Download Hydrocarbon Derivatives

• Hydrocarbon Derivatives
And Functional Groups
• Introduction
– Hydrocarbon derivatives are formed when one or more
hydrogen atoms is replaced by an element or a group of
elements other than hydrogen.
– Halogens (F2, Cl2, Br2, I2,) can all add to a hydrocarbon
to form am alkyl halide.
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•
•
•
•
When naming the halogen the –ine ending is replaced by –o
Fluorine becomes fluoro
Chlorine becomes chloro
Bromine becomes bromo
Iodine becomes iodo
• Common examples of organic halides.
– Alkenes can also add to each other in an addition reaction
to form long chains of carbon compounds.
• this is called polymerization
– The atom or group of atoms that are added to the
hydrocarbon are called functional groups.
• Functional groups usually have multiple bonds or lone
pairs of electrons that make them very reactive.
• Alcohols
– An alcohol has a hydrogen replaced by a hydroxyl (-OH)
group.
– The name of the hydrocarbon that was substituted
determines the name of the alcohol.
– The alcohol is named using the
hydrocarbon name and adding
the suffix –ol.
• If methane is substituted
with an OH group it becomes
methanol
• If a pentane group is
substituted with an OH
group it is pentanol.
• For alcohols with more than
two carbon atoms we need
the number the chain so as to
keep the alcohol group as
low as possible.
• Primary alcohols are those with
the OH at the end of the Carbon
chain.
EX:
ethanol ------------------------------------
1-propanol --------------------------------------
• Secondary alcohols are those
having the OH within the Carbon
chain.
EX:
2 - propanol ------------------------------
• Tertiary alcohols
are those that have
the OH on a
Carbon that has
only C-C bonds
EX: 2 – methyl – 2propanol
• Gasoline is a mixture of
hydrocarbons (C8H18 for
example) that contain no atoms of
oxygen. Gasohol contains ethyl
alcohol, C2H5OH, which does
contain oxygen.
• The addition of alcohol to
gasoline, therefore, adds oxygen
to the fuel. Since carbon
monoxide forms when there is an
insufficient supply of oxygen, the
addition of alcohol to gasoline
helps cut down on carbon
monoxide emissions.
If an alcohol contains two OH groups
it is a diol (sometimes called a
glycol).
An alcohol with three OH groups is
called a triol (sometimes called a
glycerol).
Addition Reactions
• A substance is added to the
double or triple bond of an
alkene or alkyne.
• The addition of water to an
alkene is called a HYDRATION
REACTION.
To make alcohol add water to ethene
H H
C=C
H H
ethene
+
H2O 
water
H OH
H–C–C–H
H H
ethanol
• The addition of HYDROGEN
to an alkene is called a
HYDROGENATION
REACTION.
H H
C=C
H H
ethene
H H
+ H2  H – C – C – H
H H
hydrogen
ethane
Ethers,
Aldehydes,
and
Ketones
Ethers
An ether has a general
formula R-O-R’. Use
“ether” ending.
EX: Diethyl ether C4H10O
CH3CH2-O-CH2CH3
• The best-known ether is the
anesthetic called diethyl ether.
• Other ethers have a wide range of
uses as solvents, refrigerants,
artificial flavours, and drugs.
• As a class of compounds, ethers are
relatively unreactive chemically.
• Ethers are isometric with the alcohols.
• For example, diethyl ether (CH3CH2-OCH2CH3) is an isomer of butanol
(CH3CH2CH2CH2-OH).
• Both have the molecular formula C4H10O.
Naming Ethers
• Ethers are named in
two ways: the
common naming
system, and the
IUPAC naming
system.
• Common Names:
The alkyl groups attached to the ether
linkage are named in alphabetical order
and are followed by the word ether.
Symmetrical ethers are named by using
the prefix di-.
• IUPAC Names:
The carbon(s) attached to the oxygen atom
are named as branches by adding the –
oxy suffix to the stem name.
• Ex. CH3-CH2-CH2-CH2-O-CH2-CH3
• Common Name: butyl ethyl ether
• IUPAC Name: ethoxybutane
Aldehydes and Ketones
• Two families of organic compounds, called
aldehydes and ketones contain the carbonyl
functional group (-C=O).
• This group consists of a carbon atom double
bonded to an oxygen atom.
–An aldehyde has a carbonyl
group (carbon double bonded
to an oxygen) attached to a
terminal carbon atom. Use “al”
ending.
• EX: Methanal CH2 O
•
H2C=O
Uses of Aldehydes
• The smaller aldehyde
molecules have sharp,
irritating odours.
• The larger ones have
flowery odours and are
diluted to make
perfumes.
• Methanal is a starting
material in the
manufacture of some
plastics.
– A ketone has a carbonyl group
attached to an internal carbon
atom. Use “one” ending.
• EX: Propanone C3H6O
CH3
C=O
CH3
• The carbonyl group (A)
is present in both
aldehydes and ketones,
as shown in (B). (C)
The simplest example
of each, with the
IUPAC name above and
the common name
below each formula.
Uses of Ketones
• The simplest ketone is
propanone (common name =
acetone).
• It is an effective solvent found
in many nail polish removers,
plastic cements, resins and
varnishes.
• It is also sold as a cleaner.
Because it is both volatile and
flammable, it should be used
only in well-ventilated areas.
Organic Acids
and
Esters
Organic acids are those acids
that are derived from living
organisms, usually from
metabolism, but sometimes as a
defense mechanism.
Long chain organic acids are
known as fatty acids.
These are also called carboxylic
acids as they contain the carboxyl
functional group (COOH)
One oxygen is double bonded to
the carbon and the other is
bonded to the carbon and to the
hydrogen both with single
• These red ants, like other ants, make the simplest
of the organic acids, formic acid.
• The sting of bees, ants, and some plants contains
formic acid, along with some other irritating
materials. Formic acid is HCOOH.
–Esters are condensation
products of carboxylic
acids with the removal
of water (also called a
dehydration synthesis).