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Chapter 7: Problem 11

What hybridization scheme would you assign to the carbon atoms in cach of the following molecules? (a) \(\mathrm{CO}_{2} ;(\mathrm{b}) \mathrm{C}_{2} \mathrm{H}_{6} ;(\mathrm{c}) \mathrm{CH}_{2} \mathrm{Cl}_{2}\) (d) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{OH} ;\) (e) \(\mathrm{CH}_{3} \mathrm{CH}=\mathrm{CHCH}_{2} \mathrm{CH}_{3}\) \((\mathrm{f}) \mathrm{COCl}_{2} ;(\mathrm{g})\left[\mathrm{CO}_{3}\right]^{2-}\)

Short Answer

Expert verified
(a) sp, (b) sp3, (c) sp3, (d) sp3, (e) sp3 and sp2, (f) sp2, (g) sp2.

Step by step solution

01

Determine Geometry of CO2

In carbon dioxide (CO2), the carbon atom forms two double bonds with oxygen atoms, and there are no lone pairs on the carbon atom. This linear molecular geometry suggests the use of sp hybridization, as the carbon atom needs two hybrid orbitals for bonding to each oxygen.
02

Analyze Geometry in C2H6

In C2H6 (ethane), each carbon atom forms four single bonds (three with hydrogen atoms and one with another carbon atom). This is characteristic of a tetrahedral arrangement, indicating sp3 hybridization for each of the carbon atoms.
03

Assess Geometry for CH2Cl2

CH2Cl2 (dichloromethane) involves a carbon atom bonded to two hydrogen atoms and two chlorine atoms. The arrangement of four bonds around the carbon resembles a tetrahedral geometry, suggesting sp3 hybridization.
04

Evaluate CH3CH2OH Structure

For CH3CH2OH (ethanol), the first carbon is bonded to three hydrogen atoms and one carbon atom, which suggests sp3 hybridization due to the tetrahedral bond arrangement. The second carbon is bonded to two hydrogens, one carbon, and one oxygen (OH group), also sp3 hybridized due to its tetrahedral arrangement.
05

Assess CH3CH=CHCH2CH3 Geometry

In CH3CH=CHCH2CH3 (pentene), the first and last carbon atoms have sp3 hybridization due to their tetrahedral bonding environment with four single bonds. The middle carbons, involved in the double bond (CH=CH), each have three bonding zones (including the double bond and single carbon bonds), indicating sp2 hybridization.
06

Determine Hybridization in COCl2

In phosgene (COCl2), the carbon atom forms a double bond with oxygen and two single bonds with chlorine atoms. The molecular geometry around carbon is trigonal planar, suggesting sp2 hybridization.
07

Analyze [CO3]2- Ion Geometry

The carbonate ion [CO3]2- features one carbon atom double-bonded with one oxygen and single-bonded with two others. The resonance structures average to a trigonal planar geometry for the carbon, indicating sp2 hybridization.

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Key Concepts

These are the key concepts you need to understand to accurately answer the question.

Molecular Geometry
Molecular geometry refers to the three-dimensional arrangement of atoms within a molecule. This plays a crucial role in determining the chemical properties and reactivity of the molecule. For example, the geometry of carbon dioxide (CO extsubscript{2}) is linear because it features two double bonds between carbon and oxygen atoms. Understanding the molecular geometry is key for predicting how molecules will interact.
  • Linear geometry: Typical for molecules with two atoms or two regions of electron density around a central atom, like CO extsubscript{2}.
  • Tetrahedral geometry: Found in molecules with four regions of electron density, such as CH extsubscript{4}.
  • Trigonal planar geometry: Common in species with three bonds or regions of electron density, such as in COCl extsubscript{2} or carbonates.
The molecular geometry affects the prediction of hybridization states and bond angles.
sp Hybridization
The term 'sp hybridization' refers to a type of hybridization where one s-orbital mixes with one p-orbital to form two equivalent sp hybrid orbitals. This type of hybridization is often associated with linear molecular geometry. For example, in carbon dioxide (CO extsubscript{2}), each carbon atom is bonded using sp hybridized orbitals. The formation of sp orbitals allows for the characteristic 180-degree bond angle in linear geometry. This results in carbon forming two pi bonds with oxygen through multiple bonding, while the hybrid orbitals form sigma bonds.
  • Formation: Mixing one s and one p orbital.
  • Geometry: Linear, with bond angles of 180掳.
  • Applications: Found in carbon compounds like CO extsubscript{2} where linear geometry is present.
sp3 Hybridization
In sp extsuperscript{3} hybridization, one s orbital and three p orbitals mix to form four equivalent sp extsuperscript{3} hybrid orbitals. This hybridization is characteristic of tetrahedral molecules, where each carbon atom forms single bonds. In ethane (C extsubscript{2}H extsubscript{6}), each carbon atom utilizes sp extsuperscript{3} hybrid orbitals.
  • Formation: One s orbital mixes with three p orbitals.
  • Geometry: Tetrahedral, with bond angles close to 109.5掳.
  • Examples: Common in alkanes like methane (CH extsubscript{4}), ethane (C extsubscript{2}H extsubscript{6}), and other saturated hydrocarbons.
This hybridization results in a stable geometry that maximizes distances between electron pairs for minimal repulsion.
sp2 Hybridization
sp extsuperscript{2} hybridization involves the mixing of one s orbital with two p orbitals, resulting in three equivalent sp extsuperscript{2} hybrid orbitals. This type of hybridization is crucial for molecules with a trigonal planar geometry, allowing for bond angles of approximately 120 degrees. For instance, in phosgene (COCl extsubscript{2}) and the carbonate ion (CO extsubscript{3} extsuperscript{2-}), the central carbon atom uses sp extsuperscript{2} hybrid orbitals to form a planar triangular structure.
  • Formation: One s orbital and two p orbitals mix.
  • Geometry: Trigonal planar, with 120掳 bond angles.
  • Examples: Seen in compounds with double bonds like alkenes and carbonyl compounds.
Molecular stability is enhanced in these structures due to the effective overlap of orbitals, crucial for the delocalization seen in resonance structures.
Ethane
Ethane (C extsubscript{2}H extsubscript{6}) is a simple alkane with a sp extsuperscript{3} hybridization of its carbon atoms. It is composed of two carbon atoms bonded together, each also forming single bonds with three hydrogen atoms. The geometry around each carbon is tetrahedral, typical for saturated hydrocarbons.
  • Hybridization: Each carbon is sp extsuperscript{3} hybridized.
  • Structure: Tetrahedral geometry around each carbon atom.
  • Bonding: Features only single sigma bonds.
These characteristics make ethane a fundamental example of how saturated hydrocarbons behave structurally and chemically, due to this stable and predictable bonding arrangement.
Dichloromethane
Dichloromethane (CH extsubscript{2}Cl extsubscript{2}), commonly known as methylene chloride, also exhibits sp extsuperscript{3} hybridization. The central carbon atom forms four bonds鈥攖wo with hydrogen atoms and two with chlorine atoms.
  • Hybridization: Carbon is sp extsuperscript{3} hybridized.
  • Geometry: Tetrahedral geometry surrounding the carbon atom.
  • Bonding: Involves two carbon-hydrogen and two carbon-chlorine sigma bonds.
Dichloromethane's tetrahedral arrangement contributes to its solvent properties in organic chemistry, as well as its phase behavior.
Phosgene
Phosgene (COCl extsubscript{2}) is an example of sp extsuperscript{2} hybridization. In this compound, the central carbon atom is double-bonded to an oxygen and single-bonded to two chlorine atoms, creating a trigonal planar geometry.
  • Hybridization: sp extsuperscript{2} hybridized carbon.
  • Structure: Trigonal planar configuration around the carbon atom.
  • Bonding: One double bond to oxygen and two single bonds to chlorine atoms.
This geometry provides insight into phosgene's reactivity and toxicity, as the planar arrangement is key to its interactions with other molecules.
Carbonate Ion
The carbonate ion ext([ ext{CO}_3]^{2-} ext) provides a classic example of sp extsuperscript{2} hybridization. The central carbon atom in the carbonate ion forms one double bond with an oxygen atom and two single bonds with two other oxygen atoms.
  • Hybridization: Carbon is sp extsuperscript{2} hybridized.
  • Geometry: A symmetrical trigonal planar structure.
  • Bonding: An average bond order due to resonance providing equal distribution of electrons.
The resonance in the carbonate ion allows for delocalization of electrons, stabilizing the ion and affecting its interactions and solubility in solution.

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Most popular questions from this chapter

Consider the molecule \(\mathrm{CO}_{2}\). (a) Use VSEPR theory to rationalize its shape. (b) Draw resonance structures for \(\mathrm{CO}_{2}\) and indicate which structure will make the major contribution to the bonding. (c) Describe the bonding in terms of a hybridization scheme, including full descriptions of the formation of \(\sigma\) - and \(\pi\) -bonds.

Write down the hybridization of the central atom in cach of the following species: (a) \(\mathrm{SiF}_{4} ;(\mathrm{b}) \mathrm{NH}_{3}\) (c) \(\left[\mathrm{NH}_{4}\right]^{+} ;(\mathrm{d}) \mathrm{BH}_{3} ;(\mathrm{e})\left[\mathrm{CoF}_{6}\right]^{3-} ;(\mathrm{f}) \mathrm{IF}_{3} ;(\mathrm{g}) \mathrm{H}_{2} \mathrm{S}\)

How many single bonds may each of the (a) \(\mathrm{N}^{-}\) (b) \(\mathrm{B}^{-}\) and \((\mathrm{c}) \mathrm{C}^{-}\) centres form while obeying the octet rule?

In which of the following molecular species does the central atom possess an octet of valence electrons? (a) \(\mathrm{BBr}_{2} \mathrm{F} ;(\mathrm{b}) \mathrm{OF}_{2} ;(\) (c) \(P H_{3} ;(d) C O_{2}\) (e) \(\mathrm{NF}_{3}\) (f) \(\left[\mathrm{PCl}_{4}\right]^{+} ;(\mathrm{g}) \mathrm{AsF}_{3} ;(\mathrm{h}) \mathrm{BF}_{3}\) (i) \(\mathrm{AlCl}_{3}\)

For each of the following, draw Lewis structures that are consistent with the central atom in each molecule obeying the octet rule: (a) \(\mathrm{H}_{2} \mathrm{O},(\mathrm{b}) \mathrm{NH}_{3}\) (c) \(\mathrm{AsF}_{3},(\mathrm{d}) \mathrm{SF}_{4}\)
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