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Copyright McGraw-Hill 20091 Chapter 9 Chemical Bonding II: Molecular Geometry and Bonding Theories

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Copyright McGraw-Hill 20092 9.1 Molecular Geometry Molecular geometry is the three- dimensional shape of a molecule. Geometry can be predicted using –Lewis dot structures –VSEPR model CCl 4

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Copyright McGraw-Hill 20093 Molecules of the type AB x will be considered –A is the central atom –B atoms surround the central atom –x commonly has integer values from 1 to 6 –Examples: All AB 1 molecules are linear.

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Copyright McGraw-Hill 20094 AB 2 AB 3

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Copyright McGraw-Hill 20095 VSEPR Model: Valence-Shell Electron- Pair Repulsion Model − Electron pairs move as far apart as possible to minimize repulsions. Lewis structure Electron-domain geometry Molecular geometry − Strategy to predict geometry: − Electron domain is a lone pair or a bond (the bond may be single, double, or triple).

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Copyright McGraw-Hill 20096 Steps to determine Geometry −Step #1: Draw the molecule’s Lewis structure. −Step #2: Count the number of electron domains on the central atom. −Step #3: Determine the electron-domain geometry. Examples H – C N:H – C N: :O: :O – N = O: – : : : : – :F – Xe – F: : : : : : : : The electron-domain geometry is based on the number of electron domains around the central atom. 23 5

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Copyright McGraw-Hill 20097 Electron domains and geometry Number of Electron Domains Electron-Domain Geometry 2Linear 3Trigonal planar 4Tetrahedral

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Copyright McGraw-Hill 20098 Number of Electron Domains Electron-Domain Geometry 5Trigonal bipyramidal 6Octahedral

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Copyright McGraw-Hill 20099 − Step #4: Determine the molecular geometry. Step #24 e ¯ domains Example: Ammonia, NH 3 The electron-domain geometry and the number of bonded atoms determine the molecular geometry. Step #1 : H – N – H – H electron-domain geometry tetrahedral Step #3 molecular geometry = trigonal pyramidal

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Copyright McGraw-Hill 200910Copyright McGraw-Hill 2009 Note:The common molecular geometries are all derived from these 5 electron-domain geometries. Linear Bent Trigonal planar Bent Trigonal pyramidal Tetrahedral T-shaped Seesaw Trigonal bipyramidal Linear T-shaped Square planar Square pyramidal Octahedral

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Copyright McGraw-Hill 200911Copyright McGraw-Hill 2009 For SF 4, which geometry is correct? or Axial and equatorial positions ax eq ax = axial eq = equatorial The 5 electron domains are not all equivalent. Why? Fewest lone-pair – bond-pair interactions at angles of 90 o 90º 120º

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Copyright McGraw-Hill 200912

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Copyright McGraw-Hill 200913

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Copyright McGraw-Hill 200914Copyright McGraw-Hill 2009 Exercise:For each of the following species, i)draw the Lewis structure. ii)determine the number of electron domains on the central atom and its electron-domain geometry. iii)predict the molecular geometry. a)NF 3 b)CO 3 2

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Copyright McGraw-Hill 200915Copyright McGraw-Hill 2009 a)NF 3 i) ii) 4 electron domains on the central atom. Electron-domain geometry: tetrahedral iii) One lone pair on the central atom. Molecular geometry: trigonal pyramidal FNF F

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Copyright McGraw-Hill 200916Copyright McGraw-Hill 2009 a)CO 3 2 i) ii) 3 electron domains on the central atom. Electron-domain geometry: trigonal planar iii) No lone pairs on the central atom. Molecular geometry: trigonal planar OCO O 22

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Copyright McGraw-Hill 200917Copyright McGraw-Hill 2009 Deviations from ideal bond angles − All electron domains repel each other. − The repulsion between domains depends on the types of domains involved. single bond triple bond double bond lone pair <<< Increasingly repulsion

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Copyright McGraw-Hill 200918Copyright McGraw-Hill 2009 lone-pair - lone-pair repulsion is greater than lone-pair - bonding-pair repulsion is greater than bonding-pair - bonding-pair repulsion

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Copyright McGraw-Hill 200919Copyright McGraw-Hill 2009 Geometry with more than one central atom CH 3 OH AX 4 No lone pairs 2 lone pairs tetrahedral bent

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Copyright McGraw-Hill 200920Copyright McGraw-Hill 2009 9.2 Molecular Geometry and Polarity + - H – F Bond dipoles are vectors and therefore are additive. The HF bond is polar and HF has a dipole moment ( ).

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Copyright McGraw-Hill 200921 Molecules with more than two atoms –Remember bond dipoles are additive since they are vectors. dipole moment > 0 dipole moment = 0 H2OH2O CO 2

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Copyright McGraw-Hill 200922Copyright McGraw-Hill 2009 cis-1,2-dichloroethene trans-1,2-dichloroethene CC = - - - - Cl H H CC = - - - - H H Example: Dichloroethene, C 2 H 2 Cl 2, exists as three isomers. polar = 1.90 D bp = 60.3ºC nonpolar = 0 D bp = 47.5ºC CC = - - - - Cl H H 1,1-dichloroethene polar = 1.34 D bp = 31.7ºC

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Copyright McGraw-Hill 200923Copyright McGraw-Hill 2009 9.3 Valence Bond Theory Electrons in molecules occupy atomic orbitals. Covalent bonding results from the overlap of atomic orbitals.

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Copyright McGraw-Hill 200924 Representation of singly-occupied and doubly-occupied s and p atomic orbitals. Singly-occupied orbitals appear light; doubly-occupied orbitals appear darker.

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Copyright McGraw-Hill 200925Copyright McGraw-Hill 2009 Example: H ( 1s 1 ) + H ( 1s 1 ) H 2

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Copyright McGraw-Hill 200926Copyright McGraw-Hill 2009 Example:F ( 1s 2 2s 2 2p 5 ) + F ( 1s 2 2s 2 2p 5 ) F 2

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Copyright McGraw-Hill 200927Copyright McGraw-Hill 2009 Example:H ( 1s 1 ) + F ( 1s 2 2s 2 2p 5 ) HF

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Copyright McGraw-Hill 200928 9.4 Hybridization of Atomic Orbitals Valence bond theory cannot account for many experimental observations. Beryllium Chloride, BeCl 2 linear both bonds equivalent VSEPR Be Cl No unpaired electrons 2 types of overlap with 2s and 2p #1 #2

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Copyright McGraw-Hill 200929

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Copyright McGraw-Hill 200930 The atomic orbitals on an atom mix to form hybrid orbitals. –Orbital shapes (boundary surfaces) are pictorial representations of wave functions. –Wave functions are mathematical functions. –Mathematical functions can be combined. Hybridization of s and p orbitals –sp hybridization

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Copyright McGraw-Hill 200931Copyright McGraw-Hill 2009 The two sp orbitals point in opposite directions inline with one another.

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Copyright McGraw-Hill 200932Copyright McGraw-Hill 2009 Each Be sp orbital overlaps a Cl 3p orbital to yield BeCl 2. 2Cl + BeCl 2 Be All bond angles 180 o.

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Copyright McGraw-Hill 200933Copyright McGraw-Hill 2009 #2 2 types of overlap with 2s and 2p #3 overlap with p-orbitals = 90 o Example: Boron trifluoride, BF 3.. F.... B F...... F...... VSEPR trigonal planar all bonds equivalent only 1 unpaired electron − sp 2 hybridization #1

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Copyright McGraw-Hill 200934Copyright McGraw-Hill 2009 The three sp 2 orbitals point to the corners of an equilateral triangle. All bond angles 120 o.

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Copyright McGraw-Hill 200935Copyright McGraw-Hill 2009 Each B sp 2 orbital overlaps a F 2p orbital to yield BF 3. B 3F + BF 3 2s 2 2p 5 All bond angles 120 o.

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Copyright McGraw-Hill 200936Copyright McGraw-Hill 2009 #2 2 types of overlap with 2s and 2p overlap with p-orbitals = 90° tetrahedral all bonds equivalent Example: Methane, CH 4 VSEPR C H H H H only 2 unpaired electrons #1 − sp 3 hybridization #3

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Copyright McGraw-Hill 200937Copyright McGraw-Hill 2009

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38Copyright McGraw-Hill 2009 The sp 3 hybrid orbitals point to the corners of a tetrahedron. All bond angles 109.5 o.

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Copyright McGraw-Hill 200939Copyright McGraw-Hill 2009 Each C 2sp 3 orbital overlaps a H 1s orbital to yield CH 4. C 4 H4 H + CH 4 1s 1 All bond angles 109.5 o.

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Copyright McGraw-Hill 200940Copyright McGraw-Hill 2009 Expanded octets − Hybridization of s, p and d orbitals Bond angles 120 o and 90 o.

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Copyright McGraw-Hill 200941Copyright McGraw-Hill 2009 Lewis structure Number of electron domains Type of hybridization

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Copyright McGraw-Hill 200942 9.5 Hybridization in Molecules Containing Multiple Bonds A sigma ( ) bond is a bond in which the shared electron density is concentrated directly along the internuclear axis between the two nuclei involved in bonding. –end-to-end overlap

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Copyright McGraw-Hill 200943 Double and triple bonds consist of both sigma ( ) and pi ( ) bonds. A pi ( ) bond forms from the sideways overlap of p orbitals resulting in regions of electron density that are concentrated above and below the plane of the molecule. –sideways overlap

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Copyright McGraw-Hill 200944Copyright McGraw-Hill 2009 Example: Ethylene, C 2 H 4 CC = - - - - H H H H number of = 3 electron domains Double bond = 1 bond + 1 bond hybridization = sp 2

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Copyright McGraw-Hill 200945Copyright McGraw-Hill 2009 Example: Acetylene, C 2 H 2 H – C C – HH – C C – H number of = 2 electron domains Triple bond = 1 bond + 2 bonds hybridization = sp

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Copyright McGraw-Hill 200946Copyright McGraw-Hill 2009 Exercise:How many pi bonds and sigma bonds are in each of the following molecules? Describe the hybridization of each C atom. (a) 4 sigma bonds (b) 5 sigma bonds, 1 pi bond (c) 10 sigma bonds, 3 pi bonds sp 3 sp 2 sp 3 sp 2 sp (a)(b)(c)

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Copyright McGraw-Hill 200947 9.6 Molecular Orbital Theory Molecular Orbital Theory (MO) –Atomic orbitals combine to form new molecular orbitals which are spread out over the entire molecule. Electrons are in orbitals that belong to the molecule as a whole. –Molecular orbitals (wave functions) result from adding and/or subtracting atomic orbitals (wave functions).

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Copyright McGraw-Hill 200948 Molecular orbital theory (MO) –Atomic orbitals combine to form new, molecular orbitals that are spread out over the entire molecule. Electrons are now in orbitals that belong to the molecule as a whole.

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Copyright McGraw-Hill 200949Copyright McGraw-Hill 2009 −Pictorial representation. H + H H 2 1s 1 1s 1 1s 2 bonding orbital antibonding orbital 1s1s1s1s H atomic orbitals H 2 molecular orbitals sum difference

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Copyright McGraw-Hill 200950Copyright McGraw-Hill 2009 Lower energy and more stable than the atomic orbitals that were added Types of molecular orbitals −Bonding molecular orbital High electron density between the nuclei

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Copyright McGraw-Hill 200951Copyright McGraw-Hill 2009 Higher energy and less stable than the atomic orbitals that were subtracted −Antibonding molecular orbital Low electron density between the nuclei node

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Copyright McGraw-Hill 200952Copyright McGraw-Hill 2009 bond order = 1/2 (2 – 0) = 1 single bond bond order = 1/2 (2 – 2) = 0 no bond Bond order

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Copyright McGraw-Hill 200953Copyright McGraw-Hill 2009 bond order = 1/2 (2 – 0) = 1 single bond bond order = 1/2 (2 – 2) = 0 no bond Examples Using Antibonding Orbitals

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Copyright McGraw-Hill 200954 Pi ( ) molecular orbitals –Wave functions representing p orbitals combine in two different ways yielding either orbitals or orbitals. –End-to-end combination yields sigma ( ) orbitals Copyright McGraw-Hill 2009 Atomic orbitals ++ -- ± 2pz2pz2pz2pz Molecular orbitals + - - + + - - sum difference bonding orbital antibonding orbital

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Copyright McGraw-Hill 200955Copyright McGraw-Hill 2009 Atomic orbitals sum difference sum difference 2px2px ± + -- 2px2px + + - + + - - + - + + - - Molecular orbitals −Sideways combination yields pi ( ) orbitals 2py2py ± + + -- 2py2py

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Copyright McGraw-Hill 200956Copyright McGraw-Hill 2009 Energy order of the 2p and 2p orbitals changes across the period. B 2, C 2, N 2 O 2, F 2, Ne 2

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Copyright McGraw-Hill 200957Copyright McGraw-Hill 2009 Molecular orbital diagram of nitrogen, N 2

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Copyright McGraw-Hill 200958Copyright McGraw-Hill 2009 Molecular orbital diagram of oxygen, O 2

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Copyright McGraw-Hill 200959 Magnetism –Diamagnetic substance A substance whose electrons are all paired. Weakly repelled by magnetic fields. –Paramagnetic substance A substance with one or more unpaired electrons. Attracted by magnetic fields.

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Copyright McGraw-Hill 200960Copyright McGraw-Hill 2009

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61 9.7 Bonding Theories and Descriptions of Molecules with Delocalized Bonding In localized bonds the and bonding electrons are associated with only two atoms. Resonance requires delocalized bonds when applying valence bond theory.

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Copyright McGraw-Hill 200962 In delocalized bonds the bonding electrons are associated with more than two atoms. Examples: NO 3 , CO 3 2 , C 6 H 6, O 3

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Copyright McGraw-Hill 200963Copyright McGraw-Hill 2009 Example: benzene, C 6 H 6 Each C atom has 3 electron domains Hybridization: sp 2

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Copyright McGraw-Hill 200964 Key Points Molecular geometry –VSEPR model Molecular geometry and polarity Valence bond theory Hybridization of atomic orbitals –s and p –s, p, and d Hybridization involving multiple bonds

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Copyright McGraw-Hill 200965 Key Points Molecular orbital theory –Bonding and antibonding orbitals –Sigma ( ) molecular orbitals –Pi ( ) molecular orbitals –MO diagrams

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