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Organic Compounds: Alkanes and Cycloalkanes
  • David Oliver
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After this chapter you should be able to:
  • Name all functional groups
  • Name alkanes and cycloalkanes
  • Discuss properties of alkanes
  • Give shapes of alkanes
  • Use cis- and trans- appropriately
  • Distinguish between isomers
    • Constitutional
    • Cis-trans
    • Stereoisomers



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Functional Groups
  • Alkanes
    • C-C single bonds
    • sp3 Hybridized
    • Name ends in -ane
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Functional Groups
  • Alkenes
    • C=C single bonds
    • sp2 Hybridized
    • Name ends in -ene
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Functional Groups
  • Alkynes
    • C=C triple bonds
    • sp Hybridized
    • Name ends in -yne
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Functional Groups
  • Arenes
    • Benzene type structures
    • sp2 Hybridized


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Functional Groups
  • Halide
    • F, Cl, Br, I attached to an organic


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Functional Groups
  • Alcohol
    • -OH group attached to an organic
    • May be primary, secondary, or tertiary
    • Name ends in -ol


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Functional Groups
  • Ether
    • Water-like structure
    • Unreactive
    • Slightly polar
    • Name ends in ether



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Functional Groups
  • Amine
    • Lewis Base
    • May be primary, secondary, or tertiary
    • Name ends in -amine


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Functional Groups
  • Nitrile
    • Cyanide group
    • Name ends in -nitrile



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Functional Groups
  • Nitro
    • Resonance stabilized
    • Auto-oxidizer




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Functional Groups
  • Sulfide
    • Same structure as water
    • Double bonding is weak
    • Name ends in  sulfide



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Functional Groups
  • Sulfoxide
    • Polar
    • Name ends in sulfoxide


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Functional Groups
  • Sulfone
    • Reactive
    • Large formal charge on sulfur
    • Name ends in sulfone
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Functional Groups
  • Thiol
    • Thio indicates sulfur
    • -ol indicates alcohol
    • Name ends in -thiol
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Functional Groups
  • Aldehyde
    • Carbonyl on the terminal hydrogen
    • Lewis acid at carbonyl carbon
    • Name ends in -al



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Functional Groups
  • Ketone
    • Carbonyl between carbons
    • Lewis acid at carbonyl carbon
    • Name ends in -one
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Functional Groups
  • Carboxylic Acid
    • Resonance stabilizes anion
    • Readily loses hydrogen
    • Name ends in –oic acid
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Functional Groups
  • Ester
    • Formed from carboxylic acid and alcohol
    • Water is eliminated in reaction
    • Name ends in -oate
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Functional Groups
  • Amide
    • A carbonyl amine
    • May be a primary, secondary or tertiary
    • Name ends in -amide
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Functional Groups
  •  Acid Chloride
    • Very reactive
    • -oyl  chloride
    • Name ends in –oyl chloride
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Functional Groups
  • Acid Anhydride
    • Dehydration of carboxylic acid
    • -oic anhydride
    • Name ends in –oic anhydride


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Alkanes
  • Methane    CH4
  • Ethane CH3CH3
  • Propane CH3CH2CH3
  • Butane CH3CH2CH2CH3
  • Pentane CH3CH2CH2CH2CH3
  • Hexane CH3CH2CH2CH2CH2CH3
  • Heptane CH3CH2CH2CH2CH2CH2CH3
  • Octane CH3CH2CH2CH2CH2CH2CH2CH3
  • Nonane CH3CH2CH2CH2CH2CH2CH2CH2CH3
  • Decane CH3(CH2)8CH3



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Alkane Isomers
  • Alkanes are not always straight chain!  Consider the C4H10
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Extra credit
  • Give structure for all isomers of C7H16 and name each.
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Alkyl Groups
  • Methyl    CH3-
  • Ethyl CH3CH2-
  • Propyl CH3CH2CH2 -
  • Butyl CH3CH2CH2CH2 -
  • Pentyl CH3CH2CH2CH2CH2 -
  • Hexyl CH3CH2CH2CH2CH2CH2 -
  • Heptyl CH3CH2CH2CH2CH2CH2CH2 -
  • Octyl CH3CH2CH2CH2CH2CH2CH2CH2 -
  • Nonyl         CH3CH2CH2CH2CH2CH2CH2CH2CH2 -
  • Decyl CH3(CH2)8CH2 -



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Degree of Alkyl Substitution
  • Primary


  • Secondary


  • Tertiary


  • Quaternary


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Nomenclature
  • Find longest continuous carbon chain with greatest number of branch points
  • Number carbons in chain giving lowest number to branch points
  • Identify and number each substituent
  • Write name as single word
  • Name complex substituents as if they were a compound with –yl ending
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Name the following
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Name the following
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Name the following
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Properties of alkanes
  • Intermolecular bonding is via London Dispersion forces
  • Melting point and boiling point are directly related to molecular weight and ability to pack molecules closely in efficient crystals.


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Contact Efficiency
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Cycloalkanes
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Cycloalkanes
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Cycloalkane Nomenclature
  • Parent is the cyclic structure
  • Number carbons in cyclic structure giving lowest number to substituents
  • Identify and number each substituent
  • Write name as single word
  • Name complex substituents as it they were a compound with –yl ending
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Name the following
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Name
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Name the following
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Name
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Cis-Trans Isomerism