What Are Hydrocarbon Derivatives?

Can you imagine life without a refrigerator? Thanks to hydrocarbon derivatives, you don't have to. In
the early 1900s, refrigeration technology evolved from chunks of ice to machine powered and
chemically cooled systems. And for more than fifty years, the best chemicals for the job were
chlorofluorocarbons, or CFCs, made of chlorine atoms, fluorine atoms and carbon atoms.
Unfortunately for the planet, CFCs are intensely damaging to the ozone layer, which is the layer of
O3 molecules high in the atmosphere that protect Earth from powerful ultraviolet rays. A chlorine
atom within a single CFC has the power to damage one hundred thousand molecules of ozone
before it breaks down. CFCs are still present as refrigerants and aerosols, but luckily the use of them
is decreasing.
Let's compare the structure of a simple CFC with an equally simple hydrocarbon and see if we can
figure out what a hydrocarbon derivative is.

Simple CFC

As you may recall, a hydrocarbon is a compound made mostly of hydrogen and carbon atoms
bonded together through the sharing of electrons. Some classic examples include methane, ethene
and benzene. The simplest hydrocarbon, methane, consists of one central carbon atom with four
hydrogens bonded to it.
 Simple Hydrocarbons

One of the simple CFCs, Freon 12, consists of one central carbon atom with two chlorines and two
fluorines bonded to it. What similarities do you notice between the two?

Hydrocarbon and CFC

In each case, there is a central carbon atom and four bonds extending out if it.
What differences do you notice? Maybe that methane only contains hydrogens and a carbon, while
Freon contains chlorine atoms, fluorine atoms and a carbon?
How about comparing methane to another hydrocarbon derivative: methanol? Methanol has a
central carbon bonded to three hydrogens and one oxygen. The oxygen is, in turn, bonded to a
hydrogen.
 Hydrocarbon and Hydrocarbon Derivative

Again, there is a central carbon that has four bonds extending from it.
Notice any patterns yet? Carbons are the central atoms in both cases. A hydrocarbon consists of
carbons and hydrogens. Hydrocarbon derivatives contain different elements attached to the
carbon instead of only hydrogen.
Perhaps you've had to look up derivatives of Latin words in the English language, or take the
derivative of a curved line in calculus. A derivative is something that is based on another source. In
our case, hydrocarbon derivatives are based on simple hydrocarbon compounds that contain only
hydrogens and carbons.
Hydrocarbon derivatives contain at least one element other than hydrogen or carbon, such as
oxygen, nitrogen or one of the halogen atoms (elements in column 7A).
Most of the time, the atoms present in a hydrocarbon derivative are attached as part of a distinct
group. These groups are known as functional groups because they affect how the compound
behaves. Sometimes functional groups affect physical properties of a compound as well.
Examples of functional groups include alcohols, aldehydes, ketones, amines and esters.

9.3- Hydrocarbon Derivatives

-Organic compounds are divided into two main classes: hydrocarbons and hydrocarbon
derivatives
-Hydrocarbon derivatives are molecular compounds of carbon and at least one other element
that is not hydrogen
-Organic halides are organic compounds in which one or more hydrogen atoms have been
replaced by halogen atoms
-Common organic halides include freons (chlorofluorocarbons) and Teflon
(polytetrafluoroethylene)
-Naming halides uses the same format as branched-chain hydrocarbons
-The branch is named by shortening the halogen name to fluoro-, chloro-, bromo-, or iodo-
-In drawing organic halides using IUPAC names, draw the parent chain and add branches at
locations specified in the name
eg.
Cl Cl
| |
H-C-C-H
| |
H H

1,2-dichloroethane

-Organic halides react fast which is explained from the idea that no strong covalent bond is
broken – the electron rearrangement does not involve separation of the carbon atoms
-Addition of halogens could be added to alkynes which results in alkenes or alkanes
-By adding halogens to alkenes, the product could undergo another addition step, by adding
halogens to the parent chain, the double bond has to become a single bond in order to
accommodate the halogens
eg.
Br Br Br Br
| | | |
H-C=C-H + Br-Br => H-C-C-H
| |
Br Br

-By adding hydrogen halides to unsaturated compounds will produce isomers

H H H H H H H H H
| | | | | | | | |
H-C=C-C-H + H-Cl => H-C-C-C-H OR H-C-C-C-H
| | | | | | |
H Cl H H HCl H

-Substitution reaction is a reaction that involves the breaking of a carbon-hydrogen bond in

an alkane or aromatic ring and the replacement of the hydrogen atom with another atom or
group of atoms
-With light energy it enables the substitution reaction to move at a noticeable rate eg. C3H8 +
BR2 + light => C3H7Br + HBR
-Through substitution reaction, in order to name the reaction product, just indicate the
location number of the replacement, followed by the halogen prefix (eg. Bromo-) and then
state the type of parent chain. Also indicate the second product created from substitution
reaction (hydrogen bromide) eg. propane + bromine => 1-bromopropane + hydrogen
bromide
-Elimination is an organic reaction in which an alkyl halide reacts with hydroxide ion to
produce an alkene by removing a hydrogen and halide ion from the molecule
 H H H H H H
| | | | | |
H-C-C-C-H + OH => H-C=C-C-H + H-O + Br
| | | | |
H BrH H H

-Alcohols have properties that can be explained by the presence of a hydroxyl (-OH)
functional group attached to a hydrocarbon chain
-Short-chain alcohols are very soluble in water because they form hydrogen bonds with water
molecules
-Alcohols are used as solvents in organic reactions because they are effective for both polar
and non-polar compounds
-To name alcohols, the –e is dropped from the end of the alkane name and is replaced with –
ol eg. Methane => methanol
-Methanol is also called wood alcohol because it was once made by heating wood shavings in
the absence of air
-These days, methanol is prepared by combining carbon monoxide and hydrogen at high
temperatures and pressure with the use of a catalyst
-Methanol, however, is poisonous to humans. Consuming a small amount could cause
blindness or death
-When naming alcohols with more than two carbon atoms, the position of the hydroxyl group
is indicated
-Alcohols that contain more than one hydroxyl group are called polyalcohols, their names
indicate the positions of the hydroxyl groups eg. 1,2-ethanediol
-Alcohols undergo elimination reactions to produce alkenes through being catalyzed by
concentrated sulfuric acid, which removes or eliminates a hydrogen atom and a hydroxyl
group
H H H H
| | | |
H-C-C-H + acid => H-C=C-H + H-O
| | |
H OH H

ethanol + acid => ethene + water

-Ethers is a family of organic compounds that contain an oxygen atom bonded between two
hydrocarbon groups, and have the general formula R1-O-R2
-To name ethers add oxy to the prefix for the smaller hydrocarbon group and join it to the
alkane name of the larger hydrocarbon group
eg.
CH3-O-C2H5

methoxyethane
-Ethers have low solubility in water, low boiling points, and have no evidence of hydrogen
bonding
-Ethers undergo chemical change only when treated with powerful reagents under vigorous
conditions
-Ethers are formed by the condensation reaction of alcohols
-Condensation reaction is the joining of two molecules and the elimination of a small
molecule, usually water
-The carbonyl functional group, -CO-, consists of a carbon atom with a double covalent bond
to an oxygen atom
-Aldehydes has the carbonyl group on the terminal carbon atom of a chain
-To name aldehydes, replace the final –e of the name of the corresponding alkane with the
suffix –al
-Small aldehyde molecules have sharp, irritating odors whereas larger molecules have
flowery odors and is used to make perfumes
-A ketone has the carbonyl group present anywhere in a carbon chain except at the end of the
chain
-The difference in position of the carbonyl group affects the chemical reactivity, and enables
us to distinguish aldehydes from ketones empirically
-To name ketones, replace the –e ending of the name of the corresponding alkane with –one
-The simplest ketone is acetone (propanone), CH3COCH3
-The family of organic compounds, carboxylic acids contain the carboxyl functional group, -
COOH, which includes both the carbonyl and hydroxyl groups
-Carboxylic acids are found in citrus fruits, and other foods with properties of having a sour
taste
-Carboxylic acids also have distinctive odors (like sweat from a person’s feet)
-The molecules of carboxylic acids are polar and form hydrogen bonds both with each other
and with water molecules
-Carboxylic acids acid properties, so a litmus test can separate these compounds from other
hydrocarbon derivatives
-To name carboxylic acids, replace the –e ending of the alkane name with –oic, followed by
the word “acid”
-Methanoic acid, HCOOH, is the first member of the carboxylic acid family
-Some acids contain two or three carbonyl groups such as oxalic acid, and citric acid
COOH CH2-COOH
| |
COOH HO-C-COOH
|
CH2-COOH

oxalic acid citric acid

-When carboxylic acids undergo a condensation reaction, in which a carboxylic acid

combines with another reactant, it forms two products – an organic compound and water
-Esterification is the condensation reaction in which a carboxylic acid reacts with an alcohol
to produce ester and water
-carboxylic acid + alcohol => ester + water
-The ester functional group is similar to that of an acid, except that the hydrogen atom of the
carboxyl group is replaced by a hydrocarbon branch
-Esters are responsible for the odors of fruits and flowers and are also added to foods for
aroma and taste
-To name an ester, determine name of the alkyl group from the alcohol used in the
esterification reaction
-Next change the ending of the acid name from “–oic acid” to “–oate”
-ethanoic acid + methanol => methyl ethanoate + water
-Artificial flavorings are made by mixing synthetic esters to give similar odors of the natural
substance
-An amide consists of a carboxyl group bonded to a nitrogen atom
-Amides could be formed in condensation reactions
-Amides occur in proteins, the large molecules found in all living organisms
-Peptide bonds is the joining of amino acids together in proteins
-To name amides, have the name of the alkane with the same number of carbon atoms, with
the final –e replaced by the suffix –amide
-Change the suffix of the carboxylic acid from “–oic acid” to –amide to have the same name
results eg. ethanamide
-Amines consist of one or more hydrocarbon groups bonded to a nitrogen atom
-Through X-Ray diffraction reveals that the amine functional group is a nitrogen atom
bonded by single covalent bonds to one, two, or three carbon atoms
-Amines are polar substances that re extremely soluble in water as they form strong hydrogen
bonds both to each other and to water
-Amines have peculiar, horrible odors (eg. smell of rotting fish)
-The name of amines include the names of the alkyl groups attached to the nitrogen atom,
followed by the suffix –amine eg. methylamine
-Amines with one, two, or three hydrocarbon groups attached to the central nitrogen atom are
referred to as primary, secondary, and tertiary
-Primary amines is when a hydrogen atom attached to the nitrogen atom is replaced by a
hydrocarbon group
-Secondary amines are when two hydrocarbon groups replaces the hydrogen atoms and
tertiary amines replaces all of the hydrogen atoms with hydrocarbon groups
-Amines are used in the synthesis of medicines
-A group of amines found in many plants are called alkaloids
-Many alkaloids influence the function of the central nervous systems of animals
-Substitution – alkane/aromatic + halogen + light => organic halide + hydrogen halide
-Elimination – alkyl halide + OH => alkene + water |+ water + halide ion
-Elimination – alcohol + acid => alkene + water
Hydrocarbons and derivatives

Hydrocarbon compounds are also known as hydrocarbons. They are compounds only containing two
elements, hydrogen and carbon. When their molecular hydrogen atoms are replaced by various kinds
of other element atoms or atom groups, we can obtain various kinds of hydrocarbon derivatives. German
chemist Schorlemmer had discovered butane and other hydrocarbons, and is thus known as the founder
of the hydrocarbon chemistry. There are many types of hydrocarbons with number of hydrocarbons with
known structure being over 2,000 kinds. Based on the connecting way of carbon bonds, they are divided
into chain hydrocarbon and cyclic hydrocarbon, two types with the former one having its carbon atoms
connected in a chain shape. According to the saturation degree of hydrogen atom on valence bonds,
they are divided into saturated and unsaturated hydrocarbons. Saturated hydrocarbons are namely
alkanes, such as methane, ethane and so on; unsaturated hydrocarbons include olefin and alkynes with
representation being ethylene and acetylene. Cyclic hydrocarbon has its intramolecular carbon bonds
connected into a closed ring. It includes two kinds, alicyclic hydrocarbons and aromatic hydrocarbons.
There are many similarities between alicyclic hydrocarbons and chain hydrocarbon. General cyclic
hydrocarbons are similar to hydrocarbons while cyclic olefin and cyclic alkyne are respectively similar as
alkenes and alkynes. Aromatic hydrocarbons mainly refer to hydrocarbons containing benzene ring
structure.

Chain hydrocarbon is also known as aliphatic hydrocarbon due to that during the initial study; it was
found that oil lipid contained many of these open chain compounds. The naming of alicyclic hydrocarbons
is due to its similar nature as aliphatic hydrocarbons. The nature of aromatic hydrocarbon is different
from other hydrocarbons while first discovered several compounds are all scented, leading to the name
which is still in use today.

Oil, gas and coal are the main source of hydrocarbons. Petroleum refining can give a variety of alkane
mixture such as gasoline, kerosene, diesel, etc; oil cracking, reforming give various kinds of olefins,
alicyclic hydrocarbons and aromatic hydrocarbons. Coal tar contains various kinds of aromatic
hydrocarbons (e.g., benzene, naphthalene, etc.). Many kinds of higher hydrocarbons are presented in
plants such as the pigments contained in tomatoes and carrots. The wax of many kinds of plants and
animals also contains higher content of alkanes. For example, beeswax contains C27H56 and C31H64;
wax of spinach leaves contains C33H68, C35H72, and C37H76; wax of cabbage leaves contains C29H60
and so on. The main component of natural rubber, polyisoprene also belongs to hydrocarbon. An
important application of hydrocarbons is being used as fuel and chemical raw materials. Through
secondary processing of petroleum, it can give ethylene, propylene, butadiene, benzene, toluene, xylene
and naphthalene, and other basic organic industrial raw materials. From these materials, we can further
prepare styrene, ethanol, acetone and other chemicals. Re-use of these raw materials can be used for
manufacturing of a variety of plastics, synthetic rubber, synthetic fibers and fine chemical products.
Hydrocarbons may also be used as food for certain bacteria to utilize with those proteins (oil protein)
excreted by these bacteria proteins being applied as feed. The national scale and level of processing
and application of hydrocarbons may reflect the extent of economic and technological development of a
country.

Hydrocarbon derivative refers to the general term of many kinds of complicated compound derived from
hydrocarbon molecules with one or more hydrogen atoms being substituted by other atoms or atoms
groups. Compounds derived from halogen substitution are called halogenated hydrocarbon; derived
from hydroxy substitution are called alcohols or phenols; derived from carboxy substitution are called
carboxylic acids. Ester, acyl halide, acid anhydride, amides, aldehydes, ketones, amines and nitriles,
etc. can be considered to be the compounds derived from hydrocarbons with intramolecular hydrogen
atoms being substituted by corresponding atoms. During early 19th century, German chemist
Schorlemmer, based on years of experimental and theoretical studies, had first defined organic
chemistry as chemistry concerning hydrocarbons and their derivatives. This definition is formulated
based on the principles of atom combination theory, being more reasonable and advanced than all the
previous definitions, thus further being adopted by many chemists. However, the problem is that it
doesn’t distinguish the difference between organic and inorganic substances. The definition of
Schorlemmer had greatly promoted the development of the theory regarding to the organic chemistry
structure. He was the first man who defined organic compound as above scientific classifications,
establishing a scientific system. He was the first man who divided organics into aliphatic and aromatic
hydrocarbons and further classified aliphatic compounds into hydrocarbons (saturated hydrocarbons and
unsaturated hydrocarbons), halocarbons, alcohols, ethers, aldehydes, ketones, acids, esters and so on.