Introduction to Organic Chemistry

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• Introduction to Organic Chemistry

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Organic Outline
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• Nomenclature
• Common and IUPAC names
• Physical Properties
• Solubility (polarity)
• Boiling point (intermolecular forces)
• Chemical Properties SCARE
• Substitution, combustion, addition,
• redox and elimination

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Organic and Inorganic
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• Organic compounds are covalent
• Organics are liquids and gases
• Organics are insoluble in water
• Organics are non-electrolytes and do not conduct
  electricity
• Organics burn
• Organic reactions are usually slow

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Functional Groups
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• Alcohols Ethers
• Thiols Amines
• Aldehydes Ketones
• Carboxylic Acids Esters
• Anhydrides Amides

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• Alcohols
• Ethers
• Thiols
• Amines
• Aldehydes

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• Ketones
• Carboxylic Acids
• Esters
• Anhydrides
• Amides

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Formulas
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• C2H6O
• Molecular
• Structural
• Condensed structural

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• Very condensed structural
• (CH3)2CH(CH2)5C(CH3)3

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• Line drawings

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Types of Carbons
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• Primary (1) attached to only one other carbon
• Secondary (2) attached to two other carbons
• Tertiary (3) attached to three other carbons
• Quaternary (4) attached to four other carbons

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Hydrocarbons
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• Aliphatic
• alkanes contain only single bonds (saturated)
• alkenes contain at least one double bond
• (unsaturated)
• alkynes contain at least one triple bond
• Aromatic
• contain a benzene ring

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Alkanes
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• 1 meth methane CH4
• 2 eth ethane C2H6
• 3 prop propane C3H8
• 4 but butane C4H10
• 5 pent pentane C5H12
• 6 hex hexane C6H14
• 7 hept heptane C7H16
• 8 oct octane C8H18
• 9 non nonane C9H20
• 10 dec decane C10H22

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Types of Alkanes
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• Straight chain
• Branched

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Side Groups
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• methyl ethyl
• n-propyl isopropyl
• n-butyl isobutyl
• sec-butyl tert-butyl
• halogens fluoro, chloro, bromo, iodo

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IUPAC Nomenclature
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• Find longest continuous carbon chain.
• Number chain in both directions
• Assign numbers to substituted carbons (the ones
  with side groups attached)
• Add numbers and find lowest total
• Alphabetize side groups
• Numbers separated by commas, numbers and name
  separated by hyphens
• Multiple side groups di, tri, tetra, penta,
  hexa, hepta, octa, nona and deca

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Examples
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• Write condensed structural formulas

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• Name

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Constitutional Isomerism
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• Organic molecules can bond in various ways. Two
  compounds are isomers if they have the same
  molecular formula.
• Find all nine of the isomers of C7H16
• Name these compounds
• Identify 1?, 2?, 3? and 4? carbons

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Cycloalkanes
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• Cyclopropane
• Cyclobutane
• Cyclopentane
• Cyclohexane

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Cis-Trans Isomerismin Cycloalkanes
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• Because bonds do not rotate, the substituents are
  fixed either above or below the plane of the
  molecule. If both are up or both are down the
  molecule is a cis isomer.
• If one substituent is up and one is down the
  molecule is a trans isomer.

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Physical Properties
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• Colorless, odorless and tasteless
• Non-polar insoluble in water
• Boiling point increases with MW
• ltC4 gases (butane C4H10)
• 5-10 liquids (octane C8H18)
• gtC11 solids (paraffin C15H32)
• Less dense than water (float)

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Chemical Properties

• S substitution
• C combustion
• A addition
• R redox
• E elimination

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Chemical Properties
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• Combustion
• _____ __ O2 ? __ CO2 __ H2O
• Substitution - Halogenation