Module 1

Review of Inorganic Chemistry

Objectives
o To understand the atomic structure of carbon.
o To understand the physical properties of carbon.
o To understand the different chemical bonding.
o To understand what an ionic bond is and how it is formed and to be able
to predict which compounds are ionic and which are covalent.
o To understand what covalent bond is and how it is formed.

Discussion
Carbon is found in many different compounds. It is in the food you eat, the
clothes you wear, the cosmetics you use and the gasoline that fuels your car. Carbon is
the sixth most abundant element in the universe. In addition, carbon is a very special
element because it plays a dominant role in the chemistry of life. Carbon, discovered in
prehistory and was known to the ancients, who manufactured it by burning organic
material making charcoal.

There are four known allotopes of carbon:
1. Amorphous
2. Graphite
3. diamond
4. fullerene.

Physical Properties of the Carbon Atom

Atomic Number : 6
Atomic Mass Average: 12.011
Melting Point: 3823 K (3550C or 6422F)
Boiling Point: 4098 K (3825C or 6917F)
Density: 2.267g/cu.cm.
Hardness Scale Mohs: 0.5

Atomic Structure of Carbon

The Carbon atom has six electrons, 4 of the electrons are in its valence shell
(outershell). The circles in the diagram show energy levels - representing increasing
distances from the nucleus.


This diagram is, however, a simplification and can be misleading. It gives the
impression that the electrons are circling the nucleus in orbits like planets around the
sun. Actually it is not possible to know exactly where the electrons are located.
A better way to look at the carbon atom is by using an energy level graph shown
below.
.



Here we see carbon has six electrons represented by arrows (the direction of the
arrow represents the electron spin) Two electrons are found in the 1s orbital close to the
nucleus. The next two will go into the 2s orbital. The remaining ones will be in two
separate 2p orbitals. This is because the p orbitals have the same energy and the
electrons would rather be in separate orbitals.

Isotopes
Isotopes are atoms which have the same atomic number but different mass
numbers. They have the same number of protons but different numbers of neutrons.
The number of neutrons in an atom can vary within small limits. For example, there are
three kinds of carbon atom 12C, 13C and 14C. They all have the same number of
protons, but the number of neutrons varies.
protons Neutrons mass number
carbon 12 6 6 12
carbon 13 6 7 13
carbon 14 6 8 14

These different types of carbon atoms are called isotopes. The fact that they have
varying numbers of neutrons makes no difference to the chemical reactions of the
carbon atom.

Uses of Carbon
1. Graphite combined with clays form the 'lead' used in pencils.
2. Diamond is used for decorative purposes, and also as drill bits.
3. Carbon added to iron makes steel.
4. Carbon is used for control rods in nuclear reactors.
5. Graphite carbon in a powdered, caked form is used as charcoal for cooking,
artwork and other uses.
6. Charcoal pills are used in medicine in pill or powder form to adsorb toxins or
poisons from the digestive system.

Chemical Bonds
A chemical bond is an attraction between atoms brought about by a sharing of
electrons between to atoms or a complete transfer of electrons.
There are three types of chemical bonds:
1. Ionic
2. Covalent
3. Polar covalent

Ionic Bonds
Ionic bonds arise from elements with low electronegativity (almost empty outer
shells) reacting with elements with high electronegativity (mostly full outer shells). In this
case there is a complete transfer of electrons.



Example:





A well known example is table salt, sodium chloride. Sodium gives up its one outer shell
electron completely to chlorine which needs only one electron to fill its shell. Thus, the
attraction between these atoms is much like static electricity since opposite charges
attract.

Covalent bond
Covalent bonds involve a complete sharing of electrons and occur most
commonly between atoms that have partially filled outer shells or energy levels. Thus if
the atoms are similar in negativity then the electrons will be shared. Carbon forms
covalent bonds. The electrons are in hybrid orbitals formed by the atoms involved as in
this example:
ethane






Diamond is strong because it involves a vast network of covalent bonds between the
carbon atoms in the diamond.

Polar Covalent Bond

These bonds are in between covalent and ionic bonds in that the atoms share
electrons but the electrons spend more of their time around on atom versus the others
in the compound. This type of bond occurs when the atoms involved differ greatly in
electronegativity. The most familiar example is water. Oxygen is much more
electronegative than hydrogen, and so the electrons involved in bonding the water
molecule spend more time there.

The fact that water is a polar covalently bonded molecule has a number of implications
for molecules that are dissolved in water. In particular, molecules with polar covalent
bonds can break apart when they encounter water molecules. They are broken apart
because of the electrical attraction between the dissimilar charges of the molecules.
Also, since ionically bonded molecules involve ions with opposite charges, water with its
polar covalent bonds can separate ions from each other and then surround the ions
which prevent them from recombining. The properties of water all relate to this polar
covalent bonding. Indeed the sorts of so called hydrophilic and hydrophobic interactions
water has with various organic compounds depend on the nature of the polar covalent
bond in water.

Types of Covalent Bond
There are three types of covalent bond depending upon the number of shared
electron pairs.
1. Single Covalent Bond
2. Double Covalent Bond
3. Triple Covalent Bond

Single Covalent Bond
A single covalent bond formed by the mutual sharing of one electron pair
between two atoms. It is denoted by single short line ( ).
Examples:



In single bond formation each atom provides one electron.



Double Covalent Bond
A double covalent bond formed between two atoms by the mutual sharing of two
electron pairs. It is denoted by double short line ( ).
Examples:



Triple Covalent Bond
A triple covalent bond formed by the mutual sharing of three electron pairs. It is
denoted by triple short line ( ).
Examples:










Assignment 1
I. True or False: Indicate whether the sentence or statement is true or
false.
1. The types of particles that are located in the nucleus of an atom are
protons and neutrons, and the types of particles that are located in
the energy levels surrounding the nucleus are electrons.
2. The atomic number of carbon is 6, so it must contain 12
electrons.
3. In salt, ionic is the nature of the bond between sodium and chlorine.
4. An ionic bond involves an attraction between ions of opposite
charge.
5. Isotope is the same number of neutron.

II. Multiple Choice : Identify the letter of the best answers.
1. The electron-dot structure of carbon has how many dots?
A. 2
B. 4
C. 6
D. 8
2. A chemical bond that occurs when atoms share electrons is a(n)
____ bond.
A. ionic
B. covalent
C. polar covalent
D. magnetic
3. What kind of chemical bond is formed when electrons are gained
and lost from atoms?
A. ionic
B. covalent
C. magnetic
D. hydrate
4. Force that holds together the atoms in a compound
A. chemical formula
B. chemical bond
C. chemical reaction
D. chemical property
5. Molecule that has oppositely charged ends
A. covalent molecule
B. polar molecule
C. ionic molecule
D. nonpolar molecule
6. Force of attraction between the opposite charges of the ions in an
ionic compound
A. ionic bond
B. polar bond
C. covalent bond
D. hydrogen bond
7. Bond that forms between atoms when they share electrons
A. covalent bond
B. polar bond
C. ionic bond
D. nonpolar bond
8. The compound NaCl is an example of
A. an ionic compound
B. a polar compound
C. nonpolar compound
D. ionic compound

9. At room temperature, most covalent compounds are ____.
A. solids
B. liquids
C. gases
D. plasma
10. At room temperature, most ionic compounds are ____.
A. solids
B. liquids
C. gases
D. plasma
11. A chemical bond is a ____ that holds together the atoms in a
compound.
A. force
B. chemical
C. physical
D. ionic
12. Chemical bonds form when atoms lose, gain, or ____ electrons.
A. share
B. multiply
C. add
D. divide
13. Carbon is
A. monovalent
B. divalent
C. trivalent
D. tetravalent
14. The smallest particle of matter that can retain the chemical
properties of carbon is
A. carbon molecule
B. carbon atom
C. carbon macromolecule
D. an element.
15. The bond formed when two atoms share a pair of electrons is
called a
A. hydrogen bond
B. covalent bond
C. nonpolar bond
D. water bond.
16. Sharing of electrons in the outer energy levels of two atoms
A. results in ion formation
B. occurs in covalent bonds
C. only occurs if both are atoms of the same element
D. is found only among carbon atoms
17. An atom that has gained or lost electrons is called a(n)
A. Molecule
B. ion
C. nucleon
D. element
18. Which of the following statements most accurately describes the
difference between an ionic bond and a covalent bond?
A. Atoms held together by ionic bonds separate when
placed in water while atoms held together by covalent
bonds do not separate in water.
B. Ionic bonds hold together atoms of two different types,
while covalent bonds hold together atoms of the same
type.
C. Electrons are exchanged between atoms held together
by an ionic bond, but they are shared between atoms
held together by a covalent bond.
D. Ionic bonds form between atoms that carry opposite
charges, while covalent bonds form between uncharged
atoms.
19. Carbon atoms are the most versatile building blocks of the
molecules used by living organisms because _____.
A. carbon is the central atom of carbon dioxide, a necessary
molecule for photosynthesis
B. carbon is the central atom in urea, a molecule used by
many living organisms to transport wastes from the body
C. each carbon atom acts as an intersection point from
which a molecule can branch off in up to four directions
D. carbon can combine with hydrogen to form hydrocarbons
20. Which of these refers to atoms with the same atomic number but
different atomic masses?
A. These atoms are different elements.
B. These atoms have different numbers of electrons.
C. These atoms are isomers.
D. These atoms are isotopes.

21. What type of bond is joining the two hydrogen atoms?


A. covalent
B. hydrogen
C. ionic
D. hydrophobic
22. A(n) _____ refers to two or more atoms held together by covalent
bonds.
A. ion
B. isotope
C. community
D. molecule
23. This atom can form up to _____ single covalent bond(s).


A. 1
B. 2
C. 3
D. 4
24. A(n) _____ bond joins these two oxygen atoms.

A. single covalent
B. ionic
C. quadruple covalent
D. double covalent

25. What type of bond joins the carbon atom to each of the hydrogen
atoms?

A. hydrogen
B. single (nonpolar) covalent
C. ionic
D. double (nonpolar) covalent

III. Answer the following
1. What is the electronic configuration of Carbon?
2. What is the atomic mass and atomic number of carbon?
3. What name is given to the bond between water molecules?
4. Differentiate ionic from covalent bond.
5. Differentiate single from double bond.

- End -















Module 2
Introduction to Organic Chemistry


To understand the meaning of Organic chemistry, we must first learn the
meaning of Chemistry. Chemistry may be defined as the science which deals with the
elements, compounds and their properties. This branch of Natural science is broadly
categorized into three different branches, namely:
(1)The Physical Chemistry
(2)The Inorganic Chemistry
(3)The Organic Chemistry
The Organic chemistry mainly deals with the Carbonic compounds which are
formed inside the living body or its derivatives. But all carbon compounds are not
organic. Example is Carbonic acid, which although does contain carbon, is inorganic
compound. So everyone must be quite careful in selecting and identifying the organic
compound. Organic compounds contain both carbon and hydrogen. Though many
organic chemicals also contain other elements, it is the carbon-hydrogen bond that
defines them as organic. Organic chemistry defines life. Just as there are millions of
different types of living organisms on this planet, there are millions of different organic
compounds, each with different chemical and physical properties. There are organic
chemicals that make up your hair, your skin, your fingernails, and so on. The diversity of
organic chemicals is due to the versatility of the carbon atom. Why is carbon such a
special element? Let's look at its chemistry in a little more detail.
Carbon (C) appears in the second row of the periodic table and has four bonding
electrons in its valence shell (use Periodic Table here). Similar to other non-metals,
carbon needs eight electrons to satisfy its valence shell. Carbon therefore forms four
bonds with other atoms (each bond consisting of one of carbon's electrons and one of
the bonding atom's electrons). Every valence electron participates in bonding, thus a
carbon atom's bonds will be distributed evenly over the atom's surface.
A carbon-carbon bond is a covalent bond between two carbon atoms. The most
common form is the single bond a bond composed of two electrons, one from each of
the two atoms. The carbon-carbon single bond is a sigma bond and is said to be formed
between one hybridized orbital from each of the carbon atoms. In ethane, the orbitals
are sp3 hybridized orbitals, but single bonds formed between carbon atoms with other
hybridizations do occur (e.g. sp2 to sp2). In fact, the carbon atoms in the single bond
need not be of the same hybridization. Carbon atoms can also form double bonds
called alkenes or triple bonds called alkynes. A double bond is formed with an sp2
hybridized orbital and a p-orbital that isn't involved in the hybridization. A triple bond is
formed with sp hybridized orbital and two p-orbitals from each atom. The use of the p-
orbitals forms a pi bond.
Carbon has the unique characteristic among all elements to form long chains of
its own atoms, a property called catenation. This coupled with the strength of the
carbon-carbon bond gives rise to an enormous number of molecular forms, many of
which are important structural elements of life, so carbon compounds have their own
field of study which is an organic chemistry.
Organic chemistry is the chemistry of the compounds of CARBON, which, in
combination with many other elements (in particular H, N, O, S, P and the halogens)
form over 5,000,000 compounds.

Many of these compounds are of immense importance, as the list below shows:
Fuels
Solvents
Explosives
Detergents
Plastics, synthetic fibers
Rubber
Wool, cotton, natural fibers
Insecticides, pesticides
Animal toxins, plant poisons
Vitamins, hormones
Synthetic pharmaceuticals
Antibiotics
Dyestuffs
Foodstuffs, flavorings and preservatives
Apart from water, living things are largely made up of organic compounds, notably
proteins, fats, carbohydrates and nucleic acids. The study of these compounds, and the
role they play in all life processes, is a special area of study called Biochemistry.

Structure of organic compounds
The carbon atoms form a "skeleton", in this example, shown belowt, a chain of
six C atoms.




Hydrogen atoms are the most common atoms found linked to carbon atoms. In
hydrocarbons, the major constituents of petroleum, they are the only atoms found linked
to carbon.

Hydrogen atoms are bound to the carbon skeleton by means of covalent bonds.
There are other ways of representing the structure of organic compounds:

represents the same molecule, without bonds being shown. Sometimes only bonds are
shown, or one uses models known as Ball-and-Stick or Filled (the colors black, red and
white represent atoms of carbon, oxygen and hydrogen respectively):

The arrangement in space of all the atoms of a molecule is called the structure of the
molecule. The complexity of the structure will clearly depend on the size of the
molecule.
For example, the structure of the particular substance with formula C6H14 might
be described in terms of a Structural Formula such as


Carbon skeletons are immensely varied: they may consist of straight chains of various
lengths, branched chains, rings of various sizes and combinations of these.



Isomerism
The two structural formula applying to molecules with molecular formula C6H14.

These two molecules are said to be isomers. Isomers are compounds which have the
same molecular formula, but different structural formula. Isomers normally also differ in
their chemical and physical properties.


Isomers do not have to belong to the same class of organic compounds. For
example, the compounds whose structural formula are shown below, are isomers. The
one on the left is a CARBOXYLIC ACID, while the one on the right is an ESTER: The
molecular formula C5H10O2.

Families of Organic Compounds: Functional Groups
The study of organic compounds is facilitated by their organization into families of
compounds. There are 20 or so different families that are of importance. Each family
contains a very large number of different compounds which have a common chemical
behavior. The common behavior within one family differs from that within another
family. The common behavior of all compounds within the same family is due to the
presence of a common functional group. A functional group is a particular atom or
type of bond or group of atoms in a particular bonding arrangement.










Functional Groups of Organic Compounds













Assignment 2
Identify the functional group of the following organic compound:

1.






2.


3.
4.


4.








5.






6.





7.





8.













9.




10.





11.


12.










13.





14.


15.







16.


17.


18.
CH3--CH2CH3

19.

20.



- End -


Module 3
Alkanes


Alkanes are the simplest family of hydrocarbons - compounds containing carbon
and hydrogen only. They only contain carbon-hydrogen bonds and carbon-carbon
single bonds. . These compounds are also called saturated hydrocarbons, because
each carbon-to-carbon bond is a single bond, and the valence of the carbon atom is,
therefore, saturated. No more atoms can be bonded to the atoms in the compound,
without breaking the compound into two or more fragments. If it contains one or more
bonds which can react with hydrogen it is called an unsaturated hydrocarbon. Almost
all other organic compounds can be named as derivatives of these simple
hydrocarbons. Alkanes which have long carbon chains are often called paraffins in
chemical industry. The most simple alkane is methane with the formula CH
4
. The
second alkane is ethane with the formula C
2
H
6
. The general formula of alkanes is
C
n
H
2n+2
. The table below shows the first ten alkanes.

IUPAC
name
Number of
Carbons
Prefix
Molecular
Formula
Structural
Formula
Methane 1 Meth- CH
4
CH
4

Ethane 2 Eth- C
2
H
6
CH
3
CH
3

Propane 3 Prop- C
3
H
8
CH
3
CH
2
CH
3

Butane 4 But- C
4
H
10
CH
3
(CH
2
)
2
CH
3

Pentane 5 Pent- C
5
H
12
CH
3
(CH
2
)
3
CH
3

Hexane 6 Hex- C
6
H
14
CH
3
(CH
2
)
4
CH
3

Heptane 7 Hept- C
7
H
16
CH
3
(CH
2
)
5
CH
3

Octane 8 Oct- C
8
H
18
CH
3
(CH
2
)
6
CH
3

Nonane 9 Non- C
9
H
20
CH
3
(CH
2
)
7
CH
3

Decane 10 Dec- C
10
H
22
CH
3
(CH
2
)
8
CH
3


Methane exists as a tetrahedral shape, but it is often represented by a flattened
structure as are most organic compounds. In many cases the structures can be further
simplified without loss of information by omitting all single bonds and writing the letter
symbol of the element close to the letter symbol of the element to which it is attached.
Thus the representation of methane as CH
4
, ethane C
2
H
6
, and propane as C
3
H
8
) is a
representation of structure as well as of molecular composition. For many simple
organic compounds representations like this are adequate for discussion and
identification purposes.
All alkanes are inflammable, the product of the burning being carbon dioxide
(CO
2
) and water (H
2
O). Methane, ethane, propane and butane are gaseous at room
temperature and are collectively referred to as natural gas. Hydrocarbons are nonpolar
allowing van der Waals forces to act between them. Short alkanes have weak van der
Walls forces. With an increase of carbon atoms the van der Waals forces increase. As
the molecular chains become longer the molecules become liquid and eventually solid.










Alkyl Groups
An alkyl is basically an alkane minus one of its hydrogen atoms. It has the
general formula CnH2n+1. An alkyl has a symbol of R.
For example:
H H
| remove one H |
H-C-H ============> H-C- or CH
3
-
| |
H H
methane methyl

H H H H
| | remove one H | |
H-C-C-H ============> H-C-C- or CH
3
CH
2
-
| | | |
H H H H
ethane ethyl





Alkyl names are used to name branched alkanes. Any branch in an alkane would
be named as the number of carbons + "yl". . The first ten alkyl group.
prefix number of carbons alkyl group
meth- 1 Methyl
eth- 2 Ethyl
prop- 3 Propyl
but- 4 Butyl
pent- 5 pentyl
hex- 6 hexyl
hept- 7 heptyl
oct- 8 octyl
non- 9 nonyl
dec- 10 decyl

The structure of ethane can be derived from that of methane by substitution of a -
CH
3
group, called a methyl group, for one of the hydrogens of methane. The structure
of propane can be derived either by substitution of a methyl group upon ethane or by
substitution of an ethyl group upon methane; either method yields the same product,
propane. Likewise, the structure of the next member of the series, butane, can be
derived by the substitution of a methyl group upon propane. The alkane series of
compounds can be extended indefinitely by this method.

Isomerism
All the alkanes with 4 or more carbon atoms in them show structural isomerism. This
means that there are two or more different structural formulae that you can draw for
each molecular formula.
For example, C
4
H
10
could be either of these two different molecules:

These are called respectively butane and 2-methylpropane.

Rules for naming Alkanes
1. First, identify the longest continuous chain in the link of carbon atoms, also
known as the parent chain. The parent chain does not have to be connected in a
straight line, it could be in "zig zag" lines only if it proves to have the most
amount of carbon atoms in its chain. Number the carbons in the parent chain
starting from the end closest to the branch(es) so that the substituents will have
the smallest possible numbers.
2. Next, find each alkyl branch and assign it a number according to which carbon
atom it is attached to. The name for the alkyl branch is followed by "-yl" to
indicate the number of carbon atoms are in a branch.
3. List the substituents (with their carbon number) in alphabetical order followed by
the name of the parent alkane. In some cases when there are more than one of
a given substituent use the prefixes di-, tri-, tetra-. Prefixes are not used to
determine alphabetical order. The structural format should look like this: (number
of location)-(branch name)(name of parent chain)
4. Use commas between numbers and dashes between numbers and words in
naming the IUPAC formulas. Do not leave spaces in the name.

Example1.
CH
3
(CH
2
)
2
CH(CH
3
)CH
2
CH
3

When viewing a condensed formula of this kind, one must recognize that
parentheses are used both to identify repeating units, such as the two methylene
groups on the left side, and substituents, such as the methyl group on the right side.
This formula is elaborated and named as follows:


The condensed formula is expanded on the left. By inspection, the longest chain
is seen to consist of six carbons, so the root name of this compound will be hexane. A
single methyl substituent (colored red) is present, so this compound is a methylhexane.
The location of the methyl group must be specified, since there are two possible
isomers of this kind. Note that if the methyl group were located at the end of the chain,
the longest chain would have seven carbons and the root name would be heptane not
hexane. To locate the substituent the hexane chain must be numbered consecutively,
starting from the end nearest a substituent. In this case it is the right end of the chain,
and the methyl group is located on carbon #3. The IUPAC name is thus:
3-methylhexane.



Example 2.

(CH
3
)
2
C(C
2
H
5
)
2

Again, the condensed formula is expanded on the left, the longest chain is identified
(five carbons) and substituents are located and named. Because of the symmetrical
substitution pattern, it does not matter at which end of the chain the numbering begins.


When two or more identical substituents are present in a molecule, a numerical prefix
(di, tri, tetra etc.) is used to designate their number. However, each substituent must
be given an identifying location number. Thus, the above compound is correctly
named: 3,3-dimethylpentane.
Note that the isomer (CH
3
)
2
CHCH
2
CH(CH
3
)
2
would be named 2,4-dimethylpentane.







Example 3.

(CH
3
)
2
CHCH
2
CH(C
2
H
5
)C(CH
3
)
3

This example illustrates some sub-rules of the IUPAC system that must be used in
complex cases. The expanded and line formulas are shown below.

In this case several six-carbon chains can be identified. Some (colored blue) are
identical in that they have the same number, kind and location of substituents. The
IUPAC name derived from these chains will not change. Some (colored magenta) differ
in the number, kind and location of substituents, and will result in a different name. The
blue chain is chosen, and it will be numbered from the right hand end. Remember the
alphabetical priority, we assign the following IUPAC name: 3-ethyl-2,2,5-
trimethylhexane.


Example 4.

Write a structural formula for the compound 3,4-dichloro-4-ethyl-5-methylheptane.
First, we draw a chain of seven carbon atoms to represent the root name "heptane".
This chain can be numbered from either end, since no substituents are yet attached.
From the IUPAC name we know there are two chlorine, one ethyl and one methyl
substituents. The numbers tell us where the substituents are located on the chain, so
they can be attached, as shown in the middle structure below. Finally, hydrogen atoms
are introduced to satisfy the tetravalency of carbon. The structural formula on the right
can then be written in condensed form as: CH
3
CH
2
CHClCCl(C
2
H
5
)CH(CH
3
)CH
2
CH
3
or
C
2
H
5
CHClCCl(C
2
H
5
)CH(CH
3
)C
2
H
5



In naming this compound it should be noted that the seven carbon chain is numbered
from the end nearest the chlorine by applying rule.


Cycloalkanes
Cycloalkanes are alkanes in which a bond is formed between the two terminal
carbons in the chain to for a cyclical or ring structure. The prefix cyclo- is written before
the name designating the carbon number in the ring (e.g. cyclohexane).
1. Substituents are named similarly to straight-chained alkanes. The carbons in the
ring are numbered so that the substituents have the smallest numbers.
2. Add the prefix cyclo- to the alkane name

Example:
The smallest cycloalkane is cyclopropane.


Cyclohexane, for example, has a ring structure which looks like this:

This is known as the "chair" form of cyclohexane - from its shape which resembles a
chair.




Uses of alkanes
Alkanes are very important substances. Most of the fuels which we now use are
made from alkanes

The table shows some uses
Alkane Uses
Methane (natural gas) used for cooking and heating
Ethane used to make polythene
Propane used in gas cylinders for homes
Butane camping gas
Octane a component of petrol


Physical Properties of Alkanes
1. Alkanes are non-polar.
2. Insoluble in water.
3. Less dense than water.
4. Boiling points increase with increasing number of carbons and decrease
with chain branching.


Chemical Reactions of alkanes
Since the alkanes are saturated contain only carbon to carbon single bonds
they are fairly unreactive 3 reactions are involved.

1. Burning
All hydrocarbons burn in a good supply of air (oxygen) to form carbon dioxide
and water.




Examples of burning equations


2. Cracking alkanes
Cracking is a method of producing smaller, more useful molecules by
heating large hydrocarbon molecules in the presence of a catalyst. The catalyst
used in the lab is aluminum oxide or silica.Cracking alkane molecules usually
produces a mixture of smaller molecules some of them alkenes. There are
insufficient hydrogen atoms in an alkane for it to produce only alkanes on
cracking. The presence of the catalyst allows the reaction to take place at a
lower temperature making the process more economical.



The products of cracking can be separated by Fractional
Distillation


3. Substitution Reactions
Since the alkanes are saturated, only have C-C single bonds, they can
not add atoms on, only substitute or change the atoms they have for different
ones.Halogens can be swopped for hydrogen atoms in the presence of light.











Assignment 3
A. Give the correct name of the following structural formula of alkanes.
1.

2.

3.






4.


5. CH
3
CH
2
CH
3

6. CH
3
CH
2
CH
2
CH
2
CH
2
CH
2
CH
2
CH
3

7.

8.


9.






10.


11.


12.

13.

14.



15.


16.


17.

18.

19.





20.



B. Draw the correct structural formula of the ff.: compounds.
1. 4-ethyl-2,4-dimethylheptane
2. 2-methyl propane
3. 3,4-diethylheptane.
4. 2-bromo-2,3,3-trichloro-4-ethyl-1-iodohexane.
5. 1,3-dimethylcyclopentane

C. Answer the following:
1. Is cyclopropane an isomer of propane? Explain
2. Which has the higher boiling point, pentane or hexane? Why?
3. Which C4H10 isomer (n-butane or methylpropane) has the higher boiling
point? Why?
-End-

Module 4
Unsaturated Hydrocarbons
(Alkenes, Alkynes, Aromatic)


Unsaturated hydrocarbons are hydrocarbons that have double or triple covalent
bonds between adjacent carbon atoms. Those with at least one double bond are called
alkenes and those with at least one triple bond are called alkynes. Alkenes with two
double bonds are called dienes.
The physical properties of unsaturated hydrocarbons are very similar to those of
the corresponding saturated compounds ( alkanes). They are slightly soluble in water.
Except for aromatic compounds, unsaturated hydrocarbons are highly reactive
and undergo addition reactions to their multiple bonds. Typical reagents added are
hydrogen halides, water, sulfuric acid, elemental halogens and alcohols.

A. Alkenes
Alkenes are a family of hydrocarbons (compounds containing carbon and
hydrogen only) containing a carbon-carbon double bond. The first two are:
ethene C
2
H
4

propene C
3
H
6

Formula of alkenes: CnH2n



Nomenclature of Alkenes
Alkenes are normally named using the IUPAC system. The rules for
alkenes are similar to those used for alkanes. The following rules summarize
alkene nomenclature.

1. Identify the longest continuous chain of carbon atoms that contains the
carbon-carbon double bond. The parent name of the alkene comes
from the IUPAC name for the alkane with the same number of carbon
atoms, except the -ane ending is changed to -ene to signify the
presence of a double bond. For example, if the longest continuous
chain of carbon atoms containing a double bond has five carbon
atoms, the compound is a pentene.
2. Number the carbon atoms of the longest continuous chain, starting at
the end closest to the double bond. Thus,
CH3-CH2-CH=CH-CH3
is numbered from right to left, placing the double bond between the
second and third carbon atoms of the chain. (Numbering the chain
from left to right incorrectly places the double bond between the third
and fourth carbons of the chain.)
3. The position of the double bond is indicated by placing the lower of the
pair of numbers assigned to the double-bonded carbon atoms in front
of the name of the alkene. Thus, the compound shown in rule 2 is 2-
pentene.
4. The location and name of any substituent molecule or group is
indicated. For example,



5-chloro-2-hexene
5. Finally, if the correct three-dimensional relationship is known about the
groups attached to the double-bonded carbons, the cis or trans
conformation label may be assigned. Thus, the complete name of the
compound in rule 4 (shown differently here)



cis-5-chloro-2-hexene
Isomerism in Alkenes
All alkenes with 4 or more carbon atoms in them show structural isomerism. This
means that there are two or more different structural formulae that you can draw for
each molecular formula.




For example, with C4H8, it isn't too difficult to come up with these three structural
isomers:


There is, however, another isomer. But-2-ene also exhibits geometric isomerism.

Geometric (cis-trans) isomerism
The terms cis and trans are from Latin, in which cis means "on the same side"
and trans means "on the other side" or "across".
The carbon-carbon double bond doesn't allow any rotation about it. That means
that it is possible to have the CH3 groups on either end of the molecule locked either on
one side of the molecule or opposite each other.



For example,



These are called cis-but-2-ene (where the groups are on the same side) or trans-
but-2-ene (where they are on opposite sides). Cis-but-2-ene is also known as (Z)-but-2-
ene; trans-but-2-ene is also known as (E)-but-2-ene.
Uses of alkenes
o Lower alkenes are used as fuel and illuminant. These may be obtained by
the cracking of kerosene or petrol.
o For the manufacture of a wide variety of polymers, e.g., polyethene,
polyvinylchloride (PVC) and teflon etc.
o As a raw material for the manufacture of industrial Chemicals such as
alcohols, aldehydes, etc.
o For producing lamp black.

Physical Properties of Alkenes
The physical properties of alkenes are comparable with those of alkanes. The
physical state depends on molecular mass (gases from ethene to butene - liquids from
pentene onwards). The simplest alkenes, ethene, propene and butene are gases.
Linear alkenes of approximately five to sixteen carbons are liquids, and higher alkenes
are waxy solids.

B. Alkynes
Aliphatic hydrocarbons with one triple bond between carbons are called alkynes.
They follow the naming convention of the alkanes except that the suffix -yne is
used instead of -ane. For alkynes above propyne the position of the double bond
must be specified in the name.

ethyne
acetylene



propyne







Alkynes are unsaturated hydrocarbons and are generally very reactive. Typical
reactions involve the addition of hydrogens or halogens.


C. Aromatic Compounds
Background : The benzene ring
All aromatic compounds are based on benzene, C6H6, which has a ring of
six carbon atoms and has the symbol:

Each corner of the hexagon has a carbon atom with a hydrogen attached.

The phenyl group
By removing one hydrogen from methane, CH4. It is called a methyl
group CH3.
By removing one hydrogen from a benzene ring, C6H6. Like a methyl or
an ethyl group, a phenyl group (C6H5) is always attached to something else.
Nomenclature
Aromatic compounds with only one group attached to the benzene ring.
Name will be based on benzene. For example,

chlorobenzene
This is a simple example of a halogen attached to the benzene ring.
The simplified formula for this is C6H5Cl, name is phenyl chloride.
Whenever you draw a benzene ring with one other thing attached to it, you are in
fact drawing a phenyl group. In order to attach something else, you have to
remove one of the existing hydrogen atoms, and so automatically make a phenyl
group. Another example,

The nitro group, NO2, is attached to a benzene ring. The simplified
formula for this is C6H5NO2 and name nitrobenzene.
The benzene ring has a methyl group attached. The old name for
methylbenzene is toluene.


The simplified formula for this is C6H5CH3.

Another example is where one of the hydrogens on the CH3 group is replaced by
a chlorine atom. Place the brackets around the (chloromethyl) in the name to
make sure that the chlorine is part of the methyl group and not somewhere else
on the ring.

(chloromethyl) benzene
If more than one of the hydrogens had been replaced by chlorine, the names
would be (dichloromethyl)benzene or (trichloromethyl)benzene. Again, notice the
importance of the brackets in showing that the chlorines are part of the side
group and not directly attached to the ring.

Benzoic acid (benzenecarboxylic acid)



Benzoic acid is the older name, but is still in common use or
benzenecarboxylic acid, it has a carboxylic acid group, -COOH, attached to the
benzene ring.

Cases where the name is based on phenyl
Remember that the phenyl group is a benzene ring minus a hydrogen
atom - C6H5. If you draw a benzene ring with one group attached, you have
drawn a phenyl group.

Phenylamine

Phenylamine is a primary amine and contains the -NH2 group attached to
a benzene ring. The old name for phenylamine is aniline or aminobenzene.

Phenylethene

This is an ethene molecule with a phenyl group attached. Ethene is a two
carbon chain with a carbon-carbon double bond. The old name for phenylethene
is styrene - the monomer from which polystyrene is made.


Phenylethanone
It consists of a two carbon chain with no carbon-carbon double bond. The
one ending shows that it is a ketone, and so has a C=O group somewhere in the
middle. Attached to the carbon chain is a phenyl group. Putting that together
gives phenylethanone.
More than one group attached to the benzene ring
Numbering the ring, any group already attached to the ring is given the
number 1 position. Where you draw it on the ring (at the top or in any other
position) that is just a question of rotating the molecule a bit. It is much easier to
get the main group at the top. The other ring positions are then numbered from 2
to 6. You can number them either clockwise or counter-clockwise. As with chain
compounds, you number the ring so that the name you end up with has the
smallest possible numbers in it. Examples will make this clear.







All of these are based on methylbenzene and so the methyl group is given the
number 1 position on the ring. Why is it 2-chloromethylbenzene rather than 6-
chloromethylbenzene? The ring is numbered clockwise in this case because that
produces a 2- in the name rather than a 6-. 2 is smaller than 6.

2-hydroxybenzoic acid
This might also be called 2-hydroxybenzenecarboxylic acid. There is a -COOH
group attached to the ring and, because the name is based on benzoic acid, that
group is assigned the number 1 position. Next to it in the 2 position is a hydroxy
group, -OH.



Benzene-1,4-dicarboxylic acid
The di shows that there are two carboxylic acid groups, -COOH, one of
them in the 1 position and the other opposite it in the 4 position.


2,4,6-trichlorophenol
This is based on phenol - with an -OH group attached in the number 1
position on the ring. There are 3 chlorine atoms substituted onto the ring in the 2,
4 and 6 positions.

Assignment 4

A. Give the name of the following sturctural formula.

1.

2.

3.





4.

5.

6.

7.



8.

9.

10.









B. Give the structural formula of the following:

1. Benzene
2. propyne
3. 2 pentyne
4. 3-nonyne
5. 3,4-dimethyl-1-pentyne
6. 4,4-diethyl-l-hexyne
7. 5-ethyl-4-propyl-2-heptyne
8. 3-methyl-1-butyne
9. 2,3 dichlorobenzene
10. Toluene

- End -










Module 5
Alcohols and Phenols


Although you may be familiar with "alcohol as a beverage, the word actually
represents an entire classification of organic molecules and not just one substance.
Alcohols contain the OH (hydroxyl) functional group attached to a saturated carbon.
Notice that we did not call this the hydroxide ion, because this group does not act as an
ionic substance. Alcohols are the family of compounds that contain one or more
hydroxyl (-OH) groups. Alcohols are represented by the general formula R-OH. The
simplest alcohol is methanol, CH3OH, which was formerly obtained by the distillation of
wood and therefore is called "wood alcohol".

Nomenclature
Alcohols are just like other substituents. Molecules with alcohols are called -ols.
For instance CH3-OH is methanol. (methane - ane + ol = methanol).
Alcohols are classified into three categories: primary (1), secondary (2) and
tertiary (3). This classification is based on the number of carbon-containing groups (R
for an alkyl or an aromatic group) attached to the carbon bearing the hydroxyl group. If
the carbon bearing the OH has one R group, the molecule is a primary alcohol. If two
R groups are attached, it is a secondary alcohol. If three R groups are attached, the
alcohol is tertiary.


CH
2
OH CH
3
CH OH CH
3
C OH CH
3
CH
3
CH
3
CH
3
ethanol
(primary)
2-propanol
(secondary)
2-methyl-2-propanol
(tertiary)






Seven structural formulae representations:
1.

2.


3.

4.


5.

6.


7. and the skeletal formula is .



Another example

2,5-heptadiol.
No cis/trans becuase it's an alkane, containing all single bonds. Rules in naming is like
in the previous topics. Here are some common names of alcohols.
Common Names
Chemical Formula IUPACName Common Name
Monohydric alcohols
CH
3
OH Methanol Wood alcohol
C
2
H
5
OH Ethanol Grain alcohol
C
5
H
11
OH Pentanol Amyl alcohol
C
16
H
33
OH Hexadecan-1-ol Cetyl alcohol


Polyhydric alcohols
C
2
H
4
(OH)
2
Ethane-1 ,2-diol Ethylene glycol
C
3
H
5
(OH)
3
Propane-1 ,2,3-triol Glycerin
C
4
H
6
(OH)
4
Butane-1 ,2,3,4-tetraol Erythritol
O
H
R
H
O
H
.
.
.
C
5
H
7
(OH)
5
Pentane-1 ,2,3,4,5-pentol Xylitol
C
6
H
8
(OH)
6
Hexane-1 ,2,3,4,5,6-hexol Mannitol , Sorbitol
C
7
H
9
(OH)
7
Heptane-1 ,2,3,4,5,6,7-heptol Volemitol
Unsaturated aliphatic alcohols
C
3
H
5
OH Prop-2-ene-1-ol Allyl alcohol
C
10
H
17
OH 3,7-Dimethylocta-2,6-dien-1-ol Geraniol
C
3
H
3
OH Prop-2-in-1-ol Propargyl alcohol
Alicyclic alcohols
C
6
H
6
(OH)
6
Cyclohexane-1 ,2,3,4,5,6-geksol Inositol
C
10
H
19
OH 2 - (2-propyl)-5-methyl-cyclohexane-1-ol Menthol

Uses of Alcohols
o methanol is used for obtaining formaldehydes, plastic masses, synthetic gasoline
and coloring matter.
o ethanol is used for alcoholic drinks and as a solvent in the industry of lacquers
and paint, also in the pharmaceutical industry.
o glycerin is used for obtaining dynamite and isolating material; it is also used as a
medicine

Physical Properties of Alcohols

Hydrogen bonding
ZnCl
2
The hydroxyl group present in all alcohols is a polar functional group. The polarity of
this group allows alcohols to form hydrogen bonds. Small chain alcohols are able to
mix with water because of the hydrogen bonding interactions that will occur between the
hydroxyl functional group and the water. If the R-group of the alcohol becomes too
large however, the solubility of the alcohol will decrease.

Chemical Properties of Alcohol
The classification of an alcohol as primary, secondary or tertiary (see above)
affects the chemical properties of the alcohols. This difference in chemical properties
can be used as a means of identification. The Lucas test and the chromic acid test are
two common methods used to distinguish among primary, secondary and tertiary
alcohols.
A. Lucas Test:
The Lucas reagent contains zinc chloride and hydrochloric acid. When the Lucas
reagent is allowed to react with an alcohol, an alkyl halide is formed. This alkyl
halide will not be soluble in water, thus cloudiness or a second layer of droplets will
form if the test is positive. With this reagent, tertiary alcohols react immediately,
secondary alcohols in 3 to 10 minutes, and primary alcohols may take an hour or
longer, or may never react.


R-OH + HCl R-Cl + H
2
O (insoluble)

R C OH
O
R C R
O
C R R
OH
R
B. Chromic Acid Test:

Chromic acid (acidified dichromate, an oxidizing agent) can also be used to
distinguish between types of alcohols by oxidizing the alcohol. Primary alcohols are
oxidized to carboxylic acids; secondary alcohols are oxidized to ketones; and tertiary
alcohols are not oxidized. During the oxidation, the orange-red color of the chromic
acid changes to a blue-green solution.



+ H
2
CrO
4
+ Cr
2
(SO
4
)
3
+ H
2
O
(primary) (red-orange) (carboxylic acid) (blue-green)


+ H
2
CrO
4
+ Cr
2
(SO
4
)
3
+ H
2
O
(secondary) (red-orange) (ketone) (blue-green)




+ H
2
CrO
4
No Reaction
(tertiary)

CH
2
OH R
CH R R
OH

Phenols

Phenol is also known as carbolic acid an organic compound with the chemical
formula C6H5OH. It is a white, crystalline solid. This functional group consists of a
phenyl, bonded to a hydroxyl (-OH). Phenols are closely related to alcohols because of
the presence of the hydroxyl (OH) group. In phenols, however, the hydroxyl group is
directly bonded to an aromatic group, such as benzene. Phenol compounds often have
curious but useful properties. Some are found in preservatives or medications. The
chemistry of phenols is different than that of alcohols. Concentrated solutions of the
compound phenol are quite toxic and can cause severe burns. Phenols sometimes
called phenolics, the structural formula is C6H5OH. The simplest way to draw the
structure of phenol is:


Another examples of phenols.
IUPAC Name Common Name Condensed
Structure
Line Structure
2-methylphenol ortho-cresol o-CH
3
C
6
H
4
OH

3-methylphenol meta-cresol m-CH
3
C
6
H
4
OH

4-methylphenol para-cresol p-CH
3
C
6
H
4
OH

1,2-benzenediol Catechol o-C
6
H
4
(OH)
2


1,3-benzenediol Resorcinol m-C
6
H
4
(OH)
2



Uses of Phenols
o Phenols involve its conversion to plastics or related materials.
o Condensation with acetone gives bisphenol-A, a key building block for
polycarbonates.
o Condensation with formaldehyde gives phenolic resins, the most famous of
which is Bakelite.
o Hydrogenation of phenol gives cyclohexanone, an intermediate en route to nylon.
o Nonionic detergents are produced by alkylation of phenol to give the
alkylphenols, which are then subjected to ethoxylation.
o Phenol is also a versatile precursor to a large collection of drugs, most notably
aspirin but also many herbicides and pharmaceuticals.
o Phenol is the preferred chemical for embalming bodies for study because of its
ability to preserve tissues for extended periods of time. However, formaldehyde
is usually preferred over phenol for embalming with intent of public viewing
because of phenol's tendency to turn tissues an unpleasant bleach-white color.
o Phenol is also used in the preparation of cosmetics including sunscreens, hair
dyes, and skin lightening preparations.
o In cosmetic surgery, phenol serves as an exfoliant.
o It is also used in phenolization, a surgical procedure used to treat an ingrown
nail, in which it is applied to the nail bed to prevent regrowth of nails. 5% Phenol
is sometimes injected near a sensory nerve in order to temporarily (up to a year)
stop it from transmitting impulses in some intractable cases of chronic
neuropathic pain.
o In molecular biology, phenol is used with chloroform to dissolve proteins and
cellular debris when purifying nucleic acids, in particular plasmid preparation.
o Phenol is also one of the main ingredients in Castellini Paint Modified, a
antiseptic used to treat Hailey-Haileys Disease (Phimpigus). It dries the scaly
skin out and helps calm the itching. It also can be used to calm the itch between
toes caused by Athletes Foot.

Physical Properties of Phenols

Pure phenol is a white crystalline solid, smelling of disinfectant. It has to be
handled with great care because it causes immediate white blistering to the skin. The
crystals are often rather wet and discoloured.


Chemical Properties of Phenols

Phenols react differently than alcohols. This is why they are given their own
functional group and are not technically alcohols. We will see this difference in the
chromic acid test and the ferric chloride test.

A. Chromic Acid Test

Phenols can be oxidized with chromic acid, but they give different types of
products than those formed from alcohols. The chromic acid test is described above,
and the same results are expected for a positive test (a blue-green solution is
formed).

B. Ferric Chloride test

Addition of aqueous ferric chloride to a phenol creates a colored solution.
Depending upon the structure of the phenol, the color can vary from green to purple.

Assignment 5
Draw the structural formula of the ff:
1. Propan-2-ol
2. 3-methylbutan-2-ol
3. 2,3-dimethyl-2-butanol
4. 1-chloro-2-methylpropan-2-ol
5. hexan-3-ol
6. 3-chloro-2-methylpropan-1-ol

7. 4-chlorobutan-2-ol
8. 4-ethyl-2-methyl-3-hexanol
9. 3-methyl-1-butanol
10. 2,2-dimethyl-1-propanol
11. 2-phenylphenol
12. Pentachlorophenol
13. 1,3 benezenediol
14. 4-Bromophenol
15. 1,2,3-Trihydroxy benzene
16. 1,2,3-Trihydroxy benzene
17. 2,4,6-trinitrophenol
18. o-Bromophenol
19. 2,4,6-trinitrophenol
20. 4-Bromophenol

-end-



Module 6
Aldehydes and Ketones

Introduction
Aldehydes ( ) and ketones ( ) are both carbonyl compounds. They
are organic compounds in which the carbonyl carbon is connected to C or H atoms on
either side. An aldehyde has one or both vacancies of the carbonyl carbon satisfied by a
H atom, while a ketone has both its vacancies satisfied by carbon. Methanal (common
name: formaldehyde) is the only aldehyde with two hydrogens attached to the carbonyl
carbon. The simplest aldehyde with one hydrogen attached to the carbonyl carbon is
ethanol ( common name: acetaldehyde). The simplest ketone is 2- propanone
(common name: dimethyl ketone, acetone).
Comparison of Aldehydes and Ketones with Alkenes







Example of Aldehydes

Example of Ketones



Nomenclature of Aldehydes and Ketones
1. The longest continuous chain must contain the carbonyl carbon.
2. The ending of the name is changed from ane to anal for aldehydes and
from ane to anone for ketones.
3. The longest continuous chain is numbered from the end that gives the
smallest number for the carbonyl carbon. For aldehydes the carbonyl carbon
is understood to be carbon -1 and the number 1 is not used in the name.

Common names for many ketones are obtained by naming the groups attached to the
carbonyl carbon followed by the word ketone. Dimethyl letone is also known as
acetone.


Examples naming simple aldehydes:
Compound Name Line Drawing
methanal
or
formaldehyde


ethanal
or
acetaldehyde

propanal

butanal

cyclobutyl
or
carboxaldehyde


pentanedial*



* note: the -e as added with the di- prefix of the dial, numbers for the two aldehydes are
not necessary.






Examples naming more complex aldehydes:

Compound Name

Line Drawing

4,4-dimethylpentanal

4-pentenal



4-amino-3-isopropylhexanal


4-chloro-2-cyclohexene
or
carboxaldehyde


2-mercapto-4-oxo-heptanal *



* note: a keto group is lower in priority than an aldehyde so it appears as an -oxo-
substituents.



Examples naming simple ketones:

Compound Name

Line Drawing

2-propanone * or dimethyl ketone or
acetone


2-butanone or ethyl methyl ketone


2-pentanone or methyl propyl ketone



3-pentanone or diethyl ketone




cyclobutanone



2,4-pentadione **



* note: the 2 in 2-propanone is redundant as the carbonyl must be located at carbon 2
for it to be a ketone.
** note: the -a as added with the di- prefix of the dione.







Examples naming more complex ketones:

Compound Name


Line Drawing


4,4-dimethyl-2-pentanone



4-penten-2-one




4-amino-3-isopropyl-2-hexanone





5-hydroxy-2-cyclohexenone




Uses of Aldehydes and Ketones:
o Aldehydes and ketons are used as solvents, starting materials and
reagents for the sysnthesis of other products.
o Formaldehyde is well recognized as formalin solution used to defend
biological specimens and to prepare Bakelite, urea-formaldehyde glues
and other polymeric products.
o Aldehyde is used primarily as an initial material in the manufacture of
acetic acid, ethyl acetic, vinyl acetate, polymers and drugs.
o Benzaldehyde is used in perfumery with in dye industries. Acetone with
ethyl methyl ketones are general industrial solvents.
o Various aldehydes and ketones exemplar, butyraldehyde, vanillin,
acetophenone, camphor, etc. are well recognized in support of their
odours and flavours.

Physical Properties of aldehydes and ketones
o Methanal is a gas at room temperature.
o Ethanal is a volatile liquid.
o Other aldehydes and ketones are liquid or solid at room temperature.
o The boiling points of aldehydes and ketones are higher than
hydrocarbons and ethers of comparable mass. It is due to weak molecular
association in aldehydes and ketones arising out of dipole-dipole
interactions.
o The boiling points of aldehydes and ketones are lower than those of
alcohols of similar molecular masses due to absence of intermolecular
hydrogen bonding.
o The lower members of aldehydes and ketones such as methanol, ethanal
and propanone are miscible in water in all proportions, because they form
hydrogen bond with water. However, the solubility of aldehydes and
ketones decreases rapidly on increasing the length of alkyl chain.
o All aldehydes and ketones are fairly soluble in organic solvents like
benzene, ether, methanol, chloroform, etc
o The lower aldehydes have sharp pungent odour. As the size of the
molecule increases, the odour becomes less pungent and more fragrant.

Chemical Properties of Aldehydes and Ketones

A. Nucleophilic addition reactions
1. Hydrogen cyanide: addition product is cyanohydrins.
2. Sodium bisulphite: addition proudct is bisulphite adduct.
3. Grignard reagent: addition intermediate product, when hydrolysed gives
alcohol.
4. Alcohol: product geminal dialkoxy compounds.

B. Nucleophilic addition reactions that involve elimination of water molecule
Aldehydes and ketones react with a number of ammonia
derivatives in weakly acidic medium to form compound containing carbon-
nitrogen double bonds with the elimination of water molecule.

1. Addition of various ammonia derivatives
i) Hydroxylamine - product oxime
ii) Hydrazine - product hydrazone
iii) Phenylhydrazine - product phenylhydrazone
iv) 2, 4 dinitrophenyl hydrazine - product 2,4 dinitrophenyl
hydrazone
v) Semicarbazide - product semicarbazone

2. Addition of Ammonia product aldehyde-ammonia ducts

C. Oxidation reactions
1. Tollen's reagent - silver mirror test
2. Fehling's solution - aldehydes give a red precipitate of cuprous oxide
3. Benedict's solutin - similar to Fehling's solution
4. Oxidation with sodium hypohalite - iodoform is the product

D. Reduction of aldehydes and ketones
1. Reduction to alcohols: aldehydes give primary alcohols. Ketones give
secondary alcohols.
2. Reduction to hydrocarbons:
i) Reduction with zinc amalgam and con HCL
ii) Reductin with basic solution of hydrazine
iii) Reductioin with HI in the presence of red phosphorus

E. Miscellaneous reactions
1. Aldol condensation
2. Cross aldol condensation
3. Cannizaro's reaction
4. Halogenation
5. Action with Schiff's reagent
6. Polymerisation
7. Substitution reactions of benzene nucleus in aldehydes and ketones.




















Assignment 6

Give the name of the following molecules:
1.

2.

3.

4.


5.


6.

7.

8.

9.


10.


11.


12.


13.


14.

15.


-end-









Module 7
Carboxylic acids and Esters

Carboxylic acids ( often referred to simply as organic acids or acids ) contain the
carboxyl group, a carbonyl group to which is attached a hydroxyl group:
O=C-OH
Carbonyl group
The carbonyl group is abbreviated as COOH or CO
2
H. The carbon of the
carbonyl group can be attached to a hydrogen as in methanoic acid ( common name:
formic acid) or to a carbon. The carbon can be part of an alkyl group as in ethanoic acid
(common name: acetic acid) or an aryl group as in benzoic acid.
Examples of carboxylic acids

Nomenclature of Carboxylic Acids
1. Carboxylic acids are named by dropping the -e ending of the parent name
and adding -oic acid.

The substituent name for a -COOH group is carboxy.

pentanoic acid or 1-carboxybutane
2. Ring compounds when one or more COOH groups are attached to a ring,
the ring is named followed by the word -carboxylic acid. The carbon atom to
which the -COOH group is attached is numbered 1 and substituents are
numbered relative to that number.

cyclobutanecarboxylic acid

3. Common names that you should know are the following:

formic acid


acetic acid


malonic acid




propionic acid


butyric acid


benzoic acid






4. Salts of carboxylic acids are named by first naming the metal, followed by a
space and then by changing the name of the acid by dropping the -oic acid
ending and adding -oate.


sodium benzoate

Sources of Carboxylic Acids
Carboxylic acids are widespread in plants and animal kingdom. They play a
significant role in biochemical processes of life. They add smell and flavor to nature, for
example, vanillin, salicylaldehyde and cinnamaldehyde contain very pleasant
fragrances.

Uses of Carboxylic acids
o Carboxylic acids are used in the production of polymers, pharmaceuticals,
solvents, and food additives. Formic acid is in ant bites.
o Many carboxylic acids are produced industrially on a large scale. They are
also pervasive in nature.
o Methanoic acid: use as rubber, textile, dyeing, leather and electroplating
industries.
o Ethanoic acid: use as solvent and as vinegar in food industry.
o Hexanedioic acid: manufacture of nylon 6:6.
o Ester of benzoic acid: use as perfumery.
o Sodium benzoate: use as a food preservative.
o Higher fatty acids: use as manufacture of soaps and detergents.

Physical Properties of Carboxylic Acids

o A carboxylic acid has a higher melting point than a different type of
organic compound with a similar molecular weight. Consequently, they are
all solids under normal conditions. The compounds with four carbons or
less are miscible with water; those with five carbons are slightly soluble,
and those with more than five carbons are generally insoluble in water.
o Carboxylic acids tend to have higher boiling points than water, not only
because of their increased surface area, but because of their tendency to
form stabilized dimers.
o Carboxylic acids are typically weak acids, meaning that they only partially
dissociate into H+ cations and RCOO anions in neutral aqueous solution.
o Carboxylic acids often have strong odors, especially the volatile
derivatives. Most common are acetic acid (vinegar) and butyric acid
(rancid butter).



Conversion of Carboxylic Acids to Esters
Carboxylic acids react with alcohols or phenols ( R = alkyl or aryl) in the presence of an
acid catalyst or enzyme to form esters:

R-COOH + HO---R RCOOR + H
2
O

The reaction, referred to as esterification, is a reversible reaction. Ester formation is
maximized by forcing the equilibrium to the right. This is accomplished by the removal of
water from the reaction mixture by running the reaction above the boling point of water.
Nomenclature of Esters
1. Name the carboxylic acid (either IUPAC or common name ) from which the
ester is derived.
2. Change the ending of the name from ic acid to ate.
3. Place the name of the substituent in the alcohol portion of the ester at the
front of the name.








Example of Esters:

propanoate



Sources of Esters
o Esters are widespread in nature and are widely used in industry. In nature,
fats are generally triesters derived from glycerol and fatty acids. Esters are
responsible for the aroma of many fruits, including apples, pears,
bananas, pineapples, and strawberries.
Uses of Esters
o Esters of fatty acids are the main components of lipids and polyamides of
aminocarboxylic acids are the main components of proteins
o Esters can be used as adhesive, solvents, perfumes, flavourings,
painkillers
Physical Properties of Esters
o Esters are more polar than ethers but less polar than alcohols.
o Esters are more volatile than carboxylic acids of similar molecular weight.






















Assignment 7
A. Draw a structure for the following compound:
1. 2-bromohexanoic acid

2. 1-cyclohexenecarboxylic acid

B. Name the following compound:
1.



2.







C. Give another name of the following compound:

1.
formic acid
2.

acetic acid

3.
malonic acid

4.

propionic acid

5.
butyric acid

6.
benzoic acid

-End-

























Module 8
Amines and Amides


Amines and amides contain a nitrogen atom bonded to one, two, or three carbon
atoms. Amides differ from amines in having a carbonyl carbon bonded to the nitrogen:
Amines are the organic versions of ammonia. An alkyl group takes the places of one,
two or three of the hydrogens. They are called primary, secondary and tertiary amines,
respectively.

Nomenclature of Amines
Amines can be named using two different systems:
as alkyl amines (naming the alkyl group or groups attached to the N)
as alkanamines (naming the alkane to which the N is attached)
Primary amines
Alkyl amine: use
the normal rules
for naming alkyl
groups as
substituents

Alkanamine: the parent alkane (the
longest chain containing the carbon to
which the N is attached) is numbered
from the end closest to the carbon
with the N on it




methyl amine or Methanamine




isopropyl amine or 2-propanamine





1-methylbutyl
amine
or 2-pentanamine

Secondary amines
Alkyl amine: if the
alkyl groups are
the same, it's a
dialkyl amine;
otherwise list the
alkyl groups in
alphabetical order
Alkanamine: the longest chain
to which the N is attached is
the parent; the other group
attached to the N is named as
an N-alkyl substituent






dimethyl amine Or N-methylmethanamine




ethyl methyl
amine
Or N-methylethanamine






1-ethylpropyl-
isopropyl amine
Or N-isopropyl-3-pentanamine



Tertiary amines
Follow the same rules as with secondary amines:



trimethyl amine Or N,N-dimethylmethanamine



ethyl dimethyl amine Or N,N-dimethylethanamine





ethyl isopropyl methyl
amine
or N-ethyl-N-methyl-2-
propanamine











Aromatic amines



is aniline; thus:









Is
2-methylaniline;

is
3-ethyl-N-
methylaniline

Functional group priorities:


is 5-amino-2-pentanol




is 4-N-methylaminophenol





Properties of Amines
o Small amines are soluble in water.
o Larger amines are less soluble because their long alkyl groups disrupt the
hydrogen bonding in water.
o Amines have strong odors.

Chemical Properties of Amines
o Amines are weak bases.

o They react with water to produce hydroxide ions (OH-), and they react with

acids to form salts.

o Amines react with acid chlorides and acid anhydrides to form amides.

Structure of Amides
The functional group of an amide consists of a carbonyl group and an amino
group.








An amide can be produced by reacting a carboxylic acid with ammonia (NH3).


The general formula for amides is RCONR'R'', where R, R', and R'' represent
alkyl groups or hydrogen

Nomenclature of Amide
The simplest of the amides are those in which the nitrogen is bonded to two
hydrogen atoms. In order to name these, start with the carboxylic acid from which the
amide is derived. Then, cross off the -ic or -oic acid and replace that ending with -
amide. Select the longest carbon chain starting with the carbon in the amide group.
Then use the alkane name for that chain but replace the -e ending with -amide to
accommodate the amide group.
More complex are the amides that have one or two alkyl groups attached to the
nitrogen atom in place of hydrogen atoms. In these case, naming alkyl groups as
attachments to the front of the name using N- to show their location.




Examples:
O
//
CH
3
-CH
2
-C
\
NH
2

Propanamide
O
//
CH
3
-CH
2
-CH-C
| \
CH
2
N-H
| |
CH
3
CH
3

2-ethyl-N-
methylbutanamide
O
//
CH
3
-CH-CH
2
-C
| \
CH
3
N-CH
2
-CH
2
-CH
3

|
CH
3

3,N-dimethyl-N-propyl-
butanamide
pentanamide
O
//
CH
3
-CH
2
-CH
2
-CH
2
-C
\
NH
2

N-ethyl-N-propylacetamide
O
//
CH
3
-C
\
N-CH
2
-CH
2
-CH
3

|
CH
2
-CH
3



Applications and occurrence of amides
o Amides are pervasive in nature and technology as structural materials.
The amide linkage is easily formed, confers structural rigidity, and resists
hydrolysis. Nylons are polyamides as are the very resilient materials. Low
molecular weight amides, such as dimethylformamide (HC(O)N(CH3)2)
are common solvents. Many drugs are amides, for example penicillin.

Physical Properties of Amides
o Low molecular weight amides are soluble in water due to the formation of
hydrogen bonds.
o Unsubstituted amides have higher melting and boiling points than
comparable substituted amides.
o Amides are very weak bases.

Chemical Properties of Amides
o Amides, unlike amines, are neutral.
o Amides undergo hydrolysis in acidic conditions to yield a carboxylic acid
and an amine salt. Hydrolysis under basic conditions produces a
carboxylate salt and an amine.





ASSIGNMENT 8
A. Give the name of the following:
1.

2.

3.

4.

5.

6.





7.


8.


9.




10. O
//
CH
3
-CH
2
-CH
2
-CH
2
-C
\
NH
2






B. Give the structural formula for each compound.

1. ethanamide

2. pentylamine

3. 2-pentanamine

4. ethyl methyl amine

5. 2-methylaniline

6. Propanamide

7. 2-ethyl-N-methylbutanamide

8. 5-amino-2-pentanol

9. trimethyl amine

10. isopropyl amine

-End-










Experiment No. 1

Methods of Purification and Separation of Organic Compounds


Organic compounds resulting from a reaction is usually impure due to the small
amounts of the materials from which it was prepares as by-products formed by
secondary reactions. These impurities may be absorbed or mixed with the compounds.
Therefore, it becomes necessary to eliminate the impurities. The following methods
may be applied:

Go to the given website and watch and answer the questions for each number.

1. Decolorization

Link to the website:

http://prezi.com/klzqraved_up/decolorization-of-brown-sugar/

Questions:

a. What is the role of activated carbon in decolorization?
b. What is another name of activated carbon/
c. Give 5 uses of activated carbon.


2. Sublimation

Link to the website:

http://www.youtube.com/watch?v=4fAOI6BeMZY

Questions:

a. What is sublimation?
b. Give the results and observation on the experiment.

3. Extraction

Link to the website:

http://www.youtube.com/watch?v=CyIA8NhMUl4

Question:

a. Give another 3 methods of purification of organic compounds with videos.



- End -
















Experiment No. 2

Hydrocarbons

Hydrocarbons are compounds containing carbon and hydrogen. The alkanes or
paraffins, constitute the saturated compounds whose carbon atoms four valence
electrons are fully satisfied with the general formula of C
n
H
2n+2
.

Alkanes are inert and do not react readily even with the most oxidizing agents or
even with strong sulfuric acid. It reacts with chlorine and bromine in the presence of
sunlight. They are insoluble in water but soluble in organic solvents like chloroform ,
carbon disulfide, etc..

Alkenes or olefinsconstitute the series with a general formula of C
n
H
2n
. Alkenes
are differentiated from alkanes by the presence of Carbon to Carbon double bond.
Alkenes respond to addition type of reaction producing saturated alkanes and
derivatives.

The alkynes are another series with a general formula of characterized by a triple
Carbon to Carbon bond.

The aromatic hydrocarbons possess a closed ring structure with benzene as the
parent compound. The compound benzene is a closed ring structure whose carbon
atoms are conjugated bonded to one another.


Go to the given website and watch and answer the questions for each number.


1. Alkanes

Link to the website:

http://www.youtube.com/watch?v=AajLtkJxPk0

Questions:

a. Physical Property of alkanes:
a.1 color
b. Note the color of flame produced in the video.
c. Give and write the chemical equation of the following chemical reaction of
alkanes.
c.1 Combustion
c.2 Cracking


2. Alkenes

Question:

a. Physical Property of alkenes:
a.1 color

b. What is the reaction of alkenes with potassium permanganate and bromine
water?




3. Alkynes

Question:

a. Physical Property of alkynes:
a.1 color

b. What is the reaction of alkynes with potassium permanganate and bromine
water?


4. Aromatic hydrocarbons

Link to the website:

http://www.youtube.com/watch?v=8czz7FdFUNk

Question:

a. Physical Property of benzene:
a.1 color

b. What is the reaction of benzene with potassium permanganate and bromine
water?

c. Write the equation involved to produce nitrobenzene.



- End -







Experiment No. 3

Alcohols

Aliphatic alcohols are derivatives of alkanes formed by replacing a hydrogen
atom by OH group. The alcohols differ from their corresponding hydrocarbons in both
physical and chemical properties. The H in OH is partially acidic because of the
electron attracting nature of oxygen that makes the H partially positive ( it forms H-
bonding with the negative end of another alcohol or water molecule.

Go to the given website and watch and answer the questions for each number.


1. Preparation of alcohol

Link to the website:

http://www.youtube.com/watch?v=znhalRdr5Zs

2. Properties of alcohol:

Link to the website:

http://www.youtube.com/watch?v=YI-os7Py8SM


Questions:

1. Give at least 4 uses of ethyl alcohol.
2. What is the role of yeast in the fermentation process?
3. Is ethyl alcohol soluble in water? CHCl
3
? CCl
4
? Rationalize each answer.

- End -

Experiment No. 4

Aldehydes and Ketones


Aldehydes are intermediate products of the oxidation of the primary alcohol while
ketones are the first oxidation products of secondary alcohols. Aldehydes and ketones
are functional isomers. Both possess the functional carbonyl ( C = O ) group. Both
groups exhibit similar reactiviries like:
1. addition of a variety of reagents at the carbonyl carbon
2. reduction of the carbonyl group, and
3. condensation and polymerization

Go to the given website and watch and answer the questions for each number.

Properties of Aldehydes and Ketones

1. Tollens Test for Aldehydes and Ketones

Link to the website:

http://www.youtube.com/watch?v=CMCVpE8p8yo

Questions:

1. Give at least 4 more tests for aldehydes and ketones.
2. Give one commercial use of aldehydes and ketones.
3. Does law permit the use of aldehydes as food preservative? Why?
4. What is the clinical indication of the presence of acetone in the urine?

- End -


Experiment No. 5

Carboxylic acids and its Derivatives

Carboxylic acid ( R-COOH ) from C
1
to C
3
have sharp odor while the other liquid
acids have foul odor. Because of strong electron donating oxygen bonded to acidic
hydrogen, acids up to C
4
hydrogen bond with water molecules that lead to water
solubility.
The alkanoic acids are weak acids ( like acetic acid). They undergo common
reactions with metals, alkali, and with alcohols in the presence of catalyst.

Go to the given website and watch and answer the questions for each number.


Preparation of Carboxylic acid ( Benzoic acid )

Link to the website:

http://www.youtube.com/watch?v=E-cBrbtuGyw

Properties of Carboxylic acid

Link to the website:

http://www.youtube.com/watch?v=KxZXlMeAxZw

Questions:

1. What are the derivatives of acids? Give example.
2. Give the equations involved in esterification of an acid. Find any website to
support your answer.
3. Compare formic acid with acetic acid and oxalic acid.

- End -

Experiment No. 6

Amines and Amides

Amines and amides contain a nitrogen atom bonded to one, two, or three carbon
atoms. Amides differ from amines in having a carbonyl carbon bonded to the nitrogen:
Amines are the organic versions of ammonia. An alkyl group takes the places of one,
two or three of the hydrogens. They are called primary, secondary and tertiary amines,
respectively.

The functional group of an amide consists of a carbonyl group and an amino
group.

An amide can be produced by reacting a carboxylic acid with ammonia (NH3).


The general formula for amides is RCONR'R'', where R, R', and R'' represent
alkyl groups or hydrogen.

Go to the given website and watch and answer the questions for each number.


Properties of Amine

Link to the website:

http://www.youtube.com/watch?v=Jgdck6SR9nU

Questions:

1. Give the chemical equation involved in the reaction on the video.
2. Find another link on the website for amide.
3. Give 2 uses of amines and amides.
- End -