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Bonding in Alkanes, Alkenes and Alkynes
Dr. K. Shahzad Baig
Memorial University of Newfoundland (MUN)
Canada
Petrucci, et al. 2011. General Chemistry: Principles and Modern Applications. Pearson Canada Inc., Toronto, Ontario.
Tro, N.J. 2010. Principles of Chemistry. : a molecular approach. Pearson Education, Inc.
Multiple Covalent Bonds
Ethylene has a carbon-to-carbon double bond in its Lewis structure
Ethylene is a planar molecule with 120o H – C – H, H – C – C and bond
angles
The hybridization scheme that produces a set of hybrid orbitals with a trigonal-planar
orientation is sp2.
The (sp2 + p) orbital set
The purple
orbitals are sp2
hybrid orbitals;
the red and blue
orbitals are 2p ,
with the colors
indicating their
phase.
The sp2 hybrid orbitals overlap along the line joining the bonded atoms a σ-bond.
The orbitals overlap in a side-to-side fashion and form a π-bond.
Notice that the phase of the p-orbitals is retained.
Bond type # σ
bonds
# π
bonds
Single (C-H) 1 0
Double (C=C) 1 1
Triple (C≡C) 1 2
Bonding
the shape of a molecule is determined only by the σ-orbitals forming bonds.
the terminal H-atoms can be easily twist or rotate about the s-bonds that join them to
a C atom.
To twist one –CH2 group out of the plane of the other, however, would reduce the
amount of overlap of the p orbitals and weaken the bond. The double bond is rigid,
and the molecule is planar.
Additionally, in carbon-to-carbon multiple bonds, the
σ-bond involves more extensive overlap than does the
π=bond. As a result, a carbon-to-carbon double bond
(σ + π) is stronger than a single bond (π) but not twice
as strong.
C - C 347 kJ/mol
C = C 611 kJ/mol
C Ξ C 837 kJ/mol
Bonding in C2H2
Bonding in acetylene, C2H2, is somewhat similar to that C2H4,
The Lewis structure of features a triple covalent bond, H – C Ξ C – H.
The molecule is linear,
In the triple bond in C2H2 one of the carbon-to-carbon bonds is a σ-bond and two are π-
bonds
Multiple covalent bonds,  11(2)
Multiple covalent bonds,  11(2)
Multiple covalent bonds,  11(2)
Multiple covalent bonds,  11(2)
Multiple covalent bonds,  11(2)

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Multiple covalent bonds, 11(2)

  • 1. Bonding in Alkanes, Alkenes and Alkynes Dr. K. Shahzad Baig Memorial University of Newfoundland (MUN) Canada Petrucci, et al. 2011. General Chemistry: Principles and Modern Applications. Pearson Canada Inc., Toronto, Ontario. Tro, N.J. 2010. Principles of Chemistry. : a molecular approach. Pearson Education, Inc.
  • 2. Multiple Covalent Bonds Ethylene has a carbon-to-carbon double bond in its Lewis structure Ethylene is a planar molecule with 120o H – C – H, H – C – C and bond angles The hybridization scheme that produces a set of hybrid orbitals with a trigonal-planar orientation is sp2. The (sp2 + p) orbital set
  • 3. The purple orbitals are sp2 hybrid orbitals; the red and blue orbitals are 2p , with the colors indicating their phase. The sp2 hybrid orbitals overlap along the line joining the bonded atoms a σ-bond. The orbitals overlap in a side-to-side fashion and form a π-bond. Notice that the phase of the p-orbitals is retained.
  • 4. Bond type # σ bonds # π bonds Single (C-H) 1 0 Double (C=C) 1 1 Triple (C≡C) 1 2
  • 5. Bonding the shape of a molecule is determined only by the σ-orbitals forming bonds. the terminal H-atoms can be easily twist or rotate about the s-bonds that join them to a C atom. To twist one –CH2 group out of the plane of the other, however, would reduce the amount of overlap of the p orbitals and weaken the bond. The double bond is rigid, and the molecule is planar. Additionally, in carbon-to-carbon multiple bonds, the σ-bond involves more extensive overlap than does the π=bond. As a result, a carbon-to-carbon double bond (σ + π) is stronger than a single bond (π) but not twice as strong. C - C 347 kJ/mol C = C 611 kJ/mol C Ξ C 837 kJ/mol
  • 6. Bonding in C2H2 Bonding in acetylene, C2H2, is somewhat similar to that C2H4, The Lewis structure of features a triple covalent bond, H – C Ξ C – H. The molecule is linear, In the triple bond in C2H2 one of the carbon-to-carbon bonds is a σ-bond and two are π- bonds

Editor's Notes

  1. One of the bonds between the carbon atoms results from the overlap of sp2 hybrid orbitals from each atom.