Billie Call Christian Institute

First Marking Period Notes

Grade 12 Chemistry
Introduction to Organic Chemistry
Introduction

Organic chemistry is the scientific study of structure, properties, and reactions

of organic compounds containing carbon atoms. The name ‘organic’ was coined
because, initially, organic chemistry was finite to compounds that were produced by
the living organisms.
This was attributed to some ‘vital force’ that was present in organic substances as
they had something that inanimate substances lacked. The above theory was
debunked when Urey Miller synthesized urea from inorganic substances but the
classification is still in use.
However, certain compounds of carbon such as the oxides, the trioxocarbonate (IV),
the metallic carbides and the cyano salts are excluded from this definition.

Types of Carbon Compounds

Carbon compounds are of two types: inorganic and organic. The compounds that
have a mineral origin fall under the category of inorganic compounds. The
compounds having plant or animal origin are classified as organic compounds.

The importance of organic chemistry in the present age is as immense as it had

been since its inception. It plays an important role in our everyday life because
food, medicines, paper, clothes, soap, perfumes, etc. are indispensable to us for
proper living. The study of organic chemistry is important for chemists and
pharmacists in synthesizing medicines for the alleviation of human suffering. The
presence of numerous organic compounds is due to the following properties of
carbon.

1. The exceptional ability of carbon atoms to catenate i.e. to combine with one
another to form straight chains, branched chains or ring compounds
containing many carbon atoms.
2. The ease with which carbon combines with hydrogen, oxygen, nitrogen and
the halogens.
3. The ability of carbon atoms to form single, double or triple covalent bonds.
4. Different arrangement of the same atoms within a molecule produces a
variety of compounds.
5. Carbon is tetravalent, forming four bonds with neighboring atoms. This allows
carbon chains to take on significant branching and provides for a vast range of
structural diversity.
 Differences between Organic And Inorganic Compounds
S/ Organic compounds Inorganic compounds
N
1 Most organic compounds are covalent Most inorganic compounds are ionic compounds
compounds
2 Reactions involving organic Reactions involving inorganic compounds are
compounds are slow fast
3 Most organic compounds have low Most in compounds have high melting and
melting and boiling points boiling points
4 Most organic compounds are highly Most inorganic compounds are not highly
volatile volatile
5 Most organic compounds are soluble Most inorganic compounds are soluble in polar
in organic solvents like ether and solvents like water
benzene
6 Most organic compounds are gases Most inorganic compounds are solids and
and liquids. liquids.
7 Most organic compounds are highly Most organic compounds are not highly
inflammable inflammable

Classification of Organic Compounds

There are a large number of organic compounds and therefore a proper systematic
classification was required. Organic compounds can be broadly classified as acyclic
(open chain) or cyclic (closed chain).

Carbon atoms can be joined together in straight chains, branched chains, or non-
aromatic rings. They can be joined by single bonds (alkanes), double bonds
(alkenes), or triple bonds (alkynes). Besides hydrogen, other elements can be bound
to the carbon chain, the most common being oxygen, nitrogen, sulfur and chlorine.

Organic compounds can be classified into the following:

1. Aliphatic
2. Alicyclic
3. Heterocyclic
4. Aromatic
Aliphatic compounds

These are compounds whose molecules composed of chains of carbon atoms. A

given carbon chain maybe straight chain e.g. hexane or branched chain e.g. 2-
methylpropane. Straight and branched chain aliphatic compounds are called acyclic
(open-chain) compounds. The simplest aliphatic compound is methane (CH 4). Most
aliphatic compounds are flammable, allowing the use of hydrocarbons as fuel, such
as methane in Bunsen burners; and acetylene in welding.
Examples of aliphatic compounds are shown in the following structures:
H H H
H H
H C C H H C C H H
H H
H C H
Ethane H H H
Isobutane
Alicyclic Compounds

An alicyclic compound is an organic compound that is both aliphatic and cyclic. They
contain one or more rings which may be either saturated or unsaturated, but do not
have aromatic character. Simple alicyclic compounds are the cycloalkanes; like
cyclopropane, cyclobutane and cyclohexane.
The structures of some alicyclic compounds are:

Cyclopropa Cyclopenta Cyclohexan

ne ne e

Heterocyclic compounds
They are compounds containing at least one atom of carbon, and at least one element
other than carbon such as sulfur, oxygen, or nitrogen within a ring structure. These
structures may comprise either simple aromatic rings or nonaromatic rings. Some examples
are pyridine (C5H5N), pyrimidine (C4H4N2) and dioxane (C4H8O2).

Aromatic compounds
These are chemical compounds that contain conjugated planar ring systems with
delocalized pi electron cloud instead of discrete alternating single and double bonds. Typical
organic compounds are benzene an toluene. Aromatic compounds are also known as
arenes. It should be noted that an aromatic compound like benzene can be represented by

the structure:
Formulas for organic compounds
We use several kinds of formulas to describe organic compounds
1. Empirical formula
The empirical formula of a chemical compound is a simple expression of the relative
numbers of each type of atom in it. Hence the empirical formula represents the
simplest whole number ratio of atoms of each element present in a compound.
 C6H12O6=CH2O

2. Molecular formula
A molecular formula simply counts the numbers of each sort of atom present in the
molecule, but tells us nothing about the way they are joined together. It is the
simples formula that gives the actual number of atoms of the various elements
present in a molecule, of any compound is called its molecular formula.
Ex. C6H6
Empirical formula is related to molecular formula by
(EF mass)n = MF mass, where EF=empirical formula, MF = molecular formula

Exercise 1.0
a. Find the empirical formula for the oxide that contains 42.0 g of nitrogen and 96.0
g of oxygen (N=14, O= 16)
b. A compound has 49.23% C, 6.85% H and 43.83% O. if the molar mass of the
compound is 146.1, find the molecular formula (C=12, H=1, O=16).
c. A compound is found to contain 47.25% copper and 52.75% chlorine. Find the
empirical formula for this compound (Cu=63.6, Cl=35.5)
d. A substance with a molecular mass of 34.0 g/mol is known to contain 5.88%
hydrogen and 94.12% oxygen. Find the empirical formula of the substance.
e. A hydrogen contains 7.7% by mass of hydrogen, and 92.3% by mass of carbon.
The relative molar mass of the compound is 78. Calculate (i) the empirical formula
and (ii) the molecular formula.
3. Structural formula
A structural formula shows all the carbon and hydrogen atoms and the bonds
attaching them. Thus, structural formulas identify the specific isomers by showing
the order of attachment of the various atoms.
 4. Condensed formula
Unfortunately, structural formulas are difficult to type/write and take up a lot
of space. Chemists often use condensed structural formulas to alleviate these
problems. The condensed formulas show hydrogen atoms right next to the
carbon atoms to which they are attached, as illustrated for butane:
5. Skeletal/Line
The ultimate condensed formula is a line-angle formula, in which carbon
atoms are implied at the corners and ends of lines, and each carbon atom is
understood to be attached to enough hydrogen atoms to give each carbon
atom four bonds. For example, we can represent pentane (CH3CH2CH2CH2CH3)
and

isopentane [(CH3)2CHCH2CH3] as follows:

Hydrocarbon Classifications
Hydrocarbons are organic compounds that contain only carbon and hydrogen. The
inherent ability of hydrocarbons to bond to themselves is known as catenation, and
allows hydrocarbon to form more complex molecules, such as cyclohexane and
benzene. Catenation comes from the fact that the bond character between carbon
atoms is entirely non-polar.
The two general classes of hydrocarbons are: aliphatic hydrocarbons (alkanes,
alkenes and alkynes) and aromatic hydrocarbons (arenes). Aromatic compounds
derive their names from the fact that many of these compounds in the early days of
discovery were grouped because they were oils with fragrant odors. The
classifications for hydrocarbons are summarized below.
Saturated hydrocarbons (alkanes) are the simplest of the hydrocarbon species. They
are composed entirely of single bonds and are saturated with hydrogen. The general
formula for saturated hydrocarbons is CnH2n+2 (assuming non-cyclic structures).
Saturated hydrocarbons are the basis of petroleum fuels and are found as either
linear or branched species. The simplest alkanes have their C atoms bonded in a
straight chain; these are called normal alkanes. They are named according to the
number of carbon atoms in the chain. The smallest alkane is methane:

Unsaturated hydrocarbons have double and/or triple bonds between carbon atoms.
Those with double bond are called alkenes and have the general formula
CnH2n (assuming non-cyclic structures). Those containing triple bonds are called
alkynes and have general formula CnH2n-2. The smallest alkene—ethene—has two C
atoms and is also known by its common name ethylene and the smallest alkyne is
ethyne, also known as acetylene.

Cycloalkanes are hydrocarbons containing one or more carbon rings to which

hydrogen atoms are attached. The prefix "cyclo" is added to the name to
communicate the ring structure. The general formula for a saturated hydrocarbon
containing one ring is CnH2n.
Aromatic hydrocarbons, also known as arenes, are hydrocarbons that have at least
one aromatic ring. Aromatic compounds contain the benzene unit. Benzene itself is
composed of six C atoms in a ring, with alternating single and double C–C bonds:

Sources of Hydrocarbons
Coal, natural gas and petroleum are the natural source of hydrocarbons. Coal is a
solid fuel, petroleum is a dark viscous liquid fuel and natural gas is a gaseous fuel.

Alkanes & the Homologous Series

Alkanes are a very important group of saturated hydrocarbons with the general
formula CnH2n+2, where n is the number of carbon atoms in the compound. The
alkanes are also called the paraffin series because of their little affinity towards a
general reagent. In other words, alkanes are inert substances.
Sources of alkanes
1. Alkanes can be obtained by the fractional distillation of crude oil.
2. Alkanes can be obtained by the hydrogenation and gasification of coal.
3. Natural gas is a source of methane, ethane and propane.
4. Alkanes are produced from solid animal and plant waste.
The table below shows the names of some members of the alkane family:
Number of Prefix IUPAC Name Substituent Molecular
carbons Name Formula
1 Meth Methane Methyl CH4
2 Eth Ethane Ethyl C2H6
3 Prop Propane Propyl C3H8
4 But Butane Butyl C4H10
5 Pent Pentane Pentyl C5H12
6 Hex Hexane Hexyl C6H14
7 Hept Heptane Heptyl C7H16
 8 Oct Octane Octyl C8H18
9 Non Nonane Nonyl C9H20
10 Dec Decane Decyl C10H22
11 Undec Undecane Undecyl C11H24
12 dodec Dodecane Dodecyl C12H26
13 Tridec Tridecane Tetradecyl C13H28
14 Tetradec Tetradecane Pentadecyl C14H30
15 Pentadec Pentadecane Hexadecyl C15H32
16 Hexadec Hexadecane Heptadecyl C16H34
17 Heptadec Heptadecane Octadecyl C17H36
18 Octadec Octadecane Nonadecyl C18H38
19 Nonadec Nonadecane Icosyl C19H40
20 Icos Icosane Henicosyl C20H42
21 Henicos Henicosane Docosyl C21H44
22 Docos Docosane Tricosyl C22H46
23 Tricos Tricosane Tricontyl C23H48
30 Tricont Tricontane Hentricont C30H62
yl
31 Hentricont Hentricontane pentaconty C31H64
l
50 pentacont Pentacontane Hectyl C50H102
100 Hect Hectane Tetradecyl C100H202
Properties of alkanes
1. The alkanes from methane to butane are gases at room temperature.
2. The alkanes from pentane up to octadecane are liquids at room temperature.
3. The alkanes above octadecane (i.e. 19 upward) are solids are room
temperature.
4. All the alkanes in the pure state are colorless.
5. The boiling point of alkanes increases down the homologous series. This is
because boiling point increases with greater intermolecular forces, which are
Van-der Waal’s forces in alkanes. Hence, boiling point increases from gas to
liquid and from liquid to solid.
6. Where there are isomers, the more branched the chain, the lower the boiling
point tends to be. In other words, the more the branches we have for a
particular alkane, the lower its boiling point. This is because Van Der Waal’s
dispersion forces are smaller for shorter molecules, and only operate over
short distances between one molecule and its neighbors.
7. The melting points of alkanes do not show a very smooth gradation with an
increase in molecular mass. For instance, the increase in melting point is
 relatively more pronounces in moving from an alkane having odd number of
carbon to higher alkane while it is relatively less in moving from an alkane
with even number of carbon atoms to the higher alkane.

Homologous series
A homologous series is a series of organic compounds having the same
general formula, arranged in an ascending order of their molecular masses.
Each member of the series is called a homologue.
Characteristics of homologous series
1. All members of a series have a general formula. For instance, all alkanes
have the general formula CnH2n+2 .
2. Each successive member differs from the next by one carbon atom and two
hydrogen atoms (-CH2).
3. The difference in molecular mass between two consecutive members is 14
amu.
4. The physical properties of homologues show a regular gradation.
5. Homologues of a series have similar chemical properties.
6. Homologues of a series have similar methods of preparation.
Examples of homologous series
Alkanes, alkenes, alkynes, alcohols, aldehydes, carboxylic acids, amines and amides
are major families of compounds that form separate homologous series.
Advantages of homologous series
The study of organic compounds becomes easier with the knowledge of homologous
series because the study of a vast number of organic compounds become restricted
to the study of a few series of homologues.
Isomerism in alkanes
Isomerism is the existence of organic compounds with the same molecular formula
but different structural formulas. All of the alkanes containing four or more carbon
atoms show structural isomerism, meaning there are two or more different
structural formulas that you can draw for each molecular formula. Isomers are
therefore compounds with the same molecular formula but different structural or
spatial arrangement of atoms. The following are the types of isomers:

Structural Isomerism Stereoisomerism

Chain Isomers Position Functional Geometric Optical
Isomers Isomers Isomers Isomers
Different The differing Differing Different Non-
 arrangement position of the positions of substituents superimposab
of a molecule’s same atoms give a around a bond le mirror
carbon atom functional different with restricted images of the
group in the functional rotation same
molecule group molecule
The positions The molecular Also referred to Commonly Optical
of the carbon formula as functional exhibited by isomers differ
atoms in the remains the group isomers alkenes, the by the
molecule can same; the type have the same presence of two placement of
be rearranged of functional molecular different different
to give group also formula but substituents on substituents,
‘branched’ remains the the atoms are both carbon around one or
carbon chains same, but its rearranged to atoms at either more atoms in
coming off the position in the give a different end of the a molecule.
main chain. molecule functional double bond Different
The name of changes. The group. The can give rise to arrangements
the molecule name of the name of the two different, of these
changes to position molecule non- substituents
reflect this, but changes to changes to superimposable can be
the molecular reflect the new reflect the new isomers due to impossible to
formula is still position of the functional the restricted superimpose-
the same. functional group. rotation of the these are
group. bond. optical
isomers
Chain Position Functional Geometric
H H H H Hisomers
H H H
Hisomers
H H H isomers isomers Cl
H
H C C C C H H C C C C H
H C C C C H C C
H H H H
H H H H Cl H
Butane But-2-ene But-2-ene (E)-1, 2-
dichloroethene

H H H H H H H Cl Cl

H C H H C C C C H H C C H C C

H H H H H C C H H H

H C C C H But-1-ene H H (Z)-1, 2-
Cyclobutane dichloroethene
H H H
2-
methylpropan
e
 Separation and purification of organic compounds

Purification of organic compounds Organic compounds are isolated either from

natural sources or from reactions mixtures. These compounds are seldom pure and
are usually contaminated with small amounts of other similar compounds, which are
found to exist together or formed during the reaction. In order to characterize them,
it is important to purify them.

The constituents of any mixture are separated by using certain common laboratory
techniques. Techniques commonly used for separating the constituents of mixture
are described below.

1. Sedimentation and decantation

This method is generally used for separating the constituents of a mixture in which
on component is a liquid, and the other is in the form of coarse particles of a solid
heavier than liquid. For example, muddy river water.

Principle: this method is based on the effect of gravity. The coarse particles of solid
being heavier than water, settle down, and the clear upper layer of the liquid is
gently poured out into another container.

Process: To separate the coarse particles of a solid from a liquid (say, muddy river
water), take the mixture in a container and allow it to stand for some time. The solid
particles settle down to the bottom of the vessel due to gravity. The process by
which insoluble heavy particles in a liquid, are allowed to settle down is called
sedimentation. During sedimentation, the larger particles settle down faster than
the finer particles. Settling down of the particles leaves the upper part of the layers
clearer.

Decantation is the process by which, a clear liquid obtained after sedimentation, is

transferred into another container, without disturbing the settled particles.

2.