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Hydrocarbons
Hydrocarbons are compounds made up of only the elements
carbon and hydrogen. They may be aliphatic or aromatic.
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Aromatic hydrocarbons
Aromatic hydrocarbons are so named because many of the
earliest known aromatic compounds had strong characteristic
odors.
The simplest aromatic hydrocarbon is benzene. The six-
membered ring and three bonds of benzene comprise a single
functional group.
When a benzene ring is bonded to another group, it is called a
phenyl group.
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Examples of Molecules Containing C-Z Bonds
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Compounds Containing the C=O Group
Compounds Containing the C=O Group:
This group is called a carbonyl group.
The polar CO bond makes the carbonyl carbon an
electrophile, while the lone pairs on O allow it to react
as a nucleophile and base.
The carbonyl group also contains a bond that is more
easily broken than a CO bond.
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Molecules Containing the C=O Group
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A functional group determines all of the
following properties of a molecule
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Intermolecular Forces
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Intermolecular Forcesvan der Waals Forces
van der Waals forces are also known as London forces.
They are weak interactions caused by momentary changes in
electron density in a molecule.
They are the only attractive forces present in nonpolar
compounds.
Even though CH4 has no
net dipole, at any one
instant its electron density
may not be completely
symmetrical, resulting in a
temporary dipole. This can
induce a temporary dipole
in another molecule. The
weak interaction of these
temporary dipoles
constitutes van der Waals
forces. 15
Intermolecular Forcesvan der Waals Forces
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Intermolecular Forcesvan der Waals Forces
van der Waals forces are also affected by polarizability.
Polarizability is a measure of how the electron cloud around an
atom responds to changes in its electronic environment.
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Intermolecular ForcesHydrogen Bonding
Hydrogen bonding typically occurs when a hydrogen
atom bonded to O, N, or F, is electrostatically attracted
to a lone pair of electrons on an O, N, or F atom in
another molecule.
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Intermolecular ForcesHydrogen Bonding
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Physical PropertiesBoiling Point
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Physical PropertiesBoiling Point
Consider the example below. Note that the relative
strength of the intermolecular forces increases from
pentane to butanal to 1-butanol. The boiling points of
these compounds increase in the same order.
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Physical PropertiesBoiling Point
Liquids having different boiling points can be separated in the
laboratory using a distillation apparatus, shown in Figure 3.3.
Figure 3.3
Schematic of a distillation
apparatus
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Physical PropertiesMelting Point
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Physical PropertiesMelting Point
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Physical PropertiesMelting Point
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Physical PropertiesMelting Point
Symmetry also plays a role in determining the melting points of
compounds having the same functional group and similar
molecular weights, but very different shapes.
A compact symmetrical molecule like neopentane packs well into
a crystalline lattice whereas isopentane, which has a CH3 group
dangling from a four-carbon chain, does not. Thus, neopentane
has a much higher melting point.
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Physical PropertiesSolubility
Solubility is the extent to which a compound, called a
solute, dissolves in a liquid, called a solvent.
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Physical PropertiesSolubility
Since butane and acetone are both organic compounds
having a CC and CH backbone, they are soluble in
the organic solvent CCl4. Butane, which is nonpolar, is
insoluble in H2O. Acetone is soluble in H2O because it
contains only three C atoms and its O atom can
hydrogen bond with an H atom of H2O.
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Physical PropertiesSolubility
To dissolve an ionic compound, the strong ion-ion
interactions must be replaced by many weaker ion-dipole
interactions.
Figure 3.4
Dissolving an ionic
compound in H2O
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Physical PropertiesSolubility
The size of an organic molecule with a polar functional group
determines its water solubility. A low molecular weight alcohol
like ethanol is water soluble since it has a small carbon
skeleton of five C atoms, compared to the size of its polar
OH group. Cholesterol has 27 carbon atoms and only one OH
group. Its carbon skeleton is too large for the OH group to
solubilize by hydrogen bonding, so cholesterol is insoluble in
water.
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Figure 3.5 Solubility summary
The nonpolar part of a molecule that is not attracted to H2O is
said to be hydrophobic.
The polar part of a molecule that can hydrogen bond to H2O is
said to be hydrophilic.
In cholesterol, for example, the hydroxy group is hydrophilic,
whereas the carbon skeleton is hydrophobic.
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Solubility ApplicationVitamins
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Solubility ApplicationVitamins
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Solubility ApplicationVitamins
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Solubility ApplicationSoap
Figure 3.6
Dissolving soap in water
Soap:
Soap molecules
have two distinct
partsa
hydrophilic
portion composed
of ions called the
polar head, and a
hydrophobic
carbon chain of
nonpolar CC
and CH bonds,
called the
nonpolar tail. 39
Solubility ApplicationThe Cell Membrane
Figure 3.7
The cell
membrane
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Solubility ApplicationThe Cell Membrane
Transport Across a Cell Membrane:
Polar molecules and ions are transported across cell membranes
encapsulated within molecules called ionophores.
Ionophores are organic molecules that complex cations. They have a
hydrophobic exterior that makes them soluble in the nonpolar interior
of the cell membrane, and a central cavity with several oxygens
whose lone pairs complex with a given ion.
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Solubility ApplicationThe Cell Membrane
Figure 3.8
Transport of ions
across a
cell membrane
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Influence of Functional Groups on Reactivity
Recall that:
Functional groups create reactive sites in molecules.
Electron-rich sites react with electron poor sites.
All functional groups contain a heteroatom, a bond or
both, and these features create electron-deficient (or
electrophilic) sites and electron-rich (or nucleophilic)
sites in a molecule. Molecules react at these sites.
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Influence of Functional Groups on Reactivity
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Influence of Functional Groups on Reactivity
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Influence of Functional Groups on Reactivity
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Biomolecules
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Figure 3.9 Simple and complex biomolecules
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