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Carbon

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Title: Carbon


1
Chapter 22
  • Carbon Hydrocarbons

2
Chapter 22 Vocabulary
  • Diamond
  • Graphite
  • Fullerenes
  • Delocalized electrons
  • Organic compounds
  • Catenation
  • Hydrocarbons
  • Isomers
  • Structural formula
  • Structural isomers
  • Geometric isomers
  • Saturated hydrocarbon
  • Alkanes
  • Cycloalkanes
  • Alkyl groups
  • Natural gas
  • Petroleum
  • Unsaturated hydrocarbons
  • Alkynes
  • Aromatic hydrocarbons
  • benzene

3
Chapter 22 Vocabulary
  • Diamond is a colorless, crystalline, solid form
    of carbon
  • Graphite is a soft, black, crystalline form of
    carbon that is a fair conductor of electricity
  • Fullerenes are dark colored solids made of
    spherically networked carbon atom cages.
  • Delocalized electrons are electrons shared by
    more than two atoms
  • Organic compounds covalently bonded compounds
    containing carbon, excluding carbonates and
    oxides.
  • Catenation the covalent bonding of an element to
    itself to form chains or rings.
  • Hydrocarbons are composed of only carbon and
    hydrogen they are the simplest organic
    compounds.
  • Compounds that have the same molecular formula
    but different structures are called isomers.
  • Structural formula indicates the number and types
    of atoms present in a molecule and also shows the
    bonding arrangement of the atoms.

4
Chapter 22 Vocabulary
  • Structural isomers are isomers in which the atoms
    are bonded together in different orders.
  • Geometric isomers are isomers in which the order
    of atom bonding is the same but the arrangement
    of atoms in space is different.
  • Saturated hydrocarbons are hydrocarbons in which
    each carbon atom in the molecule forms four
    single covalent bonds with other atoms.
  • Hydrocarbons that contain only single bonds are
    alkanes.
  • Cycloalkanes are alkanes in which the carbon
    atoms are arranged in a ring, or cyclic,
    structure.
  • Alkyl groups are groups of atoms that are formed
    when one hydrogen atom is removed from an alkane
    molecule
  • Natural gas is a fossil fuel composed primarily
    of alkanes containing one to four carbon atoms
  • Petroleum is a complex mixture of different
    hydrocarbons that varies greatly in composition.
  • Unsaturated hydrocarbons are hydrocarbons in
    which not all carbon atoms have four single
    covalent bonds.

5
Chapter 22 Vocabulary
  • Structural isomers are isomers in which the atoms
    are bonded together in different orders.
  • Geometric isomers are isomers in which the order
    of atom bonding is the same but the arrangement
    of atoms in space is different.
  • Alkenes are hydrocarbons that contain double
    covalent bonds.
  • Hydrocarbons with triple covalent bonds are
    alkynes.
  • Aromatic hydrocarbons are hydrocarbons with six
    membered carbon rings and delocalized electrons
  • Benzene is the primary aromatic hydrocarbon

6
Alkanes and Aromatic Hydrocarbons
  • Organic Compounds
  • Bonding in Hydrocarbons
  • Naming Alkanes
  • Properties of Alkanes

7
Organic Chemistry and Hydrocarbons
  • _________ originally meant chemicals that came
    from ______________.
  • 1828 German chemist Friedrich Wohler synthesized
    urea in a lab
  • Today, organic chemistry is the chemistry of
    virtually all compounds containing the element
    ___________.

8
Friedrich Wohler 1800 1882 Used inorganic
substances to synthesize urea, a carbon compound
found in urine. This re-defined organic chemistry.
9
Organic Chemistry and Hydrocarbons
  • Over a million organic compounds, with numerous
    properties
  • Why so many? Carbons unique bonding ability!
  • Lets start with the simplest of the organic
    compounds Hydrocarbons

10
Organic Compounds
  • Contain _________________
  • Have ______________ bonds
  • Have low _____________ points
  • Have low _______________ points
  • Burn in air (oxygen)
  • Are soluble in _____________ solvents
  • Form large ________________

11
Alkanes
  • Contain ______ and _________ only
  • Contain ____________ bonds C-C
  • Have _____ bonds to every carbon (C) atom
  • Are ________________

12
Alkanes
Structural Formulas
  • Show the bonds between each of the atoms
  • H H
  • ? ?
  • H ? C ? H H C H
  • ? ?
  • H H
  • CH4 - methane

13
Alkanes
Structural Formulas
  • H H Condensed Structural
    Formulas
  • H C C H CH3 CH3
  • H H Ethane
  • H H H
  • H C C C H CH3 CH2 CH3
  • H H H Propane

14
Alkanes
Structural Formulas
  • H H H
  • H C C C H
  • H H H
  • CH3 CH2 CH3
  • CH3CH2CH3

Structural Formula
Condensed Structural Formula
Condensed Formula
15
Alkanes
Structural Formulas
Examples
Condensed__________________
_____________ formula
16
Alkanes
17
Organic Naming Prefixes
18
Naming Alkanes
  • Name carbons Structural Formula
  • ____ane 1 CH4
  • ____ane 2 CH3CH3
  • ____ane 3 CH3CH2CH3
  • ____ane 4 CH3CH2CH2CH3
  • ____ane 5 CH3CH2CH2CH2CH3

19
Naming Alkanes
  • Name carbons Structural Formula
  • ___ane 6
    CH3CH2CH2CH2CH2CH3
  • ____ane 7 CH3CH2CH2CH2CH2CH2C
    H3
  • ___ane 8 CH3CH2CH2CH2CH2CH2CH2CH3
  • ___ane 9 CH3 CH2 CH2CH2CH2CH2CH2CH2CH3
  • ___ane 10 CH3CH2CH2CH2CH2CH2CH2CH2CH2CH3

20
Practice Problems
  • A. What is the condensed formula for
  • H H H H
  • H C C C C H
  • H H H H
  • B. What is its molecular formula?
  • C. What is its name?

21
Reactions of Alkanes
  • Combustion
  • alkane O2 CO2 H2O heat

Combustion In the Cell
  • Metabolic oxidation is combustion
  • C6H12 O6 6O2 6CO2 6H2O heat
  • glucose

22
Combustion Example
  • Complete the combustion reaction for
  • C3H8 O2
  • Balance your equation

23
Practice Problem
  • Complete and balance the reaction for the
    complete combustion of C7H16

24
Alkanes and Aromatic Hydrocarbons
  • Branched Alkanes
  • Structural Formulas

25
Alkyl Groups
  • Branches on carbon chains
  • H
  • H C CH3 _________
  • H
  • H H
  • H C C CH3CH2 _________
  • H H

26
Alkyl Groups
27
Branched Alkanes
  • CH3
  • CH3CHCH3
  • methyl groups
  • CH3 CH3
  • CH3CHCH2CHCH3

28
Naming Branched Alkanes
  • CH3 methyl branch
  • CH3CH2CH2CHCH2CH3
  • 6 5 4 3 2 1 Count


29
Naming Branched Alkanes
  • CH3 methyl branch
  • CH3CH2CH2CHCH2CH3
  • 6 5 4 3 2 1 Count
  • 3-Methylhexane
  • on third C CH3 six carbon chain
  • group

30
Naming Alkanes
31
Naming Alkanes Example
32
Naming Practice Problems
  • A. CH3 CH3
  • CH3CHCH2CHCH3
  • B. CH3 CH3
  • CH3CH2CHCH2CCH2CH3
  • CH3

33
Practice Problems
  • Write a condensed structure for
  • A. 3,4-dimethylheptane
  • B. 2,2-dimethyloctane

34
Isomers
  • Same _____________ formula
  • Same ________ and ______ of atoms
  • Different ________________ of atoms
  • Also have different properties, such as b.p.,
    m.p., and reactivity

35
Structural Isomers
___________________ are isomers in which the
atoms are bonded together in different orders.
36
Geometric Isomers
  • ____________________ are isomers in which the
    order of atom bonding is the same but the
    arrangement of atoms in space is different.

37
Examples of Isomers
  • The formula C4H10 has two different structures
  • CH3
  • CH3CH2CH2CH3 CH3CHCH3
  • Butane 2-methylpropane
  • When a CH3 is is used to form a branch, it makes
    a new isomer of C4H10.




38
Practice Problem
  • Write 3 isomers of C5H12 and name each.

39
Practice Problems
  • Write the structural formulas of 3 isomers that
    have the formula C5H12. Name each.

40
Alkanes and Aromatic Hydrocarbons
  • Cycloalkanes
  • Aromatic Hydrocarbons

41
Cycloalkanes
  • _____________ CH2
  • CH2 CH2
  • _____________ CH2 CH2
  • CH2 CH2

42
More Cycloalkanes
  • ____________ CH2
  • CH2 CH2
  • CH2 CH2
  • ____________
  • CH2
  • CH2 CH2
  • CH2 CH2
  • CH2

43
Naming Cycloalkanes with Side Groups
  • Number of Naming
  • side groups
  • One Side group name goes in front of the
    cycloalkane name.
  • Two or more Number the ring in the direction
    that gives the lowest numbers to the side
    groups.

44
Cycloalkanes with Side Groups
45
Practice Problems
46
Aromatic Compounds and Benzene
  • ___________________ contain __________.
  • Benzene, C6H6 , is represented as a ______
    carbon ring with _____ double bonds.
  • Two possible can be drawn to show benzene in
    this form.

47
Benzene Structure
  • The structures for ______________ can also be
    written as a single structure where the
    alternating double bonds are written as a circle
    within the ring.
  • Benzene
  • structure

48
Aromatic Compounds in Nature and Health
  • Many aromatic compounds are common in
    _____________ and in _____________.

49
Naming Aromatic Compounds
  • Aromatic compounds are named with benzene as the
    parent chain. One side group is named in front of
    the name benzene.
  • methylbenzene chlorobenzene
  • (toluene)

50
Naming Aromatic Compounds
  • When two groups are attached to benzene, the
    ring is numbered to give the lower numbers to the
    side groups. The prefixes ortho (1,2), meta
    (1,3-) and para (1,4-) are also used.

51
Some Common Names
  • Some substituted benzene rings also use a common
    name. Then naming with additional more side
    groups uses the ortho-, meta-, para- system.

52
Practice Problems
  • Write the structural formulas for each of the
    following
  • A. 1,3-dichlorobenzene
  • B. Ortho-chlorotoluene

53
Practice Problems
  • Select the names for each structure
  • 1. Chlorocyclohexane
  • 2. Chlorobenzene
  • 3. 1-chlorobenzene
  • 1. Meta-methyltoluene
  • 2. Meta-dimethylbenzene
  • 3. 1,3-dimethylbenzene

54
Haloalkanes, Alkenes, and Alkynes
  • Alkenes and Alkynes

55
Saturated and Unsaturated Compounds
  • Saturated compounds (alkanes) have the maximum
    number of hydrogen atoms attached to each carbon
    atom
  • Unsaturated compounds have fewer hydrogen atoms
    attached to the carbon chain than alkanes
  • Unsaturated compounds contain double or triple
    bonds alkenes alkynes

56
Alkenes
  • Carbon-carbon _____________ bonds
  • Names end in -___________
  • H2CCH2 ethene (ethylene)
  • H2CCH-CH3 propene (propylene)
  • cyclohexene

57
Alkenes
58
Alkynes
  • Carbon-carbon __________ bonds
  • Names end in -_________
  • HC?CH ethyne(acetylene)
  • HC?C-CH3 propyne

59
Naming Alkenes and Alkynes
  • When the carbon chain has 4 or more C atoms,
    number the chain to give the lowest number to
    the double or triple bond.
  • 1 2 3 4
  • CH2CHCH2CH3 1-butene
  • CH3CHCHCH3 2-butene
  • CH3CH?CHCH3 2-butyne

60
Naming Alkenes
Slide 35
61
Naming Alkenes
62
Naming Alkynes
Slide 35
63
Practice Problem
  • Write the names for each of the following
    unsaturated compounds
  • A. CH3CH2C?CCH3
  • CH3
  • B. CH3CCHCH3 C.

64
Hydrogenation
  • Adds a hydrogen atom to each carbon atom of a
    double bond
  • H H H H
  • Ni
  • HCCH H2 HCCH
  • H H
  • ethene ethane

65
Products of Hydrogenation
  • Adding H2 to vegetable oils produces compounds
    with higher melting points
  • Margarines
  • Soft margarines
  • Shortenings (solid)

66
Trans Fats
  • In the US, it is estimated that 2-4 of our total
    Calories is in the form of trans fatty acid.
  • trans fatty acids behave like saturated fatty
    acids in the body.
  • Several studies reported that trans fatty acids
    raise LDL-cholesterol. Some studies also report
    that trans fatty acid lower HDL-cholesterol
  • The trans fatty acids controversy will continue
    to be debated.

67
Unsaturated Fatty Acids
  • Fatty acids in vegetable oils are omega-6 acids
    (the first double bond occurs at carbon 6
    counting from the methyl group)
  • A common omega-6 acid is linoleic acid
  • CH3CH2CH2CH2CH2CHCHCH2CHCH(CH2)7COOH
  • 6
  • linoleic acid, a fatty acid

68
Trans Fats
  • In vegetable oils, the unsaturated fats usually
    contain cis double bonds.
  • During hydrogenation, some cis double bonds are
    converted to trans double bonds (more stable)
    causing a change in the fatty acid structure
  • If a label states partially or fully
    hydrogenated, the fats contain trans fatty
    acids.

69
Fats and Atheroschlerosis
  • Inuit people of Alaska have a high fat diet and
    high blood cholesterol levels, but a very low
    occurrence of atherosclerosis and heart attacks.
  • Fat in the Intuit diet was primarily from fish
    such as salmon, tuna and herring rather than from
    land animals (as in the American diet).

70
Omega-3 Fatty Acids
  • Fatty acids in the fish oils are mostly the
    omega-3 type (first double bond occurs at the
    third carbon counting from the methyl group).
  • linolenic acid 18 carbon atoms
  • CH3CH2CHCHCH2CHCHCH2CHCH(CH2)7COOH
  • ?
  • eicosapentaenoic acid (EPA) 20 carbon atoms
    CH3CH2(CHCHCH2)5(CH2)2COOH

71
Atherosclerosis
  • Plaques of cholesterol adhere to the walls of the
    blood vessels
  • Blood pressure rises as blood squeezes through
    smaller blood vessels
  • Blood clots may form
  • Omega-3 fatty acids decrease the sticking of
    blood platelets (fewer blood clots)
  • Omega-3 fatty acids can increase bleeding time

72
Questions
  • (1) Ture or (2) False
  • A. ____ There are more unsaturated fats in
    vegetable oils.
  • B. ____ Vegetable oils have more omega-3 oils
    than found in fish.
  • C. ____ Hydrogenation of oils converts some
    cis-double bonds to trans- double bonds.
  • D. ____ Animal fats have more saturated fats.

73
Natural Gas
  • Fossil fuels provide much of the worlds energy
  • Natural gas and petroleum contain mostly the
    aliphatic (or straight-chain) hydrocarbons
    formed from marine life buried in sediment of the
    oceans
  • Natural gas is an important source of alkanes of
    low molecular mass

74
Natural Gas
  • Natural gas is typically
  • 80 methane, 10 ethane, 4 propane, and 2
    butane with the remainder being nitrogen and
    higher molar mass hydrocarbons
  • also contains a small amount of He, and is one of
    its major sources

75
Natural Gas
  • Natural gas is prized for combustion, because
    with adequate oxygen, it burns with a hot, clean
    blue flame
  • CH4 2O2 ? CO2 2H2O heat
  • Incomplete burning has a yellow flame, due to
    glowing carbon parts, as well as making carbon
    monoxide

76
Petroleum
  • The compounds found in petroleum (or crude oil)
    are more complex than those in natural gas
  • Usually straight-chain and branched-chain
    alkanes, with some aromatic compounds also
  • Crude oil must be refined (separated) before
    being used

77
Petroleum
  • It is separated by distillation into fractions,
    according to boiling pt.
  • Fractions containing higher molar mass can be
    cracked into more useful shorter chain
    components, such as gasoline and kerosene
  • involves catalyst and heat
  • starts materials for plastics and paints

78
Citations
  • http//www.karentimberlake.com/
  • http//www.cottonchemistry.bizland.com/chem/chemno
    tes1.htm
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