Organic Chemistry – Study of Hydrocarbons & their derivatives

Organic Chemistry is the study of compounds based on hydrocarbons and their derivatives.

Hydrocarbon
A Hydrocarbon is a compound which is made of hydrogen and carbon only.

We are going to learn about four main homologous series; they are Alkane, Alkene, Alcohol and
carboxylic acid.

Homologous series
The Homologous series is a family or group of hydrocarbons or derivatives having the same
functional group, same general formula and similar chemical properties. They also have a similar
trend in physical properties.

Functional Group
The functional group is simply an atom or group of atoms attached to the organic compound which
dictates its chemical property. Gives its own chemical property. Also in some cases, it gives rise
to some unique physical properties too. Do not worry if you are still confused about what a
functional group is. I have explained this concept with some examples in this blog, that will make
everything clear.

General Formula
The General Formula is the formula to find out the molecular formula for an organic compound
which is in a certain homologous series.

The general formula of a homologous series gives the formula which shows how many hydrogen
or another kind of atoms will be there for a given number of carbon atoms.

For example, the General Formula of Alkane is CnH2n+2 . Which means, if an alkane has one
carbon atom, then it will have 2(1)+2 = 4 Hydrogen atoms. This is how easily we use the general
formula to easily determine how many atom(s) of each element are present.
Simple differentiating of the four homologous series:

Alkane
Alkane is the simplest of all the homologous series. It only has simple C-H bonds throughout its
whole structure. The General Formula of the alkane is CnH2n+2 . It does not have any functional
group, hence alkanes are quite inert in nature.

For example, Butane is an alkane with four carbon atoms. We can use the general formula of
alkane to easily figure out its molecular formula.

The number of Carbon atoms are 4, hence n=4. Hence the molecular formula of Butane is
C4H2(4)+2 = C4H6.
Alkene
Similarly to Alkanes, alkenes also contains C-H bonds. But it also contains one C=C (carbon to
carbon double bond) attached as the functional group, it’s general formula is CnH2n

The functional group of alkenes gives it some unique chemical properties.

For example, butene is an alkene with four carbon atoms. We can easily use the general formula
of alkene to determine the molecular formula of butene.

Butene has four carbon atoms, hence n=4. Hence the molecular formula of butene is C 4H2(4) =
C4H8

Alcohol
In Alcohol, there is also C-H bonds present. The –OH(Hydroxide) attached acts as the functional
group, general formula CnH2n+2O.

Similar to alkanes and alkenes, we can also use the general formula to determine the molecular
formula of specific alcohols.

For example butanol is an alcohol with four carbon atoms.

Carboxylic acid
 C-H present, but with –COOH bond attached as the functional group. General Formula CnH2nO2

For Example: butanoic acid, a carboxlylic acid with four carbon atoms. Please note, the carbon
atom within the functional group is also taken into consideration.

Butanoic Acid

Naming an organic compound

Naming an organic compound is one of the most important things to do. In IGCSE chemistry
exams, they give the formula and ask you to name it. So read this section very carefully as I dive
into details of how to name an organic compound.

The name of an organic compound indicates four things:

1 The number of carbons atom(s) in the compound.

2 If an alkyl group attached or not. If yes, then its name and position number.
3 Indicating to which homologous series the organic compound belongs to and the position
number of the functional group if any present.

The number of carbon atom(s) present is indicated by the prefix (beginning part of name).

The homologous series to which the compound belongs to is indicated by the suffix (end part).

The alkyl group position number and name is indicated before the prefix.

The position no. of the functional group is placed between the suffix and prefix.

So the name of an organic compound is in the following format:

m code Alkylname prefix-n-suffix

m- Position of alkyl group

n- position of functional group

Code- di-(two) , tri-(three), tetra-(four)

List of prefixes
No. of carbons prefix Alkyl Radical
1 Meth- Methyl-
2 Eth- Ethyl-
3 Prop- Propyl-
4 But- Butyl-
5 Pent- Pentyl-
6 Hex- Hexyl-
7 Hep- Heptyl-
8 Oct- …..
9 Non- ……
10 Dec- ……

Suffix, indicating the homologous series

Homologous series suffix
alkane -ane
alkene -ene
alcohol -ol
Carboxylic acid -oic

Examples:
Example 1: An alkane made of 5 carbons:
Prefix→Pent- Suffix→ -ane so Name → Pentane

Example 2: An alkene made of 6 carbons:

Prefix→ Hex- Suffix→ -ene so Name→Hexene
▪ In the case of alcohol and carboxylic acid, you have to add an extra “an” after the prefix
▪ An alcohol made of 3 carbon atoms:
Prefix →Prop- (add an extra “an” after it) Suffix→- ol so Name→Propanol

Example 3: A carboxylic acid made of 2 carbon atoms:

Prefix→ Eth- (add an extra “an” after it) Suffix→ -oic so Name→ Ethanoic acid

Naming an Organic Compound by interprating the formula:

▪ C3H8 – the following formula satisfies the general formula of alkane, and consists of 3 carbon
atoms. Name- Propane
▪ C5H10 – the following formula satisfies the general formula of alkene and consists of 5 carbon
atoms. Name- pentene
▪ C3H7OH- the following is an alcohol as we can see a –OH group is attached to it, with three
carbon atoms. Name- propanol
▪ C3H7COOH- the following is a carboxylic acid group as we can see a –COOH group attached,
with 4 carbon atoms (we also include the carbon from the functional group when naming).
▪ Name- butanoic acid

Different types of formulas in organic chemistry

 In organic chemistry, the organic compounds are usually expressed in three types of formulas:
▪ Molecular Formula
▪ Structural Formula
▪ Displayed Formula
To show the show the difference between them I am going to show butane in these three different
types of formulas.

Molecular Formula
The molecular formula shows only the number of atoms present from each element. It provides no
information about the type of bonding between the atoms. It also does not give any hint about the
structure, like how the atoms are arranged in the molecule. Whether there is any sort of branching
or not.
Example: C4H10

Structural Formula
Gives an idea about the structure, the compound is expressed as small groups of each carbon atoms
and hydrogen atoms attached to it, bonding is shown between each group by dashes, but the
bonding between the carbon and hydrogen atoms are not shown.
Example: CH3-CH2-CH2-CH3

Displayed Formula
The displayed formula shows all the individual bonds in an organic compound. You will even have
to show the bonds between the individual carbon and hydrogen atoms.

If there is an alcohol, you will have to show the bonding between the hydrogen and oxygen atom.

Usually in IGCSE chemistry exams, there are two mark questions which asks you to draw the
displayed formula of specific organic compounds.

Structural Isomerism
Up to now, all the organic compounds we have seen, all the carbon atoms were neatly lined up in
a straight line. But in reality that might not be the case.

In reality instead of following one carbon after another, they can form branches. Different types
of alkyl groups might be connected to the carbon atom.

It is not considered a valid branching if the alkyl group is connected to the end carbon atoms.

We count the position number from the end where it would be less.

I know this is a bit confusing. Please have a look at the examples below, I strongly believe they
will clear things up! Also please refer to the Alkyl radical table above.

Isomers
Isomers are simply organic compounds with same molecular formula but different structural
formulas.

To simply put isomers are different structural variations of the same organic compound.

For example, the molecular formula of pentene is C5H12 . It contains 5 carbon atoms and 10
hydrogen atoms. All the isomers of pentene will have 5 carbon atoms and 10 hydrogen atoms,
meaning the same molecular formula. But their structures will be different, hence they will have
different structural formulas.
Examples:

Isomers of Pentene
▪ I have listed below all the different Isomers of pentene (C5H10) along with names and displayed
formula.
▪ Please remember, when you are naming an isomer. Make sure to mention the position number
of the carbon to carbon double bond. Also, mention the position number of the alkyl radical.
Isomers of butanol:
Physical properties of Alkanes, Alkenes, alcohols and carboxylic acids:
Organic compounds which are in the same homologous series show a similar trend in physical
properties.

For example, the melting and boiling points of alkanes increases as their carbon number increase
(or their size increases). Because as their size increases the intermolecular forces between the
molecules increases. Hence takes more energy to overcome. Therefore the lighter alkanes are
usually gas at room temperature while the heavier alkanes are liquid.

The alkenes also show the same physical trend due to the same reason. But even though the trend
is similar all the alkenes comparatively have lower melting and boiling points than alkanes. This
because due to the carbon to carbon double bonds, the intermolecular forces are not that strong as
it is in alkanes.

The alcohol and carboxylic acids have much higher melting and boiling points than both the
alkanes and alkenes. This is due to their ability to form strong hydrogen bonding between the
molecules as they are the -OH functioanl group attached. So most alcohols and carboxylic acids
are liquids at room temperature.
All the organic compounds which are in the same homologous series have similar chemical
properties.
 Chemical Reactions of Alkane, Alkene, and Alcohols:
Alkanes: alkanes are the most inert of all the homologous series, due to the presence of only C-H
bond which is quite stable or inert.

The alkanes undergo only two types of reactions combustion with oxygen/air and substitution
reaction with halogens.

Reaction name Reaction(with an example) and conditions(if any)

Combustion (reaction with oxygen) Alkane+ Oxygen→ carbon dioxide+water

CH4(g) + 2O2(g)→ CO2(g) +2H2O(l)

(insufficient supply of oxygen causes incomplete combustion and produces
carbon monoxide or soot(carbon) instead of carbon dioxide
Substitution (reaction with halogens) Alkane + Halogen→ Hydrogen Halide+ Halogenoalkane

CH4(g)+Br2(g)→CH3Br(g)+HBr(g)
Condition: presence of UV light

Important Note, comes in IGCSE Chemistry exams: Carbon monoxide is a poisonous gas,
attaches with hemoglobin more efficiently than oxygen, which reduces the supply of oxygen to
the brain and causes death.

Alkenes: alkenes are more reactive than alkanes due to the presence of carbon to carbon double
bond as the functional group. If there is any carbon to carbon double present in an organic
compound, it is said to be unsaturated. If no carbon to carbon double bond is present in an
organic compound, then it is called saturated.

Here are the two basic reactions of alkenes; another one is during the production of alcohol.

Reaction name Reaction(with example) and conditions (if any)

Combustions (reaction with oxygen) Alkene+oxygen→Carbon dioxide+water

C2H4(g)+O2(g)→ 2CO2(g)+2H2O(l)
Addition(reaction with halogens) Alkene+Halogen→dihalogenoalkane

C2H4(g)+Br2(l)→ C2H4Br2(l)

Test of Unsaturation (presence of carbon-carbon double bond)

 Test for unsaturation means testing whether carbon to carbon double bond is present in an organic
compound. This is an extremely common question which frequently appears in IGCSE chemistry
exams.

Bromine is water is simply water with bromine mixed with it. When bromine mixes with water it
forms an orange-brown solution, which is called bromine water.

When an organic compound is unsaturated (contains carbon to carbon double bond). If you add
bromine water to it, then the bromine water will be decolorized. In simple words, it would turn
from orange-brown to colorless.

Alcohols: Two basic reactions of alcohols are combustion(reaction with oxygen) and
dehydration(loss of water from compound) :

Reaction Relevant equations and conditions

name
Combustion Alcohol+oxygen→ carbon dioxide+ water

C2H5OH(l)+3O2(g)→2CO2(g)+3H2O(l)
Dehydration Alcohol→Alkene+water

Conditions: heat, aluminum oxide as catalyst

Ethanol→Ethene+ water
C2H5OH(g)→ C2H4(g)+ H2O(l)

Production of ethanol
There are two reactions by which ethanol is mass produced, by Hydration and Fermentation.
Here are the conditions and reactions that occur in these two processes.

Process name Relevant equations and conditions

Fermentation Yeast is mixed with starch/sugar solution, and left in a sealed container, at 30-40◦C,
the yeast respires anreobically, produces an enzyme which converts glucose to ethanol
and carbon dioxide gas
 C6H12O6→ 2C2H12OH(aq) + 2CO2(g)
Hydration Ethane+ steam→ethanol

Temperature:300◦C, Pressure: 60-70 atm

Catalyst: phosphoric acid
C2H4(g)+ H2O(g)→CH5OH(g)
Only small portion of ethene reacts. The ethanol produced is condensed as a liquid and the
unreacted ethene is recycled.

Comparison between fermentation and hydration of ethane

Fermentation Hydration of ethene

Use of resources Uses renewable sources- sugar beet
or sugar cane, corm or other starchy
materials.
Type of process A batch process- everything is mixed
together in a reaction vessel and then
left for several days. That batch is then
removed and a new reaction is set up-
this is inefficient
Rate of reaction Slow, taking several days for each
batch
Quality of Produces very impure ethanol that
product needs further processing
Reaction Uses gentle temperature and ordinary
Conditions pressures
Uses finite resources- once all oil has been used up
there won’t be anymore
A continuous process- a stream of reactants is
constantly passed over the catalyst. This is more
efficient than a batch process.
rapid
Produces much purer ethanol
Uses high temperatures and pressures, needing a
high input of energy.

Ethanol is used as biofuel, it is renewable and produced by fermentation. But it is not such a bright
idea to plant crops for fuel instead of food.

What is crude oil (petroleum)?

Crude oil, also known as petroleum is a viscous brwon liquid. It is obtained from underground or
under the seabed. Millions of years ago creatures in the sea died and their bodies remained on the
seabed. Their bodies got covered by sediments and rocks. Under high temperature and pressure
their bodies converted to crude oil. Crude oil is a fossil fuel because it’s formed from the fossils
of dead creatures. Crude oil is a mixture of hydrocarbons of various sizes.
By hydrocarbon I simply mean alkanes and alkenes. Crude oil simply contains alkanes and alkenes
of various sizes, all mixed together.

Properties of hydrocarbons as their size increases

As the size of the hydrocarbon increases, the intermolecular forces between the molecules increase.
This is because, as the size of the molecules increases, the intermolecular forces between them
also increases. This results in the following:
 ▪ High melting and boiling point
▪ The liquids becomes less volatile (evaporates less easily)
▪ The liquid becomes viscous
▪ Bigger hydrocarbons do not burn so easily as the smaller ones. This limits the use of bigger ones
as fuels.

Separation of crude oil

The different fractions of crude oil are separated by the process of fractional distillation. The
crude oil is heated and inserted into a fractionating column. Fractions of the crude oil which have
lower boiling points, turn to gas and moves up the fractionating column. The fraction of the crude
oil having higher boiling point remains at the bottom which the ones with lower boiling points turn
to gas and moves up.

This is how different fractions of the crude oil are collected at different heights of the fractionating
column.

Please view the diagram and the table below to learn more about the different fractions of crude
oil and how we use them.

Fraction Use
Refinery gas Mixture of methane, ethane ,propane, butane , in LPG(Liquefied Petroleum Gas)
used for domestic heating and cooking
Gasoline Used as fuels for cars
kerosine Used as aviation fuel, domestic heating
Diesel(Gas oil) Used for buses, trucks, lorries, trains
Fuel oil Used for ships and industrial heating
Bitumen To make roads

Cracking
cracking is a useful process in which large hydrocarbon molecules are broken into smaller ones.
The big hydrocarbon molecules in gas oil, for example, can be broken down into smaller ones
needed for petrol.

Why cracking?
There is a very high demand for lighter hydrocarbons such as petrol because they burn easily. But
in crude oil, there are not enough fraction of the lighter hydrocarbons to provide for this demand.
To fulfill this high demand, the larger fractions of crude oil are cracked to produce extra lighter
hydrocarbon,s. The larger fractions are quite unreactive and cannot be used as fueld, for this reason
they must be cracked.

Cracking also produces hydrocarbons with carbon to carbon double bonds (alkene), which are very
useful as they are quite reactive. These are used by the chemical industries to produces different
types of chemicals such as shampoos, pesticides etc.

How cracking works?

The larger fraction of hydrocarbon is converted to gas by heating, then passed over the catalyst of
mixed silicon dioxide and aluminium oxide at temperatures of about 600-700◦C. If catalysts are
not used, then the higher temperature is needed, which is a waste of energy.

Cracking is a random process, so the smaller fractions produced during cracking might not be the
same.

Cracking produces a mixture of alkanes and alkenes.

For example a large alkane C13H28 can breakdown into several combinations of alkanes and
alkenes

C13H28 → C2H4 + C3H6 + C8H18

C13H28 → 2C2H4 + C9H20
C13H28 → 2C2H4 + C3H6 + C6H14
C13H28 → 2C2H4 + C3H6 + C6H12 + H2

Polymers
Polymerisation is the process of joining small molecules called monomers to form a big molecule
called polymer.

There are two types of polymerization, addition polymerization, and condensation

polymerization.

Addition Polymerisation
In addition polymerization, the monomers are unsaturated (have a carbon to carbon double bonds).
The monomers are of the same types; they join up to form a polymer. There is no byproduct.
Condensation Polymerisation
In condensation polymerization, the polymers are of two types, in this type of polymerization,
water is produced as a byproduct.

Naming of addition polymer, Poly(monomer name)

Examples of addition polymers

Poly(ethane):
Monomer: ethene (C2H4)

In terms of repeating unit

Uses of poly(ethene)
There are two types of poly (ethene):
Low density poly (ethene) [LDPE] : soft, flexible
High density poly(ethene)[HDPE]: more rigid
Uses of LDPE: shopping bags
Uses of HDPE: plastic bottles

Poly(propene):
Monomer: propene

In terms of repeating unit:

Uses of poly(propene): to make crates, ropes [stronger than poly(ethane)]

Short form: PP

Poly(chloroethene)/PVC(poly vinyl chloride)

In terms of repeating unit:

PVC is quite rigid

Uses of PVC: drain pipes, replacement windows, floor covering sheets, electrical insulator.

Examples of condensation polymers:

Nylon:
Monomers: hexanedioic acid (HOOCCH2CH2CH2CH2COOH)
Two carboxylic acid (-COOH) groups attached at both ends
1, 6-diaminohexane (H2NCH2CH2CH2CH2CH2CH2NH2)
Two amine (-NH2) groups attached at both ends
Uses of nylon: textiles, ropes, cogs, and bearings for machines