Hydrocarbons Part 2

Aromatic Hydrocarbons, Alkyl Halides and Alcohols

Hazel Jane M. De Felipe

MAT-Science
 Aromatic Hydrocarbons
• Aromatic hydrocarbons are also known as arenes,
these hydrocarbons contain at least one aromatic
ring. These are termed aromatic because most of
these compounds have strong fragrant odors. One of
the best known aromatic compound is benzene.
The electronic structure of benzene may be represented as a resonance
hybrid.

Benzene resonance structure.

The representation shows that all of the carbon-carbon bonds are equivalent
and that each one intermediate between a single bond and a double bond.
Geometric structure of benzene molecule

The entire structure is planar, and all of the bond

angles are 120º.
Friedrich August Kekule von Stradonitz (1829-1896)

Friedrich August Kekule von Stradonitz (1829-1896) is a German

organic chemist. He was a professor at Ghent, Belgium from
1858-1896, and at Bonn from 1867-1896. He studied various
carbon compounds, especially benzene, developing the ring
theory which describes benzene’s molecular structure. This
theory is of fundamental importance to modern chemistry.
Benzene was recognized as the first aromatic hydrocarbon. It is
characterized by alternating double and single bond between
carbon atoms. Its structure can also be illustrated with a circle
inside to show the six electron floating around its ring. The nature
of its bonding was first recognized by Friedrich August Kekule in the
19th century. Examples of benzene are methylbenzene,
naphthalene, phenanthrene and TNT trinitrotoluene.

Methylbenzene (Toluene)
There are three position isomers of any disubstituted benzene derivatives.

o-xylene m-xylene p-xylene

See how the example below is named.

o-dibromobenzene or 1,2-dibromobenzene

The prefix ortho (o), meta (m), and para (p) are used to designate the position of the
two substituent groups.
 Naming Aromatic Compounds
Naming aromatic compounds often has more than one
name
That is acceptable and it is not uncommon to find the
old names still in use as well.

Example: methylbenzene (Toluene)

The name is so obvious that the group attached to the
ring is added to the word benzene.

chlorobenzene nitrobenzene
Compounds, which the two substituted groups are
different, are named accordingly. Thus,
 Uses of Benzene
In the 19th century, benzene was used for the following
puposes:

• as an after-shave lotion because of its pleasant smell;

• as an industrial solvent especially for degreasing metal;
• to decaffeinate coffee which was popularized by Ludwig
Roselius; and
• to make rubbers, lubricants, dyes, detergents,
drugs(ibuprofen,aspirin), explosives, and pesticide.
• However, benzene is toxic.
• Exposure to benzene can cause serious health effects. It is a
global health problem that we need to face.
– Benzene targets the internal organs like liver, kidney, lungs
and heart.
– It damages the brain and could break DNA strand causing
chromosomal damage.
• Low levels of benzene in outdoor air comes from tobacco
smoke, automobile service stations, exhaust from motor
vehicles, and industrial emissions.
• Benzene is also classified as carcinogenic. It was first reported
to induce cancer in humans in the 1920’s.
 Alkyl Halides
Alkyl halides are hydrocarbons in which one or more hydrogen
atoms have been replaced by halogen atoms. Alkyl halides
have the general formula R-X, where R is an alkyl group and X
is the halogen replacing one hydrogen atom.

Examples: ethyl chloride (CH3CH2Cl), propyl chloride

(CH3CH2CH3Cl),
The simplest common alkyl halides are chloroform and
carbon tetrachloride. Chloroform was used as a medical
anesthetic in the past, but has been found to be
carcinogenic. Carbon tetrachloride has also been used in
fire extinguishers, as a fabric cleaner, and as a solvent,
but is now known to damage the liver.

Chloroform Carbon tetrachloride

 PROPERTIES OF ALKYL HALIDES
• The melting and boiling points of alkyl halides are greater
than those of hydrocarbons of comparable molecular
weights.
• The melting and boiling points of alkyl halides increases
with the molecular weight.
• CH3F, CH3Cl, CH3Br, and C2H5Cl are gases at room
temperature.
• The alkyl halides up to C18 are colorless liquids while
higher members are colorless solids.
• Alkyl halides are insoluble in water but soluble in organic
solvents.
 PROPERTIES OF ALKYL HALIDES
• They burn on copper wire with green edge flame.
• Alkyl bromides and iodides are heavier than water.
• Alkyl chlorides and fluorides are lighter than water.
• Alkyl Iodide become violet or brown in color on
exposure as they decompose in light.
• Alkyl halides are in general toxic compounds and
cause unconsciousness when inhaled in large
amounts.S
 Chlorofluorocarbons (CFCs)
• Alkanes whose hydrogen atoms are substituted with
chlorine and fluorine are called Chlorofluorocarbons
(CFCs), CFCs have been used as dispersing gases in
aerosol cans, as foaming agents for plastics, and as
refrigerants. They are also known as Freons.

tricholorofluoromethane(Freon 11) and

dichlorofluoromethane (Freon 12)

• The use of CFCs has been sharply reduced because they
pose danger to the ozone layer. It is estimated that
chlorine can remain in the atmosphere for years,
destroying thousands of ozone molecules (O3). CFCs in
the atmosphere also contributed to the green house
effect.

• Alkyl halides are used as industrial solvents (such as 1,2-

dichloroethane), inhaled anesthetics in medicine (such as
Halothane). Bromomethane is used as fumigant, but is
known to have adverse effects on human health and the
environment.
 Functional Group
Functional group determines the structure, properties
and chemical reactions of organic compounds.
Functional group hold onto their properties
regardless of the molecule in which they are found.
They are formed through a base molecule and an R
(hydrocarbon) group.
 Alcohols
• Alcohol is an organic compound commonly used as
reagent, solvent, and fuel. It is colorless and also
transparent. It has an OH group attached to a single
bond alkyl group, alkane. Four most common
alcohols are methyl alcohol, ethyl alcohol, propyl
alcohol, and isopropyl alcohol.
• Alcohol is an organic compound commonly used as
reagent, solvent, and fuel. It is colorless and also
transparent. It has an OH group attached to a single
bond alkyl group, alkane. Four most common
alcohols are methyl alcohol, ethyl alcohol, propyl
alcohol, and isopropyl alcohol.
Alcohols are classified as primary(1º), Secondary (2º),
or Tertiary (3º), depending on the number of carbon
subtituents bonded to the hydroxyl,bearing carbon.
 Naming Alcohols
To name alcohols locate the longest chain of carbon
that holds the OH group. Write the location number
of the OH group without considering where the alkyl
group is. Name the alkane attached to the OH group.
Replace the –e with an –ol.
OH CH3

CH3CHCHCH3
•The parent chain is butane
•The OH group location is on the second carbon atom
•Methyl (CH3) is attached in the third carbon atom
•Alkane name is therefore 3-methylbutane
•Alcohol name will be 3-methyl-2-butanol

OH CH3

CH3CHCHCH3
 Uses of Alcohols
• Ethanol, with the chemical formula C2H5OH, is the most
commonly used alcohol. It is produced through
fermentation and is consumed by humans through
alcoholic beverages.

• On the other hand, methanol (CH3OH), The simplest

alcohol is obtained from the distillation of wood, and
therefore, called as the “wood alcohol”. Unlike ethanol,
methanol is extremely toxic. It can cause blindness once
sipped even in as little amount as 10 mL.