FUNCTIONAL GROUPS

What is a Functional Group (FG) ?

..an atom or bond or a group of
atoms or bonds that is attached to one or
more C atoms that has a..

characteristic chemical behavior

Functional Groups and Reactivity

FGs change reactivity and physical
properties of a molecule
Reactivity is the rate at which a molecule is
converted to product or its behavior
toward specific reagents.

Functional Groups

Functional Groups

FGs Also Change a Molecules Physical

Properties

FGs Also Change a Molecules Physical

Properties
Property

Ethane(C2H6)

Ethanol (EtOH)

b.p.

-89 C

78 C

Soluble in
water?
Rxn w
H3PO4/?

Identify the Functional Groups

The C-O Group

The C=C Group

The C=O Group

The Phenyl Group

Functional Groups

Functional group determines all of the

following properties of a molecule :
bonding & shape
type & strength of intermolecular forces
physical properties
nomenclature
chemical reactivity

Intermolecular Forces (I.F.)

Intermolecular Forces-ionic

Intermolecular Forces-non-ionic
van der Waals forces
dipole-dipole interactions
hydrogen bonding

Van der Waals Forces

Van der Waals Forces

 Polarizability is a measure of how the electron cloud around an

atom responds to changes in its electronic environment.

Dipole-Dipole Interactions

Hydrogen Bonding

Intermolecular Forces & Physical Properties

Physical PropertiesBoiling Point

The stronger the intermolecular forces, the

higher the boiling point.
For compounds with approximately the same
molecular weight:

Physical PropertiesBoiling Point

Physical PropertiesBoiling Point

For two compounds with similar functional groups:

The larger the surface area, the higher the boiling point.
The more polarizable the atoms, the higher the boiling
point.

Introduction to Organic Molecules and Functional Groups

Physical PropertiesBoiling Point
Liquids having different boiling points can be separated in the
laboratory using a distillation apparatus, shown in Figure 3.4.

Introduction to Organic Molecules and Functional Groups

Physical PropertiesMelting Point
The melting point is the temperature at which a solid is
converted to its liquid phase.
In melting, energy is needed to overcome the attractive
forces in the more ordered crystalline solid.
The stronger the intermolecular forces, the higher the
melting point.
Given the same functional group, the more symmetrical
the compound, the higher the melting point.

Introduction to Organic Molecules and Functional Groups

Physical PropertiesMelting 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:

Introduction to Organic Molecules and Functional Groups

Physical PropertiesMelting Point
The trend in melting points of pentane, butanal, and 1butanol parallels the trend observed in their boiling
points.

Introduction to Organic Molecules and Functional Groups

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 CH 3 group
dangling from a four-carbon chain, does not. Thus, neopentane
has a much higher melting point.

Introduction to Organic Molecules and Functional Groups

Physical PropertiesSolubility
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
and the solvent.

Introduction to Organic Molecules and Functional Groups

Physical PropertiesSolubility
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 since it is capable of
hydrogen bonding with a solute. Many organic solvents
are either nonpolar, like carbon tetrachloride (CCl 4) and
hexane [CH3(CH2)4CH3], or weakly polar, like diethyl ether
(CH3CH2OCH2CH3).
Most ionic compounds are soluble in water, but insoluble
in organic solvents.

Introduction to Organic Molecules and Functional Groups

Physical PropertiesSolubility
An organic compound is water soluble only if it contains
one polar functional group capable of hydrogen bonding
with the solvent for every five C atoms it contains. For
example, compare the solubility of butane and acetone in
H2O and CCl4.

Introduction to Organic Molecules and Functional Groups

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.

Introduction to Organic Molecules and Functional Groups

Physical PropertiesSolubility
To dissolve an ionic compound, the strong ion-ion
interactions must be replaced by many weaker ion-dipole
interactions.

Introduction to Organic Molecules and Functional Groups

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.

Introduction to Organic Molecules and Functional Groups

Physical PropertiesSolubility
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.

Are these molecules water soluble?

Polarity is the basis of micelle formation

Introduction to Organic Molecules and Functional Groups

ApplicationThe Cell Membrane

Introduction to Organic Molecules and Functional Groups

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.

Introduction to Organic Molecules and Functional Groups

ApplicationThe Cell Membrane
Transport Across a Cell Membrane:

Introduction to Organic Molecules and Functional Groups

ApplicationThe Cell Membrane
Several synthetic ionophores have also been prepared, including
one group called crown ethers.
Crown ethers are cyclic ethers containing several oxygen atoms
that bind specific cations depending on the size of their cavity.

Functional Groups and Reactivity (E.N. atom)

Example of an Electrophilic Alkyl Halide( RX)

Functional Groups and Reactivity (lone pairs)

Functional Groups and Reactivity ( bonds)

Example of a Nucleophilic bond