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The Number of Bonds That Carbon Can Make and Its Ability to Make Chains and Rings

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The largest database of organic compounds lists about 10 million substances, which include compounds originating from living organisms and those synthesized by chemists

The number of potential organic compounds has been estimated at 1060—an astronomically high number. The existence of so many organic molecules is a consequence of the ability of carbon atoms to form up to four strong bonds to other carbon atoms, resulting in chains and rings of many different sizes, shapes, and complexities.

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The three dimensional shape or configuration of a molecule is an important characteristic. This shape is dependent on the preferred spatial orientation of covalent bonds to atoms having two or more bonding partners. Three dimensional configurations are best viewed with the aid of models. In most cases the focus of configuration is a carbon atom so the lines specifying bond directions will originate there. As defined in the diagram on the right, a simple straight line represents a bond lying approximately in the surface plane. The two bonds to substituents A in the structure on the left are of this kind. A wedge shaped bond is directed in front of this plane (thick end toward the viewer), as shown by the bond to substituent B; and a hatched bond is directed in back of the plane (away from the viewer), as shown by the bond to substituent D

Some texts and other sources may use a dashed bond in the same manner as we have defined the hatched bond, but this can be confusing because the dashed bond is often used to represent a partial bond (i.e. a covalent bond that is partially formed or partially broken). The following examples make use of this notation, and also illustrate the importance of including non-bonding valence shell electron pairs (colored blue) when viewing such configurations. In the three examples shown above, the central atom (carbon) does not have any non-bonding valence electrons; consequently the configuration may be estimated from the number of bonding partners alone. For molecules of water and ammonia, however, the non-bonding electrons must be included in the calculation. In each case there are four regions of electron density associated with the valence shell so that a tetrahedral bond angle is expected. The measured bond angles of these compounds (H2O 104.5º & NH3 107.3º) show that they are closer to being tetrahedral than trigonal or linear. Of course, it is the configuration of atoms (not electrons) that defines the the shape of a molecule, and in this sense ammonia is said to be pyramidal (not tetrahedral). The compound boron trifluoride, BF3, does not have non-bonding valence electrons and the configuration of its atoms is trigonal. Nice treatments of VSEPR theory have been provided by Oxford and Purdue.

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Hydrocarbons are organic molecules consisting entirely of carbon and hydrogen. We often use hydrocarbons in our daily lives: for instance, the propane in a gas grill and the butane in a lighter are both hydrocarbons. They make good fuels because their covalent bonds store a large amount of energy, which is released when the molecules are burned (i.e., when they react with oxygen to form carbon dioxide and water). Methane, the simplest hydrocarbon molecule, consists of a central carbon atom bonded to four hydrogen atoms. The carbon and the four hydrogen atoms form the vertices of a three-dimensional shape known as a tetrahedron, which has four triangular faces; because of this, methane is said to have a tetrahedral geometry. More generally, when a carbon atom is bonded to four other atoms, the molecule (or part of a molecule) will take on a tetrahedral shape similar to that of methane. This happens because the electron pairs that make up the bonds repel each other, and the shape that maximizes their distance from each other is a tetrahedron. Most macromolecules are not classified as hydrocarbons, because they contain other atoms in addition to carbon and hydrogen, such as nitrogen, oxygen, and phosphorus. However, carbon chains with attached hydrogens are a key structural component of most macromolecules (even if they are interspersed with other atoms), so understanding the properties of hydrocarbons is important to understanding the behavior of macromolecules. Carbon’s ability to form bonds with four other atoms goes back to its number and configuration of electrons (Asimov, I., 1962). Carbon has an atomic number of six (meaning six protons, and six electrons as well in a neutral atom), so the first two electrons fill the inner shell and the remaining four are left in the second shell, which is the valence (outermost) shell. To achieve stability, carbon must find four more electrons to fill its outer shell, giving a total of eight and satisfying the octet rule. Carbon atoms may thus form bonds to as many as four other atoms. For example, in methane (CH_4 start subscript, 4, end subscript), carbon forms covalent bonds with four hydrogen atoms. Each bond corresponds to a pair of shared electrons (one from carbon and one from hydrogen), giving carbon the eight electrons it needs for a full outer shell (Reece, J

B., Urry, L. A., 2011).

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To sum up, the main source of the carbon in organic compounds is carbon dioxide in the atmosphere. Plants use sunlight to convert carbon dioxide and water (inorganic compounds) into sugar (an organic compound) through the process of photosynthesis. Other important sources of carbon are fossil fuels such as coal, petroleum and natural gas. This is because fossil fuels are themselves formed from the decaying remains of dead organisms.

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Asimov, I. (1962). The world of carbon (new, rev. ed.). New York, NY: Collier Books.

Hybrid orbitals. (n.d.). Retrieved July 22, 2015 from UC Davis ChemWiki: http://chemwiki.ucdavis.edu/Organic_Chemistry/Fundamentals/Hybrid_Orbitals.

Reece, J. B., Urry, L. A., Cain, M. L., Wasserman, S. A., Minorsky, P. V., and Jackson, R. B. (2011). The chemical context of life. In Campbell Biology (10th ed., pp. 28-43). San Francisco, CA: Pearson.

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