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2.6 Primary Interatomic Bonds  •  37


                                       2p
                                       2s
                   Energy
              (a)
                                       1s

                                 promotion
                                 of election

                                        2p
                                        2s
                   Energy                                    sp 3
              (b)                                                                         H
                                                                                         1s
                                        1s
                                                                                               3
                                                                                              sp
                                                                 109.5°              3
                                    sp 3          sp 3                              sp
                                 hybridization              C                                   sp 3
                                                                      sp 3       H        C
                                                                                 1s
                                                                                                   H
                                       2sp 3                                                       1s
                                                     sp 3                            H    sp 3
                   Energy
              (c)                                                                    1s
                                        1s        Figure 2.14  Schematic                     Region of overlap
                                                                     3
                                                  diagram showing four sp
                                                  hybrid orbitals that point to   Figure 2.15  Schematic
              Figure 2.13  Schematic diagram      the corners of a tetrahedron;   diagram that shows bonding of
                                     3
              that shows the formation of sp  hy-  the angle between orbitals   carbon sp  hybrid orbitals to the
                                                                                      3
              brid orbitals in carbon. (a) Promo-  is 109.5 .                  1s orbitals of four hydrogen atoms
              tion of a 2s electron to a 2p state; (b)   (From J. E. Brady and F.   in a molecule of methane (CH 4 ).
              this promoted electron in a 2p state;   Senese, Chemistry: Matter   (From J. E. Brady and F. Senese,
                       3
              (c) four 2sp  orbitals that form by   and Its Changes, 4th edition.   Chemistry: Matter and Its Changes,
              mixing the single 2s orbital with the   Reprinted with permission of   4th edition. Reprinted with permis-
              three 2p orbitals.                  John Wiley & Sons, Inc.)     sion of John Wiley & Sons, Inc.)
                                    Other types of hybrid bonds are possible for carbon, as well as other substances.
                                                2
                                 One of these is sp , in which an s orbital and two p orbitals are hybridized. To achieve
                                 this configuration, one 2s orbital mixes with two of the three 2p orbitals—the third p
                                 orbital remains unhybridized; this is shown in Figure 2.16. Here, 2p z  denotes the unhy-
                                                        2
                                                9
                                 bridized p orbital.  Three sp  hybrids belong to each carbon atom, which lie in the same
                                 plane such that the angle between adjacent orbitals is 120   (Figure 2.17); lines drawn
                                 from one orbital to another form a triangle. Furthermore, the unhybridized 2p z  orbital
                                                                               2
                                 is oriented perpendicular to the plane containing the sp  hybrids.
                                    These  sp 2  bonds are found in graphite, another form of carbon, which has a
                                 structure and properties distinctly different from those of diamond (as discussed in
                                 Section 12.4). Graphite is composed of parallel layers of interconnecting hexagons.
                                 Hexagons form from planar sp 2  triangles that bond to one another in the manner
                                                                                                   2
                                 presented in Figure 2.18—a carbon atom is located at each vertex. In-plane sp  bonds
                                 are strong; by way of contrast, weak interplanar bonding results from van der Waals
                                 forces that involve electrons originating from the unhybridized 2p z  orbitals. The struc-
                                 ture of graphite is shown in Figure 12.17.



              9 This 2p z  orbital has the shape and orientation of the p z  shown in Figure 2.5c. In addition, the two p orbitals found
                    2
              in the sp  hybrid correspond to the p x  and p y  orbitals of this same figure. Furthermore, p x , p y , and p z  are the three
                           3
              orbitals of the sp  hybrid.
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