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Chapter 3

Chapter 3. Functional groups. Alkanes and alkyl groups. IUPAC name of alkanes Properties of alkane. IUPAC name of cycloalkanes. Properties of cycloalkanes. Functional groups. alkane. alkene. alkyne. arene. halide. Functional group. carbonyl. water. aldehyde. H. alcohol. ketone.

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Chapter 3

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  1. Chapter 3 • Functional groups. • Alkanes and alkyl groups. • IUPAC name of alkanes • Properties of alkane. • IUPAC name of cycloalkanes. • Properties of cycloalkanes. Chapter 3 - Alkane

  2. Functional groups alkane alkene alkyne arene halide Chapter 3 - Alkane

  3. Functional group carbonyl water aldehyde H alcohol ketone ether acid thiol ester sulfide amide amine Chapter 3 - Alkane

  4. Functional group … and others, … see page 76 Table 3.1 Chapter 3 - Alkane

  5. Chapter 3 • Functional groups. • Alkane and alkyl groups. • IUPAC name of alkanes • Properties of alkane. • IUPAC name of cycloalkanes. • Properties of cycloalkanes. Chapter 3 - Alkane

  6. Alkanes • Hydrocarbons, Aliphatic, Paraffins • Saturated - CnH2n+2 • Straight, open, normal, and branched chain • Constitutional Isomers • Naming: methane to decane Chapter 3 - Alkane

  7. Alkanes - Straight, open, normal, and branched chain C3H8 C4H10 branched C5H12 C6H14 C7H16 Straight, open, normal Chapter 3 - Alkane

  8. Alkanes - Constitutional Isomers See Table 3.2 on p82 Graph theory - 1874 C6H14 6 5 4 3 Chapter 3 - Alkane

  9. Alkanes - Names of straight chain Table 3.3 on p83 - Methane - Decane Chapter 3 - Alkane

  10. Alkyl groups • Partial structure of alkane - H atom removed. • Unstable. • Name - replacing -ane by -yl. • 1o, 2o, 3o, 4o. Chapter 3 - Alkane

  11. Alkyl groups • -CH3 … methyl • -CH2CH3 … ethyl • -CH2CH2CH3 … propyl • -CH2CH2CH2CH3 … butyl • -CH(CH3)2 … iso-propyl • -C(CH3)3 … tert-butyl • see Tables 3.4 (p 84) & Figure 3.3 (p 85). Chapter 3 - Alkane

  12. Alkyl groups - 1o, 2o, 3o, 4o 2o 3o 1o 4o Chapter 3 - Alkane

  13. Chapter 3 • Functional groups. • Alkanes and alkyl groups. • IUPAC name of alkanes • Properties of alkane. • IUPAC name of cycloalkanes. • Properties of cycloalkanes. Chapter 3 - Alkane

  14. IUPAC Name of alkanes • Find the parent hydrocarbon (i.e. the longest chain). • Number the atoms in the main chain. • Identify and number the substituents. • Write the name in a single word. • Name a complex substituent just as though it were itself a compound. Chapter 3 - Alkane

  15. 6 5 4 3 2 1 1 2 4 5 6 3 IUPAC Name of alkanes 2,2,3,3-Tetramethyl -hexane Chapter 3 - Alkane

  16. Chapter 3 • Functional groups. • Alkanes and alkyl groups. • IUPAC nameof alkanes • Properties of alkane. • IUPAC name of cycloalkanes. • Properties of cycloalkanes. Chapter 3 - Alkane

  17. Alkane Properties • Non-polar. • Low energy barrier rotation. • Chemically inert. • CnH2n+2 + [(3n+1)/2]O2(g)  nCO2(g) + (n+1)H2O(g) • CH4 + Cl2 Chapter 3 - Alkane

  18. Van der Wall forces Alkane Properties - non-polar Chapter 3 - Alkane

  19. Chapter 3 - Alkane

  20. Alkane Properties - Low energy barrier rotation Chapter 3 - Alkane

  21. Alkane Properties - reactions Chemically inert, except ... Chapter 3 - Alkane

  22. Chapter 3 • Functional groups. • Alkanes and alkyl groups. • IUPAC nameof alkanes • Properties of alkane. • IUPAC name of cycloalkanes. • Properties of cycloalkanes. Chapter 3 - Alkane

  23. Cycloalkane • Alicyclic alkane. • CnH2n • Less flexible than straight chain (C3-C7). • Non-polar. • Naming. • Stereoisomers. Chapter 3 - Alkane

  24. Alicyclic alkane cyclopropane cyclobutane cyclopentane cyclohexane cyclohexane cyclohexane cycloheptane cyclooctane Chapter 3 - Alkane

  25. Less flexible n = 11 n = 3 cyclopropane cycloundecane Chapter 3 - Alkane

  26. IUPAC Name of cycloalkane • Find the parent. • Number the substituents 1,4-Dimethylcyclohexane 3-Cyclobutylpentane 1- Methy-3-propylcyclopentane 1-Bromo-4-ethylcyclodecane 1-tert-butyl-2-methylcyclohexane 4-Bromo-1-tert-butyl-2-methylcycloheptane Chapter 3 - Alkane

  27. Bicycloalkane Bridge 6 4 Bridgehead carbon 3 5 1 2 Chapter 3 - Alkane

  28. Stereoisomers of cycloalkane Constitutional isomers Stereoisomers Chapter 3 - Alkane

  29. Stereoisomers of cycloalkane Chapter 3 - Alkane

  30. Stereoisomers of cycloalkane • Identify the carbon as 1o, 2o, 3o, 4o. • Give the IUPAC name Chapter 3 - Alkane

  31. Stereoisomers of cycloalkane Which stereoisomer is energetically more stable? Chapter 3 - Alkane

  32. Chapter 3 • Functional groups. • Alkanes and alkyl groups. • IUPAC name of alkanes • Properties of alkane. • IUPAC name of cycloalkanes. • Properties of cycloalkanes. Chapter 3 - Alkane

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