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Organic Chemistry 4e Carey | |||||
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Alkanes |
Chapter 2: Alkanes |
Simplest organic molecules with only C and H atoms. Commercially important as fuels and oils.
Nomenclature:
Functional group suffix = -ane (review)
Functional group prefix = alkyl-
Physical
Properties:
The low polarity of all the bonds in alkanes means that the only intermolecular
forces between molecules of alkanes are the very weak induced dipole - induced
dipole forces, which are easily overcome. As a result, compared
to other functional groups, alkanes tend to have low melting and boiling points
and very low solubility in polar solvents such as water (remember "oil and water
don't mix" and the adage "like dissolves like").
Structure:
Alkanes are the simplest organic compounds, comprised of only sp3
hybridized C and H atoms connected by s bonds.
They have a generic formula of CnH2n+2 (a relationship
that also defines the maximum number of hydrogen atoms that can be present for
a given number of C atoms).
Structures of the simple C1 to C4 alkanes are shown below in a variety of representations.
As the number of C atoms increases then other isomeric structures
are possible
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CH4 (b.pt. = -160oC) |
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C2H6 (b.pt. = -89oC) |
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C3H8 (b.pt. = -42oC) |
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C4H10 (b.pt. = -0.4oC) |
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Isomeric
Alkanes:
The molecular formula for the C1 to C3 alkanes lead to single, unique structures.
However for C4H10, there are two possible constitutional
isomers. It is important to be able to recognize isomers because there can have
different chemical, physical properties and biological properties. The constitutional
isomers of C4H10 are shown below along with some properties:
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m.pt.= -139oC
b.pt. = -0.4oC DHf = -125.6 kJ/mol (-30.0 kcal/mol) DHc = -2877 kJ/mol (-687 kcal/mol) |
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m.pt.= -161oC
b.pt. = -10.2oC DHf = -135.6 kJ/mol (-32.4 kcal/mol) DHc =-2868 kJ/mol (-685 kcal/mol) |
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C5H12
has three possible constitutional isomers:
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b.pt. = 36.1 oC DHf = -147 kJ/mol (-35.1 kcal/mol) DHc = - 3509 kJ/mol |
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b.pt. = 30 oC DHf = -154.1 kJ/mol (-36.8 kcal/mol) DHc = -3502 kJ/mol |
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| neopentane |
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b.pt. = 9.5 oC DHf = -168.0 kJ/mol (-40.1 kcal/mol) DHc = -3493 kJ/mol (- 835 kcal/mol) |