Amines and Amides

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dekupar
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68129
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Amines and Amides
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2011-02-28 15:54:39
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Amines Amides
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Amines and Amides Chapter 16
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  1. Amines
    • bases, substituted ammonia
    • biologically significant: amino acids, DNA, RNA bases, alkaloids
  2. General formula for primary amine
    R-NH2
  3. General formula for secondary amine
    R2-NH
  4. General formula for tertiary amine
    R3-N
  5. General formula for quaternary
    R4-N+X-
  6. More information on amines
    • organic derivative of ammonia (NH3) in which 1 or more hydrogen atoms have been replaced by an alkyl, acycloakly, or an aryl group (beneze ring)
    • N has 5 valence e-, 3 covalent bonds, and 1 nonbonding electron pair
    • N is also less electronegative than O
    • N is one of the elements involved in the formation of H+ bonding
  7. Properties of amines
    • N is very electronegative (although less than O)
    • Results in:
    • -N-H bond being very polar
    • -hydrogen bonding being possible
    • -high boiling points
    • -amines being organic bases
  8. Classification of amines
    • determined by the number of carbon atom directly boned to the N atom
    • classified as: primary, secondary, or tertiary
    • Note: t-butyl alcohol is a t-alcohol, while t-butyl amine is a primary amine
  9. Causes of isomers in amines
    • different carbon atom arrangements produce isomers
    • different positioning of the nitrogen atom on a carbon chain
  10. Causes of isomers for secondary and tertiary amines
    • different partititioning of carbon atoms among the carbon chain
    • ex: CH3CH2NHCH2CH3- diethyl amine
    • CH3NHCH2CH2CH3- methylpropyl amine
    • CH3NHCH[2(CH3)]
  11. Amine nomenclature
    • Both common and IUPAC names are used
    • Simple amines are named by listing the alkyl group or groups attched to the N atom in alphabetical order and adding the suffix -amine
    • appears as 1 word
    • prefix di and tri are used when identical groups are bonded to the N atom
  12. Naming diamines
    • in diamines the final -e of the carbon chain is retained
    • ex.1,4- butanediamine
    • NH2CH2CH2CH2CH2NH2
  13. Nomenclature of secondary & tertiary amines
    • treat additional branches as a substituent on the nitrogen
    • base name is based on longest chain that contains the amine
    • name other chain as alkyl substituent of the N
    • use N- at front of a branch name to indicate that substituant is on the nitrogen
  14. Naming aromatic amines
    • aniline is the simplest aromatic amine
    • compounds are named as substituted anilines
    • anitalic "N" is used to indicate that an alkyl group is attached to the nitrogen and not to the ring
  15. Physical properties of amines
    • methylamines and ethylamines are gases at room temp & have ammonia like odor
    • most other amines are liquid & have odor resembling fish
    • have the ability to form H-bonding
  16. Boiling points of amines
    boiling points are intermediate b/w those of alcohols and alkenes of similar molecular masses
  17. solubility of amines
    low molecular mass amines are very soluble in water
  18. Amines+acid--->
    • amines+acid--->salt
    • ex. R-NH2+HCl---> R-NH3+ + Cl-
  19. Basicity of amines
    NH3 + water---> NH4+ + OH-
  20. Basicity of amines generalizations
    • substituted ammonia ions are always charged species rather than neutral molecules
    • N atom in the structure participates in 4 bonds
    • substituted ammonium ions have common names derived from the names of the "parent" amines w/ the words ammonium ion replacing amine
    • -examples in notes
  21. Production from ammonia and an alcohol uses:
    Al2O3 & heat
  22. Preparation of amines:
    ammonia + alkylhalide in the presence of a base
    ex.ammonia+ ethyl bromide+ sodium hydroxide--->aminoethane+sodiumbromide+water
  23. Preparation of amines:
    amine+water--->
    amine+water---> ammonium ion+hydroxide
  24. Preparation of amines:
    amine salt+base--->
    amine salt+base--->amine+salt+water
  25. Neutralization formula of an amine
    • RNH2+HCl--->RNH3+ Cl-
    • Note: no H2O os produced in this reaction
    • Amine salts are the only product
  26. Neutralization
    • 1.salts exist as white crystalline solids
    • 2.reliatively high melting points
    • 3.salts are always more soluble
    • 4.many drugs are prepared and administered as salts b/c of their solublitiy
  27. General formula for amides
    R-C(=O)NH2
  28. amide nomenclature
    drop -e ending and replace w/ -amide
  29. Amide formation
    amines react w/ acid chlorides or acid anhydrides to form amides
  30. Preparation of amides
    production from a carboxylic acid uses:
    NH3 & heat

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