1. Hydrocarbon Compounds
22.1 Hydrocarbons
22.2 Unsaturated Hydrocarbons
22.3 Isomerism
22.4 Hydrocarbon Rings
22.5 Hydrocarbons from Earth’s Crust
Updated 11/11/2018
Created by C. Ippolito July 2007

2. Created by C. Ippolito July 2007
Hydrocarbons
Objectives
Describe the relationship between the number of valence electrons and bonding in carbon
Define and describe alkanes
Relate the polarity of hydrocarbons to their solubility
Updated 11/11/2018
Created by C. Ippolito July 2007

3. Organic Chemistry and Hydrocarbons
originally compounds thought to be made only in living things
now study of compounds with BOTH carbon and hydrogen
Hydrocarbons
simplest organic compounds
contain only carbon and hydrogen
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Alkanes
only single covalent bonds between carbons
Saturated Hydrocarbons
contain the maximum number of hydrogen atoms per carbon atom
Straight Chain Alkanes
homologous series – group of compounds that have a constant incremental change
1 = meth-
3 = prop-
5 = pent-
7 = hept-
9 = non-
2 = eth-
4 = but-
6 = hex-
8 = oct-
10 = dec-
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Created by C. Ippolito July 2007

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Formulas
Molecular Formula – C4H10
Structural Formula –
Condensed Structural Formulas
CH3-CH2-CH2-CH3
CH3CH2CH2CH3
CH3(CH2)2CH3
Carbon Skeleton – C-C-C-C
Line Angle Formula -
section 1
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Created by C. Ippolito July 2007

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Branched Chains
Parent Chain
longest continuous carbon chain
Substituents
atoms or atom groups replacing a hydrogen atom
Alkyl Groups
hydrocarbon substituents
CH3― methyl group
CH3CH2― ethyl group
CH3CH2CH2― propyl group
Updated 11/11/2018
Created by C. Ippolito July 2007

7. IUPAC Naming Rules for Alkanes
Find longest chain (parent)
Number carbons and use root name with –ane ending
Add numbers to substituent groups
Use prefixes for multiple appearances of same group
List substituents in alphabetical order
Use punctuation but no spaces
Updated 11/11/2018
Created by C. Ippolito July 2007

8. Naming Branched Alkanes
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9. Drawing Branched-Chain Alkanes
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Properties of Alkanes
Hydrocarbons are NONPOLAR
weak van der Waals forces
low mass tend to be gases or liquids with low boiling points
insoluble in water
Updated 11/11/2018
Created by C. Ippolito July 2007

11. Unsaturated Hydrocarbons
Objectives
Describe the difference between unsaturated and saturated hydrocarbons
Distinguish between the structures of alkenes and alkynes
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Alkenes
contain one or more carbon-carbon double covalent bond
Unsaturated Hydrocarbon
contain less than the maximum number of hydrogen per carbon atom
Updated 11/11/2018
Created by C. Ippolito July 2007

13. IUPAC Naming Rules for Alkenes
Find longest chain with double bond (parent)
Number carbons and use root name with ending –ene so that double bond has lowest number possible
Add numbers to substituent groups
Use prefixes for multiple appearances of same group
List substituents in alphabetical order
Use punctuation but no spaces
Updated 11/11/2018
Created by C. Ippolito July 2007

14. Created by C. Ippolito July 2007
Alkenes
contain one or more carbon-carbon triple covalent bond
Unsaturated Hydrocarbon
contain less than the maximum number of hydrogen per carbon atom
Updated 11/11/2018
Created by C. Ippolito July 2007

15. IUPAC Naming Rules for Alkynes
Find longest chain with triple bond (parent)
Number carbons and use root name with ending –yne so that double bond has lowest number possible
Add numbers to substituent groups
Use prefixes for multiple appearances of same group
List substituents in alphabetical order
Use punctuation but no spaces
Updated 11/11/2018
Created by C. Ippolito July 2007

16. Created by C. Ippolito July 2007
Isomerism
Objectives
Explain why structural isomers have different properties
Describe the conditions under which geometric isomers are possible
Identify optical isomers
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Structural Isomers
compounds with the same molecular formula but different structures
different physical and chemical properties
section 2 May 1 section 3 May 2
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Stereoisomers
atoms joined in same order but positions in space are different
Geometric Isomers
related to rigid double bond
Optical Isomers
asymmetrical carbon
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Geometric Isomers
Geometric Isomers
orientation around rigid double bond
cis configuration
groups on same side of double bond
trans configuration
groups on different sides of double bond
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Optical Isomers
Optical Isomers
four different groups attached to an asymmetric carbon
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21. Objectives Identify cyclic ring structures Describe bonding in benzene
Hydrocarbon Rings
Objectives
Identify cyclic ring structures
Describe bonding in benzene
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Cyclic Hydrocarbons
hydrocarbon chain forms a ring
cyclopropane
cyclobutane
cyclopentane
cyclohexane
section 1 May 3
Updated 11/11/2018
Created by C. Ippolito July 2007

23. Aromatic Hydrocarbons
contains a benzene ring
electrons shared evenly
“resonance”
phenyl group
benzene sub
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Substituted Benzene
dimethyl benzene – 3 isomers
ortho-
1,2 dimethyl benzene
o-xylene
meta-
1,3 dimethyl benzene
m-xylene
para-
1,4 dimethyl benzene
p-xylene
may 3 section 2
Updated 11/11/2018
Created by C. Ippolito July 2007

25. Hydrocarbons from Earth’s Crust
Objectives
Identify three important fossil fuels and describe their origins.
Describe the composition of natural gas, petroleum, and coal.
Describe what happens when petroleum is refined
Updated 11/11/2018
Created by C. Ippolito July 2007

26. Created by C. Ippolito July 2007
Natural Gas
source of alkanes of low molar mass
80% methane
10% ethane
4% propane
CH4(g) + 2O2(g)  CO2(g) + 2H2O(g) + heat
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Petroleum
Fractional Distillation
separation by boiling points
Cracking
heat to form smaller chains from larger ones
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Coal
Classified by its hardness and carbon content
Peat
soft, brown, spongy, fibrous material
high water content
Lignite
harder, less fibrous, 50% carbon
Bituminous Coal
“soft” coal, 70%-80% carbon
Anthracite Coal
“hard” coal, over 80% carbon
Updated 11/11/2018
Created by C. Ippolito July 2007