Carbon bonding tetrahedral arrangement

Both carbon and silicon have their normal bonding tetrahedrally arranged. 

The simplest hydrocarbon molecule, methane, has a tetrahedral shape, with the carbon atom at the center of the tetrahedron and the four hydrogen atoms at the corners. Every carbon atom in a saturated hydrocarbon molecule has its bonds tetrahedrally arranged. This arrangement allows the hydrogen atoms bonded to carbon atoms to be located as far as possible from one another. 

Place the equatorial bonds so as to approximate a tetrahedral arrangement of the bonds to each carbon The equatorial bond of each carbon should be parallel to the ring bonds of its two nearest neighbor carbons... 

Stereochemistry refers to chemistry in three dimensions Its foundations were laid by Jacobus van t Hoff and Joseph Achille Le Bel m 1874 Van t Hoff and Le Bel mde pendently proposed that the four bonds to carbon were directed toward the corners of a tetrahedron One consequence of a tetrahedral arrangement of bonds to carbon is that two compounds may be different because the arrangement of their atoms m space IS different Isomers that have the same constitution but differ m the spatial arrangement of their atoms are called stereoisomers We have already had considerable experience with certain types of stereoisomers—those involving cis and trans substitution patterns m alkenes and m cycloalkanes... 

Our discussion to this point has been limited to molecules m which the chirality center IS carbon Atoms other than carbon may also be chirality centers Silicon like carbon has a tetrahedral arrangement of bonds when it bears four substituents A large number of organosilicon compounds m which silicon bears four different groups have been resolved into their enantiomers... 

Stereochemical inversion of the tetrahedral arrangement of bonds to the carbon at which substitution occurs... 

The optical activity of quartz and certain other materials was first discovered by Jean-Baptiste Biot in 1815 in France, and in 1848 a young chemist in Paris named Louis Pasteur made a related and remarkable discovery. Pasteur noticed that preparations of optically inactive sodium ammonium tartrate contained two visibly different kinds of crystals that were mirror images of each other. Pasteur carefully separated the two types of crystals, dissolved them each in water, and found that each solution was optically active. Even more intriguing, the specific rotations of these two solutions were equal in magnitude and of opposite sign. Because these differences in optical rotation were apparent properties of the dissolved molecules, Pasteur eventually proposed that the molecules themselves were mirror images of each other, just like their respective crystals. Based on this and other related evidence, in 1847 van t Hoff and LeBel proposed the tetrahedral arrangement of valence bonds to carbon. 

When we try to apply VB theory to methane we run into difficulties. A carbon atom has the configuration [HeJ2s22pvl2p l,1 with four valence electrons (34). However, two valence electrons are already paired and only the two half-filled 2/ -orbitals appear to be available for bonding. It looks as though a carbon atom should have a valence of 2 and form two perpendicular bonds, but in fact it almost always has a valence of 4 (it is commonly tetravalent ) and in CH4 has a tetrahedral arrangement of bonds. 

FIGURE 3.14 Each C H bond in methane is formed by the pairing of an electron in a hydrogen U-orbital and an electron in one of the four sp hybrid orbitals of carbon. Therefore, valence-bond theory predicts four equivalent cr-bonds in a tetrahedral arrangement, which is consistent with experimental results. 

In ethene each carbon atom has four electron pairs in its valence shell, which may be considered to occupy four domains with an approximately tetrahedral arrangement. Two of these pairs are forming the double bond, so that the two tetrahedra are sharing an edge, giving an... 

The manual separation of the enantiomorphous crystals of sodium ammonium tartrate tetrahydrate (Figure 1) by Pasteur in 1848 (1) is historically significant, because it laid the foundations of modem stereochemistry. This experiment demonstrated for the first time that certain classes of molecules display enan-tiomorphism even when dissolved in solvent. These observations eventually paved the way for the inspired suggestion, made more than two decades later, by van t Hoff (2) and Le Bel (3), of a tetrahedral arrangement of bonds around the carbon atom. 

The carbon atom now has four unpaired electrons and can form four bonds, but we still have not explained why these bonds adopt a tetrahedral arrangement. To do this, we introduce the concept of hybridisation. 

We have already explained. In terms of hybridisation, how a carbon atom can form four sp hybrid orbitals (see p. 47). We can apply this concept to explain the bonding in alkanes. Ethane is taken as an example of a typical alkane. The four sp hybrid orbitals on each carbon atom will overlap end-on with four other orbitals three hydrogen Is orbitals and one sp hybrid orbital on the other carbon atom. Four cr bonds will be formed and they will adopt a tetrahedral arrangement. This is illustrated for ethane in the diagram. 

An intermediate, often transient, appearing in a chemical or enzymatic reaction in which a carbon atom, which had been double-bonded (i.e., in a trigonal structure) in a particular molecular entity, has been transformed to a carbon center having a tetrahedral arrangement of substituents. Tetrahedral intermediates of proteases have been stabilized with cryoenzymological tech-niques ... 

For a final example, let s consider methane, CH with four bonding electrons surrounding the central carbon atom. VSEPR predicts a tetrahedral arrangement with bond angles of 109.5°. 

Conformational isomerism in propane Propane is a three-carbon- (sp -hybridized) atom-containing linear alkane. All are tetrahedrally arranged. When a hydrogen atom of ethane is replaced by a methyl (CH3) group, we have propane. There is rotation about two C-C cr bonds. 

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