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Which types of orbital overlap are present in the bonding of a cumulene molecule?
A
Sigma bonds formed by hybrid orbitals and one set of pi bonds formed by orbitals in the same plane
B
Sigma bonds formed by hybrid orbitals and pi bonds formed by hybrid orbitals
C
Sigma bonds formed by hybrid orbitals and two perpendicular sets of pi bonds formed by unhybridized orbitals
D
Only sigma bonds formed by hybrid orbitals; no pi bonds are present
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1
Identify the hybridization of the central carbon atoms in a cumulene molecule. Since cumulenes have consecutive double bonds, the carbons involved are typically sp hybridized.
Recall that sp hybridization involves mixing one s orbital and one p orbital, resulting in two sp hybrid orbitals oriented linearly (180° apart), which form sigma bonds.
Understand that the remaining two unhybridized p orbitals on each sp hybridized carbon are perpendicular to each other and to the axis of the sigma bonds.
Recognize that these two sets of unhybridized p orbitals form two perpendicular pi bonds, one set in one plane and the other set in a plane perpendicular to the first.
Conclude that the bonding in cumulenes consists of sigma bonds formed by sp hybrid orbitals and two perpendicular sets of pi bonds formed by unhybridized p orbitals.