1.9 sp Hybrid Orbitals and the Structure of Acetylene
2 min read•may 7, 2024
Carbon atoms can mix their orbitals to form new hybrid orbitals. In , one s and one combine to create two sp orbitals. These sp orbitals are key to understanding 's structure and bonding.
Acetylene, with its , showcases sp in action. Each carbon atom uses its sp orbitals to form sigma bonds, while unhybridized p orbitals create pi bonds. This results in acetylene's unique linear shape and strong .
sp Hybridization and Acetylene Structure
Formation of sp hybrid orbitals
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- sp hybridization involves mixing one s orbital and one p orbital in a carbon atom
- Creates two oriented 180° apart from each other ()
- Each contains one electron for bonding
- Formation process combines one 2s orbital and one 2p orbital (usually 2p)
- Remaining two 2p orbitals (2p and 2p) are unhybridized and perpendicular to the sp orbitals
- have equal contributions from s and p orbitals (50% s character, 50% p character)
- Higher s character makes sp orbitals more electronegative than sp and sp orbitals (greater attraction for electrons)
Sp orbitals in acetylene structure
- Acetylene (CH) is a linear molecule with a carbon-carbon triple bond
- Each carbon atom in acetylene undergoes sp hybridization forming two orbitals
- One sp orbital forms a bond with the other carbon atom
- The other sp orbital forms a bond with a hydrogen atom (C-H bond)
- Unhybridized 2p orbitals on each carbon atom overlap sideways above and below the internuclear axis
- Forms two bonds between the carbon atoms
- Carbon-carbon triple bond in acetylene consists of one bond and two bonds
- Shorter and stronger than double or single bonds due to increased
- Linear geometry of acetylene results from the 180° orientation of sp hybrid orbitals on each carbon atom
- This orientation determines the in acetylene (180°)
Acetylene vs other carbon molecules
- Acetylene (sp hybridization):
- Carbon-carbon triple bond length: 120 pm
- Carbon-carbon bond energy: 837 kJ/mol
- Linear geometry
- Ethene (sp hybridization):
- Carbon-carbon double bond length: 134 pm
- Carbon-carbon bond energy: 614 kJ/mol
- Trigonal planar geometry
- Ethane (sp hybridization):
- Carbon-carbon single bond length: 154 pm
- Carbon-carbon bond energy: 347 kJ/mol
- Tetrahedral geometry
- Bond length decreases and bond strength increases in the order: single < double < triple
- Due to increasing s character and greater orbital overlap in the bonding orbitals (sp < sp < sp)
Valence Bond Theory and Molecular Geometry
- explains the formation of covalent bonds through orbital overlap
- Hybridization of atomic orbitals determines the of compounds
- sp hybridization results in linear molecular geometry (e.g., acetylene)
- sp hybridization leads to trigonal planar geometry (e.g., ethene)
- sp hybridization produces tetrahedral geometry (e.g., ethane)
Key Terms to Review (22)
Acetylene: Acetylene is a colorless, flammable gas with the chemical formula C₂H₂. It is the simplest alkyne and is known for its unique bonding structure and reactivity, which are important in the context of sp hybrid orbitals and the calculation of the degree of unsaturation.
Alkyne: An alkyne is a hydrocarbon compound containing a carbon-carbon triple bond. Alkynes are a class of unsaturated organic compounds that play a crucial role in various topics within organic chemistry, including sp hybridization, functional groups, degree of unsaturation, nomenclature, and synthetic transformations.
Bond angle: The bond angle is the geometric angle between two adjacent bonds originating from the same atom. In the context of sp3 hybrid orbitals and the structure of methane, it refers to the angle between any two covalent bonds that join atoms to the central carbon atom.
Bond Angle: The bond angle refers to the angle formed between the covalent bonds of a molecule. It is a crucial parameter that determines the three-dimensional structure and geometry of molecules, which in turn influences their physical and chemical properties.
Carbon-Carbon Triple Bond: A carbon-carbon triple bond is a type of covalent bond where three pairs of electrons are shared between two carbon atoms, resulting in a very strong and stable connection. This structural feature is found in organic compounds known as alkynes and has important implications for their physical and chemical properties.
Ethyne: Ethyne, also known as acetylene, is a simple hydrocarbon compound with the chemical formula C₂H₂. It is a linear, unsaturated molecule with a triple bond between the two carbon atoms, making it the simplest alkyne. Ethyne is an important industrial chemical and has a wide range of applications, including in the context of sp hybrid orbitals, the structure of acetylene, naming alkynes, and the reduction of alkynes.
Hybridization: Hybridization is a fundamental concept in chemistry that describes the process of mixing atomic orbitals to form new hybrid orbitals, which are used to explain the geometry and bonding patterns of molecules. This term is closely related to the development of chemical bonding theory, valence bond theory, and molecular orbital theory, as well as the structure and properties of various organic compounds.
Linear Geometry: Linear geometry refers to the spatial arrangement of atoms or molecules where the bonding atoms are arranged in a straight line. This geometric configuration is particularly relevant in the context of sp-hybridized orbitals and the structure of acetylene.
Molecular Geometry: Molecular geometry refers to the three-dimensional arrangement of atoms within a molecule, which significantly influences the molecule's physical and chemical properties. The shape of a molecule is determined by the arrangement of its constituent atoms and the presence of lone pairs of electrons, which can repel bonded atoms and alter the geometry. Understanding molecular geometry is crucial for predicting molecular behavior, reactivity, and interactions.
Orbital Overlap: Orbital overlap refers to the interaction and sharing of electron density between two or more atomic orbitals, which is a fundamental concept in understanding the formation of chemical bonds. This term is particularly relevant in the context of valence bond theory, sp3 hybrid orbitals, and sp hybrid orbitals.
P Orbital: The p orbital is a type of atomic orbital in an atom's electron cloud that has a dumbbell-like shape with a node (a point where the wavefunction is zero) at the nucleus. The p orbitals are higher energy orbitals that can hold up to 6 electrons and are important in the context of hybridization and the structure of organic molecules.
Pi Bond: A pi (π) bond is a type of covalent chemical bond formed by the side-to-side overlap of atomic orbitals, resulting in electron density concentrated above and below the internuclear axis between two atoms. Pi bonds are crucial in the structure and reactivity of many organic compounds.
Sigma Bond: A sigma bond is a type of covalent chemical bond formed by the overlap of atomic orbitals along the internuclear axis between two atoms. Sigma bonds are the strongest type of covalent bonds and are responsible for the structural stability and geometry of molecules.
Sp hybrid: sp hybrid orbitals are formed when one s orbital mixes with one p orbital from the same atom, creating two equivalent orbitals that are linearly oriented 180 degrees apart. This hybridization occurs in molecules like acetylene (C2H2), facilitating the formation of triple bonds between carbon atoms.
Sp hybrid orbitals: Sp hybrid orbitals are formed when one s orbital and one p orbital mix together in an atom, creating two new, identical orbitals that are linearly oriented 180 degrees apart. This hybridization occurs in molecules where carbon forms triple bonds, such as acetylene (C2H2), contributing to their unique structure and bonding characteristics.
Sp Hybrid Orbitals: sp Hybrid Orbitals are a type of atomic orbital that result from the combination of one s orbital and one p orbital on an atom. These hybridized orbitals have a specific spatial arrangement and are crucial in understanding the structure and bonding of certain organic compounds, particularly acetylene.
Sp Hybridization: sp Hybridization is a concept in organic chemistry that describes the formation of hybrid atomic orbitals through the combination of one s orbital and one p orbital, resulting in the creation of two equivalent sp hybrid orbitals. This hybridization is particularly important in understanding the structure and bonding patterns of certain organic compounds, such as alkynes.
Sp Orbital: The sp orbital is a type of hybrid orbital that results from the combination of one s orbital and one p orbital. This hybridization occurs in certain molecular geometries, such as the linear structure of acetylene, and is crucial in understanding the bonding and reactivity of these compounds.
Triple Bond: A triple bond is a covalent bond in which three pairs of electrons are shared between two atoms, resulting in a very strong and stable chemical connection. This type of bond is particularly important in the context of organic chemistry, as it is a key structural feature in certain classes of compounds known as alkynes.
Triple bonds: A triple bond is a chemical bond where three pairs of electrons are shared between two atoms. It is the strongest and shortest type of covalent bond found in molecules.
Valence bond theory: Valence bond theory explains how atoms in a molecule are bonded together by overlapping their atomic orbitals to share electron pairs. It combines the concepts of orbital hybridization and resonance to account for the molecular shape and stability.
Valence Bond Theory: Valence bond theory is a model used to describe the formation of chemical bonds between atoms. It focuses on the pairing of unpaired valence electrons between atoms to create stable covalent bonds, allowing atoms to achieve a more stable electronic configuration.