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Amines versus
Alkyl Halides and Alcohols
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Common Names of Amines
•  Substituents are in alphabetical order followed
by “amine.”
•  They are all written as one word.
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Systematic Names of Amines
•  The suffix “amine” denotes the amine
functional group.
•  The “e” at the end of the alkane name is
replaced by “amine.”
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Systematic Names of Amines
•  A substituent on the chain is indicated by a number.
•  A substituent on the nitrogen is indicated by an “N.”
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Quaternary Ammonium Salts
When there are four groups bonded to the N,
the groups are stated in alphabetical order
followed by ammonium and then the name of the anion.
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Summary of Nomenclature
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The Structure of an Alkyl Halide
The C—X bond of an alkyl halide becomes longer and weaker
as the size of the halogen increases.
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The Structure of an Alcohol
Resembles the Structure of Water
An alcohol is structurally like water with one H replaced by an R.
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The Structure of an Alcohol
Resembles the Structure of Water
An ether is structurally like water with both Hs replaced by Rs.
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Structures of Amines
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Boiling Points
The greater the attractive forces between molecules,
the higher the boiling point.
attractive forces
van der Waals forces
dipole–dipole interactions
hydrogen bonds
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Boiling Points
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Methane
Ethane
Propane
Butane
Pentane
Hexane
Heptane
Octane
167.7
–88.6
–42.1
–0.5
36.1
68.7
98.4
125.7
C
C
C
C
C
C
C
C
induced dipole-induced dipole
interactions
van der Waals forces
The greater the surface area of the molecule, the higher the bp.
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Branching Lowers the Boiling Point
cigar
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tennis ball
Dipole–Dipole Interactions
Dipole–dipole interactions are
stronger than van der Waals forces.
Van der Waals
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Van der Waals
dipole–dipole
Comparative Boiling Points
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Comparative Boiling Points
The larger the halogen, the more polarizable it is.
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Hydrogen Bonds in H2O and NH3
CH4 –167.7 °C
H2O 100 °C
no hydrogen bonds
hydrogen bonds
Hydrogen bonds are stronger than other dipole–dipole interactions.
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Hydrogen Bonds in Water
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Hydrogen Bonds in Amines
Hydrogen bonds are stronger in primary amines than in secondary amines
because primary amines have stronger dipole–dipole interactions.
Tertiary amines cannot form hydrogen bonds with each other.
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Hydrogen Bonds in Proteins
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Hydrogen Bonds in DNA
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Compounds with Similar Shapes and Properties
Often Have Similar Physiological Activities
Drugs bind to their receptors by van der Waals interactions,
dipole-dipole interactions, and hydrogen bonding.
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Melting Points
The mp is influenced by the packing of the molecules in the crystal lattice
alkanes with an odd number of carbons pack less tightly.
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Solubility
like dissolves like
Polar compounds dissolve in polar solvents (H2O).
Nonpolar compounds dissolve in nonpolar solvents (hexane).
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Solvation
Solvation is the interaction between solute molecules and solvent molecules.
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