Hybrid AO's and polyatomic MO's. CH101 Fall 2012 Boston University
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1 CH101 Fall 2012 Boston University
2 Figures on slides 4 9 are used with permission from Clayden et al., Organic Chemistry (Oxford University Press, 2000), 2007 Oxford University Press. Figures on slides 23, 25 and 39 are used with permission from Mahaffy et al., Chemistry: Human Activity, Chemical Reactivity (Nelson, 2011), 2011 Nelson Education Ltd. 2
3 Hybridized AO s account for central atom electron pair geometry 3
4 Central atom AO mixing: Hybrid AO s Unmixed AO s have the wrong central atom geometry 4
5 An s and a p AO make two sp hybrid AO s 180 o angle, for SN = 2 Two p s are unchanged on each atom 5
6 sp hybrids account for linear geometry 180 o angle, for SN = 2 Two p s are unchanged on each atom 6
7 An s and two p AO s make three sp 2 hybrid AO s 120 o angle, for SN = 3 One p is unchanged on each atom 7
8 sp 2 hybrids account for trigonal planar geometry 120 o angle, for SN = 3 One p is unchanged on each atom 8
9 An s and three p AO s make four sp 3 hybrid AO s 109 o angle, for SN = 4 sp 3 hybrids account for tetrahedral geometry 9
10 Which hybridization to use? steric number electron pair geometry hybridization steric number = attached atoms + lone pairs steric number electron pair geometry hybridization molecular geometry H 2 O 4 tetrahedral sp 3 bent at 109 NH 3 4 tetrahedral sp 3 trigonal pyramidal CH 4 4 tetrahedral sp 3 tetrahedral SO 2 3 trigonal planar sp 2 bent at 120 BH 3 3 trigonal planar sp 2 trigonal planar CO 2 2 linear sp linear at
11 Examples CO 2, carbon dioxide H 2 CO, formaldehyde HCO 2, formate SO 2, sulfur dioxide 11
12 Polyatomic MO recipe Overview σ framework of single bonds and lone pairs π framework of additional bond pairs π framework can be delocalized (spread) over more than two atoms. 12
13 Polyatomic MO recipe 1. Use the Lewis structure to get the number of electron pairs make hybrid AO s on each atom (except H) 2. Sketch the σ framework and place pairs in each bonding σ MO in each nonbonding hybrid AO 3. Sketch the π framework MO s, mark as bonding, nonbonding, antibonding place remaining pairs (Auf Bau) get the π bond order 13
14 σ framework recipe Hybridization of terminal atoms the same as their central atom Terminal H never hybridized One pair in each hybrid AO σ bonding MO One pair in each non bonded hybrid AO 14
15 CO 2 sp σ framework sp hybrids overlap to make two sp σ bonding MO s, leaving two sp nonbonding AO s. These can hold 15
16 CO 2 sp σ framework sp hybrids overlap to make two sp σ bonding MO s, leaving two sp nonbonding AO s. These can hold 16
17 CO 2 sp σ framework sp hybrids overlap to make two sp σ bonding MO s, leaving two sp nonbonding AO s. These can hold 4 pairs of electrons. 17
18 CO 2 sp σ framework sp hybrids overlap to make two sp σ bonding MO s, leaving two sp nonbonding AO s. These can hold 4 pairs of electrons. The remaining 4 pairs are in the 18
19 CO 2 π framework 19
20 π framework recipe Unused p AO s form same number of π MO s Number of loops and AO overlap determine whether π MO is bonding (π) nonbonding (π n ) antibonding (π*) 20
21 CO 2 π framework 4 pairs are in the (delocalized) π framework 2 pairs in π (bonding) and 2 pairs in π n (nonbonding); bond order 2 21
22 H 2 CO sp 2 σ framework 6 pairs in Lewis structure, 5 pairs in σ framework, and so 1 pair in (localized) π framework. 22
23 H 2 CO sp 2 σ framework 6 pairs in Lewis structure, 5 pairs in σ framework, and so 1 pair in (localized) π framework. 23
24 H 2 CO π framework 1 pair in (localized) π framework 1 pair in π (bonding); bond order 1 24
25 H 2 CO π framework 1 pair in (localized) π framework 1 pair in π (bonding); bond order 1 25
26 HCOO sp 2 σ framework 9 pairs in Lewis structure, 7 pairs in σ framework, and so 2 pairs in (delocalized) π framework. 26
27 HCOO π framework 2 pairs in (delocalized) π framework 1 pair in π (bonding) and 1 pair in π n (nonbonding); bond order 1 27
28 SO 2 sp 2 σ framework 9 Boston pairs University in Slideshow Lewis Title structure, Goes Here 7 pairs in σ framework, and so 2 pairs in (delocalized) π framework. 28
29 SO 2 π framework 2 pairs in (delocalized) π framework 1 pair in π (bonding) and 1 pair in π n (nonbonding); bond order 1 29
30 SO 2 correlation diagram
31 Do these on your own HCOOH, formic acid allyl: [H 2 C=CH CH 2 ], anion; [H 2 C=CH CH 2 ] +, cation H 2 C=C=CH 2, allene H 2 C=CH CH=CH 2, 1,3 butadiene O 3, ozone For each one, Write the Lewis structure Sketch the σ framework and assign its pairs Sketch the π framework MO s, identify localization or delocalization, bonding, nonbonding, antibonding, and assign its pairs, and get the π bond order 31
32 HCOOH, formic acid Formate, HCOO π, is planar and has 9 pairs 7 pairs in σ framework 1 pair in a delocalized bonding π 1 orbital 1 pair in a delocalized nonbonding π 2n orbital What about formic acid? 9 pairs 8 pairs in σ framework 1 pair in localized bonding π 1 orbital 32
33 H 2 C=CH CH 2, allyl (radical) What about allyl? Use CH 2 sp 2, to have increased delocalization: 8 ½ pairs 7 pairs in σ framework 1 pair in delocalized bonding π 1 orbital ½ pair (1 electron) in delocalized nonbonding π 2n orbital 33
34 [H 2 C=CH CH 2 ] +, allyl cation What about allyl cation? 8 pairs 7 pairs in σ framework 1 pair in delocalized bonding π 1 orbital 34
35 [H 2 C=CH CH 2 ], allyl anion What about allyl anion? If CH 2 is sp 3, then 9 pairs 8 pairs in σ framework 1 pair in localized bonding π 1 orbital If CH 2 is sp 2, then 7 pairs in σ framework 1 pair in delocalized bonding π 1 orbital 1 pair in delocalized nonbonding π 2n orbital Increased delocalization makes CH 2 is sp 2 more stable (extension to recipe) 35
36 H 2 C=C=CH 2, allene What about allene? 8 pairs 6 pairs in σ framework 2 pair in two localized bonding π 1 orbitals 36
37 H 2 C=CH CH=CH 2, 1,3 butadiene What about 1,3 butadiene? 11 pairs 9 pairs in σ framework 1 pair in delocalized bonding π 1 orbital 1 pair in delocalized bonding π 2 orbital 37
38 O 3, ozone What about ozone? 9 pairs 7 pairs in σ framework 1 pair in delocalized bonding π 1 orbital 1 pair in delocalized nonbonding π 2n orbital Ozone is polar. Why? The two electrons in the nonbonding MO are each only on the terminal O s! 38
39 O 3 ozone σ and π frameworks 39
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