Académique Documents
Professionnel Documents
Culture Documents
SM CH 0308
SM CH 0308
Chapter 3
Functional Groups
Prepared by Rabi Ann Musah
State University of New York at Albany
Copyright © The McGraw-Hill Companies, Inc. Permission required for reproduction or display.
1
Organic Molecules and Functional Groups
Functional Groups:
2
Organic Molecules and Functional Groups
Functional Groups: Hydrocarbons
Hydrocarbons are compounds made up of only the elements
carbon and hydrogen. They may be aliphatic or aromatic.
3
Organic Molecules and Functional Groups
Functional Groups: Heteroatoms
4
Functional Groups: Carbonyl groups
5
Organic Molecules and Functional Groups
Functional Groups:
• Heteroatoms and bonds confer reactivity on a particular
molecule.
Heteroatoms have lone pairs and create electron-
deficient sites on carbon.
Bonds are easily broken in chemical reactions. A
bond makes a molecule a base and a nucleophile.
Don’t think that the C—C and C—H bonds are unimportant.
They form the carbon backbone or skeleton to which the
functional group is attached. 6
Organic Molecules and Functional Groups
Functional Groups:
• Ethane: This molecule has only C—C and C—H bonds, so it has
no functional group. It has no polar bonds, no lone pairs, and
no bonds, so it has no reactive sites. It is very unreactive.
• Ethanol: This molecule has an OH group attached to its
backbone. It is called a hydroxy functional group. Ethanol has
lone pairs and polar bonds that make it reactive with a variety
of reagents.
The hydroxy group makes the properties of ethanol very
different from the properties of ethane.
7
Organic Molecules and Functional Groups
Functional Groups:
• 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.
8
Organic Molecules and Functional Groups
Functional Groups:
9
Organic Molecules and Functional Groups
Functional Groups:
Compounds Containing the C=O Group:
• This group is called a “carbonyl group”.
• The polar C—O 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 C—O bond.
10
Organic Molecules and Functional Groups
Functional Groups:
Molecules Containing the C=O Functional Group
11
Organic Molecules and Functional Groups
Functional Groups:
It should be noted that the importance of a functional
group cannot be overstated.
14
Organic Molecules and Functional Groups
Intermolecular Forces: van 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 interactions of this
type constitutes van der
Waals forces. 15
Organic Molecules and Functional Groups
Intermolecular Forces: van der Waals Forces
• All compounds exhibit van der Waals forces.
• The surface area of a molecule determines the strength of the
van der Waals interactions between molecules. The larger the
surface area, the larger the attractive force between two
molecules, and the stronger the intermolecular forces.
16
Organic Molecules and Functional Groups
Intermolecular Forces: van 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.
18
Organic Molecules and Functional Groups
19
Organic Molecules and Functional Groups
Intermolecular Forces: Summary
Note: as the polarity of an organic molecule increases,
so does the strength of its intermolecular forces.
20
Organic Molecules and Functional Groups
Physical Properties: Boiling Point
• The boiling point of a compound is the temperature at
which liquid molecules are converted into gas.
• In boiling, energy is needed to overcome the attractive
forces in the more ordered liquid state.
• The stronger the intermolecular forces, the higher the
boiling point. For compounds with approximately the
same molecular weight:
21
Organic Molecules and Functional Groups
Physical Properties: Boiling 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.
23
Organic Molecules and Functional Groups
24
Organic Molecules and Functional Groups
Physical Properties: Melting Point
• Because ionic compounds are held together by
extremely strong interactions, they have very high
melting points.
• With covalent molecules, the melting point depends
upon the identity of the functional group. For
compounds of approximately the same molecular
weight:
25
Organic Molecules and Functional Groups
26
Organic Molecules and Functional Groups
Physical Properties: Melting 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.
27
Organic Molecules and Functional Groups
Physical Properties: Solubility
• Solubility is the extent to which a compound, called a
solute, dissolves in a liquid, called a solvent.
• In dissolving a
compound, the
energy needed to
break up the
interactions
between the
molecules or ions
of the solute comes
from new
interactions
between the solute
28
and the solvent.
Organic Molecules and Functional Groups
Physical Properties: Solubility
• To dissolve an ionic compound, the strong ion-ion
interactions must be replaced by many weaker ion-dipole
interactions.
Figure 3.4
Dissolving a ionic
compound in H2O
29
Organic Molecules and Functional Groups
Physical Properties: Solubility
• Compounds dissolve in solvents having similar kinds
of intermolecular forces. “Like dissolves like.”
• Polar compounds dissolve in polar solvents. Nonpolar
or weakly polar compounds dissolve in nonpolar or
weakly polar solvents.
• Water and organic solvents are two different kinds of
solvents. Water is very polar and is capable of
hydrogen bonding with a solute. Many organic
solvents are either nonpolar, like carbon tetrachloride
(CCl4) and hexane [CH3(CH2)4CH3], or weakly polar, like
diethyl ether (CH3CH2OCH2CH3).
• Most ionic compounds are soluble in water, but
insoluble in organic solvents.
30
Organic Molecules and Functional Groups
31
Organic Molecules and Functional Groups
Physical Properties: Solubility
• Since butane and acetone are both organic compounds
having a C—C and C—H 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.
32
Organic Molecules and Functional Groups
Physical Properties: Solubility
• 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.
33
Organic Molecules and Functional Groups
Physical Properties: Solubility
• 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.
Figure 3.5
Solubility
summary
34
Organic Molecules and Functional Groups
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.
35
Organic Molecules and Functional Groups
Influence of Functional Groups on Reactivity:
36
Organic Molecules and Functional Groups
Influence of Functional Groups on Reactivity:
• An electron-deficient carbon (electrophilic) reacts
with a nucleophile, symbolized as :Nu¯.
• An electron-rich carbon (nucleophilic) reacts with an
electrophile, symbolized as E+.
Example 1: alkenes contain an electron rich double
bond, and so they react with electrophiles E+.
37
Organic Molecules and Functional Groups
Influence of Functional Groups on Reactivity:
Example 2: alkyl halides possess an electrophilic
carbon atom due to the electron withdrawing effect of
the halogen atom, so they react with electron-rich
nucleophiles.
38
Organic Chemistry, Second Edition
End Chapter 3
Copyright © The McGraw-Hill Companies, Inc. Permission required for reproduction or display.
39