylic acid
  with an alcohol in the presence of a small amount
  of an inorganic acid.
• The reaction mixture will contain some ester and
  water, as well as unreacted acid and alcohol.

118
Some Derivatives of Carboxylic Acids

• Esters are usually called by their common names.
• Many simple esters occur naturally and have
  pleasant odors.
• Esters are frequently used in fragrances and as
  artificial flavors.

119
Some Derivatives of Carboxylic Acids

• Fats are solid esters of glycerol and (mostly)
  saturated acids at room temperature.
• Oils are liquid esters of glycerol and primarily
  unsaturated acids at room temperature.
• The "acid" parts of fats and oils usually contain
  even numbers of C atoms in naturally occurring
  fats and oils.
• 16 and 18 carbon chains are the most commonly
  found chain sizes in nature.

120
Some Derivatives of Carboxylic Acids

• Some acids that are found (as their esters) in
  fats and oils include

121
Some Derivatives of Carboxylic Acids

• Stearic acid is often found in beef fat.

122
Some Derivatives of Carboxylic Acids

• Triglycerides are the triesters of glycerol.
• The common name for triglycerides is tri (acid
  stem) plus an -in suffix.
• For example, tripalmitin.

123
Some Derivatives of Carboxylic Acids

• Waxes are esters of long chain fatty acids and
  alcohols other than glycerol.
• Commonly, waxes are derived from monohydric
  alcohols.
• Beeswax and carnauba wax are esters of myricyl
  alcohol, C30H61OH.

124
Some Derivatives of Carboxylic Acids

• Carnauba wax is often used in car waxes.

125
Some Derivatives of Carboxylic Acids

• Dihydric alcohols (2 OHs per molecule) can
  react with dicarboxylic acids (2 COOHs per
  molecule) to form polyesters.
• Ester linkages are formed at both ends of both
  molecules to give polymeric esters with very high
  molecular weights.

126
Some Derivatives of Carboxylic Acids
127
Some Derivatives of Carboxylic Acids

• Amides are derivatives of organic acids and
  primary or secondary amines.
• The functional groups of amides are

128
Some Derivatives of Carboxylic Acids

• Amides are also named as derivatives of
  carboxylic acids.
• The suffix -amide is substituted for -ic acid or
  -oic acid.

129
Some Derivatives of Carboxylic Acids

• When an aryl or alkyl substituent is present on
  the N atom, the letter N and the name of the
  substituent are prefixed to the name of the
  unsubstituted amide.

130
Some Derivatives of Carboxylic Acids

• Acetaminophen Tylenol - is an amide.

131
Summary of the Functional Groups

• A summary of the functional groups is

132
(No Transcript)
133
Substitution Reactions

• In a substitution reaction an atom or group of
  atoms attached to a carbon atom is replaced
  (substituted for) by another atom or group of
  atoms.
• There is no change in the degree of saturation at
  the reactive carbon atom.
• Halogenation reactions are an important class of
  substitution reactions.
• Chlorine reacts with alkanes in free radical
  chain reactions (also substitution reactions).

134
Substitution Reactions

• Free radical chain reactions
• The halogenation of methane is one example.

135
Substitution Reactions
136
Substitution Reactions
137
Substitution Reactions

• Free radical chain reactions
• Many substitution reactions of alkanes produce
  more than one product.

138
Substitution Reactions
139
Substitution Reactions
140
Substitution Reactions

• Nitration reaction of an aromatic hydrocarbon
  replaces an H atom attached to an aromatic ring
  with a nitro, -NO2, group.

141
Addition Reactions

• An addition reaction involves an increase in the
  number of groups attached to carbon.
• The degree of saturation of the molecule is
  increased.

142
Addition Reactions

• Hydrogenation is a very important kind of
  addition reaction.
• Hydrogenation is used to convert unsaturated fats
  and oils to saturated fats or oils.

143
Elimination Reactions

• An elimination reaction involves the removal of
  groups attached to carbon.
• The degree of unsaturation increases.

144
Elimination Reactions

• Dehydration is an important kind of elimination
  reaction.

145
Polymerization Reactions

• A polymer is a large molecule that consists of a
  high-molecular weight chain of small molecules.
• The small molecules that have been joined to form
  the polymer are called monomers.
• Synthetic polymers are a relatively new class of
  molecules.
• The first one, bakelite, was discovered in 1909.
• Nylon, which is still extensively used, was
  discovered in 1930s.

146
Polymerization Reactions

• Addition polymerization is a large commercial
  process in the United States.
• Polyethylene is the addition polymer made in the
  largest quantities in the United States.
• Polyethylene is used to make Coke bottles,
  plastic bags, etc.

147
Polymerization Reactions

• Addition polymerization
• Polyethylene formation

148
Polymerization Reactions

• Addition polymerization
• Teflon is the material used in nonstick frying
  pans and other kitchen utensils.

149
Polymerization Reactions

• Formation of rubber
• Natural rubber is a polymer made of isoprene
  (2-methyl-1,3-butadiene) units that form a unique
  stereoisomeric structure.

150
Polymerization Reactions

• Vulcanization of rubber
• Natural rubber is a sticky, soft compound when
  heated which limited its commercial potential.
• Charles Goodyear discovered in 1839 that heating
  rubber with sulfur removed the stickiness and
  made the substance elastic.
• This is the basis of modern tire production.
• Vulcanization provides disulfide cross-linking
  bonds between the isoprene units.

151
Polymerization Reactions

• Copolymers
• If two different monomers are mixed and the
  polymerized, copolymers are formed.
• Styrene butadiene rubber - SBR - is an important
  copolymer used in tire production.

152
Polymerization Reactions

• Copolymers

153
Polymerization Reactions
154
Polymerization Reactions

• Condensation Polymers
• Condensation polymers occur when two molecules
  react and eliminate a small molecule.
• Molecules eliminated commonly are water and HCl.
• Important condensation polymers include nylon,
  dacron, and kevlar.
• Dacron is used in clothing to make it wrinkle
  free.
• Blood does not clot in contact with dacron thus
  it is used in artificial arteries.

155
Polymerization Reactions

• Condensation Polymers
• Dacron formation

156
Polymerization Reactions
157
Polymerization Reactions

• Condensation Polymers
• Nylon was first made by Wallace Carothers in the
  1930s.
• Nylon is widely used in a variety of commercial
  products including stockings, rope, guitar
  strings, fire-proof clothing.

158
Polymerization Reactions

• Condensation Polymers
• Nylon 66 formation

159
Polymerization Reactions
160
Synthesis Question

• TNT, the explosive ingredient in dynamite, has
  the correct name of 2,4,6-trinitrotoluene. Draw
  the structure of TNT.

161
Synthesis Question
162
Group Question

• Aerobic respiration produces carbon dioxide and
  water as its end products. Anaerobic respiration
  has different end products. What are the end
  products of anaerobic respiration? How could you
  easily detect that someone has switched from
  aerobic to anaerobic respiration?

163
End of Chapter 27

• There are more organic compounds than any other
  type of chemical species.