Other Organic Compounds

1
CHAPTER 21

• Other Organic Compounds

2
Functional Groups

• Functional Group
• An atom or group of atoms that is responsible for
  the specific properties of an organic compound.
• The bonds within functional groups are often the
  site of chemical reactivity.

3
Classes of Organic Compounds

• Alcohols
• Organic compounds that contain one or more
  hydroxyl groups.
• The general formula for alcohols
• R-OH
• Systematic names of organic compounds indicate
  which functional groups are present in a molecule.

4
Classes of Organic Compounds

• Rules for naming alcohols
• 1. Name the parent compound.
• Locate the longest continuous chain of carbon
  atoms that contains the hydroxyl group.
• If there is only one hydroxyl group, add the
  suffix -ol to the prefix corresponding to the
  number of carbon atoms in this chain.

5
Classes of Organic Compounds

• If there is more than one hydroxyl group, use the
  full name of the corresponding alkane and add the
  suffix modified to indicate the number of
  hydroxyl groups.
• -diol 2, -triol 3, and so on.
• 2. Number the carbon atoms in the parent chain.
• Number so the hydroxyl group has the lowest
  possible number.

6
Classes of Organic Compounds

• 3. Insert position numbers.
• Place the hydroxyl position number or numbers
  immediately before the name of the parent
  alcohol.
• 4. Punctuate the name.
• Separate numbers from the name with hyphens, and
  if there is more than one position number,
  separate with commas.

7
Classes of Organic Compounds

• Example
• Name the following alcohol.

8
Classes of Organic Compounds

• Example
• Name the following alcohol

9
Classes of Organic Compounds

• Example
• Name the following alcohol

10
Classes of Organic Compounds

• Example
• Draw condensed structures for the following
  alcohols
• Methanol
• 2-Propanol
• 1,2-Propanediol
• 1,2-Ethanediol

11
Classes of Organic Compounds

• You can read about the properties and uses of
  alcohols on pages 664 - 666.

12
Classes of Organic Compounds

• Alkyl Halides
• Organic compounds in which one or more halogen
  atoms - fluorine, chlorine, bromine, or iodine -
  are substituted for one or more hydrogen atoms in
  a hydrocarbon.
• General formula for Alkyl Halides
• R-X

13
Classes of Organic Compounds

• Rules for naming alkyl halides
• 1. Name the parent compound.
• Locate the longest continuous chain of carbon
  atoms that contains the halogen.
• Add the prefixes for the attached halogen atoms
  to the name of the alkane corresponding the the
  number of carbon atoms in the chain.

14
Classes of Organic Compounds

• The prefixes to use are
• Fluoro- fluorine
• Chloro- chlorine
• Bromo- bromine
• Iodo- iodine
• If more than one kind of halogen atom is present,
  add the halogen prefixes in alphabetical order.

15
Classes of Organic Compounds

• If there is more than one atom of the same
  halogen, add the appropriate prefix (di-, tri-,
  and so on).
• 2. Number the carbon atoms in the parent chain.
• Number the carbon-atom chain so that the sum of
  the halogen numbers is as low as possible.

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Classes of Organic Compounds

• If there are different halogen atoms in
  equivalent positions, give the lower number to
  the one that comes first in alphabetical order.
• 3. Insert position numbers.
• Place the halogen position number or numbers
  immediately before the halogen prefixes.
• 4. Punctuate the name.

17
Classes of Organic Compounds

• Example
• Name the following alkyl halide

18
Classes of Organic Compounds

• Example
• Name the following alkyl halide

19
Classes of Organic Compounds

• Example
• Name the following alkyl halide

20
Classes of Organic Compounds

• Examples
• Draw condensed structures for the following alkyl
  halides
• 2-iodopropane
• 1,1,1,2-tetrabromobutane
• 1,1-difluoropropane
• Dichloromethane

21
Classes of Organic Compounds

• You can read about the properties and uses of
  alkyl halides on pages 668 - 669.

22
Classes of Organic Compounds

• Ethers
• Organic compounds in which two hydrocarbon groups
  are bonded to the same atom of oxygen.
• General formula for ethers
• R-O-R
• In this formula, R may be the same hydrocarbon
  group as R or a different one.

23
Classes of Organic Compounds

• Rules for naming ethers
• 1. Name the parent compound.
• The word ether will come at the end of the name.
• 2. Add the names of the alkyl groups.
• If there are two different alkyl groups, arrange
  the names in alphabetical order in front of the
  word ether.

24
Classes of Organic Compounds

• If both alkyl groups are the same, the prefix
  di- is added to the name of the alkyl group in
  front of the word ether.
• 3. Leave appropriate spaces in the name.
• There should be spaces between the names of the
  alkyl groups and the word ether.

25
Classes of Organic Compounds

• Example
• Name the following ether

26
Classes of Organic Compounds

• Example
• Name the following ether

27
Classes of Organic Compounds

• Example
• Name the following ether

28
Classes of Organic Compounds

• Example
• Name the following ether

29
Classes of Organic Compounds

• Example
• Draw condensed structures for the following
  ethers
• Dimethyl ether
• Ethyl propyl ether
• Dicyclohexyl ether
• Butyl methyl ether

30
Classes of Organic Compounds

• You can read about the properties and uses of
  ethers on page 671.

31
Classes of Organic Compounds

• Aldehydes and Ketones
• Aldehydes and Ketones contain the carboxyl group
  shown below
• The difference between aldehydes and ketones is
  the location of the carboxyl group.

32
Classes of Organic Compounds

• Aldehydes
• Organic compounds in which the carboxyl group is
  attached to a carbon atom at the end of a
  carbon-atom chain.
• General formula for aldehydes

33
Classes of Organic Compounds

• Rules for naming aldehydes
• 1. Name the parent compound.
• Locate the longest continuous chain that contains
  the carboxyl group.
• Add the suffix -al to the prefix corresponding
  to the number of carbon atoms in this chain.

34
Classes of Organic Compounds

• Example
• Name the following aldehyde

35
Classes of Organic Compounds

• Example
• Name the following aldehyde

36
Classes of Organic Compounds

• Example
• Name the following aldehyde

37
Classes of Organic Compounds

• Example
• Draw condensed structures for the following
  aldehydes
• Butanal
• Hexanal
• Octanal
• Heptanal

38
Classes of Organic Compounds

• Ketones
• Organic compounds in which the carboxyl group is
  attached to carbon atoms within the chain.
• General formula for ketones

39
Classes of Organic Compounds

• Rules for naming ketones
• 1. Name the parent compound.
• Locate the longest continuous chain that contains
  the carboxyl group.
• Add the suffix -one to the prefix corresponding
  to the number of carbon atoms in this chain.

40
Classes of Organic Compounds

• 2. Number the carbon atoms in the chain.
• Number the carbon atoms in the chain so that the
  carbon atom in the carboxyl group has the lowest
  possible number.
• 3. Insert position numbers.
• 4. Punctuate the name.

41
Classes of Organic Compounds

• Example
• Name the following ketone

42
Classes of Organic Compounds

• Example
• Name the following ketone

43
Classes of Organic Compounds

• Example
• Name the following ketone

44
Classes of Organic Compounds

• Example
• Draw condensed structures for the following
  ketones
• 3-heptanone
• Cyclohexanone
• 2-octanone
• 2-hexanone

45
Classes of Organic Compounds

• You can read about the properties and uses
  aldehydes and ketones on page 673.

46
Classes of Organic Compounds

• Carboxylic Acids
• Organic compounds that contain the carboxyl
  functional group.
• The carboxyl group always comes at the end of a
  carbon-atom chain.
• General formula for carboxylic acids

47
Classes of Organic Compounds

• Rules for naming carboxylic acids
• 1. Name the parent compound.
• Locate the longest continuous chain that contains
  the carboxyl group.
• If there is only one carboxyl group, add the
  suffix -oic acid to the prefix corresponding to
  the number of carbon atoms in this chain.

48
Classes of Organic Compounds

• If there is more than one carboxyl group, use the
  full name of the corresponding alkane, and add
  the suffix modified to indicate the number of
  carboxyl groups.
• For example
• -dioic acid 2
• -trioic acid 3

49
Classes of Organic Compounds

• Example
• Name the following carboxylic acid

50
Classes of Organic Compounds

• Example
• Name the following carboxylic acid

51
Classes of Organic Compounds

• Example
• Name the following carboxylic acid

52
Classes of Organic Compounds

• Example
• Draw condensed structures for the following
  carboxylic acids.
• Ethanoic acid
• Propanedioic acid
• Heptanoic acid
• 1,4-butanedioic acid

53
Classes of Organic Compounds

• You can read about the properties and uses of
  carboxylic acids on page 674.

54
Classes of Organic Compounds

• Esters
• Organic compounds with carboxylic acid groups in
  which the hydrogen of the hydroxyl group has been
  replaced by an alkyl group.
• General formula for esters

55
Classes of Organic Compounds

• Rules for naming esters
• 1. Name the parent compound.
• Name the carboxylic acid from which the ester was
  formed.
• Change the -oic acid ending in the name of this
  acid to -oate.
• This gives the second half of the esters name.

56
Classes of Organic Compounds

• 2. Add the name of the alkyl group.
• Identify the name of the alkyl group that has
  replaced the hydrogen of the hydroxyl group.
• Add the name of the alkyl group to the front of
  the name.

57
Classes of Organic Compounds

• 3. Leave appropriate spaces in the name.
• There should be a space between the name of the
  alkyl group and the name of the parent compound.

58
Classes of Organic Compounds

• Example
• Name the following ester

59
Classes of Organic Compounds

• Example
• Name the following ester

60
Classes of Organic Compounds

• Example
• Draw condensed structures for the following
  esters
• Butyl ethanoate
• Ethyl methanoate
• Propyl Propanoate
• Methyl Butanoate

61
Classes of Organic Compounds

• You can read about the properties and uses of
  esters on page 676.

62
Classes of Organic Compounds

• Amines
• Organic compounds that can be considered to be
  derivatives of ammonia, NH3.
• General formula for amines

63
Classes of Organic Compounds

• Rules for naming amines
• 1. Name the parent compound.
• The end of the name will be -amine.
• 2. Add the names of the alkyl groups.
• Arrange the names of the alkyl groups attached to
  the nitrogen atom in alphabetical order.

64
Classes of Organic Compounds

• Add the prefixes di- or tri- in front of the
  group name if two or three, respectively, of the
  same kind are included in the amine.
• Combine these names in front of -amine to form
  one word.

65
Classes of Organic Compounds

• Example
• Name the following amines

66
Classes of Organic Compounds

• Example
• Name the following amines

67
Classes of Organic Compounds

• Example
• Name the following amines

68
Classes of Organic Compounds

• Example
• Draw condensed structures for the following
  amines
• Dimethylpropylamine
• Dibutylethylamine
• Butyl amine
• Diethylmethylamine

69
Classes of Organic Compounds

• Amines are categorized as primary, secondary, or
  tertiary, depending on the number of hydrogen
  atoms that have been replaced in the ammonia
  molecule.
• Primary amine
• One hydrogen atom of an ammonia molecule has been
  replaced by an alkyl group.

70
Classes of Organic Compounds

• Secondary amine
• Two hydrogen atoms of an ammonia molecule have
  been replaced by alkyl groups.
• Tertiary amine
• All three hydrogen atoms of an ammonia molecule
  have been replaced by alkyl groups.

71
Classes of Organic Compounds

• You can read about the properties and uses of
  amines on pages 677 - 679.

72
Organic Reactions

• Substitution Reactions
• Reaction in which one or more atoms replace
  another atom or group of atoms in a molecule.
• The reaction between an alkane and a halogen is
  an example of a substitution reaction.

73
Organic Reactions

• Additional compounds can be formed by replacing
  the other hydrogen atoms remaining in the methane
  molecule.
• The products are dichloromethane,
  trichloromethane, and tetrachloromethane.

74
Organic Reactions

• CFCs are formed by further substitution
  reactions between chloroalkanes and HF.

75
Organic Reactions

• Addition Reactions
• Reaction in which an atom or molecule is added to
  an unsaturated molecule and increases the
  saturation of the molecule.
• A common type of addition reaction is
  hydrogenation.
• In hydrogenation, one or more hydrogen atoms are
  added to an unsaturated molecule.

76
Organic Reactions

• Vegetable oils contain unsaturated fatty acids,
  long chains of carbon atoms with many double
  bonds.
• Example
• When hydrogen gas is blown through an oil,
  hydrogen atoms may add to the double bonds in the
  oil molecule.

77
Organic Reactions

• When you see the word hydrogenated on a food
  product, you know that an oil has been converted
  to a fat by this process.

78
Organic Reactions

• Condensation Reactions
• Reaction in which two molecules or parts of the
  same molecule combine.
• A small molecule, such as water, is usually
  removed during the reaction.
• An example is the reaction between two amino
  acids, which contain both amine and carboxyl
  groups.

79
Organic Reactions
80
Organic Reactions

• Elimination Reactions
• Reaction in which a simple molecule, such as
  water or ammonia, is removed from adjacent carbon
  atoms of a larger molecule.
• A simple example of an elimination reaction is
  the heating of ethanol in the presence of
  concentrated sulfuric acid.

81
Organic Reactions

• Another example of an elimination reaction is the
  dehydration of sucrose with concentrated sulfuric
  acid.

82
Polymers

• Polymers are large molecules made of many small
  units joined to each other through organic
  reactions.
• The small units are monomers.
• A polymer can be made from identical or different
  monomers.
• A polymer made from two different monomers is a
  copolymer.

83
Polymers

• Some of the most common natural polymers include
  starch, cellulose, and proteins.
• Some synthetic polymers are plastics and
  synthetic fibers.
• Polymers can be classified by the way they behave
  when heated.
• A thermoplastic polymer melts when heated and can
  be reshaped many times.

84
Polymers

• A thermosetting polymer does not melt when heated
  but keeps its original shape.
• The thermal properties of polymers can be
  explained by whether their structure is linear,
  branched, or cross-linked.

85
Polymers

• Linear polymers
• Free to move. They slide back and forth against
  each other easily when heated.
• Linear polymers are thermoplastic.

86
Polymers

• Branched Polymers
• Contain side chains that prevent the molecules
  from sliding across each other easily.
• More heat is required to melt a branched polymer
  than a linear polymer.
• Branched polymers are thermoplastic.

87
Polymers

• Cross-Linked Polymers
• Adjacent molecules in the polymer have formed
  bonds with each other.
• Individual molecules are not able to slide past
  each other when heated.
• Cross-linked polymers retain their shape when
  heated and a thermosetting.

88
Polymers

• An addition polymer is a polymer formed by chain
  addition reactions between monomers that contain
  a double bond.
• For example, molecules of ethene can polymerize
  with each other to form polyethene (polyethylene).

89
Polymers

• The letter n shows that the addition reaction can
  be repeated multiple times to form a polymer n
  monomers long.
• In fact, this reaction can be repeated hundreds
  or thousands of times.

90
Polymers

• Forms of Polyethylene and related polymers
• 1. High-density polyethylene (HDPE)
• A linear polymer.
• It has a high density because linear molecules
  can pack together closely.
• One use of HDPE is in plastic containers such as
  milk and juice bottles because HDPE tends to
  remain stiff and rigid.

91
Polymers

• 2. Low-density polyethylene (LDPE)
• Tends to be less rigid than HDPE and is used in
  plastic bags.
• 3. Cross-linked polyethylene (CLPE)
• Is even tougher and more rigid than HDPE.
• It is used for objects that need to be very
  strong.

92
Natural and Synthetic Rubber

• Natural rubber is produced by the rubber tree,
  Hevea brasiliensis.
• It is formed as the result of an addition
  reaction.
• The monomer in this reaction is
  2-methyl-1,3-butadiene, commonly called isoprene.

93
Natural and Synthetic Rubber

• Natural rubber has relatively few practical
  applications.
• When warmed, individual molecules of polyisoprene
  slide easily back and forth past each other.
• The rubber gets soft and gooey, making it useless
  for many purposes.

94
Natural and Synthetic Rubber

• In 1839, Charles Goodyear found that the addition
  of sulfur to molten rubber produces a material
  that remains very hard and tough when cooled.
• He called this process vulcanization.
• Vulcanization
• Is a cross-linking process between adjacent
  polyisoprene molecules that occurs when the
  molecules are heated with sulfur atoms.

95
Natural and Synthetic Rubber

• Vulcanization enabled rubber to be used in a wide
  variety of products, such as hoses, rainwear, and
  tires.
• In the first year of WWII, Japan controlled large
  portions of SE Asia, where most of the worlds
  natural rubber is obtained.
• The US and other Allied nations were forced to
  develop synthetic substitutes for natural rubber.

96
Natural and Synthetic Rubber

• Some synthetic rubbers have superior properties
  to natural rubber.
• Styrene-butadiene rubber, SBR, is a copolymer
  made in the reaction between styrene and
  butadiene.
• SBR is mainly used in tires.
• Another subsitute, neoprene, is formed during the
  polymerization of 2-chlorobutadiene.

97
Condensation Polymers

• A condensation polymer is a polymer formed by
  condensation reactions.
• Monomers of condensation polymers must contain
  two functional groups.
• This allows each monomer to link with two other
  monomers by condensation reactions.
• Condensation polymers are usually copolymers with
  two monomers in an alternating order.

98
Condensation Polymers

• One example of a condensation polymer is nylon
  66.
• Nylon 66 was invented by Dr. Wallace Carothers in
  1935 and is one of the most widely used of all
  synthetic polymers.
• Nylon 66 is an example of a polyamide polymer
  (presence of the amide group).

99
Condensation Polymers

• Polyamides have become commercial successes
  because they can be fabricated into so many
  different forms.
• Examples
• They can be knitted and woven to make stockings
  and other types of clothing.
• When treated with radiation, extensive
  corss-linking occurs and the final product
  becomes very rigid and strong (Kevlar).

100
Condensation Polymers

• Polyesters are another common type of
  condensation polymer.
• Polyethylene terephthalate, PET, is a polyester
  formed when terephthalic acid reacts with
  ethylene glycol.
• PET has a vast range of uses, such as in tires,
  photographic film, food packaging, and bottles.

101
Condensation Polymers

• Its best known use may be as a fiber called
  polyester, which is widely used in permanent
  press clothing.
• Polyester fabric is made wrinkle resistant by the
  cross-linking of its polymer strands.