Chapter 4. Molecular Structure and Orbitals

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1 Chapter 4 Molecular Structure and Orbitals

2 Chapter 4 Table of Contents (4.1) (4.2) (4.3) (4.4) (4.5) (4.6) (4.7) Molecular structure: The VSEPR model Bond polarity and dipole moments Hybridization and the localized electron model The molecular orbital model Bonding in homonuclear diatomic molecules Bonding in heteronuclear diatomic molecules Combining the localized electron and molecular orbital models

3 Chapter 4 Question to Consider The spicy flavor of chili peppers is attributed to a complex molecule with multiple hybridizations What is the name of this molecule?

4 Section 4.1 Molecular Structure: The VSEPR Model The VSEPR Model Molecular structure is the three-dimensional arrangement of atoms in a molecule Valence shell electron-pair repulsion (VSEPR) model The structure around a given atom is determined principally by minimizing electron pair repulsions

5 Section 4.1 Molecular Structure: The VSEPR Model Electron Structures Linear structure can be observed in BeCl 2 Each electron pair on Be is shared with a Cl atom BF 3 shows a trigonal planar structure Each electron pair is shared with a fluorine atom

6 Section 4.1 Molecular Structure: The VSEPR Model Electron Structures When there are four pairs of electrons around an atom, they take up a tetrahedral structure The bond angle for such a structure is degrees In the presence of a lone pair, the molecular structure is a trigonal pyramid

7 Section 4.1 Molecular Structure: The VSEPR Model Electron Structures Consider the structure of NH 3, which has one lone pair The arrangement of electron pairs is tetrahedral, but the arrangement of atoms is not

8 Section 4.1 Molecular Structure: The VSEPR Model Lone Pair Trends Bonding pairs are shared between two nuclei Electrons can be close to either nucleus Lone pairs center around just one nucleus, and both electrons choose that nucleus Lone pairs need more space than bonding pairs They compress the angles between bonding pairs

9 Section 4.1 Molecular Structure: The VSEPR Model Electron Structures When there are five electron pairs, the structure that produces minimal repulsion is a trigonal bipyramid It consists of two trigonal-based pyramids that share a common base The best arrangement for six pairs of electrons around a given atom is the octahedral structure This structure has 90-degree bond angles

10 Section 4.1 Molecular Structure: The VSEPR Model Table Structures of Molecules that have Four Electron Pairs Around the Central Atom

11 Section 4.1 Molecular Structure: The VSEPR Model Table Structures of Molecules with Five Electron Pairs Around the Central Atom

12 Section 4.1 Molecular Structure: The VSEPR Model Table Structures of Molecules with Five Electron Pairs Around the Central Atom (Contd)

13 Section 4.1 Molecular Structure: The VSEPR Model Concept Check Determine the shape and bond angles for each of the following molecules: HCN PH 3 SF 4 O 3 KrF 4

14 Section 4.1 Molecular Structure: The VSEPR Model Problem Solving Strategy - Steps to Apply the VSEPR Model Draw the Lewis structure for the molecule Count the electron pairs and arrange them in the way that minimizes repulsion Put the pairs as far apart as possible Determine the positions of the atoms from the way the electron pairs are shared Determine the name of the molecular structure from the positions of the atoms

15 Section 4.1 Molecular Structure: The VSEPR Model Interactive Example Prediction of Molecular Structure II When phosphorus reacts with excess chlorine gas, the compound phosphorus pentachloride (PCl 5 ) is formed. In the gaseous and liquid states, this substance consists of PCl 5 molecules, but in the solid state it consists of a 1:1 mixture of PCl 4+ and PCl 6 ions. Predict the geometric structures of PCl 5, PCl 4 +, and PCl 6.

16 Section 4.1 Molecular Structure: The VSEPR Model Interactive Example Prediction of Molecular Structure II Solution The Lewis structure for PCl 5 is shown Five pairs of electrons around the phosphorus atom require a trigonal bipyramidal arrangement When the chlorine atoms are included, a trigonal bipyramidal molecule results:

17 Section 4.1 Molecular Structure: The VSEPR Model Interactive Example Prediction of Molecular Structure II The Lewis structure for the PCl 4+ ion [5 + 4(7) 1 = 32 valence electrons] is shown below There are four pairs of electrons surrounding the phosphorus atom in the PCl 4+ ion, which requires a tetrahedral arrangement of the pairs Since each pair is shared with a chlorine atom, a tetrahedral PCl 4+ cation results

18 Section 4.1 Molecular Structure: The VSEPR Model Interactive Example Prediction of Molecular Structure II The Lewis structure for PCl 6 [5 + 6(7) + 1 = 48 valence electrons] is shown below Since phosphorus is surrounded by six pairs of electrons, an octahedral arrangement is required to minimize repulsions, as shown below in the center Since each electron pair is shared with a chlorine atom, an octahedral PCl 6 anion is predicted

19 Section 4.1 Molecular Structure: The VSEPR Model The VSEPR Model and Multiple Bonds While using the VSEPR model, a double bond must be considered as one effective pair The two pairs involved in the double bond are not independent pairs The double bond acts as one center of electron density that repels other electron pairs With molecules that exhibit resonance, any one of the resonance structures can be used to predict its molecular structure using the VSEPER model

20 Section 4.1 Molecular Structure: The VSEPR Model Interactive Example Structures of Molecules with Multiple Bonds Predict the molecular structure of the sulfur dioxide molecule. Is this molecule expected to have a dipole moment? Solution First, determine the Lewis structure for the SO 2 molecule, which has 18 valence electrons The expected resonance structures are:

21 Section 4.1 Molecular Structure: The VSEPR Model Interactive Example Structures of Molecules with Multiple Bonds To determine the molecular structure, count the electron pairs around the sulfur atom In each resonance structure the sulfur has one lone pair, one pair in a single bond, and one double bond Counting the double bond as one pair yields three effective pairs around the sulfur A trigonal planar arrangement is required, which yields a V- shaped molecule

22 Section 4.1 Molecular Structure: The VSEPR Model Interactive Example Structures of Molecules with Multiple Bonds Thus the structure of the SO 2 molecule is expected to be V- shaped, with a 120-degree bond angle The molecule has a dipole moment directed as shown: Since the molecule is V-shaped, the polar bonds do not cancel

23 Section 4.1 Molecular Structure: The VSEPR Model Molecules Containing No Single Central Atom The VSEPR model can accurately determine the structure of complicated molecules such as methanol Lewis structure: There are four pairs of electrons around the C and O atoms, which give rise to a tetrahedral arrangement Space requirements of the lone pairs distort the arrangement

24 Section 4.1 Molecular Structure: The VSEPR Model Figure The Molecular Structure of Methanol (a) The arrangement of electron pairs and atoms around the carbon (b) The arrangement of bonding and lone pairs around oxygen (c) The molecular structure

25 Section 4.1 Molecular Structure: The VSEPR Model Accuracy of the VSEPR Model It aptly predicts the molecular structures of most molecules formed from non-metallic elements It can be used to predict the structures of molecules with hundreds of atoms It fails to determine the molecular structure in certain instances Phosphine (PH 3 ) and ammonia (NH 3 ) have similar Lewis structures but different bond angles 94 degrees and 107 degrees, respectively

26 Section 4.2 Bond Polarity and Dipole Moments Dipole Moment A molecule that has a center of positive charge and a center of negative charge is said to be dipolar or to possess dipole moment It is represented by an arrow pointing to the negative charge center The tail indicates the positive charge center

27 Section 4.2 Bond Polarity and Dipole Moments Dipole Moment Electrostatic potential diagrams can also be used to represent dipole moment The colors of visible light are used to show variation in distribution of charge Red - Most electron-rich region Blue - Most electron-poor region

28 Section 4.2 Bond Polarity and Dipole Moments Bond Polarity Trends Any diatomic molecule with polar bonds will exhibit dipole moments This behavior can also be exhibited by polyatomic molecules Few molecules possess polar bonds but lack dipole moment Occurs when the individual bond polarities are arranged in a manner that they cancel each other out

29 Section 4.2 Bond Polarity and Dipole Moments Table Types of Molecules with Polar Bonds but No Resulting Dipole Moment

30 Section 4.2 Bond Polarity and Dipole Moments Example Bond Polarity and Dipole Moment For each of the following molecules, show the direction of the bond polarities and indicate which ones have a dipole moment: HCl Cl 2 SO 3 (planar molecule with the oxygen atoms spaced evenly around the central sulfur atom) CH 4 (tetrahedral with the carbon atom at the center) H 2 S (V-shaped with the sulfur atom at the point)

31 Section 4.2 Bond Polarity and Dipole Moments Example Bond Polarity and Dipole Moment Solution The HCl molecule: The electronegativity of chlorine is greater than that of hydrogen Thus the chlorine will be partially negative, and the hydrogen will be partially positive The HCl molecule has a dipole moment:

32 Section 4.2 Bond Polarity and Dipole Moments Example Bond Polarity and Dipole Moment The Cl 2 molecule: The two chlorine atoms share the electrons equally No bond polarity occurs and the Cl 2 molecule has no dipole moment

33 Section 4.2 Bond Polarity and Dipole Moments Example Bond Polarity and Dipole Moment The SO 3 molecule: The electronegativity of oxygen is greater than that of sulfur This means that each oxygen will have a partial negative charge, and the sulfur will have a partial positive charge The bond polarities arranged symmetrically as shown cancel, and the molecule has no dipole moment

34 Section 4.2 Bond Polarity and Dipole Moments Example Bond Polarity and Dipole Moment The CH 4 molecule: Carbon has a slightly higher electronegativity than does hydrogen This leads to small partial positive charges on the hydrogen atoms and a small partial negative charge on the carbon: The bond polarities cancel, and the molecule has no dipole moment

35 Section 4.2 Bond Polarity and Dipole Moments Example Bond Polarity and Dipole Moment The H 2 S molecule: Since the electronegativity of sulfur is slightly greater than that of hydrogen, the sulfur will have a partial negative charge, and the hydrogen atoms will have a partial positive charge, which can be represented as:

36 Section 4.2 Bond Polarity and Dipole Moments Example Bond Polarity and Dipole Moment This case is analogous to the water molecule, and the polar bonds result in a dipole moment oriented as shown:

37 Section 4.3 Hybridization and the Localized Electron Model Hybridization It refers to the mixing of the native atomic orbitals to form special orbitals for bonding Atoms may adopt a different set of atomic orbitals or hybrid orbitals from those in the free state

38 Section 4.3 Hybridization and the Localized Electron Model sp 3 Hybridization It can be observed upon combination of one 2s and three 2p orbitals Whenever an atom requires a set of equivalent tetrahedral atomic orbitals, this model assumes that the atom adopts a set of sp 3 orbitals The atom becomes sp 3 hybridized

39 Section 4.3 Hybridization and the Localized Electron Model Figure The Formation of sp 3 Hybrid Orbitals

40 Section 4.3 Hybridization and the Localized Electron Model Concept Check What is the valence electron configuration of a carbon atom? Why can t the bonding orbitals for methane be formed by an overlap of atomic orbitals?

41 Section 4.3 Hybridization and the Localized Electron Model Concept Check Why can t sp 3 hybridization account for the ethylene molecule?

42 Section 4.3 Hybridization and the Localized Electron Model sp 2 Hybridization Gives a trigonal planar arrangement of atomic orbitals with bond angles of 120 degrees It occurs on the combination of one 2s and two 2p orbitals One p orbital is not used It is oriented perpendicular to the plane of the sp 2 orbitals

43 Section 4.3 Hybridization and the Localized Electron Model Types of sp 2 Hybridized Bonds Sigma ( ) bond Electron pair is shared in an area centered on a line running between the atoms Pi ( ) bond Forms double and triple bonds by sharing electron pair(s) in the space above and below the σ bond using the unhybridized p orbitals A double bond always consists of one bond and one bond If an atom is surrounded by three effective pairs, a set of sp 2 hybrid orbitals is required

44 Section 4.3 Hybridization and the Localized Electron Model Figure A Carbon Carbon Double Bond

45 Section 4.3 Hybridization and the Localized Electron Model sp Hybridization It occurs upon combination of one s and one p orbital Two effective pairs around an atom always require sp hybridization of that atom It follows a linear arrangement of atomic orbitals p orbitals that remain unchanged upon hybridization are used in the formation of bonds

46 Section 4.3 Hybridization and the Localized Electron Model Figure Bonding in CO 2 Part (a)

47 Section 4.3 Hybridization and the Localized Electron Model Concept Check Draw the Lewis structure for HCN Which of the hybrid orbitals are used? Draw HCN and: Show all the bonds between the atoms Label each or bond

48 Section 4.3 Hybridization and the Localized Electron Model dsp 3 Hybridization It is a combination of one d, one s, and three p orbitals It results in a trigonal bipyramidal arrangement of five equivalent hybrid orbitals The image illustrates hybrid orbitals in a phosphorus atom

49 Section 4.3 Hybridization and the Localized Electron Model d 2 sp 3 Hybridization An atom is d 2 sp 3 hybridized when there is a combination of two d, one s, and three p orbitals It results in an octahedral arrangement of six equivalent hybrid orbitals The image illustrates the orbitals in a sulfur atom

50 Section 4.3 Hybridization and the Localized Electron Model Interactive Example The Localized Electron Model IV How is the xenon atom in XeFe 4 hybridized? Solution XeFe 4 has six pairs of electrons around xenon that are arranged octahedrally to minimize repulsions An octahedral set of six atomic orbitals is required to hold these electrons, and the xenon atom is d 2 sp 3 hybridized

51 Section 4.3 Hybridization and the Localized Electron Model Interactive Example The Localized Electron Model IV

52 Section 4.3 Hybridization and the Localized Electron Model Concept Check For each of the following molecules, determine: (a) Bond angle (b) Expected hybridization of the central atom NH 3 SO 2 KrF 2 CO 2 ICl 5

53 Section 4.3 Hybridization and the Localized Electron Model Figure The Relationship of the Number of Effective Pairs, their Spatial Arrangement, and the Hybrid Orbital set Required

54 Section 4.3 Hybridization and the Localized Electron Model Figure The Relationship of the Number of Effective Pairs, their Spatial Arrangement, and the Hybrid Orbital set Required (Contd)

55 Section 4.3 Hybridization and the Localized Electron Model Problem Solving Strategy: Using the Localized Electron Model Draw the Lewis structure(s) Determine the arrangement of electron pairs, using the VSEPR model Specify the hybrid orbitals needed to accommodate the electron pairs

56 Section 4.3 Hybridization and the Localized Electron Model Interactive Example The Localized Electron Model V For each of the following molecules or ions, predict the hybridization of each atom, and describe the molecular structure a. CO b. BF 4 c. XeF 2 Solution a. CO The CO molecule has 10 valence electrons, and its Lewis structure is : C O : Each atom has two effective pairs, which means that both are sp hybridized

57 Section 4.3 Hybridization and the Localized Electron Model Interactive Example The Localized Electron Model V The triple bond consists of a σ bond produced by the overlap of an sp orbital from each atom and two bonds produced by the overlap of 2p orbitals from each atom The lone pairs are in the sp orbitals Since the CO molecule has only two atoms, it must be linear

58 Section 4.3 Hybridization and the Localized Electron Model Interactive Example The Localized Electron Model V b. BF 4 The BF 4 ion has 32 valence electrons The Lewis structure shows four pairs of electrons around the boron atom, which means a tetrahedral arrangement: This requires sp 3 hybridization of the boron atom

59 Section 4.3 Hybridization and the Localized Electron Model Interactive Example The Localized Electron Model V Each fluorine atom also has four electron pairs and can be assumed to be sp 3 hybridized The BF 4 ion s molecular structure is tetrahedral

60 Section 4.3 Hybridization and the Localized Electron Model Interactive Example The Localized Electron Model V c. XeF 2 The XeF 2 molecule has 22 valence electrons The Lewis structure shows five electron pairs on the xenon atom, which requires trigonal bipyramidal arrangement: Note that the lone pairs are placed in the plane where they are 120 degrees apart

61 Section 4.3 Hybridization and the Localized Electron Model Interactive Example The Localized Electron Model V To accommodate five pairs at the vertices of a trigonal bipyramid requires that the xenon atom adopt a set of five dsp 3 orbitals Each fluorine atom has four electron pairs and can be assumed to be sp 3 hybridized The XeF 2 molecule has a linear arrangement of atoms

62 Section 4.4 The Molecular Orbital Model Properties of Molecular Orbitals The electron probability of both MOs is centered along the line passing through the two nuclei MO 1 - Greatest electron probability is between the nuclei MO 2 - Greatest electron probability is on either sides of the nuclei MO 1 and MO 2 are referred to as sigma (σ) molecular orbitals In the molecule, only the molecular orbitals are available for occupation by electrons

63 Section 4.4 The Molecular Orbital Model Properties of Molecular Orbitals MO 1 is lower in energy than the 1s orbitals of free atoms, while MO 2 is higher in energy than the 1s orbitals A bonding molecular orbital is lower in energy than the atomic orbitals from which it is composed An antibonding molecular orbital is higher in energy than the atomic orbitals from which it is composed Each molecular orbital can hold 2 electrons with opposite spins

64 Section 4.4 The Molecular Orbital Model Figure Bonding and Antibonding Molecular Orbitals (MOs)

65 Section 4.4 The Molecular Orbital Model Properties of Molecular Orbitals The MO model is physically reasonable In bonding MOs, electrons have a higher probability of being between the nuclei In antibonding MOs, electrons are mainly outside the space between the nuclei The labels on MOs indicate their symmetry, the parent atomic orbitals, and whether they are bonding or antibonding Molecular electron configurations can be written in a manner similar to atomic electron configurations

66 Section 4.4 The Molecular Orbital Model Properties of Molecular Orbitals The number of orbitals are conserved The number of MOs will always be equal to the number of atomic orbitals used to construct them

67 Section 4.4 The Molecular Orbital Model Fig Molecular Orbital Energy-Level Diagram of the H 2 Molecule

68 Section 4.4 The Molecular Orbital Model Bond Order It refers to the difference between the number of bonding electrons and the number of antibonding electrons divided by 2 2 is considered given the fact that electrons are taken in the form of pairs Bond order = number of bonding electrons number of antibonding electrons 2 Larger bond order is generally related to greater bond strength

69 Section 4.4 The Molecular Orbital Model Calculation of Bond Order for a H 2 ion Bond order = = 1 2

70 Section 4.5 Bonding in Homonuclear Diatomic Molecules Homonuclear Diatomic Molecules These molecules are composed of two identical atoms The valence orbitals significantly contribute to the MO of a particular molecule Electron probability in such molecules is high above and below the line between the nuclei Both orbitals are pi ( ) molecular orbitals Bonding MO - 2p Antibonding MO - 2p *

71 Section 4.5 Bonding in Homonuclear Diatomic Molecules Bonding and Antibonding in Homonuclear Diatomic Molecules

72 Section 4.5 Bonding in Homonuclear Diatomic Molecules Paramagnetism Paramagnetism causes a substance to be attracted into the inducing magnetic field Associated with unpaired electrons Diamagnetism causes a substance to be repelled from the inducing magnetic field Associated with paired electrons

73 Section 4.5 Bonding in Homonuclear Diatomic Molecules Interactive Example The Molecular Orbital Model II Use the molecular orbital model to predict the bond order and magnetism of each of the following molecules Solution (a) Ne 2 (b) P 2 (a) Ne 2 The valence orbitals for Ne are 2s and 2p Construct the MO structure The Ne 2 molecule has 16 valence electrons (8 from each atom) Placing these electrons in the appropriate molecular orbitals produces the following diagram:

74 Section 4.5 Bonding in Homonuclear Diatomic Molecules Interactive Example The Molecular Orbital Model II σ 2p * 2p * E 2p σ 2p σ 2s * σ 2s The bond order is (8 8)/2 = 0, and Ne 2 does not exist

75 Section 4.5 Bonding in Homonuclear Diatomic Molecules Interactive Example The Molecular Orbital Model II (b) P 2 The P 2 molecule contains phosphorus atoms from the third row of the periodic table Assume that the diatomic molecules of the Period 3 elements can be treated in a way very similar which has been seen so far Draw the MO diagram for P 2 analogous to that for N 2 The only change will be that the molecular orbitals will be formed from 3s and 3p atomic orbitals The P 2 molecule has 10 valence electrons (5 from each phosphorus atom)

76 Section 4.5 Bonding in Homonuclear Diatomic Molecules Interactive Example The Molecular Orbital Model II The resulting molecular orbital diagram is: σ 3p * 3p * E σ 3p 3p σ 3s * σ 3s The molecule has a bond order of 3 and is expected to be diamagnetic

77 Section 4.6 Bonding in Heteronuclear Diatomic Molecules Heteronuclear Diatomic Molecules These molecules are composed of two different atoms They may also involve, in special cases, molecules that contain atoms adjacent to each other in the periodic table They are best described by the MO model

78 Section 4.6 Bonding in Heteronuclear Diatomic Molecules Energy-Level Diagram of Heteronuclear Diatomic Molecules - An Example (HF) Consider the HF molecule and assume that fluorine uses only its 2p orbitals to bond to hydrogen The MOs for HF are composed of fluorine 2p and hydrogen 1s orbitals The fluorine 2p orbital is lower in energy than the hydrogen 1s orbital The σ MO holding the binding electron pairs will show higher electron probability closer to fluorine Electron pairs are not equally shared

79 Section 4.6 Bonding in Heteronuclear Diatomic Molecules Energy-Level Diagram of Heteronuclear Diatomic Molecules - An Example (HF) Partial MO energy-level diagram Electron probability distribution

80 Section 4.6 Bonding in Heteronuclear Diatomic Molecules Interactive Example The Molecular Orbital Model III Use the molecular orbital model to predict the magnetism and bond order of the NO + and CN ions Solution The NO + ion has 10 valence electrons ( ) The CN ion also has 10 valence electrons ( ) Both ions are therefore diamagnetic and have a bond order derived from the equation 8 2 = 3 2

81 Section 4.6 Bonding in Heteronuclear Diatomic Molecules Interactive Example The Molecular Orbital Model III The molecular orbital diagram for these two ions is the same σ 2p * 2p * E σ 2p 2p σ 2s * σ 2s

82 Section 4.7 Combining the Localized Electron and Molecular Orbital Models An Introduction The ideal bonding model must contain the following: Simplicity of the localized electron model Delocalization feature of the molecular orbital model Combining both models will help describe molecules that require resonance σ bond can be described as being localized bonding can be treated as being delocalized

83 Section 4.7 Combining the Localized Electron and Molecular Orbital Models Figure (a) The Molecular Orbital System in Benzene

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