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Magazine Chapter 4: Problem 30
Which hybrid orbitals are used by carbon atoms in the following molecules? \(\mathrm{CH}_{3}-\mathrm{CH}_{3} ;\) (b) \(\mathrm{CH}_{3}-\mathrm{CH}=\mathrm{CH}_{2} ;\) (c) \(\mathrm{CH}_{3}-\mathrm{CH}_{2}-\mathrm{OH} ;\) (d) \(\mathrm{CH}_{3}-\mathrm{CHO}\) (e) \(\mathrm{CH}_{3} \mathrm{COOH}\)
Short Answer
Expert verified
(a) \(sp^3\), (b) \(sp^3, sp^2, sp^2\), (c) \(sp^3, sp^3\), (d) \(sp^3, sp^2\), (e) \(sp^3, sp^2\).
Step by step solution
01
Analyze Ethane (\(\mathrm{CH}_3-\mathrm{CH}_3\))
In ethane, \(\mathrm{CH}_3-\mathrm{CH}_3\), each carbon forms four single bonds, three with hydrogen atoms and one with the other carbon atom. In such cases, carbon undergoes \(sp^3\) hybridization, which is optimal for forming tetrahedral angles of 109.5 degrees with single (sigma) bonds.
02
Analyze Propene (\(\mathrm{CH}_3-\mathrm{CH} = \mathrm{CH}_2\))
In propene, the first carbon \(\mathrm{CH}_3-\) forms all single bonds, indicating \(sp^3\) hybridization. The second carbon \(-\mathrm{CH}=\) forms a double bond with the third carbon and single bonds otherwise, indicating \(sp^2\) hybridization for trigonal planar structures. The third carbon \(-=\mathrm{CH}_2\) forms a double bond with the second carbon and single bonds otherwise, also showing \(sp^2\) hybridization.
03
Analyze Ethanol (\(\mathrm{CH}_3-\mathrm{CH}_2-\mathrm{OH}\))
In ethanol, the first carbon \(\mathrm{CH}_3-\) and the second carbon \(-\mathrm{CH}_2-\) both form only single bonds with the surrounding atoms, indicating \(sp^3\) hybridization, which is consistent with the tetrahedral structures of these carbons.
04
Analyze Acetaldehyde (\(\mathrm{CH}_3-\mathrm{CHO}\))
In acetaldehyde, the first carbon \(\mathrm{CH}_3-\) is \(sp^3\) hybridized since it forms all single bonds. The second carbon \(-\mathrm{CHO}\), which forms a double bond with oxygen and a single bond with the other carbon, is \(sp^2\) hybridized, allowing for planar bonding geometry with the oxygen and hydrogen.
05
Analyze Acetic Acid (\(\mathrm{CH}_3\mathrm{COOH}\))
In acetic acid, the first carbon \(\mathrm{CH}_3-\) is \(sp^3\) hybridized due to all single bonds. The second carbon \(-\mathrm{COOH}\), involved in a double bond with oxygen and one single bond with another carbon atom, is \(sp^2\) hybridized to accommodate the planar arrangements and the resonance structures, if any.
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Key Concepts
These are the key concepts you need to understand to accurately answer the question.
sp3 hybridization
Understanding \(sp^3\) hybridization is essential when studying carbon compounds. This type of hybridization occurs when one s orbital and three p orbitals from the same atom combine to form four new equivalent orbitals. These new orbitals are known as \(sp^3\) hybrid orbitals.
- Each \(sp^3\) hybrid orbital is in charge of forming a single covalent bond.
- In most organic molecules, carbon atoms undergo \(sp^3\) hybridization when they form four sigma bonds.
- The overall spatial arrangement of these bonds is tetrahedral, which means that the bonds are oriented as if towards the corners of a tetrahedron.
sp2 hybridization
In \(sp^2\) hybridization, one s orbital mixes with two p orbitals, creating three \(sp^2\) hybridized orbitals. This setup leaves one unhybridized p orbital.
- \(sp^2\) hybridization occurs in carbon atoms that form a combination of sigma bonds and a pi bond, often seen in alkenes.
- The three \(sp^2\) hybrid orbitals lie in a planar arrangement, forming 120-degree angles between them.
- Alkenes, such as propene (\(\mathrm{CH}_3\!\!-\mathrm{CH}=\mathrm{CH}_2\)), exhibit this type of hybridization for carbons involved in the double bond.
sigma bonds
Sigma bonds are a fundamental type of covalent bond and are crucial in understanding hybridization in organic molecules. These bonds are characterized by the head-on overlapping of atomic orbitals.
- They are the strongest type of covalent bonds and form the backbone of organic compounds.
- The creation of a sigma bond involves the sharing of a pair of electrons symmetrically along the axis connecting the bonded atoms.
- In molecules with \(sp^3\) hybridized carbons, each hybrid orbital forms a single sigma bond.
tetrahedral angles
Tetrahedral angles are associated with molecules where central atoms exhibit \(sp^3\) hybridization. A tetrahedral arrangement provides maximum separation between electron pairs, reducing repulsion.
- In a perfect tetrahedron, the angle between bonds is approximately 109.5 degrees.
- This arrangement allows for a stable structure as it minimizes electron pair repulsion according to the VSEPR theory.
- Tetrahedral geometry is present in many types of molecules, particularly alkanes where each carbon atom forms three bonds with hydrogens and one bond with another carbon.
