Atomic Structure

Atoms contain protons, neutrons, and electrons. Protons have positive charge while neutrons has

neutral charge but same mass as protons. Since an atom is electrically neutral, electrons has to carry a

negative charge and the amount of electrons is the same as the amount of protons

Particle Symbol Relative mass Charge

proton p 1 a.m.u +1

electron e- -1
a.m.u

neutron n 1 a.m.u 0

a.m.u. = atomic mass unit = 1/12 the mass of a carbon-12 atom

The protons and neutrons in each atom are tightly packed in a positively charged nucleus.

These make up the nucleon number.

Electrons move around nucleus in an orbit called electron shells.

PROTON NUMBER is the number of protons in an atom. The number of protons in an atom or

ion determines what element it is. For example, if a particle has 6 protons in it, it must be

carbon.

The atomic number of an atom or an ion is equal to its number of protons eg.

Page | 1
If you look up potassium (K) in the periodic table, it has an atomic number of 19, meaning that all

potassium atoms and all potassium ions contain 19 protons.

NUCLEON NUMBER is the number of protons and neutrons in nucleus of an atom.

Atomic Mass Number = (# of Protons) + (# of Neutrons)

Therefore, to find the number of neutrons, we subtract proton number from nucleon number,

i.e.: Nucleon number – Proton number = Neutrons

Example: A particle with 6 protons and an atomic mass number of 14 has 8 neutrons.

In an atom because there is no overall charge the number of electrons equals the number of

protons.

A particle’s name will sometimes include the atomic mass number of the particle.

For example, chlorine-37 is a chlorine atom that has an atomic mass number of 37, meaning that

Page | 2
it has a total of 37 protons and neutrons in its nucleus.

Since the atomic number for chlorine is 17, any chlorine atom or ion always has 17 protons.

Therefore, a chlorine-37 atom has 20 neutrons, because 37 minus 17 equals 20.

Ions = Charged Particles

1. Ions are formed when atoms gain or lose electrons.

2. Positive ions (cations) are formed when a neutral atom loses

electrons.

3. Negative ions (anions) are formed when a neutral atom gains

electrons.

4. Metallic atoms tend to lose electrons to form positive ions

(also known as cations).

5. Nonmetallic atoms tend to gain electrons to form negative

ions (a.k.a. anions).

ISOTOPES are atoms of the same element with different number of neutrons.

Therefore, their nucleon number is different.

Therefore, isotopes have the following characteristics:

Page | 3
 1. Isotopes have the same atomic number (same number of protons),

but a different atomic mass number (a different number of

neutrons).

2. Isotopes behave the same chemically, because they are the same

element. The only difference is that one is heavier than the other,

because of the additional neutrons.

For example, carbon-12 and carbon-14 are both isotopes of carbon.

Carbon-12 has 6 neutrons; carbon-14 has 8 neutrons.

Element Symbols

ELECTRONIC CONFIGURATION

Page | 4
Electrons are placed in orbits/ energy levels and each energy level can hold only up to a

maximum number of electrons.. First shell contains maximum 2 electrons. Second shell and so

and so for has maximum of 8 electrons.

This is summarised in the table below:

Energy level or 'shell' Max no of electrons

1st 2

2nd 8

3rd 18

4th 32

5th 50

A oxygen atom containing 8 electrons has an electron arrangement of 2,6. Two electrons filling

the first shell, and six electrons are filling the second shell.

A magnesium atom containing 12 electrons has an electron arrangement of 2, 8, 2. Two

electrons filling the first shell, eight electrons filling the second shell and two electrons in the

outer third shell.

Page | 5
However, these models of electron arrangement are simple and a more advance one can now

be used. It is possible to break these energy levels into sub-shells.

Electrons are impossible to locate exactly at any one time. It is however, possible to indicate a

region or volume where the electron is most likely to be found. This region is called an Orbital.

Each orbital is capable of holding a maximum of 2 electrons. Orbitals can be divided into s, p, d,

and f types. Each type has its own characteristic shape.

The shape of s and p orbitals are shown below:

s orbitals have a spherical shell shape

Page | 6
 p orbitals are pairs of 'dumb-bells' aligned along the x, y and z axis at 90o to each other.

 There are three p orbitals

Structure and Properties of Materials

Elements: An Element is a substance that cannot be broken down into simpler substances by

chemical nor physical methods.

Classifying Elements

- Classifying by state. E.g. some elements are solids, some liquids, some gases.

- Classifying by metals and non-metals. E.g. most elements are metals, semi-metals are

metalloids (having properties of metals & non-metals), some are non-metals

- Classifying by periodicity. From left-right elements change from metal to non-metal

Composition of elements

Page | 7
Elements are made of atoms. An Atom is smallest unit of an element, having properties of that

element.

A Molecule is group of two or more atoms chemically joined together, e.g. chlorine molecule

has 2 chlorine atoms

Chemical formula shows the number and kinds of atoms in a molecule, e.g. chlorine molecule

has formula Cl2, where Cl is chlorine symbol and the subscript number (2) shows that there are

2 atoms in a chlorine gas molecule.

Compounds

A Compound is substance containing 2 or more elements chemically joined together e.g.

Magnesium is an element; oxygen is an element – they can only be burnt to form magnesium

oxide compound.

Composition of compounds

Ions or molecules make up compounds. Ions are atoms having electrical charge E.g. NaCl made

up of 2 ions; positively charged Na, negatively charged Cl.

Mixtures

Mixture contains 2 or more substances not chemically joined together. e.g. seawater is made

up of water and NaCl (salt); oxygen in air varies.

Page | 8
Pure compound Mixture
has fixed % by mass of each has variable composition by mass of
element each element
has a chemical formula does not have a chemical formula
cannot be separated into its can be easily separated into its
elements by physical means components by physical means
has fixed melting and boiling
no fixed melting and boiling points
points

Chemical bonding

Ionic bonding

Ionic bonding is the transfer of electrons from one atom to another to become achieve an inert

gas configuration, forming ions.

Ionic bonds are formed between METALLIC and NON- METALLIC ATOMS ONLY.

- Metals lose electrons to form positive ions (cations)

- Non-metals gain electrons to form negative ions (anions)

The formation of ions is resulted from transfer of atoms from one atom to another atom(s),

which the ions produced are of opposite charges, and unlike charges attract, causing them to

be held together with a strong force.

Example: Formation of NaCl

Page | 9
  Sodium atom loses an electron by transferring the electron to chlorine atom, making
both stable.
 The loss of electron forms cation, Na+, and the gain of electron forms anion, Cl-.

 The opposite charges acquired by both ions attract to each other, forming a strong ionic
bond of NaCl.

Covalent bond

Covalent bonding is the sharing a pair of electrons to gain electronic configuration of an inert

gas, usually for molecules.

Covalent bonds occur between NON-METALLIC ATOMS ONLY.

In covalent bond, we try to subtitute the short of electrons of two/more atoms between each

other to form the 2 or 8 valence electrons. the shared electrons appear in pairs!

Example: H2 molecule

 Hydrogen atom has one valency.

 To become stable with hydrogen atom, it needs one more electron, just like helium
which has 2 valency.

Page | 10
  When 2 hydrogen atoms join, they share their electrons, on which, the share becomes 2
electrons, which is now a noble gas configuration, being shared between these 2 atoms.

 We write the bond as H – H single bond, which means they share an electron pair (2
electrons).

Example: Cl2 molecule

 Cl atom has 7 valency and needs one electron, each, to form a noble gas configuration
between two Cl atoms.
 Hence they share an electron EACH to hence share 2 electrons between the atoms.

 Hence, each Cl atom now has 8 valency which is a noble gas configuration.

Example: O2 molecule

 An O atom has 6 valency and needs 2 electrons, each, to form a noble gas configuration.
 Hence, EACH SHARE THE AMOUNT OF ELECTRONS EACH SHORT OF, in this case – 2
electrons, to form stable molecule.

 The contribution hence now become 4 electrons and what left on each oxygen atom is 4
electrons.

 We combine each 4 electrons on oxygen atom with the 4 electrons shared and hence
we get 8 valency for each oxygen atom – a noble gas configuration!

Example: H2O molecule

Page | 11
  Apart from oxygen sharing between oxygen atoms, it can have electrons with other
atoms.
 Oxygen needs 2 electrons and when bonded with hydrogen, which need an atom each,
they combine to provide 2 electrons on both sides of oxygen bonded with hydrogen
atoms.

 Each hydrogen with oxygen atom form a single bond: O – H.

Example: CO2 molecule

 Carbon needs 4, oxygen needs 2.

 We share two from oxygen part, WHICH HAS THE SMALLEST NUMBER OF SHORT
ELECTRONS, TO SHARE THE AMOUNT OF ELECTRONS THAT ATOM NEEDS, to form 4
shared atoms.

 Now oxygen is stable but carbon needs 2 more, which we now know they can get from
another oxygen atom.

 The atoms are now stable and since each bond has 2 pairs of electrons, we call this
double bond: C = O.

Intermolecular forces

Intermolecular attractions are attractions between one molecule and a neighbouring molecule. All
molecules experience intermolecular attractions, although in some cases those attractions are very
weak.

Page | 12
 All molecules experience intermolecular attractions, although in some cases those attractions are very
weak.

3 types of intermolecular forces ( weak forces between molecules)

1. van der Waals forces: London or dispersion forces occurs are weak forces occur between
non- polar molecules , eg: CH4, Cl2, CO2. These types of attractive forces are caused by a
phenomenon known as instantaneous dipole formation. In this process, electron distribution in
the individual molecules suddenly becomes asymmetrical, and the newly formed dipoles are
now attracted to one another.

The origin of van der Waals dispersion forces

Temporary fluctuating dipoles

Attractions are electrical in nature. In a symmetrical molecule like hydrogen, however, there
doesn't seem to be any electrical distortion to produce positive or negative parts. But that's
only true on average.

The lozenge-shaped diagram represents a small symmetrical molecule - H 2, perhaps, or Br2. The
even shading shows that on average there is no electrical distortion. But the electrons are
mobile, and at any one instant they might find themselves towards one end of the molecule,
making that end -. The other end will be temporarily short of electrons and so becomes +

An instant later the electrons may well have moved up to the other end, reversing the polarity of the molecule.

This constant "sloshing around" of the electrons in the molecule causes rapidly fluctuating dipoles even in the
most symmetrical molecule

How temporary dipoles give rise to intermolecular attractions

Imagine a molecule which has a temporary polarity being approached by one which happens to be entirely
non-polar just at that moment. (A pretty unlikely event, but it makes the diagrams much easier to draw! In
reality, one of the molecules is likely to have a greater polarity than the other at that time - and so will be the

Page | 13
dominant one.)

As the right hand molecule approaches, its electrons will tend to be attracted by the slightly positive end of the
left hand one. This sets up an induced dipole in the approaching molecule, which is orientated in such a way
that the + end of one is attracted to the - end of the other.

An instant later the electrons in the left hand molecule may well have moved up the other end. In doing so,
they will repel the electrons in the right hand one.

The polarity of both molecules reverses, but you still have + attracting -. As long as the molecules stay close
to each other the polarities will continue to fluctuate in synchronisation so that the attraction is always
maintained.

There is no reason why this has to be restricted to two molecules. As long as the molecules are close together
this synchronised movement of the electrons can occur over huge numbers of molecules.

This diagram shows how a whole lattice of molecules could be held together in a solid using van der Waals
dispersion forces. An instant later, of course, you would have to draw a quite different arrangement of the
distribution of the electrons as they shifted around - but always in synchronisation.

The strength of dispersion forces

Dispersion forces between molecules are much weaker than the covalent bonds within molecules. It isn't
possible to give any exact value, because the size of the attraction varies considerably with the size of the

Page | 14
molecule and its shape.

2. Dipole-dipole forces are forces occur between polar molecules, eg HCl , H 2S, SO2. Dipole-dipole attractions
take place when two or more neutral, polar molecules are oriented such that their positive (+)

and negative (-) ends are close to each other.

Because of the attraction between unlike charges, this is a fairly strong type of intermolecular force, and
molecules held together by dipole-dipole forces tend to be in the solid or liquid state. Also, for molecules that
are about the same size and weight, the strength of the dipole-dipole forces increases as the degree of polarity
increases. In other words, the more polar a molecule is, the stronger the dipole-dipole forces it will form with
itself and other molecules.

Hydrogen bonding is the electrostatic attraction forces between H atom bonded to a very electronegative atom
and the lone pair of electrons from a very electronegative atom such as. F,O or N atom (eg HF, NH3,
H2O ,amines and alcohols) Hydrogen bonding causes higher boiling points of hydrides, solubility of carboxylic
acids, alcohols and amines, dimerisation of carboxylic acids and low density of ice.

The hydrogen is attached directly to one of the most electronegative elements, causing the hydrogen to
acquire a significant amount of positive charge.

are a stronger intermolecular force than either Dispersion forces or dipole-dipole interactions since the
hydrogen nucleus is extremely small and positively charged and fluorine, oxygen and nitrogen being very
electronegative so that the electron on the hydrogen atom is strongly attracted to the fluorine, oxygen or
nitrogen atom, leaving a highly localised positive charge on the hydrogen atom and highly negative localised

Page | 15
charge on the fluorine, oxygen or nitrogen atom. This means the electrostatic attraction between these
molecules will be greater than for the polar molecules that do not have hydrogen covalently bonded to either
fluorine, oxygen or nitrogen. An electronegative atom such as fluorine, oxygen, or nitrogen is a hydrogen bond
acceptor, regardless of whether it is bonded to a hydrogen atom or not

Introduction to Organic Chemistry

Organic chemistry is the study of compounds containing hydrogen and carbon and of

compounds containing other elements in addition to carbon and hydrogen.

Why are there many different carbon compounds? This is mainly due to:

Carbon readily bonding to itself and to most other elements including metals (organometallic)

Carbon can bond in a variety of ways giving rise to chains, rings and cages.

Page | 16
Importance of Carbon in Organic Chemistry

In organic chemistry, carbon (C) is the most important element. It has remarkable properties,

which allow carbon a great diversity of combinations and bonds with other molecules.

Carbon has four valence electrons. This means that it can make four covalent bonds with other

molecules. Also, it has a moderate electronegativity and a rather small (right) size. So, it can

bond to other molecules easily and to itself and make infinite structures. Double bonds or even

triple bonds are also possible with the carbon atom.

Definition of an organic molecule (definition of organic chemistry)

An organic molecule consists of many carbons and hydrogen atoms, which form bonds with the
carbons. In addition, it has functional groups attached to the whole complex. The carbon-
hydrogen bonds are assumed to be neutral as the difference in electronegativity is practically
neutral anyway. Functional groups make up the polar part of an organic molecule.

Compounds that only contain carbon and hydrogen are called hydrocarbons. They are classified

as aliphatic or aromatic. Aromatic compounds contain one or more arene rings. They have

distinctive, usually pleasant smells. All the other organic compounds are aliphatic. For example,

all alkanes and alkenes are aliphatic and benzene is an aromatic compound

There are different types of hydrocarbon molecules:

Aromatic hydrocarbon: These are hydrocarbon rings, which have double or triple bonds.

Saturated hydrocarbon: The formula of the hydrogen-carbon ratio is given by: CnH2n+2 ,

assuming a non-cyclic (ring) structure. Saturated hydrocarbons only consist of single bonds and

Page | 17
the very easiest appearance of a saturated hydrocarbon is an alkane.

Unsaturated hydrocarbon: The ratio of hydrogen and carbon is given by: CnH2n , where again a

non-cyclic structure is assumed. Unlike saturated hydrocarbons, it has double bonds and the

simplest appearance of an unsaturated hydrocarbon is an alkene.

There is a second type of unsaturated hydrocarbons which has the ration formula given by:

CnH2n-2. Once again, a non-cyclic structure is assumed and this type of hydrocarbon only makes

triple bonds. The simplest structure is an alkyne.

Cyclic hydrocarbons are quite similar to aromatic hydrocarbons. Both are rings, but the

difference lies in the bonds. Cyclic hydrocarbons only have saturated rings (only single bonds).

Types of formula

In organic chemistry, there are many ways of representing a formula.

For the compound butane, with 4 carbon atoms and 10 hydrogen atoms

Page | 18
Carbon chains
Hydrocarbons
Hydrocarbons are compounds of carbon and hydrogen only.
 A saturated hydrocarbon has single bonds only.

 An unsaturated hydrocarbon contains a multiple carbon carbon bond.

Alkanes

Carbon atoms can bond with other carbon atoms to form an enormous range of compounds

with different carbon-chain lengths. The simplest organic compounds are a family of saturated

hydrocarbons called the alkanes, shown below.

Page | 19
Note the following points.
 The name of the alkane ends with –ane.
 The prefixes (meth-, eth-, …) are used to represent the number of carbon atoms. You
will need to use these many times in organic chemistry and they must be learnt.

General formula

Page | 20
Functional groups

Saturated hydrocarbon chains are comparatively unreactive. The reactivity is increased by the

presence of a functional group – the reactive part of a carbon compound.

Common functional groups

It is essential that you can instantly identify a functional group within a molecule. The main

functional groups are shown below.

Named according
functional Group Example:
to:

Name Structure prefix- -suffix Name Structure

[single C-C - -ane propane

bond]
see alkanes

-
[double -ene propene
C=C bond]
see alkenes

[triple C≡C - -yne propyne

bond]
naming
alkynes

Page | 21
Halogen fluoro- -fluoride 1-
(X = F, Cl, chloro- -chloride chloropropan
Br or I) bromo- -bromide e
haloalkanes iodo- -iodide

Hydroxyl hydroxy -ol propanol

(Alcohol) -
naming
alcohols

Amine amino- -amine propylamine

naming
amines

Carbonyl :
Carbonyl groups exist in both aldehydes and ketones

(Aldehyde) oxo- -al propanal

naming
aldehydes

(Ketone) oxo- -one propanone

naming
ketones

Carboxyl carboxy- -oic acid propanoic

(Carboxylic acid
Acid)
naming
carboxylic
acids

Ester - -oate methyl

naming propanoate
esters

Page | 22
Acid - -oyl propanoyl
Chloride chloride chloride
(Acyl
Chloride)
naming
acid
chlorides

Amide amido- -amide propanamide

naming
amides

Acid - -oic propionic

Anhydride anhydrid anhydride
naming e
acid
anhydrides

Nitrile cyano- -nitrile propanenitrile

naming
nitriles

Naming organic compounds

There are two way of naming organic compounds:

Common names

Systematic names (IUPAC names

Page | 23
IUPAC NOMENCLATURE OF ORGANIC COMPOUNDS: INTRODUCTION

In the earlier days, the conventional names for organic compounds were mainly derived from

the source of occurrence. However organic chemists realized the need for a systematic naming

for organic compounds since a large number of organic compounds are synthesized in due

course. This leads to setting up a system of nomenclature by "International Union of Pure and

Applied Chemistry, IUPAC" .

The IUPAC system of nomenclature is a set of logical rules framed which are mainly aimed at

giving an unambiguous name to an organic compound. By using this system, it is possible to

give a systematic name to an organic compound just by looking at its structure and it is also

possible to write the structure of organic compound by following the IUPAC name for that

compound.

On this page, I have given a logical introduction to IUPAC nomenclature. A concise and unified

approach is followed to help in giving IUPAC names to almost all types of compounds. This is

not an exhaustive reference to IUPAC nomenclature. However this is more than suffice to all

the students at various levels of their learning curve.

SYSTEMATIC IUPAC NAME

The systematic IUPAC name of an organic compound consists of four parts.

1. Root word

2. Suffix(es) and

Page | 24
 3. Prefix(es)

4. infix

The suffix is again divided into primary and secondary.

The complete systematic IUPAC name can be represented as:

* The root word and 1osuffix together is known as base name.

* The Prefix(es), infix and 2o suffix may or may not be required always.

1) Root word: It indicates the number of carbon atoms in the longest possible continuous carbon chain

also known as parent chain chosen by a set of rules. The root words used for different length of carbon

chain (upto 20) are shown below.

Number of Root word

carbon

atoms in the

Page | 25
parent chain

1 Meth

2 Eth

3 Prop

4 But

5 Pent

6 Hex

7 Hept

8 Oct

9 Non

10 Dec

11 Undec

12 Dodec

13 Tridec

14 Tetradec

15 Pentadec

16 Hexadec

17 Heptadec

18 Octadec

19 Nonadec

20 Icos

Page | 26
2) Suffix: It is again divided into two types.

i. Primary suffix and

ii. Secondary suffix

i) Primary suffix: It is used to indicate the degree of saturation or unsaturation in the main chain. It is

added immediately after the root word.

Type of carbon chain Primary suffix

Saturated (all C-C bonds) -ane

Unsaturated: one C=C -ene

Unsaturated: two C=C -diene

Unsaturated: one C≡C -yne

Unsaturated: two C≡C -diyne

Unsaturated: one C=C &

-enyne
one C≡C

ii) Secondary suffix: It is used to indicate the main functional group in the organic compound
and is added immediately after the 1o suffix.

Note: If there are two or more functional groups in a compound, the functional group with higher
priority is to be selected as main functional group, which must be indicated by a secondary
suffix. The remaining functional groups with lower priority are treated as substituents and are
indicated by prefixes.

Page | 27
The suffixes as well as prefixes used for some important functional groups are shown in the
following table in the decreasing order of their priority.

Also note that different suffix is used when carbon atom of the functional group is not part of the
main chain.

Suffix
Suffix
When
When
carbon of
carbon of
Name of the
the
Functional Representation functional Prefix
functional
group group is
group is NOT
part of the
part of the
parent
parent chain
chain

carboxylic -carboxylic
-COOH -oic acid carboxy-
acid acid

Acid -oic -carboxylic

-
anhydride anyhydride anhydride

alkyl - alkoxycarbonyl
Ester -COOR alkyl -oate
carboxylate -

-carbonyl
Acid halide -COX -oyl halide halocarbonyl-
halide

-
Acid amide -CONH2 -amide carbamoyl-
carboxamide

Nitrile -CN -nitrile -carbonitrile cyano-

-
Aldehyde -CHO -al carbaldehyd oxo-
e

Ketone -CO- -one - oxo-

Alcohol -OH -ol - hydroxy

Thiol -SH -thiol - mercapto

Page | 28
 Amine -NH2 -amine - amino-

Imine =NH -imine - imino-

Alkene C=C -ene - -

Alkyne C≡C -yne - -

Note: This is not the complete reference.

3) Prefix: The prefix is used to indicate the side chains, substituents and low priority functional
groups (which are considered as substituents). The prefix may be added immediately before the
root word or before the infix.

The prefixes used for some common side chains and substituents are shown below. (the prefixes
for functional groups are already given)

Side chain or
Prefix
Substituent

-CH3 methyl-

-CH2CH3 (or) -C2H5 ethyl-

-CH2CH2CH3 propyl-

isopropyl-

-CH2CH2CH2CH3 butyl

sec-butyl
(or)
(1-methyl)propyl

isobutyl
(or)
(2-methyl)propyl

tert-butyl
(or)
(1,1-dimethyl)ethyl

-X halo-

Page | 29
 -OR alkoxy-

-NO2 -nitro

Remember that the alkyl groups along with halo, nitro and alkoxy have the same preference.
They have lower priority than double and triple bonds.

3) Infix: The infixes like cyclo, spiro, bicyclo are added between the prefix(es) and root word to
indicate the nature of parent chain.

* The "Cyclo" infix is used to indicate the cyclic nature of the parent chain.

* The "Spiro" infix is used to indicate the spiro compound.

* The "Bicyclo" infix is used to indicate the bicyclic nature of the parent chain.

The infixes are some times called as primary prefixes.

STEPS INVOLVED IN GIVING IUPAC NAME

1) The first step in giving IUPAC name to an organic compound is to select the parent chain and
assign a root word.

2) Next, the appropriate primary prefix(es) must be added to the root word to indicate the
saturation or unsaturation.

3) If the molecule contains functional group or groups, a secondary suffix must be added to
indicate the main functional group. This is optional and not necessary if the molecule contains
no functional group.

4) Prefix the root word with the infix "cyclo" if the parent chain is cyclic; or with the infix "spiro"
if it is a spiro compound; or with the infix "bicyclo" if the compound is bicyclic.

5) Finally add prefix(es) to the name if there are side chains or substituents on the parent
chain.

E.g. The IUPAC name of the following compound is arrived in steps mentioned below.

Page | 30
 Step- How many carbons are Root word =
4
1 there in the parent chain? "but"

Step- Saturated or
Saturated 1osuffix = "ane"
2 Unsaturated?

Yes. There is an
Step- Is there any functional
alcohol group 2osuffix = "2-ol"
3 group?
on 2nd carbon.

Yes. There is a
Step- Are there any side chains 2oprefix = "3-
methyl group
4 or substituents? methyl"
on 3rd carbon.

Now add them to makeup the IUPAC name of the compound.

You will learn how to select a parent chain?; how to number the carbon atoms and give the
locants to the functional groups, side chains ? etc., in the following section.

IUPAC RULES

The following rules are helpful in assigning the systematic IUPAC name of an organic
compound.

1) The selection of parent chain: The first step in naming an organic compound is to select the
parent chain and give the root word depending on the number of carbons in it.

The longest continuous carbon chain containing as many functional groups, double bonds, triple
bonds, side chains and substituents as possible is to be selected as parent chain.

Illustrations:

i) In the following molecule, the longest chain has 6 carbons. Hence the root word is "hex-".
Note that the parent chain may not be straight.

Page | 31
ii) The root word for the following molecule is "hept-" since the longest chain contains 7
carbons.

Do not come under the impression that the ethyl groups (-C2H5) are side chains and the longest
chain contains 5 carbons.

The shaded part shows the longest chain that contains 7 carbons. Also look at the alternate way
of writing this molecule in which the ethyl groups are expanded to -CH2CH3.

iii) In the following molecule, there are three chains of equal length (7 carbons).

However the chain with more number of substituents (that with 3 substituents as shown in the
following diagram) is to be taken as the parent chain.

iv) The double bonds and triple bonds have more priority than the alkyl side chains and some
other substituents like halo, nitro, alkoxy etc. Hence, whenever there are two or more chains

Page | 32
with equal number of carbons, the chain that contains double or triple bond is to be selected as
the parent chain irrespective of other chain containing more number of substituents.

There are two chains with 6 carbons. But the chain with the a double bond as shown in the
diagram (II) is to be selected as the parent chain.

Note: The double bond has more priority than the triple bond.

v) However, the longest chain must be selected as parent chain irrespective of whether it
contains multiple bonds or not.

E.g. In the following molecule, the longest chain (shaded) contains no double bond. It is to be
selected as parent chain since it contains more carbons (7) than that containing double bond
(only 6 carbons).

vi) The chain with main functional group must be selected as parent chain even though it
contains less number of carbons than any other chain without the main functional group.

The functional group overrides all of above rules since it has more priority than the double
bonds, triple bonds, side chains and other substituents.

E.g. The chain (shaded) with 6 carbons that includes the -OH functional group is to be selected
as parent chain irrespective of presence of another chain with 7 carbons that contains no
functional group.

Page | 33
There are other situations which will decide the parent chain. These will be dealt at appropriate
sections.

2) Numbering the parent chain:

i) The positions of double bonds or triple bonds or substituents or side chains or functional
groups on the parent chain are to be indicated by appropriate numbers (or locants). The locants
are assigned to them by numbering carbon atoms in the parent chain.

Even though two different series of locants are possible by numbering the carbon chain from
either sides, the correct series is chosen by following the rule of first point of difference as
stated below.

The rule of first point of difference: When series of locants containing the same number of
terms are compared term by term, that series which contains the lowest number on the
occasion of the first difference is preferred.

For example, in the following molecule, the numbering can be done from either side of the
chain to get two sets of locants. However the 2,7,9 is chosen since it has lowest number i.e., 2
on the first occasion of difference when compared with the other set: 3,4,9.

Actually the so called “Least Sum Rule” is the special case of above “Rule of First point of
Difference”. Though looking simple, the least sum rule is valid only to chains with two
substituents, a special case. However use of Least sum rule is not advisable when there are
more than two substituents since it may violate the actual rule of first point of difference.

Therefore, while deciding the positions, we should always use "the rule of first point of
difference" only.

ii) If two or more side chains are at equivalent positions, the one to be assigned the lower
number is that cited first in the name.

Page | 34
In case of simple radicals, the group to be cited first in the name is decided by the alphabetical
order of the first letter in case of simple radicals. While choosing the alphabetical order, the
prefixes like di, tri, tetra must not be taken into account.

In the following molecule, 4-ethyl-5-methyloctane, both methyl and ethyl groups are at
equivalent positions. However the ethyl group comes first in the alphabetical order. Therefore
it is to be written first in the name and to be given the lowest number.

Note: The groups: sec-butyl and tert-butyl are alphabetized under "b". However the Isobutyl
and Isopropyl groups are alphabetized under "i" and not under "b" or "p".

iii) However, if two or more groups are not at equivalent positions, the group that comes first
alphabetically may not get the least number.

E.g. In the following molecule, 5-ethyl-2-methylheptane, the methyl and ethyl groups are not at
equivalent positions. The methyl group is given the least number according to the rule of first
point of difference.

But note that the ethyl group is written first in the name.

iv) The multiple bonds (double or triple bonds) have higher priority over alkyl or halo or nitro or
alkoxy groups, and hence should be given lower numbers.

E.g. In the following hydrocarbon, 6-methylhept-3-ene, the double bond is given the lower
number and is indicated by the primary suffix 3-ene. The position of methyl group is indicated
by locant, 6.

Page | 35
v) The double bond is preferred over the triple bond since it is to be cited first in the name.

Therefore the double bond is to be given the lower number whenever both double bond and
triple bond are at equivalent positions on the parent chain.

E.g. In the following hydrocarbon, hept-2-en-5-yne, both the double and triple bonds are at
equivalent positions. But the position of double bond is shown by 2-ene. The counting of
carbons is done from the left hand side of the molecule.

vi) However, if the double and triple bonds are not at equivalent positions, then the positions are
decided by the rule of first point of difference.

E.g. In the following hydrocarbon, hept-4-en-2-yne, the double and triple bonds are not at
equivalent positions. The triple bond gets the lower number.

Again note that the 4-ene is written first.

vii) Nevertheless, the main functional group must be given the least number even though it
violates the rule of first point of difference. It has more priority over multiple bonds also.

For example, in the following organic molecule, 6-methyloct-7-en-4-ol, the -OH group gets
lower number (i.e., 4) by numbering the carbons from right to left.

Page | 36
3) Grammar to be followed in writing the IUPAC name:

i) The IUPAC name must be written as one word. However there are exceptions.

ii) The numbers are separated by commas.

iii) The numbers and letters are separated by hyphens.

iv) If there are two or more same type of simple substituents they should be prefixed by di, tri,
tetra, penta etc.

E.g. The number of methyl groups are indicated by di and tri in the following cases.

v) If the side chains themselves contain terms like di, tri, tetra etc., the multiplying prefixes like
bis, tris, tetrakis etc., should be used.

E.g. The two 1,2-dimethylpropyl groups are indicated by the prefix "bis" as shown below.

vi) If two or more side chains of different nature are present, they are cited in alphabetical
order.

* In case of simple radicals, they are alphabetized based on the first letter in the name of simple
radical without multiplying prefixes.

E.g. In the following molecule, the ethyl group is written first since the letter 'e' precedes the
letter 'm' of methyl in the alphabetical order. We should not compare 'e' in the word 'ethyl' and
'd' in the word 'dimethyl'

Page | 37
* However the name of a complex radical is considered to begin with the first letter of its
complete name.

E.g. In the following case, “dimethylbutyl” is considered as a complete single substituent and is
alphabetized under "d".

Organizing organic reactions

There are several organic reactions, which include:

Acid-base reactions, for example, Ethanoic acid reacts with sodium hydroxide to form sodium
ethanoate and water: CH3COOH (aq) + NaOH (aq) CH3COONa (aq) + H2O (l)

Redox reactions, for example, between ethanol and oxygen:

CH3CH2OH (aq) + O2(g) CH3COOH (aq) + H2O (l)

Substitution reactions, which involves replacing an atom by another atom. For example, the
bromine atom in bromoethane is substituted by the
–OH group to form ethanol when it is warmed with sodium hydroxide:

CH3CH2Br (l) + OH- (aq) CH3CH2OH (aq) + Br- (aq)

Addition reactions, which involve 2 molecules combining to make only one new molecule. For
example, if ethene and steam is passed over a hot phosphoric acid catalyst, ethanol is produced
CH2=CH2(g) + H2O (g) CH3CH2OH (g)

Page | 38
Elimination reactions, which involve the removal of a molecule from a larger one. For example,
is ethanol is passed over a hot catalyst of pumice, a water molecule is eliminated:
CH3CH2OH (g) CH2=CH2(g) + H2O (g)

Hydrolysis reactions involve breaking covalent bonds by the reaction with water. For example,
when bromoethane is mixed with water, ethanol is formed along with hydrogen bromide:
CH3CH2Br (l) + H2O (l) CH3CH2OH (aq) + HBr (aq)

Breaking bonds in different ways

A covalent bond consists of a pair of electrons between 2 nuclei in which they are attracted to
the nuclei. This binds the 2 nuclei together. Covalent bonds can be broken in many ways. For
example, if HCl is broken into H and Cl atoms, each atom takes one electron from the covalent
bond. Atoms with unpaired electrons are called free radicals. When a covalent bond is broken
to form 2 free radicals, the process is called homolytic fission. The energy for this process is
usually provided by UV light or high temperature. Unpaired electrons are represented by a dot.

 In the example above, a covalent bond breaks so that one of the bonding electrons goes to
each of A and B.
 Homolytic fission forms two free-radicals.
 A free radical is a species with an unpaired electron
 Heterolytic fission


 NOTE:
 Homolytic fission → free radicals
 Heterolytic fission → ions

An electrophile is an electron-loving (and an electron-poor) species and is a proton acceptor

and is attracted to electron-rich molecules, leading to the formation of a new covalent bond

between the electrophile and thee molecule.

Page | 39
A nucleophile (nucleus-lover) is an electron-pair donor which is attracted to an atom with a

partial positive charge, leading to the formation of a new covalent bond between the

nucleophile and the molecule under attack.

Isomerism

Isomers have the same molecular formula but a different structural formula. Isomerism is due

to a number of reasons, which include the ability of carbon being able to bond to itself and to

most other carbon atoms in the periodic table.

Structural isomerism

Structural isomers have different structural arrangements but still have the same molecular

formula. 3 types of structural isomers:

(i) Chain Isomers: These isomers arise because of the possibility of branching in

carbon chains. For example, there are two isomers of butane, C 4H10. In one of

them, the carbon atoms lie in a "straight chain" whereas in the other the

chain is branched.

Page | 40
(ii) Positional isomers: In position isomerism, the basic carbon skeleton remains
unchanged, but important groups are moved around on that skeleton. For
example, there are two structural isomers with the molecular formula
C3H7Br. In one of them the bromine atom is on the end of the chain, whereas
in the other it's attached in the middle.

Another similar example occurs in alcohols such as C4H9OH

These are the only two possibilities provided you keep to a four carbon chain,
but there is no reason why you should do that. You can easily have a mixture of
chain isomerism and position isomerism - you aren't restricted to one or the
other.

So two other isomers of butanol are:

(iii) Functional group isomers: In this variety of structural isomerism, the

isomers contain different functional groups - that is, they belong to different
families of compounds (different homologous series). For example, a
molecular formula C3H6O could be either propanal (an aldehyde) or
propanone (a ketone).

Page | 41
 There are other possibilities as well for this same molecular formula - for
example, you could have a carbon-carbon double bond (an alkene) and an -OH
group (an alcohol) in the same molecule.

Another common example is illustrated by the molecular formula C 3H6O2.

Amongst the several structural isomers of this are propanoic acid (a carboxylic
acid) and methyl ethanoate (an ester).

Stereoisomerism

In stereoisomerism, the same atoms are joined to each other in different spatial arrangements.

Geometric and optical isomerism are two types of this stereoisomerism.

Geometric (or cis-trans) isomerism

The atoms on either side of a carbon-carbon single bond can rotate freely, but the atoms

around a carbon=carbon double bond cannot. For example, but-2ene, CH 3CH=CHCH3 has 2 cis-

trans isomers.

Hydrocarbons

Page | 42
Homologous series: a family of organic compounds with a general formula and similar chemical

properties.

Characteristics of a Homologous Series

 All members of homologous series have same general formula
 Formula of each member differs by –CH2 group

 Physical properties changes gradually in the increase of carbon atoms

 The members have similar chemical properties

Alkanes
The homologous series of the alkanes have the following properties:

• They have a general formula of CNH2N+2

• They are non-polar molecules with only C-H and C-C bonds

• All the C-C bonds are single bonds so the alkanes are described as saturated hydrocarbons

Chemical properties of alkanes

Combustion in air

Alkanes make excellent fuels. Complete combustion in air produces carbon dioxide and water.

For example, the combustion of butane:

C4H10 (g) + 6½ O2 (g) 4 CO2 (g) + 5 H2O (g)

The incomplete combustion of butane in an insufficient amount of oxygen produces carbon

monoxide and water instead of carbon dioxide:

C4H10 (g) + 4½ O2 (g) 4 CO (g) + 5 H2O (g)

Page | 43
Carbon monoxide is a toxic gas as it has no smell and colour and readily bonds to the iron

groups of haemoglobin in the blood. This causes the haemoglobin to become unable to carry

oxygen which may cause death in serious cases.

The substitution reaction of alkanes

Alkanes are inert compounds as they are non-polar. The carbon and hydrogen in the alkanes

have very similar electronegativities and so they are non-polar. This also means that they are

not attacked by common chemical reagents like acids, alkalis, water, etc. which are highly polar,

and initiate the reaction by their attraction to the polar groups. These polar reagents don’t

react with the alkanes. Some non-polar reagents will react with the alkanes. These include the

group IV elements chlorine, bromine, etc. that will react with alkanes under ultraviolet light,

which will substitute the hydrogen atoms in the alkane with halogen atoms.

For example, when chlorine is mixed with methane under UV light, chloromethane is formed

and hydrogen chloride gas is evolved:

CH4 (g) + Cl2 (g) CH3Cl (g) + HCl (g)

This is a photochemical reaction as it requires UV light to begin. The mechanism involves a

chain reaction. During a chain reaction, for every reactive species you start off with, a new one

is generated at the end - and this keeps the process going.

Chain initiation
The chain is initiated (started) by UV light breaking a chlorine molecule into free radicals. This is
called photodissociation. Homolytic fission occurs and 2 free radicals of chlorine form

Page | 44
 Cl2 2Cl

Chain propagation reactions

These are the reactions which keep the chain going. The reaction of a chlorine free radical with

a methane molecule produces hydrogen chloride and a methyl free radical. A methyl radical can

react with a chlorine molecule to make chloromethane and new chlorine radical.

CH4 + Cl CH3 + HCl

CH3 + Cl2 CH3Cl + Cl

Chain termination reactions

These are reactions which remove free radicals from the system without replacing them by new ones.

2Cl Cl2
CH3 + Cl CH3Cl
CH3 + CH3 CH3CH3

When the reagents are used up, no more chloromethane and hydrogen chloride are formed.

The reaction can end in three ways as shown above

i) Either that the chlorine free radicals recombine to make chlorine molecules,

ii) The methyl free radicals recombine to make an ethane molecule

iii) methyl free radicals and chlorine free radicals combine to form chloromethane

Hydrocarbons: Alkenes

Physical properties of alkenes

• Simple alkenes are hydrocarbons that contain one C=C double bond.

Page | 45
• The simplest is ethene, CH2=CH2.

• The general formula of the homologous series of the alkenes is CnH2n

Reactions of Alkenes
1) Combustion

 Burns in air to form carbon dioxide and water

Example: Ethene burns in air. Write the balanced equation for the reaction
C2H4 (g) + 3O2 (g) --> 2CO2 (g) + 2H2O (l)
 Incomplete combustion forms soot and CO. It’s produced more than alkane

2) Addition Reaction

 Is the reaction of 2 or more molecules to form a single product

a. Addition of hydrogen:

 Alkenes react with hydrogen to form alkanes, called hydrogenation. Must use nickel as
catalyst and heat.

CH2=CH2 (g) + H2 (g) CH3-CH3 (g)

b. Addition of bromine
 Bromine adds to C = C double bond of alkane molecules.
 Phosphoric acid (H3PO4), high temperature of 300oC and 60-70 atm pressure are needed
as catalyst.

 When an alkene such as propene is bubbled through a solution of bromine at room

temperature, the bromine solution is rapidly decolourized. This reaction doesn’t need
UV light to occur. The bromine joins to propene to form 1,2-dibromopropane:

CH3CH=CH2 + Br2 CH3CHBrCH2Br

Page | 46
c. Addition of water
 Alkene reacts with water, in the form of steam, to produce alcohol.
 Alkene + steam is passed over phosphoric acid (H3PO4) catalyst and temperature of
300oC.

 H2O molecule adds to C = C bonds to form alcohol.

CH2=CH2 (g) + H2O (g) CH3CH2OH

c) Addition of hydrogen halides

Hydrogen halides also react with alkenes in addition reactions. Ethene produces chloroethane
when it is bubbled through concentrated hydrochloric acid

CH2=CH2 (g) + HCl (aq) CH3CH2Cl (l)

The reactivity of the hydrogen halides increases from HF to HI, following the order of
decreasing bond energy. Alkenes such as propene can give rise to 2 different products.

The addition of H-X to an unsymmetrical alkene like propene

An unsymmetrical alkene is one like propene or but-1-ene in which the groups or atoms
attached to either end of the carbon-carbon double bond are different.

For example, in propene there are a hydrogen and a methyl group at one end, but two
hydrogen atoms at the other end of the double bond.

With these unsymmetrical alkenes, it is possible to get two different products during some
addition reactions.

Definition of Markovnikov’s rule

"In the addition of hydrogen halides to unsymmetrically constituted [unsaturated]

hydrocarbons, the halogen atom becomes attached to the carbon bearing the lesser number of
hydrogen atoms."

Page | 47
3) Polymerization

 The joining of several identical alkene molecules to form a big molecule

Eg: Ethene --> poly(ethene)

During the polymerisation of ethene, thousands of ethene molecules join together to make
poly(ethene) - commonly called polythene.

4) Reactions of alkenes with manganate (VII) ions

Alkenes undergo a different type of reaction with manganate (VII) ions, depending on the
conditions:

o With cold, acidified or alkaline dilute potassium manganate (VII) ions, the alkenes react
readily at room temperature. The purple colour disappears and a diol is formed.

CH2=CH2 + H2O + [O] HOCH2CH2OH

Hydroxy compounds – Alcohols

Characteristics
 Are homologous series with general formula CnH2n+1OH
 They have –OH functional group (hydroxyl group)

 All alcohols end with suffix -ol

Page | 48
  First three members of the series (so that you’d have idea on the next)

- Methanol, CH3OH
- Ethanol, C2H5OH or CH3CH2OH
- Propanol, C3H7OH or CH3CH2CH2OH
 For alcohol, the –OH is not of hydroxide ion, OH-, but is covalent bond between oxygen and
hydrogen, O – H

The different types of alcohols

There are three types of alcohols:

1. Primary alcohols:

In primary alcohols, the –OH group is attached to a carbon atom which is attached to only one

alkyl group (or no alkyl group as in methanol):

Examples include:

CH3CH2-OH CH 3CH2CH2-OH

Ethanol Propanol

2. Secondary alcohols:

In secondary alcohols, the –OH group is attached to a carbon atom which is attached to 2 alkyl
groups:

Examples include:

Page | 49
3. Tertiary alcohols:

In tertiary alcohols, the –OH group is attached to a carbon atom which is attached to 3 alkyl
groups:

Examples include:

Reactions of alcohols

1) Combustion

 Alcohols burn in air to produce carbon dioxide and water.

E.g. combustion of ethanol
C2H5OH (aq) + 3O2 (g) --> 2CO2 (g) + 3H2O (l)

2) Mild oxidation

Oxidation is the addition of oxygen. The oxidizing agent used here is potassium dichromate(VI)
acidified with dilute sulphuric acid. If oxidation occurs, the orange colour of potassium
dichromate solution changes into a green solution containing chromate ions.

With primary alcohols

Primary alcohols can be oxidized into aldehydes or carboxylic acids, depending on the reaction
conditions. Carboxylic acids are formed when aldehydes formed are oxidized further.

a) Partial oxidation

Aldehydes are produced if you use an excess of alcohol and if the aldehyde is distilled as it is

formed (there is not enough oxidizing agent to oxidise the aldehyde).

The reaction is:

CH3-CH2-OH + [O] CH3-CHO + H2O

Page | 50
Here the colour of the solution changes from orange to green.

b) Full oxidation

Here an excess of an oxidizing agent is used and the mixture is heated under reflux, making sure that no
aldehyde can escape.

CH3-CH2-OH + [O] CH3-CHO + H2O

Then:

CH3CHO + [O] CH3COOH

With secondary alcohols

Secondary alcohols are oxidised into ketones only. For example, heating propan-2-ol with acidified
potassium dichromate(VI), Propanone formed.

With tertiary alcohols

No reaction occurs, because the oxidizing agent has to remove one hydrogen from the –OH group and
another from the same carbon atom.

The dehydration of ethanol to give ethene

This is a simple way of making gaseous alkenes like ethene. If ethanol vapour is passed over heated
aluminium oxide powder, the ethanol is essentially cracked to give ethene and water vapour.

Page | 51
Uses of alcohols

Uses of ethanol

Drinks

The "alcohol" in alcoholic drinks is simply ethanol.

Industrial methylated spirits (meths)

Ethanol is usually sold as industrial methylated spirits which is ethanol with a small quantity of methanol
added and possibly some colour. Methanol is poisonous, and so the industrial methylated spirits is unfit
to drink. This avoids the high taxes which are levied on alcoholic drinks (certainly in the UK!).

As a fuel

Ethanol burns to give carbon dioxide and water and can be used as a fuel in its own right, or in mixtures
with petrol (gasoline). "Gasohol" is a petrol / ethanol mixture containing about 10 - 20% ethanol.
Because ethanol can be produced by fermentation, this is a useful way for countries without an oil
industry to reduce imports of petrol.

As a solvent

Ethanol is widely used as a solvent. It is relatively safe, and can be used to dissolve many organic
compounds which are insoluble in water. It is used, for example, in many perfumes and cosmetics.

Uses of methanol

As a fuel

Methanol again burns to form carbon dioxide and water.

It can be used a a petrol additive to improve combustion, or work is currently being done on its use as a
fuel in its own right.

As an industrial feedstock

Most methanol is used to make other things - for example, methanal (formaldehyde), ethanoic acid, and
methyl esters of various acids. In most cases, these are in turn converted into further products.

Page | 52
Carboxylic Acids

Characteristics
 homologous series with general formula CnH2n+1COOH (first series, n = 0, ascending)
 They have –COOH functional group (carboxyl group)

 All carboxylic acids end with suffix –oic acid

 First three members of the series (so that you’d have idea on the next)

- Methanoic acid, HCOOH

- Ethanoic acid, CH3COOH
- Propanoic acid, C2H5COOH

Preparation Of Carboxylic Acids

1. From natural gas

 Natural gas is passed over air and catalyst to form ethanoic acid and water.

E.g. production of ethanoic acid from methane

2CH4 (g) + 2O2(g) CH3COOH (aq) + 2H2O (l)

2. Oxidation

Propanoic acid

Page | 53
Properties Of Carboxylic Acids
 Carboxylic acids are weak acids (partially ionises in water)
 Carboxylic acids react with metals to form metal ethanoate (salt) and hydrogen

E.g. Reaction between calcium and ethanoic acid forming calcium ethanoate and hydrogen
Ca (s) + 2CH3COOH (aq) ---> Ca(CH3COO)2 (aq) + H2 (g)

 Carboxylic acids react with bases to form salt and water (neutralization)

E.g. Ethanoic acid reacts with sodium hydroxide to form sodium ethanoate and water.
CH3COOH (aq) + NaOH (aq) ---> CH3COONa (aq) + H2O(g)

 Carboxylic acids react with carbonates and bicarbonates to form salt, carbon dioxide
and hydrogen.

E.g. Ethanoic acid reacts with sodium carbonate to form sodium ethanoate and water.
2CH3COOH (aq) + Na2CO3 (aq) ---> 2CH3COONa (aq) + CO2 (g) + H2O (g)

Esterification
 Ester is an organic compound made from carboxylic acid and alcohol with the removal
of one molecule of water.
 Sulfuric acid is added as catalyst then heat mixture.

 The reaction is reversible.

 We can add sodium hydroxide and heat mixture to obtain carboxylic acid and alcohol
from ester --> This is hydrolysis.

Page | 54
Amines and Amides
Amines are organic chemical compounds that include the functional group -NH2

That is, amines are a class or category of organic chemical compounds that include a nitrogen
atom connected to two hydrogen atoms by single covalent bonds between the nitrogen and
each of the hydrogen atoms.

Classification and Classification and Amines

• Amines and amides are abundant in nature. They are a major component of proteins and
enzymes, nucleic acids, alkaloid drugs, etc. (Alkaloids are N containing, weakly basic organic
compounds; thousands of these substances are known.)

• Amines are organic derivatives of ammonia, NH3, in which one or more of the three H’s is
replaced by a carbon group.

• Amines are classified as primary (1°), secondary (2°), or tertiary (3°), depending on how many
carbon groups are connected to the nitrogen atom.

Primary Amines

These have two hydrogen atoms and one alkyl or aryl group attached to the nitrogen to form
the amine or amino group -NH2.

methylamine (aminomethane), , ,

Secondary Amines

These have one hydrogen atom and two alkyl or aryl groups attached to the nitrogen

dimethylamine

Page | 55
Tertiary Amines

These have no hydrogen atom and three alkyl or aryl groups attached to the nitrogen

trimethylamine

Naming Amides

Definition of Amides:

Amides are organic chemical compounds that include the -amide functional group:

That is, amides are a class or category of organic chemical compounds that (usually*) include a part consisting
of a carbon atom connected to both:

 a nitrogen atom connected to two hydrogen atoms by single covalent bonds between the nitogen and
each of the hydrogen atoms (that is an -amine group).
AND
 an oxygen atom (connected to the carbon atom by a double covalent bond).

Amide molecules can vary in size up to very long molecules most of which consist of carbon atoms attached to
each other and also to hydrogen atoms.

Names and Structures of simple Linear Amides

The homologous series of linear amides with the -amide group attached to the first (=last!)
carbon atom is shown below.

Numb Name Simple Structure Other Names =

er Synonyns
carbo and simple formula showing bond types but not accurate (*Examples not
ns in bond angles complete lists)
chain

Page | 56
  Methanamide

 1-Methanamide

 Methanamid

 Carbamaldehyde
formamide (CH3NO)
1  Formimidic acid
HCONH2  Formic acid,
amide

 Formamid

 Formic amide
 Acetamide

 Acetic acid
amide

 Acetimidic acid

 Methanecarboxa
ethanamide (C2H5NO) mide
2  Ethanimidic acid
CH3CONH2
 Acetamid

 Ethionamide

 Ethanamid

 Acetimidic acid
 n-Propanamide
3 propanamide (C3H7NO)
 Propylamide
CH3CH2CONH2  n-Propylamide

 Propionamide

 Propionic amide

 Propanimidic
acid

 Propionimidic
acid

 Propionic acid

Page | 57
  Propionic acid
amide

 Propyzamide

 Protionamide
 n-Butanamide

 Butyramide
butanamide (C4H9NO)  n-Butyramide
4
CH3CH2CH2CONH2  n-Butylamide

 Butanimidic acid
 n-Pentanamide

 Valeramide
pentanamide (C5H11NO)
5  n-Valeramide
CH3CH2CH2CH2CONH2
 Pentanimidic
acid
 n-Hexanamide

 Caproamide

 n-Caproamide

 Capronamide

 Hexylamide
hexanamide (C6H13NO)
6  Hexamide
CH3CH2CH2CH2CH2CONH2
 Hexanoamide

 Policapram

 n-Capronamide

 n-Caproic amide
 n-Heptanamide
7 heptanamide (C7H15NO)
 Enanthamide
CH3CH2CH2CH2CH2CH2CONH2  Octanoylamide

 Heptamide

 Enanthic acid

Page | 58
 amide

octanamide (C8H17NO)  n-Octanamide

8
CH3CH2CH2CH2CH2CH2CH2CON  Caprylamide
H2
 n-Nonanamide

 Nonamide

 Pelargonamide
nonanamide (C9H19NO)
9  Nonan-1-amide
CH3CH2CH2CH2CH2CH2CH2CH2
CONH2  Nonanoic acid
amide

 Nonan-1-amide

decanamide (C10H21NO)

CH3CH2CH2CH2CH2CH2CH2CH2
10
CH2CONH2

Introduction to polymers
A polymer is a large molecule (macromolecule) composed of repeating structural units. These
sub-units are typically connected by covalent chemical bonds. Although the term polymer is
sometimes taken to refer to plastics, it actually encompasses a large class of compounds
comprising both natural and synthetic materials with a wide variety of properties.

Types of Polymers:

Page | 59
There are many types of polymers including synthetic and natural polymers.

Natural polymers are discussed in other web pages and include:

Proteins - silk, collagen, keratin.
Carbohydrates - cellulose, starch, glycogen
DNA - RNA

Other Natural polymers: Rubber (hydrocarbon base) and silicones (alternating silicon and
oxygen).

Classification of Polymers:

Homopolymers - consist of chains with identical bonding linkages to each monomer unit. This
usually implies that the polymer is made from all identical monomer molecules.
These may be represented as : -[A-A-A-A-A-A]-

Copolymers - consist of chains with two or more linkages usually implying two or more
different types of monomer units.
These may be represented as : -[A-B-A-B-A-B]-

Further more,depending on the arrangement of the types of monomers in the polymer chain,
we have the following classification:

In random copolymers two or more different repeating units are distributed randomly

-A-A-B-A-B-B-A-B-A-A-B-A-A-A-B-A-B-B-A-B-B-B-A-A-B-A-A-

Alternating copolymers are made of alternating sequences of the different monomers

-A-B-A-B-A-B-A-B-A-B-A-B-A-B-A-B-A-B-A-B-A-B-A-B-A-B-A-

In block copolymers long sequences of a monomer are followed by long sequences of

another monomer

-A-A-A-A-A-A-A-A-A-B-B-B-B-B-B-B-B-B-B-B-B-A-A-A-A-A-A-

Graft copolymers consist of a chain made from one type of monomers with branches of

another type.

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 |

-A-A-A-A-A-A-A-A-A-A-A-A- A-A-A-A-A-A-A-A-A-A-A-A-A-A-

| |

B B

| |

B B

| |

B B

| |

B B

| |

Classification Based on Structure

1. Linear polymers

These polymers consist of long and straight chains. The examples of Polymers are high density
polythene, polyvinyl chloride, etc. These are represented as:

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2.Branched chain polymers
These polymers contain linear chains having some branches, e.g., low density polythene. These
are depicted as follows:

3. Cross linked or Network polymers

These are usually formed from bi-functional and tri-functional monomers and contain strong
covalent bonds between various linear polymer chains, e.g. bakelite, melamine, etc. These
polymers are depicted as follows:

Classification Based on Mode of Polymerisation

Polymers can also be classified on the basis of mode of polymerisation into two sub groups.

1. Addition polymers
The addition polymers are formed by the repeated addition of monomer molecules possessing
double or triple bonds, e.g., the formation of polythene from ethene and polypropene from
propene. However, the addition polymers formed by the polymerisation of a single monomeric
species are known as homopolymers, e.g., polythene.

The product of this addition process is a very long hydrocarbon chain.

Addition polymers can be made from any alkene:

Eg propene poly(propene)

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Eg but-2-ene poly(but-2-ene)

Many useful polymers are addition polymers made by this process:

 polyethene is used in plastic bags and in crates

 polypropene is used in plastic tubing

 polychloroethene (polyvinylchloride) is used in waterproof clothing and records

 polyphenylethene (polystyrene) is used in packaging

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Addition polymerisation reactions are carried out at high pressure in the presence of a suitable
catalyst.

ii) Properties of addition polymers

Addition polymers (polyalkenes) are long chain hydrocarbons which are saturated and non-
polar. Their structure results in their having a number of characteristic properties:

a) Since the hydrocarbon chains are often very long, the Van der Waal's forces between the
chains are often very strong and the polymers have relatively high melting and boiling
points. Since the chain length is variable, most polymers contain chains of a variety of
different lengths. Thus the Van der Waal's forces are of variable strength and these
polymers tend to melt gradually over a range of temperatures rather than sharply at a fixed
temperature. As the chains are not rigidly held in place by each other, polymers tend to be
reasonably soft.

b) Since the chains are non-polar, addition polymers are insoluble in water. Since the
intermolecular forces between the molecules are strong and the chains are often tangled,
they are generally insoluble in non-polar solvents as well. In fact the long saturated
hydrocarbon chains result in polyalkenes being very unreactive generally, as they cannot
react with electrophiles, nucleophiles or undergo addition reactions.

This results in their widespread use as inert materials - they are very useful as insulators, as
packaging and in making containers.

However their low reactivity means that they are not easily decomposed in nature and as a
result have a very long lifetime. Such substances are said to be non-biodegradable, and

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 constitute an environmental hazard as they are very persistent in nature and thus difficult
to dispose of.

c) The density and strength of addition polymers varies widely. They depend to a certain
extent on the length of the hydrocarbon chain, but depend much more strongly on the
nature and extent of the branching on the chain.

Polymers which have very few branches are very compact and the chains can thus pack
together very efficiently:

These polymers tend to have a very high density. Since the chains are closely packed, the
Van der Waal's forces between the chains are strong and these polymers tend to be
stronger and harder as well.

Polymers which are highly branched cannot pack together as well, and there tend to be large
spaces in the structure:

These polymers have a much lower density. Since the chains are not closely packed, the van
der Waal's forces between the chains are weaker and these polymers tend to be weaker
and softer.

2. Condensation polymers
The condensation polymers are formed by repeated condensation reaction between two
different bi-functional or tri-functional monomeric units. In these polymerisation reactions, the

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elimination of small molecules such as water, alcohol, hydrogen chloride, etc. take place. The
examples are terylene (dacron), nylon 6, 6, nylon 6, etc.

i) Polyesters

It has been shown that if a carboxylic acid or acyl chloride is reacted with an alcohol, then an
ester is formed and a water molecule is lost.

Eg ethanoyl chloride + ethanol  ethyl ethanoate + HCl

Eg benzoic acid + methanol  methyl benzoate + H2O

These are examples of condensation reactions – combination of two or more molecules

followed by the elimination of a small molecule.

It follows that if a dicarboxylic acid is reacted with a diol, then the -COOH group at each end of
the dicarboxylic acid should join to an -OH group, and the -OH group at each end of the diol
should join to a -COOH group. It should therefore be possible for all the molecules to link
together and form a polymer.

Eg benzene-1,4-dicarboxylic acid and ethan-1,2-diol

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 benzene-1,4-dicarboxylic acid ethan-1,2-diol

These two compounds can link together to form a polymer, and water is given off:

This polymer can be represented by the following repeating unit:

The overall equation can be represented as:

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The monomer units are linked together by the ester group:

Polymers containing this type of linkage are therefore known as polyesters.

The above polymer is known as terylene. It is used in fire-resistant clothing (eg racing drivers)

The same polyester can also be formed by the combination of a diacyl chloride and a diol:

Eg benzene-1,4-diacyl chloride and ethan-1,2-diol

These two monomer units link together to form the same polymer. The only difference is that
HCl instead of H2O is given off.

The overall equation can be represented as:

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The polymerisation reaction with diacyl chlorides produces a much better yield than the
corresponding polymerisation reaction with dicarboxylic acids. This is because acyl chlorides are
more reactive than carboxylic acids and also because the HCl produced is gaseous and thus
escapes, making the reaction more difficult to reverse.

Thus dicarboxylic acids are generally converted to diacyl chlorides (by addition of PCl 5) before a
polymerisation is carried out.

ii) Polyamides

It has been shown that if a carboxylic acid or acyl chloride is reacted with a primary amine, an
N-substituted amide is formed:

Eg propanoic acid + ethylamine == N-ethylpropanamide + H2O

Eg ethanoyl chloride + 1-aminopropane  N-propylethanamide + HCl

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It follows that if a dicarboxylic acid is reacted with a diamine, the -COOH group at each end of
the dicarboxylic acid with join to an -NH2 group, and the -NH2 group at each end of the diamine
will join to a -COOH group. It should therefore be possible for each of the molecules to join
together and form a polymer.

Eg hexanedioic acid + 1,6-diaminohexane

These two compounds can link together to form a polymer, and water is given off.

The polymer can be represented by the following repeating unit:

The overall equation can be represented as:

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The monomers are linked together by the amide, or peptide link:

Polymers containing this type of linkage are therefore known as polyamides.

The above polymer is known as nylon 66. It is a man-made fibre used in clothing

The same polyamide can be formed by the combination of the diacyl chloride and the diamine:

These two monomer units link together to form the same polyamide. The only difference is that
HCl is given off instead of water.

The overall equation can be represented as:

The polymerisation reaction with diacyl chlorides gives a much better yield than with the
corresponding dicarboxylic acid for the same reasons as with the polyesterification reaction.
Dicarboxylic acids are therefore converted to the corresponding diacyl chloride (by addition of
PCl5) before the polymerisation is carried out.

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Polyesters and polyamides are collectively known as condensation polymers because they are
the product of condensation reactions.

iii) Properties and uses of condensation polymers

Condensation polymers tend to consist largely of straight chains with few branches. This is
because they are formed by reactions with heterolytic mechanisms, which are much less
random than homolytic mechanisms. Addition polymers are formed by free radical addition
mechanisms which always lead to a variety of products and consequently much more
branching.

Since there are few branches in condensation polymers, they are usually linear and can thus
pack closely tegether. Condensation polymers are therefore more rigid than addition polymers
and have a higher tensile strength.

The strength of the intermolecular forces between the different chains in polyamides is further
enhanced by the presence of hydrogen bonding.

Polyamides are therefore generally very strong. In some natural polyamides, such as proteins,
intramolecular hydrogen bonding is possible and the molecule curls up to form a helical
structure:

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Polyamides and polyesters are both used largely in high-strength synthetic fibres.

Polyesters are used as wool and cotton substitutes in clothing (esp jumpers, T-shirts, shirts etc)
and also in carpets and rugs. Bullet-proof vests and some flame-retardant clothing are made
from polyesters.

Polyamides are more elastic and used in underwear, fishing nets and other synthetic fibres.

Perhaps the most important difference between condensation polymers and addition polymers
is that condensation polymers are made up of chains containing polar bonds; i.e. C-N and C-O
bonds which link every polymer unit. These polar carbon atoms can be readily attacked by
nucleophiles and as a result the polymers can be broken up and the constituent monomers
reformed. Condensation polymers are hence biodegradable, and so clearly constitute a smaller
environmental hazard than addition polymers, whose chains are made up entirely of non-polar
C-C bonds and which are hence non-biodegradable.

The break-up of these polymers is carried out in aqueous solution and can be classed as
hydrolysis reactions:

Polyesters are best hydrolysed in strongly alkaline conditions, in which they undergo
saponification:

Polyamides are best hydrolysed in strongly acidic conditions:

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The biodegradability of condensation polymers may compromise their effectiveness, since
physical and chemical durability is one of the reasons for their widespread use. A balance must
be struck between practical durability and long-term biodegradability.

Disposal And Recycling Of Polymers

The disposal of non-biodegradable polymers is a significant problem. There are three options:

- burying in landfill sites

This is widespread in all developed countries but is a completely unsustainable practice, as
each landfill site will eventually fill up. Landfill sites are also unsightly and unhygienic.

- burning
This is also common, but burning polymers releases greenhouses gases such as carbon
dioxide and can also release toxic gases, depending on exactly what polymer is being
burned

- recycling
This is environmentally preferable to burying or burning, but it is not easy. Different plastics
need to be collected, separated and cleaned. They then need to be melted down before
being recast into the new item. Often this process can cost more than it costs to
manufacture the plastic from crude oil.

Some plastics cannot be melted – they burn or harden instead of melting. It is even more
difficult to recycle these plastics as they can only be used in the same shape in which they
were originally cast.

The above problems mean that the continued manufacture of non-biodegradable polymers is a
cause for environmental concern.

Biodegradable polymers decompose naturally, so burying them is slightly less environmentally

unsustainable as they will eventually break down.

They can be recycled, broken down into their original components and reused, but they still
need to be collected, separated and cleaned.

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Amino Acids and Proteins
Protein molecules are polymers composed of monomers called amino acids. Wonderfully varied
in size and shape, they have a wide range of roles in our bodies. For example, proteins provide
the underlying structure of our cells, form antibodies that fight off invaders, regulate many
necessary chemical changes, and help to transport molecules through the blood stream. All but
one of the twenty kinds of amino acids found in proteins have the following general form:

There is a central carbon atom attached to a hydrogen, a carboxylic acid group, an amine group
and an alkyl group. Amino acids are thus all chiral except for glycine, in which the R is another H
atom.

The R represents a group called a side-chain that distinguishes one amino acid from another

Amino acids are linked together by a peptide bond, created when the carboxylic acid group of
one amino acid reacts with the amine group of another amino acid to form an amide functional
group. The product is called a peptide.

Although the language used to describe peptides is not consistent among scientists, small
peptides are often called oligopeptides, and large peptides are called polypeptides.

Because the reaction that links amino acids produces water as a by-product, it is an example of
a condensation reaction, a chemical change in which a larger molecule is made from two
smaller molecules accompanied by the release of water or another small molecule.

Since amino acids have both acid and amine groups, two molecules can therefore react with
each other to form a molecule containing a peptide or amide link:

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This reaction is called a condensation reaction because two amino acid molecules join together
and one molecule of water is eliminated.

All protein molecules are polypeptides.

Protein molecules are described in terms of their primary, secondary, and tertiary structures.

Primary Structure: The unique sequence of amino acids that makes up a protein or polypeptide chain.
The primary structure of a protein is the linear sequence of its amino acids.

Secondary Structure: The way in which the primary structure of a polypeptide chain folds. The
arrangement of atoms that are close to each other in the polypeptide chain is called the
secondary structure of the protein.

Tertiary Structure: The final 3D structure of a protein is its Tertiary Structure, which pertains to
the shaping of the secondary structure. This may involve coiling or pleating, often with straight
chains of amino acids in between.
Tertiary structure is held together by four different bonds and interactions:
 Disulphide Bonds - Where two Cysteine amino acids are found together, a strong
double bond (S=S) is formed between the Sulphur atoms within the Cysteine monomers.
 Ionic Bonds - If two oppositely charged 'R' groups (+ve and -ve) are found close to each
other, and ionic bond forms between them.

 Hydrogen Bonds - Your typical everyday Hydrogen bonds.

 Hydrophobic and Hydrophilic Interactions - Some amino acids may be hydrophobic

while others are hydrophilic. In a water based environment, a globular protein will
orientate itself such that it's hydrophobic parts are towards its centre and its hydrophilic
parts are towards its edges

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Wool
Wool fibres are composed of a polymer called keratin which is constructed from monomer
units of amino acids. This makes wool a protein. Keratin has a helical configuration in which the
degree of polymerisation is unknown since there are quite a large number of possible amino
acid combinations. Keratin is composed of twenty amino acids of variable sequence. In general,
the amino acids arginine, cystine and glutamic acid constitute at least one third of the wool
polymer. The helical keratin structure is referred to as alpha-keratin. If the wool fibre is
stretched, the alpha-keratin can unfold giving rise to a new configuration called beta-keratin. A
beta-keratin arrangement will always try and revert back to the 'relaxed' helical alpha-keratin
configuration.

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The peptide group of keratin can be hydrolysed by acids leaving the disulphide bonds which
cross link the wool polymer intact. Whist this would weaken the fibre, it would not result in
complete decomposition. On the other hand, wool dissolves readily in alkali conditions. This is
because the disulphide bond holding the fibre together are hydrolysed by alkali.
Ultra violet wavelengths of sunlight break the peptide and disulphide bonds at the fabric
surface causing yellowing and dulling of colour.
Wool is quite difficult to ignite. It will burn but not readily.

Silk

The name silk is thought to have originated from the greek word seres. In Old English, silk was
sioloc. Most of the worlds silk is derived from the cocoons of the moth Bombyx mori which
lives exclusively on the leaves of Morus alba, the white mulberry tree. There are other species
of silkworm but their contribution to world silk is small. One cocoon is made of a single silk
thread between 300 and 900 metres long. A silk strand consists of two silk filaments encased
by a protein called sericin. The sericin can be dissolved in mild alkaline leaving the pure silk
threads.

Their are similarities in the structure of silk and wool in as much as both polymers are proteins

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composed of amino acids, the general structure of proteins can be found here. It is interesting
to note that the peptide group in silk (and wool) is identical to the amide group found in nylon.
Chemically, both silk and nylon are polyamides. It was in part the polyamide nature of silk
which directed the research which led to the synthesis of nylon (nylon was designed to replace
silk as a synthetic textile fibre)

The silk polymer is a linear molecule composed of the protein fibroin. This protein is composed
of sixteen amino acids of which three - alanine, glycine and serine - constitute 80% of the
polymer. There are no amino acids containing sulphur in fibroin and so no disulphide bonds.
The silk polymer system is about 65-70% crystalline giving a high tensile strength to the fibres.

Acids can degrade silk fairly easily since once the peptide groups are hydrolysed there are no
disulphide bonds (as are found in wool) to hold the structure together. Alkali causes the silk
fibre to swell. Prolonged exposure to alkali results in the complete degradation of the polymer
structure.

The Silk Polymer

The silk polymer is a linear, fibroin polymer. It differs fron the wool polymers as follows :

1. Silk is composed of sixteen different amino acids compared with the twenty amino acids of
the wool polymer. Three of these sixteen amino acids, namely alanine, glycine and serine,
make up about four-fifths of the silk polymers composition.

2. The silk polymers are not composed of any amino acids containing sulphur. Hence, the
polymer system of silk does not contain any disulphide bonds.

3. The silk polymer occurs only in the beta-configuration. It is thought that silk polymer is about
as long as (140 nm), or only slightly longer than the wool polymer, and about 0.9 nm thick. Silk
may be considered to have the same composition as that of wool except that the silk polymer
system contains no disulphide bonds.

Physical properties
1. Tenacity - The silk filament is strong.This strength is due to its linear, beta-configuration
polymers and very crystalline polymer system. These two factors permit many more hydrogen
bonds to be formed in a much more regular manner. When wet, silk loses strength. This is due
to water molecules hydrolysing a significant number of hydrogen bonds and in the process
weakning the silk polymer.

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2. Elastic-plastic nature - Silk is considered to be more plastic than elastic because its very
crystalline polymer system does not permit the amount of polymer movement which could
occur in a more amorphous system. Hence, if the silk material is stretched excessively, the silk
polymers, which are already in a stretched state (they have a beta-configuration) will slide past
each other. The process of stretching ruptures a significant number of hydrogen bonds. When
stretching ceases, the polymers do not return to their original position, but remain in their new
positions. This disorganises the polymer system of silk, which is seen as a distortion and
wrinkling or creasing of the silk textile material. The handle of the silk is described as a
medium, and its very crystalline polymer system imparts a certain amount of stiffness to the
filaments. This is often misinterpreted, in that the handle is regarded as a soft, because of the
smooth, even and regular surface of silk filaments.

3. Hygroscopic nature - Because silk has a very crystalline polymer system, it is less absorbent
than wool. The greater crystallinity of silk's polymer system allows fewer water molecules to
enter than does the amorphous polymer system of wool. The other hygroscopic properties of
silk are rather similar to those of wool.

4. Thermal properties - Silk is more sensitive to heat than wool. This is considered to be partly
due to the lack of any covalent cross links in the polymer system of silk, compared with the
disulphide bonds which occur in the polymer system of wool. The existing peptide bonds, salt
linkages and hydrogen bonds of the silk polymer system tend to break down once the
temperature exceeds 100 degree C.

Chemical Properties
1. Effect of acids - Silk is degraded more readily by acids than is wool. This is because, unlike
the wool polymer system with its disulphide bonds, there are no covalent cross-links between
silk polymers. Thus perspiration, which is acidic, will cause immediate breakdown of the
polymer system of silk. This is usually noticed as a distinct weakning of the silk textile material.

2. Effect of alkalis - Alkaline solutions cause the silk filament to swell. This is due to partial
separation of the silk polymers by the molecules of alkali. Salt linkages, hydrogen bonds and
van der Waals' forces hold the polymer system of silk together. Since these inter-polymer
forces of attraction are all hydrolysed by the alkali, dissolution of the silk filament occurs
readily in the alkaline solution. It is interesting to note that initially this dissolution means only
a separation of the silk polymers from each other. However, prolonged exposure would result
in peptide bond hydrolysis, resulting in a polymer degradation and complete destruction of the
silk polymer.

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3. Effect of sunlight and weather - The resistance of silk to the environment is not as good as
that of wool. This lower resistance is due mainly to the lack of covalent crosslinks in the
polymer system of silk.

Carbohydrates
Carbohydrate is a general name for sugars, starches, and cellulose. The name derives from an
earlier belief that these substances were hydrates of carbon, because many of them have the
general formula (CH2O)n. Today, chemists also refer to carbohydrates as saccharides after the
smaller units from which they are built. Sugars are monosaccharides and disaccharides.
Starches and cellulose are polysaccharides. Carbohydrates serve many different functions in
nature. For example, sugar and starch are important for energy storage and production in both
plants and animals, and cellulose provides the support structure of woody plants.

Monosaccharides

Monosaccharides are simple sugars, having 3 to 7 carbon atoms. They can be bonded together
to form polysaccharides.

The names of most sugars end with the letters ose.

Example: Glucose, fructose, and galactose are monosaccharides; their structural formula is
C6H12O6.

Glucose and other kinds of sugars may be linear molecules as shown below but in aqueous
solution they become a ring form.

There are two isomers of the ring form of glucose. They differ in the location of the OH group
on the number 1 carbon atom (in red below).

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The number 1 carbon atom (numbered in red above) of the linear form of glucose is attached
to the oxygen on the number 5 carbon atom.

Simple sugars store energy for cells. Details concerning energy storage and release by glucose
are in the chapter on cellular respiration.

Cells also use simple sugars to construct other kinds of organic molecules.

Disaccharides

Disaccharides are composed of 2 monosaccharides joined together by a condensation reaction.

Examples:

Sucrose (table sugar) is composed of glucose and fructose.

Like glucose, sucrose stores energy. Plants synthesize sucrose to transport to

nonphotosynthetic parts of the plant.

Lactose is found in milk. It is formed when glucose bonds to galactose.

The digestion of complex carbohydrates (polysaccharides) typically involves hydrolysis

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reactions in which the molecules are broken down to maltose, a disaccharide. Maltose is then
further broken down to produce two glucose molecules.

Polysaccharides

Monosaccharides may be bonded together to form long chains called polysaccharides.

Starch and Glycogen

Starch and glycogen are polysaccharides that function to store energy. They are composed of
glucose monomers bonded together producing long chains.

Animals store extra carbohydrates as glycogen in the liver and muscles. Between meals, the
liver breaks down glycogen to glucose in order to keep the concentration of glucoses in the
blood stable. After meals, as glucose levels in the blood rise, it is removed from and stored as
glycogen.

Plants produce starch to store carbohydrates.

Amylopectin is a form of starch that is very similar to glycogen. It is branched but glycogen has
more branches. Amylose is a form of starch that is unbranched.

Below: Glycogen or Starch

Cellulose and Chitin

Cellulose and Chitin are polysaccharides that function to support and protect the organism. The
cell walls of plants are composed of cellulose. The cell walls of fungi and the exoskeleton of
arthropods are composed of chitin.

Cellulose is composed of beta-glucose monomers; starch and glycogen are composed of alpha-
glucose. The bond orientation between the glucose subunits of starch and glycogen allows the
polymers to form compact spirals. The monomers of cellulose and chitin are bonded together in
such a way that the molecule is straight and unbranched. The molecule remains straight

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because every other glucose is twisted to an upside-down position compared to the two
monomers on each side. Cellulose fibers are composed of long parallel chains of these
molecules. The chains are attached to each other by hydrogen bonds between the hydroxyl
groups of adjacent molecules.

Below: Cellulose

Cotton and wood are composed mostly of cellulose. They are the remains of plant cell walls.

Cotton - Structure and properties

The word cotton is derived from the Arabic. Depending upon the arabian dialect, it is
pronounced kutan, qutn, qutun etc. As soon as the cotton fiber is obtained from a plant it is
classified as a natural, cellulose, seed, mono-cellular, staple fiber.

Macro structure of cotton

Under a microscope, a cotton fiber appears as a very fine, regular fiber. It ranges in length from
about 10mm to 65 mm, depending upon the quality of the fiber. Cotton is a very fine fiber with
little variation in fiber diameter; compared with wool for instance, its fiber diameter is not
considered as critical a fiber dimension as its length. The fiber length to breadth ratio of cotton
ranges from about 6000:1 for the longest and best types, to about 350:1 for the shortest and
coarsest cotton types. The greater this ratio, the more readily can the cotton fibers be spun into
yarn. Cotton fibers vary in colour from near white to light tan.

Polymer system of cotton

The cotton polymer is a linear, cellulose polymer. The repeating unit in the cotton polymer is
cellobiose which consists of two glucose units. The cotton polymer system consists of about
5000 cellobiose units, that is its degree of polymerisation is about 5000. It is a very long, linear
polymer, about 5000 nm in length and about 0.8 nm thick. Cotton is a crystalline fiber. Its
polymer system is about 65 to 70 per cent crystalline and, correspondingly, about 35-30 per
cent amorphous. Therefore, the cotton polymers are, in the main, well oriented and probably
no further apart than 0.5 nm, in the crystalline regions.

Physical properties of cotton

(1) Tenacity - The strength of cotton fibers is attributed to the good alignment of its long
polymers (that is its polymer system is about 70 per cent crystalline), the countless, regular,

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hydrogen bond formations between adjacent polymers, and the spiralling fibrils in the primary
and secondary cell walls.It is one of the few fibers which gains strength when wet. It is thought
this occurs because of a temporary improvement in polymer alignment in the amorphous
regions of the polymer system. The improved alignment when wet results in an increase in the
number of hydrogen bonds, with an approximate 5 per cent increase in fiber tenacity.

(2) Elastic plastic nature - The cotton fiber is relatively inelastic because of its crystalline
polymer system, and for this reason cotton textiles wrinkle and crease readily. Only under
considerable strain will cotton polymers give and slide past one another.

(3) Hygroscopic nature - The general crispness of dry cotton textile materials may be attributed
to the rapidity with which the fibers can absorb moisture from the skin of the fingers. This rapid
absorption imparts a sensation of dryness which, in association with the fibers inelasticity or
stiffness, creates the sensation of crispness. The hygroscopic nature ordinarily prevents cotton
textile materials from developing static electricity.

Differences and similarities between starch and cellulose

Cellulose and starch are both polymers composed if sugar monomers. Compare the differences
between cellulose and starch. Discuss the use of cellulose as a possible souce of raw material
for the production of polymers.

Starch and cellulose are very similar polymers. They are both made up so similar monomers;
starch is made up on alpha glucose while cellulose is made up on beta glucose. The monomer of
starch is one unit of glucose where as the monomer of cellulose is not one unit of glucose, but
two units of glucose joined by a beta linkage. Cellulose is a lot stronger than starch. Starch is
practically useless as a material, but cellulose is strong enough to make fibers from, and hence
rope, clothing, etc. Cellulose doesn't dissolve in water the way starch will, and doesn't break
down as easily. Starch can be eaten, but cellulose is not digestible by the human body. Starch is
broken down into glucose to sustain the body, but the body is not equipped with the enzymes
that can break down cellulose into glucose.

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Difference between starch and cellulose

Cellulose is repeating units of beta-Glucose, whilst starch is repeating units of alpha-glucose.

Cellulose and starch are two very similar polymers. The monomer of starch is one unit of
Glucose whereas the monomer of cellulose is not one unit of glucose, but two units of glucose
joined by a beta-linkage. Both cellulose and starch are results of condensational polymerisation.
The different linkage creates a significant difference between starch and cellulose. The most
important difference is the fact that Cellulose cannot be digested whilst starch is a regularly
consumed source of food.
Cellulose is strong enough to make ropes, clothing and fibres, and unlike starch, it does not
dissolve in water. This suggests that cellulose is much stronger than starch, and is hence a more
useful material, making it a possible source of raw material for the production of polymers.

Starch

starch

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