Science 30

Chemistry
Chapter 2: Chemical legacy of
human activity.

Body Chemistry

2.1- Organic compounds

3 main types of organic compounds:

Alkanes single bonds, saturated.

Alkenes- double bonds, unsaturated.

General formula CnH2n+2

General formula CnH2n

Alkynes- triple bonds, unsaturated.

General formula CnH2n-2

Classifications of Hydrocarbons

Hydrocarbons can be classified as follows:

A) Naming system for

Hydrocarbons
1.

2.

Name the longest chain

for root of the word see Data Booklet pg 10
(meth, eth . . .)
Ending = ane, ene or yne
Number the chain so branches are at the lowest
possible position numbers.
- If a double or triple bond, number closest to the bond.

3.

Name the branches

Root of word same as above
Ending = yl

Naming cont.
4. Put names together in this order: position #,
branch, parent chain
Multiple branches? Put branches in
alphabetical order.
Numbers are separated by commas.
Words and numbers are separated by dashes.
Multiples of the same kind of branch use a
prefix to indicate how many (di, tri . . .).
Double or triple bonds must have the carbon
# inserted and then the ending.

Name the Following

Hydrocarbons
H H H H H H H H
H C C C C C C C C H
H H H H H H H H
H
C
H

H
C

CH = C-CH2-CH2-CH3

B) Cyclic Hydrocarbons
These are hydrocarbons that form rings;
are also referred to as aromatic or phenyl
rings.
Are double bonded alkenes; general
formula is CnHn

Benzene is a hexagonal structure, all

aromatic compounds are.

naphthalene

benzene

Benzene
Aromatics are naturally occurring, present
in natural resources (coal and petroleum).
Benzene is a carcinogen and the level in
natural gas is regulated in Canada.
When natural gas spills, the soil is
contaminated with water soluble
aromatics.
Clean up must be completed through
remediation (removal from groundwater,
soil or surface water).

1) Remediation
Involves the removal or breakdown of
hydrocarbons in the gasoline.
Harmful aromatics can contaminate
drinking water, ground water and cause
illness.
Bacteria in soil naturally breakdown
organics, but benzene is very stable and is
not easily broken down.
Because of the high stability, benzene is
classified as a POP (persistent organic
pollutant).

Soil remediation

Whyte Avenue soil remediation

Bioremediation

2) Benzene structure and

stability

Benzene has properties similar to both

alkanes and alkenes.

Resonance is responsible for this:

Stability- high stability similar to alkenes.

Reactivity- high reactivity similar to alkanes.
Within aromatic ring, electrons are shared by all
carbons.
Responsible for stability.

High temperatures needed to break down

benzene = contained in gasoline emissions.

3) PAHs
Polycyclic Aromatic hydrocarbons produced
by incomplete combustion of oils.
Found on charbroiled foods, smoke in
forest fires and vehicle exhaust,
Combine with DNA to form structures that
result in mutations.

Benzopyrene

C) Functional groups

In addition to hydrogen and carbon organic

compounds can also contain other elements, often
in specific arrangements.
Functional Group:
certain arrangement of atoms within a molecule
determines properties of the molecule
Molecules are classified based on functional group
Example of a functional group
Hydroxyl
functional group for alcohol
R OH
NOTE: R represents any # of carbons

Halogenated Hydrocarbons

Functional group:
One or more H is replaced by a halogen
Halogens include:
fluorine, chlorine, bromine, and iodine
Naming Halogenated Hydrocarbons:
Use a prefix to indicate the number of halogens
Write chloro, fluoro, bromo, or iodo to indicate which
halogen is present
Name the parent chain
Examples:
trichloromethane

tetrachloromethane

CFCs

Was used as a cleaner,

found to be a carcinogen

Damages
ozone layer

CFCs
(ChloroFluoroCarbons
formed from carbon and
halogens) are products
common in air
conditioners, aerosols,
solvents and styrofoam
packaging. These
products make their way
to the upper atmosphere
and break ozone down.
Cl + O3 = ClO + O2
ClO + O = Cl + O2

Ozone Layer

A single chlorine atom removes about 100,000 ozone

molecules before it is taken out of operation by other
substances.

Ozone
The chemical formula for ozone is O3. It can be
produced in the upper atmosphere when UV rays strike
O2.
O2 + UV -> O + O (1)
O + O2 -> O3 (2)

Ozone is also continually being broken down by UV

rays.
O3 + UV->

O2 + O

(3)

O + O3 ->

O2 + O 2

(4)

A balance between these two reactions has resulted in a

layer of ozone surrounding the planet.

These reactions are

responsible for
absorption of 9799% of the sun's
high frequency UV
waves..

Ultraviolet light is light with

wavelengths between 150
and 300nm

UV-B radiation exposure causes

increased cancer, eye cataracts,
weakened immune system and
reduced plant yields.

"There has been a great deal of recent attention to the

suspected increase in amphibian deformities. However, most
reports have been anecdotal, and no experiment in the field
under natural conditions had been performed previously,"

Even though the ozone is

being destroyed naturally, it
is disappearing faster than
possible without other
factors influencing it.

The first global agreement to restrict CFCs came

with the signing of the MONTREAL PROTOCOL in
1987 ultimately aiming to reduce them by half by the
year 2000. The main CFCs will not be produced by
any of the signing countries after the end of 1995,
except for a limited amount for essential uses, such
as for medical sprays.

Other Halogenated
Compounds

Many other compounds cause damage to

the environment:

DDT used for mosquito control

Dioxin byproduct of chlorinated processes
Furan byproduct of chlorinated processes

2.2) Alcohols, Carboxylic Acids

and Esters

3 types of functional groups in organic

compounds:

Alcohols: OH group
Carboxylic acids: COOH
Esters: OH and COOH

a) Alcohols

Have hydroxyl in them (OH)

and end in ol.
Hydroxyl group attracts water
particles; causes antifreeze to
slow freezing of gas lines.
Uses and common examples:

Solvents, fuels, disinfectants,

pharmaceuticals.
Methanol, ethanol, glycol and
isopropanol.

Alcohols contain Hydroxyl

Naming Alcohols:
Omit e at end of the name
Change ending to ol
Properties:
Hydroxyl group does not dissociate in water, therefore
alcohols are NOT basic
Liquid at room temp
Distinct odour
Examples:

Methanol

poisonous

Ethanol

in alcoholic
beverages

isopropanol

Rubbing alcohol

b) Carboxylic acids
Carbon atom joined to a
single oxygen atom and one
oxygen joined to a
hydrogen (COOH).
Lactic acid is the name of a
carboxylic acid produced
during exercise;
biphosphate is used to
buffer it in the body.

Carboxylic Acids Contain

Carboxyl Groups

Naming Carboxylic Acids:

Properties:

Omit e at end of the name

Change ending to oic acid

Weak acids because the OH donates a proton

NOTE: the OH in carboxylic acids behaves differently
than the OH in alcohols

Examples:

Vinegar
Citric acid
Lactic acid

c) Esters

Formed by carboxylic acids and

alcohols reacting.
Naturally occurring (fatty acids in
bodies) and artificially
(cosmetics/food industry).
Water is a by product of the
formation of an ester.
Used to add a smell or color to a
compound (e.g. Licorice).

Esters

Examples of esters:
Cologne
Aftershave
pleasant odours / flavours in food
Alcohols and carboxylic acids react to form esters
An H is removed from the alcohol and an OH from
the acid- water is formed.
Functional group for ester:
Naming an ester:
R is the alcohol, change the ending to yl
R is the acid drop ic acid and change ending
to ate

d) Polyesters
Polyester forms plastic: created by many
alcohols and carboxylic acids reacting,
forming long chains (polymers).
These filaments are used to make many
products:

Towropes
PFD straps
T-shirts
Wakeboards
Dacron

e) Bioplastics
Plastics are not
biodegradable; they do
not breakdown in land
fills (up to 300 years).
Bioplastics are
completely
biodegradable but have
the strength of plastics.
Produced by tissues of
plants or from bacteria
cells.

Water Pollution