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Organic Functional

Groups: Halocarbons

Representing Covalent
Bonds
The valence electrons of elements
are often represented using dot
diagrams

Dot diagrams can be used to show bonding pairs


of electrons for elements and compounds.

Hybrid Diagrams Are Also


Used
Bonding pairs are shown as dashes;
lone pairs are shown as dots.

Non-Polar Covalen Bonds


In elements that form covalent
bonds, electrons are shared equally
between atoms.

These bonds are called non-polar,


because the electrical charge is
evenly distributed

Polar Covalent Bonds


In many compounds, atoms of different
elements share their electrons unequally
one element gets them a bigger share
of the time than the other one.

The chlorine atom is more


electronegative, that is, it attracts the
electron more than the hydrogen does.

Consequences of Bond
Polarity
Carbon and hydrogen share their
electrons equally they form nonpolar covalent bonds.
Compounds with non-polar bonds
tend to have weaker attractive
forces, lower melting points and
boiling points.
Small non-polar molecules tend to be
gases, larger ones liquids at room
temperature.

Polar Covalent Bonding


The halogens are more electronegative than
carbon, making for more polar covalent bonds.
Halocarbon compounds have small dipoles,
partially positive and negative ends, which
change the physical and chemical properties of
compounds significantly.
Halocarbons have greater intermolecular forces,
higher melting and boiling temperatures, and are
often liquids at room temperature.

One Atom Really Makes a


Difference!
C-Cl bond is polar

All nonpolar
bonds

Methane
Boiling Point: -160C

Chloromethane
Boiling Point: -24C

Functional Groups
When a highly electronegative element (one that
attracts electrons) is part of an organic compound,
they are often called functional groups.
Functional groups have a profound affect on the
physical and chemical properties of atoms.
We shall look at three classes of organic compounds
with polar functional groups: halocarbons,
oxygenated compounds such as alcohols, ethers,
carbonyl compounds, and esters, and nitrogenous
compounds like amines and amides.

The
Halogens

The Halogens:
Periodic Table, Group 17
So far we have considered organic
compounds containing only two elements.
Now we will expand our horizons further.
First we will consider a group of elements
collectively known as the halogens.
On the periodic table, elements in columns
are known as groups or families.
Elements in the same group have similar
chemical and physical properties, and make
similar kinds of compounds.

Group 17: The Halogens


The halogens are in the second column from the
right.
Astatine (At) is not included: it is unstable and
extremely rare.
Halogens each have seven valence electrons
three more than carbon.
Halogens are very hungry to gain an 8 th electron.
When they do, the eight electrons collectively drop
in energy and are more stable.
The halogens tend to share electrons, but not
equally. They tend to make polar covalent bonds
with other elements on the right side of the
periodic table.

Halogens form diatomic


elements
Halocarbons do not generally exist in
nature. Because of their reactivity,
halogens are always found as negative
ions, which do not react with hydrocarbons.
Halocarbons are made in the laboratory
using the halogen elements in their pure
form, which is a diatomic molecule:
F2 Cl2 Br2

I2

For fluorine:

Naming Halocarbons
Naming a halocarbon is similar to
naming a hydrocarbon.
You need to specify the name of the
halogen, the number of halogens (if
greater than one), and their positions
on the hydrocarbon.
Halogens written as prefixes such as
chloro-, fluoro-, bromo-, etc.

Name the Following


CH3CHFCH3
CCl2HCH2CH2CH2Cl
CCl2F2
CH3Br
CH3CH2CHICH3
Cl2C=CCl2
CCl4

Draw the Following


Halocarbons

2-Chloro pentane
1,1,1 trichloro ethane
3-fluoro propene
2,4 dibromo hexane
1,2 diiodo butane

Halocarbon Reactions
Saturated Hydrocarbons
Halogens will replace a hydrogen
atom:
CH3CH3(g) + Cl2(g) CH3CH2Cl (l) +
HCl(g)
This is called a substitution reaction.

Halocarbon Reactions
Unsaturated Hydrocarbons
Like hydrogen, halogens break the
double bond and add to the molecule
in two places:
H2C=CH2 + F2 CH2FCH2F
product!

name the

This is called an addition reaction.

Substitution or Addition?
CH4
C2H4
C3H4
C4H8
C5H12
C6H10
C6H14

Halocarbon Uses
Halocarbons are not naturally occurring
Their most important use is to build
large organic molecules their ability to
substitute for hydrogen is matched by
their ability to be removed!
Many industrial uses of halocarbons
have been limited because of their
toxicity, but they are still widely used.

Classes of Halocarbons
CFCs chloroflurocarbons formerly
used in air conditioners, hairspray, and
refrigerators

HFCs hydrofluorcarbons currently


used as a replacement for CFCs, these
are major greenhouse gases

PCBs polychlorinated biphenyls


used in heating and cooling systems;
they degrade into dioxins, which
very toxic substances

Organochlorine pesticides
compounds such as DDT, which
concentrate up the food chain, are
still used in the developing world.