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Discover the abundance and significance of carbon, the various allotropes like diamond, graphite, and fullerenes, and the fundamental concepts of organic compounds and hydrocarbons. Learn about the structure, bonding, isomerism, nomenclature, and properties of saturated and unsaturated hydrocarbons.
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Chapter 20: Carbon and Hydrocarbons • 20.1 – Abundance and Importance of Carbon • 20.2 – Organic Compounds • 20.3 – Saturated Hydrocarbons • 20.4 – Unsaturated Hydrocarbons
Structure and Bonding of Carbon • Carbon, the first member of Group 14, has mostly nonmetallic properties. Carbon atoms tend to form four single bonds. This bonding results in a tetrahedral shape.
Allotropes of Carbon • Carbon occurs in several solid allotropic forms that have dramatically different properties. • Diamond – Colorless, crystalline, solid form of carbon • Graphite – soft, black, crystalline form of carbon that is a fair conductor of electricity. • Fullerenes – dark colored solids made of spherically networked carbon atom cages
Allotropes of Carbon - Diamond • The hardest material known to man • Carbon atoms are bonded covalently in a network fashion • Conducts heat 5x better than silver or copper • Does not conduct electricity
Allotropes of Carbon - Graphite • Soft, crumbles easily and feels greasy • Used as a lubricant and as lead • Good conductor of electricity • Stronger and lighter than steel
Allotropes of Carbon - Fullerenes • Discovered in the 1980s (N.P. 1996) • Structure consists of near spherical cages • Scientists are currently trying to find practical uses for these substances
Organic Compounds • Covalently bonded compounds containing carbon, excluding carbonates and oxides • The diversity of organic compounds results from the uniqueness of carbon’s structure and bonding
Carbon – Carbon Bonding • Catenation – Carbon atoms are unique in their ability to form long chains and rings of covalently bonded atoms.
Carbon Bonding to Other Elements • Hydrocarbons – composed of only carbon and hydrogen; they are the simplest organic compounds. • Most contain hydrocarbon backbones and have other elements added on (O, S, and N)
Arrangement of Atoms • Isomer – Compounds that have the same molecular formula but different structures • As the number of carbons increases so does the number of possible isomers
Structural Formula • Indicates the number and types of atoms present in a molecule and also shows the bonding arrangement of the atoms • Structural formulas do not accurately represent the three dimensional shape of the molecule.
Isomers – Structural • Structural Isomers – isomers in which the atoms are bonded together in different orders
Isomers - Geometric • Isomers in which the order of atom bonding is the same but the arrangement of atoms in space is different • In order for geometric isomers to exist, there must be a rigid structure in the molecule to prevent free rotation around a bond
Saturated Hydrocarbons • Hydrocarbons in which each carbon atom in the molecule form four single covalent bonds with other atoms
Alkanes CnH2n+2 • Hydrocarbons that contain only single bonds • Homologous series – one in which adjacent members differ by a constant unit. • Alkyl groups- groups of atoms that are formed when one hydrogen atom is removed from an alkane molecule
Cycloalkanes • Alkanes in which the carbon atoms are arranged in a ring, or cyclic, structure
Alkane Nomenclature Unbranched Chain • Count the longest continuous chain. • Use greek prefix (at right) • End with -ane
Alkane Nomenclature Branched Chain • Name the longest chain (See previous) • Add the name of the alkyl group • Insert position numbers • Punctuate
Cycloalkane Nomenclature • Name the longest chain • Add Cyclo- • Add names of alkyl groups • Number the carbons (lowest numbers) • Inset position numbers • Punctuate
Example • Give the name of the following molecule • 6 carbons = hexane • CH3 = methyl • Number around the circle • 1,3 - dimethlycyclohexane
Example • Draw 1,1- dimethylcyclobutane
Unsaturated Hydrocarbons • Hydrocarbons in which not all carbon atoms have four single covalent bonds
Alkenes CnH2n • Hydrocarbons that contain double covalent bonds
Alkene Nomenclature • Name the same as Alkane • Locate the longest continuous chain that contains the double bond(s). • Double bond should have lowest number
Alkynes CnH2n-2 • Hydrocarbons with triple covalent bonds • Named the same as others • Find the longest chain containing a triple bond • Number so triple bond has lowest number
Example • Name the following
Aromatic Hydrocarbons • Hydrocarbons with six membered carbon rings and delocalized electrons • Benzene – the primary aromatic hydrocarbon
Aromatic Nomenclature • Name the parent Hydrocarbon (Usually benzene) • Name the Alkyl groups • Number the carbon atoms • Insert position numbers • Add Punctuation
Example • Name the following