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Unformatted text preview: 15 Chapter Organic Compounds and the Atomic Properties of Carbon 15.1 Methane (natural gas) CH 4 Acetic Acid (in vinegar) C 2 H 4 O 2 Calcium Carbonate CaCO 3 Sodium Bicarbonate NaHCO 3 15.2 In the early 19 th century, many prominent thinkers believed that an unobservable spiritual energy, a "vital force," existed within compounds from living things, which made them impossible to synthesize and fundamentally different from compounds of the mineral world. The finding that urea (present in mammal urine) could be synthesized from inorganic ammonium cyanate led to the downfall of vitalism. 15.3 a) Carbon's position in the periodic table gives it an electronegativity midway between the most metallic and nonmetallic elements of period 2. Therefore, carbon shares electrons to attain a filled shell, bonding covalently in molecules, networks, and polyatomic ions. b) Carbon has four electrons in its outer shell, so it needs to form four covalent bonds to fulfill its octet requirement. c) Formation of carbon ions is energetically impossible under ordinary conditions. Its ionization energy and electron affinity values are not conducive to ion formation. d) Carbon forms relatively short, strong bonds as a result of its small size, which allows close approach to another atom and thus greater orbital overlap. e) The C C bond is short enough to allow the formation of multiple bonds using the 2p orbitals. 15.4 a) Carbon bonds to C, H, O, N, P, S, and halogens. b) Heteroatoms are all atoms other than C or H. c) N, O, F, Cl, and Br are more electronegative. H and P are less electronegative. S and I have the same electronegativity as carbon. d) Since carbon can bond to a wide variety of atoms, this means it can form many different compounds. 15.5 Atomic and bonding properties produce three crucial differences between carbon and Si. Si is larger, forms weaker bonds, and unlike C, has d orbitals available. 15.6 Oxidation states of carbon range from - 4 to + 4. In carbon dioxide (CO 2 ) carbon has a + 4 oxidation state. In methane (CH 4 ) carbon has a - 4 oxidation state. 15.7 The C Li bond is the most reactive, since it shows the greatest difference in electronegativity. C I and C O would be less reactive, with C H and C C least so. 15.8 a) An alkane and a cycloalkane contain only single C C bonds, while an alkene contains a C C double bond and an alkyne contains a C C triple bond. A cycloalkane contains a ring of C atoms. b) C n H 2n + 2 ; C n H 2n ; C n H 2n ; C n H 2n- 2 , respectively. c) Both alkanes and cycloalkanes are saturated. 15.9 a) Constitutional isomers are those with different sequences of bonded atoms. b) Geometric isomers have different orientation of groups around a double bond or a cyclic structure....
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- Spring '07