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Seager
Michael R. Slabaugh
www.cengage.com/chemistry/seager
Chapter 12
Unsaturated Hydrocarbons
Jennifer P. Harris
UNSATURATED HYDROCARBONS
• Unsaturated hydrocarbons contain carbon-carbon multiple
bonds.
• Alkenes contain carbon-carbon double bonds (C=C ).
• Alkynes contain carbon-carbon triple bonds (C≡C).
• Aromatics contain benzene rings.
NAMING ALKENES
• Step 1: Name the longest chain that contains the C=C bond.
Use the IUPAC root and the –ene ending.
• Step 2: Number the longest chain so the C=C bond gets the
lowest number possible.
• Step 3: Locate the C=C bond with the lower-numbered
carbon.
Examples:
1 2 3 4
CH3-CH=CH-CH3
2-butene
6 5 4 3 2 1
CH3-CH2-CH2-CH=CH-CH3
2-hexene
NAMING ALKENES (continued)
• Step 4: Locate and name attached groups.
• Step 5: Combine all the names.
NAMING ALKENES
WITH MULTIPLE DOUBLE BONDS
• Step 1: Follow the same naming instructions for alkenes with
one double bond, except use the endings –diene, – triene,
and the like to denote the number of double bonds.
• Step 2: Indicate the location of all the multiple bonds.
• EXAMPLES:
THE GEOMETRY OF ALKENES
• In C=C bonds, sp2 hybrid orbitals are formed by the carbon
atoms, with one electron left in a 2p orbital. A representation
of sp2 hybridization of carbon:
THE GEOMETRY OF ALKENES (continued)
• During hybridization, two of the 2p orbitals mix with the single
2s orbital to produce three sp2 hybrid orbitals. One 2p orbital
is not hybridized and remains unchanged.
THE GEOMETRY OF ALKENES (continued)
• This gives a planar shape for the sp2 bonding orbitals with
the unhybridized p orbital perpendicular to the plane of the
three sp2 hybridized orbitals.
THE GEOMETRY OF ALKENES (continued)
• The planar geometry of the sp2 hybrid orbitals and the
ability of the 2p electron to form a “pi bond” bridge locks
the C=C bond firmly in place.
THE GEOMETRY OF ALKENES (continued)
• Because there is no free rotation about the C=C bond,
geometric isomerism is possible.
• cis- isomers have two similar or identical groups on the
same side of the double bond.
• trans- isomers have two similar or identical groups on
opposite sides of the double bond.
THE GEOMETRY OF ALKENES (continued)
• Geometric isomers have different physical properties.
PHYSICAL PROPERTIES OF ALKENES
• Similar to alkanes
• Nonpolar
• Insoluble in water
• Soluble in nonpolar solvents
• Less dense than water
• Unpleasant, gasoline-like odors
PHYSICAL PROPERTIES OF ALKENES
ALKENE REACTIONS
• Alkenes are quite chemically reactive.
• Alkene reactions follow the pattern:
• Examples:
THE GEOMETRY OF ALKYNES
• In C≡C bonds, sp hybrid orbitals are formed by the carbon
atoms, with two electrons left in unhybridized 2p orbitals. A
representation of sp hybridization of carbon:
THE GEOMETRY OF ALKYNES (continued)
• During hybridization, one 2p orbital mixes with the single 2s
orbital to produce two sp hybrid orbitals. Two 2p orbitals are
not hybridized and remain unchanged.
• This gives a linear shape for the sp bonding orbitals with the
unhybridized p orbitals perpendicular to the line of the two sp
hybridized orbitals.
THE GEOMETRY OF ALKYNES (continued)
• A carbon-carbon sigma bond forms by the overlap of one sp
hybrid orbital of each carbon atom.
• The other sp hybrid orbital of each carbon atom overlaps with
a 1s orbital of a hydrogen atom to form a carbon-hydrogen
sigma bond.
• The remaining pair of unhybridized p orbitals of each carbon
atom overlap sideways to form a pair of pi bonds between
the carbon atoms.
ALKYNE PROPERTIES
• PHYSICAL PROPERTIES OF ALKYNES
• Similar to alkanes and alkenes
• Nonpolar
• Insoluble in water
• Soluble in nonpolar solvents
• Less dense than water
• Low melting and boiling points