Organic Chemistry Exam 1 Review

Alkane Nomenclature

• Name Recognition: Be familiar with alkanes up to decane, including their chemical formulas and common representations:

  • Methane: ext{CH}_4

  • Ethane: ext{C}2 ext{H}6 (condensed: ext{CH}3 ext{CH}3)

  • Propane: ext{C}3 ext{H}8 (condensed: ext{CH}3 ext{CH}2 ext{CH}_3)

  • Butane: ext{C}4 ext{H}{10}

  • Pentane: ext{C}5 ext{H}{12}

  • Hexane: ext{C}6 ext{H}{14}

  • Heptane: ext{C}7 ext{H}{16}

  • Octane: ext{C}8 ext{H}{18}

  • Nonane: ext{C}9 ext{H}{20}

  • Decane: ext{C}{10} ext{H}{22}

• Bond-Line Structures: Every endpoint and corner in a bond-line structure represents a carbon atom, with implicit hydrogens to satisfy carbon's four-bond valency.

IUPAC Nomenclature for Substituted Alkanes

• Steps for Naming Alkanes:

  1. Identify the Longest Carbon Chain: This is the parent chain. For example, a six-carbon chain is hexane, a seven-carbon chain is heptane, an eight-carbon chain is octane.

  2. Number the Parent Chain: Number the chain in a way that gives the lowest possible numbers to the substituents.

     • Example: For methylhexane, 3-methylhexane is preferred over 4-methylhexane.

  3. Identify and Name Substituents:

     • One-carbon substituent: Methyl

     • Two-carbon substituent: Ethyl

     • Three-carbon substituent: Propyl

     • Branched three-carbon substituent: Isopropyl

     • Branched four-carbon substituent (attached at carbon 2): sec-butyl

     • Branched four-carbon substituent (tertiary carbon attachment): tert-butyl

  4. Handle Multiple Identical Substituents: Use prefixes such as