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Carbon and Hydrocarbons: Structure and Bonding

Learn about the abundance and importance of carbon, different allotropes of carbon, the bonding of carbon, and the structure and naming of saturated and unsaturated hydrocarbons.

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Carbon and Hydrocarbons: Structure and Bonding

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  1. Chapter 20: Carbon and Hydrocarbons • 20.1 – Abundance and Importance of Carbon • 20.2 – Organic Compounds • 20.3 – Saturated Hydrocarbons • 20.4 – Unsaturated Hydrocarbons

  2. 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.

  3. 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

  4. 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

  5. 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

  6. 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

  7. 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

  8. Carbon – Carbon Bonding • Catenation – Carbon atoms are unique in their ability to form long chains and rings of covalently bonded atoms.

  9. 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)

  10. 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

  11. 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.

  12. Isomers – Structural • Structural Isomers – isomers in which the atoms are bonded together in different orders

  13. 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

  14. Cis and Trans

  15. Saturated Hydrocarbons • Hydrocarbons in which each carbon atom in the molecule form four single covalent bonds with other atoms

  16. 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

  17. Cycloalkanes • Alkanes in which the carbon atoms are arranged in a ring, or cyclic, structure

  18. Alkane Nomenclature Unbranched Chain • Count the longest continuous chain. • Use greek prefix (at right) • End with -ane

  19. Alkane Nomenclature Branched Chain • Name the longest chain (See previous) • Add the name of the alkyl group • Insert position numbers • Punctuate

  20. Example

  21. Cycloalkane Nomenclature • Name the longest chain • Add Cyclo- • Add names of alkyl groups • Number the carbons (lowest numbers) • Inset position numbers • Punctuate

  22. Example • Give the name of the following molecule • 6 carbons = hexane • CH3 = methyl • Number around the circle • 1,3 - dimethlycyclohexane

  23. Example • Draw 1,1- dimethylcyclobutane

  24. Unsaturated Hydrocarbons • Hydrocarbons in which not all carbon atoms have four single covalent bonds

  25. Alkenes CnH2n • Hydrocarbons that contain double covalent bonds

  26. Alkene Nomenclature • Name the same as Alkane • Locate the longest continuous chain that contains the double bond(s). • Double bond should have lowest number

  27. Example

  28. 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

  29. Example • Name the following

  30. Aromatic Hydrocarbons • Hydrocarbons with six membered carbon rings and delocalized electrons • Benzene – the primary aromatic hydrocarbon

  31. Aromatic Nomenclature • Name the parent Hydrocarbon (Usually benzene) • Name the Alkyl groups • Number the carbon atoms • Insert position numbers • Add Punctuation

  32. Example • Name the following

  33. Example

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