1.14 the orbital view of bonding:
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1 1.14 the orbital view of bonding: The sigma bond Dr. Abdullah Saleh/
2 A limitation of Lewis Theory of Bonding It does not explain the three dimensional geometries of molecules! Dr. Abdullah Saleh/
3 Molecular Orbital Theory (MO) Only s and p orbitals are very important in organic chemistry Orbital: a region in space where the probability of finding an electron is large The typical representation of orbitals are those volumes which contain the electron 90-95% of the time Dr. Abdullah Saleh/
4 1s and 2s orbitals are spheres centered around the nucleus Each orbital can accommodate 2 electrons The 2s orbital is higher in energy and contains a nodal surface (probability of finding electrons = 0) in its center Each 2p orbital has two nearly touching spheres (or lobes) One sphere has a positive phase sign and the other a negative phase sign; a nodal plane separates the spheres There are three 2p orbitals which are perpendicular (orthoganol) to each other Each p orbital can accommodate 2 electrons for a total of 6 electrons All three p orbitals are degenerate (equal in energy) The 2p orbitals are higher in energy than the 1s or 2s Dr. Abdullah Saleh/
5 Dr. Abdullah Saleh/
6 Figure 1.2 Shapes of the s and p orbitals used by valence electrons of a carbon Dr. Abdullah Saleh/
7 As two atoms approach each other their atomic orbitals (AOs) overlap to become molecular orbitals (MOs) The number of MOs that result must always equal the number of AOs used Example: H 2 molecule As the hydrogen atoms approach each other their 1s orbitals begin to overlap The MOs that form encompass both nuclei The electrons are not restricted to the vicinity of one nucleus or another Each MO has a maximum of 2 spin-paired electrons The two electrons between the nuclei serve to attract the nuclei towards each other (covalent bond) Dr. Abdullah Saleh/
8 The sigma bond A sigma (σ) orbital lies along the axis between two bonded atoms; a pair of electrons in a sigma orbital is called a sigma bond. Dr. Abdullah Saleh/
9 Figure 1.3 The molecular orbital representation of covalent bond formation Dr. Abdullah Saleh/
10 Figure 1.4 Orbital overlap to form σ bonds Dr. Abdullah Saleh/
11 1.15 Carbon sp 3 Hybrid Orbitals 1.16 Tetrahedral Carbon; the Bonding in Methane Dr. Abdullah Saleh/
12 The Structure of Methane and Ethane: sp 3 Hybridization The structure of methane with its four identical tetrahedral bonds cannot be adequately explained using the electronic configuration of carbon Hybridization of the valence orbitals (2s and 2p) provides four new identical orbitals which can be used for the bonding in methane Orbital hybridization is a mathematical combination of the 2s and 2p wave functions to obtain wave functions for the new orbitals Dr. Abdullah Saleh/
13 Figure 1.5 Distribution of the six electrons in a carbon atom Dr. Abdullah Saleh/
14 When one 2s orbital and three 2p orbitals are hybridized four new and identical sp 3 orbitals are obtained When four orbitals are hybridized, four orbitals must result Each new orbital has one part s character and 3 parts p character The four identical orbitals are oriented in a tetrahedral arrangements The four sp 3 orbitals are then combined with the 1s orbitals of four hydrogens to give the molecular orbitals of methane Each new molecular orbital can accommodate 2 electrons Dr. Abdullah Saleh/
15 Figure 1.6 Unhybridized vs sp 3 hybridized orbitals on carbon Dr. Abdullah Saleh/
16 Dr. Abdullah Saleh/
17 Figure 1.7 sp 3 orbitals extending in one direction Dr. Abdullah Saleh/
18 An sp 3 orbital looks like a p orbital with one lobe greatly extended Often the small lobe is not drawn The extended sp 3 lobe can then overlap well with the hydrogen 1s to form a strong bond The bond formed is called a sigma (σ) bond because it is circularly symmetrical in cross section when view along the bond axis Dr. Abdullah Saleh/
19 Figure 1.7 Examples of sigma bonds formed from sp 3 hybrid orbitals Dr. Abdullah Saleh/
20 A variety of representations of methane show its tetrahedral nature and electron distribution a. calculated electron density surface b. ball-and-stick model c. a typical 3-dimensional drawing Dr. Abdullah Saleh/
21 Figure 1.9 Methane Dr. Abdullah Saleh/
22 Figure 1.10 Planes in methane Dr. Abdullah Saleh/
23 Ethane (C 2 H 6 ) The carbon-carbon bond is made from overlap of two sp 3 orbitals to form a σ bond The molecule is approximately tetrahedral around each carbon Dr. Abdullah Saleh/
24 The representations of ethane show the tetrahedral arrangement around each carbon a. calculated electron density surface b. ball-and-stick model c. typical 3-dimensional drawing Generally there is relatively free rotation about σ bonds Very little energy (13-26 kcal/mol) is required to rotate around the carbon-carbon bond of ethane Dr. Abdullah Saleh/
25 1.17 Classification According to Molecular Framework Dr. Abdullah Saleh/
26 1.17.a Acyclic Compounds Acyclic: not cyclic Have chains of carbon atoms but no rings The chains may be unbranched or branched. unbranched chain of eight carbons branched chain of eight carbons Dr. Abdullah Saleh/
27 Figure 1.11 Examples of natural acyclic compounds Dr. Abdullah Saleh/
28 1.17.b Carbocyclic Compounds Carbocyclic: contain rings of carbon atoms The smallest possible carbon ring has 3 carbon atoms. Rings may have chains of carbon atoms attached to them And may contain multiple bonds Dr. Abdullah Saleh/
29 Figure 1.12 Examples of natural carbocyclic compunds with rings of various sizes and shapes Dr. Abdullah Saleh/
30 1.17.c Heterocyclic Compounds Heterocyclic: at least 1 atom in the ring must be a heteroatom, an atom that is not carbon The most common heteroatoms are, oxygen, nitrogen, and sulfur, but heterocyclics with other elements are also known Heterocyclic rings come in many sizes, and may contain multiple bonds, may have carbon chains or rings attached to them Found in many natural products Dr. Abdullah Saleh/
31 Figure 1.13 Examples of natural heterocyclic compounds Dr. Abdullah Saleh/
32 1.18 Classification According to Functional Groups Dr. Abdullah Saleh/
33 Functional Groups Are Groups of atoms that have characteristic chemical properties regardless of the molecular framework to which they are attached Dr. Abdullah Saleh/
34 Dr. Abdullah Saleh/
35 Dr. Abdullah Saleh/
36 End of Chapter 1 Dr. Abdullah I. Saleh Dr. Abdullah Saleh/
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