Ochem 1

• Drawing organic structures


  Lewis structures, condensed and line-angle structures
• Topics for Exam I


  • Drawing organic structures
  • Functional groups
  • Introduction to nomenclature
  • Nomenclature of alkanes, alkyl halides, and cycloalkanes
  • Isomerism
• Learning objectives for Exam I


  • Draw valid Lewis structures, including formal charges if appropriate
  • Draw condensed and line-angle structures from Lewis structures, and vice versa
  • Determine molecular formula from structures
  • Identify and draw functional groups
  • Identify nomenclature prefixes, infixes, and suffixes
  • Draw or identify common substituents
  • Name and draw structures for alkanes and cycloalkanes
  • Define and identify cis-trans stereoisomers
  • Define and identify constitutional isomers
• Planned schedule


  • Review, continued
  • Condensed and line-angle structures
  • No Class – MLK Day
  • Functional groups
  • Introduction to nomenclature; saturation
  • Nomenclature: alkanes, alkyl halides, and cycloalkanes
  • Isomers
  • Exam 1 (65 points)
• Additional worksheets in D2L


  • Organic Molecules and Functional Groups
  • Alkane/Cycloalkane Nomenclature and Isomerism
  • Nomenclature Problems (part I)
• Draw Lewis structures


  • C2H6
  • CH4O
  • C3H6 (contains C=C)
  • C4H10 (multiple possible answers)
  • CH5N
• Remember to keep in mind total available valence electrons and try to minimize formal charges when drawing Lewis structures
• The following Lewis structures are incorrect. Determine the problems and correct them.


  • C2H4
  • CH2O
  • CN-
• Molecular representations


  Lewis structure, Condensed/Partially condensed structure, Skeletal/Bond-line structure/Line-angle drawing
• Lone pairs on line-angle drawings


  Formal charges must be shown, Lone pairs may be omitted, and can be determined from structure
• Drawing line-angle structures


  • HCOCH2OH
• Interpreting line-angle structures


  • How many carbons are shown?
  • How many hydrogens are bonded to the indicated carbons?
• Interpreting line-angle structures


  • What is the molecular formula for the following?
  • What is the molecular formula for adrenaline?
  • What is the molecular formula for thalidomide?
• Molecular representations


  • How many hydrogens on each carbon atom?
  • (CH3)3CCH2COCHCH2
• 3D organic structures


  Use dashes and wedges to show 3D structure
• Functional groups


  • Hydrocarbons
  • Compounds containing O
  • Compounds containing N
  • Compounds containing S
• Alkane


  Absence of other functional groups; only single bonds
• Cycloalkane


  Carbons form a ring with single bonds
• Alkene


  At least one double bond
• Cycloalkene


  Double bond in ring
• Alkyne


  At least one triple bond
• Aromatic (arene)


  Contains a benzene ring
• Alkyl halide


  1. X, R = any carbon group, X = halogen
• Carbonyl group


  C=O, found in aldehydes, ketones, carboxylic acids and carboxylic acid derivatives
• Compounds containing oxygen


  • Alcohol
  • Ether
  • Aldehyde
  • Ketone
  • Carboxylic acid
  • Acid halide
  • Ester
  • Amide
  • Acid anhydride
• Compounds containing nitrogen


  • Amine
  • Amide
  • Nitrile
• Compounds containing sulfur


  • Thiol
  • Sulfide
  • Sulfoxide
• Summary of functional groups (and examples)
• Draw an example of each of the following. You can draw Lewis or line-angle structures. There is more than one correct possible answer to each question.


  • An alkane with 6 carbons
  • An alkane with 6 carbons that is different from the one you drew in part (a)
  • An alkene with 4 carbons
• Nomenclature


  The naming of organic molecules
• 1800s: named by discoverers, 1892: IUPAC system
• Nomenclature


  All names have Substituents-MainChain, Substituents are groups attached to the main chain, MainChain consists of Parent-Infix-Suffix
• Parent


  • meth-
  • eth-
  • prop-
  • but-
  • pent-
  • hex-
  • hept-
  • oct-
  • non-
  • dec-
  • undec-
  • dodec-
• Infix


  • -an- = only carbon-carbon single bonds (saturated)
  • -en- = an alkene (double bond) is present (unsaturated)
  • -yn- = an alkyne (triple bond) is present (unsaturated)
• Suffix


  • -ol (alcohol)
  • ether
  • -amine (amine)
  • -nitrile (nitrile)
  • -thiol (thiol)
  • sulfide
  • -al (aldehyde)
  • -one (ketone)
  • -oic acid (carboxylic acid)
  • -oate (ester)
  • -amide (amide)
  • -oyl chloride (acid chloride)
  • -oic anhydride (acid anhydride)
• Nomenclature


  • 2-hexanol
  • octanoic acid
  • 4-methyl-2-pentanamine
• Substituents


  Groups attached to the main chain
• Main Chain


  Consists of Parent-Infix-Suffix
• Parent


  Tells you number of carbons in main chain
• Infix


  Tells you if the carbon-carbon bonds are single bonds (saturated molecule) or double or triple bonds (unsaturated molecules)