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ORGANIC CHEMISTRY

Class -11

Bheshraj Subedi
bheshraj.subedi@trinitycollege.edu.np
Department of Chemistry
Trinity International S.S. & College
Dillibazar, Kathmandu - Nepal
Course content
 Introduction of organic compounds and organic
chemistry with vital force theory
 Difference between organic and inorganic compounds
 Source and importance of organic compounds
 Unique nature of carbon atom
 Classification of organic compounds
 Functional group and homologous series
 Cracking and Reforming
 Quality of gasoline (Octane number & Cetane number)
 Gasoline additives
 Some important questions for exam
Organic Chemistry
Introduction
The branch of science that deals with structure,
composition, preparation, properties and uses of
various chemical compounds is known as chemistry.
There are main two classes of chemical
compounds i.e. organic and inorganic compounds.
The chemical compounds which were obtained from
mineral and earth crust are called inorganic
compounds. For example, salt, marble, glass, alum,
metals, non metals etc.
The compounds which were obtained from
vegetable and animal origin are called organic
compounds. For example, carbohydrate, fat, oil,
protein, vitamin petroleum product etc.
This classification of chemical compound was
first given by a Swedish chemist J.J. Berzelius in 18th
century. The word organic has been derived from
‘organism’ which means living body. Thus the
compounds which were originated from living body
i.e. plants, animals and micro-organism are called
organic compounds and the systematic study of
such compounds is called organic chemistry.
Vital force theory
(Origin of organic compounds)
In the early stage of development of chemistry
it was considered that, all organic compound could
be originated from plants and animals only through
some mysterious natural force. This concept of
involvement of living being in the production of
organic compounds for the first time was proposed
by Berzelius in 1815 which is called as ‘vital force
theory’.
The word vital has been derived from Latin word
‘vita’ which means life. Therefore, the organic compound
could only produced by some mysterious natural life force
(god force) existing in living organism.
The laboratory synthesis of organic compound was
considered impossible due to absence of vital force
or living force.
Failure of Vital force theory
The vital force theory was in belief for long
time. Later on in 1828, a German chemist Friedrich
Wohler obtained typical organic compound ‘urea’
from inorganic compound ‘ammonium cyanate’ on
heating.
This synthesis of an organic compound from
inorganic compound broke down the old concept of
origin of organic compound i.e. vital force theory is
failed out and is discarded.

Hennel (1828) ⟶ Ethyl alcohol (C₂H₅-OH)


Kolbe (1845) ⟶ Acetic acid (CH₃-COOH)
Berthelot (1856) ⟶ Methane (CH₄)
Now a days more than 95% of organic
compounds are synthesized in lab by using different
chemical compounds from artificial method.
Modern definition of organic chemistry
After the failure of vital force theory, the new
concept of organic compound is developed. So
organic compound should be defined with wider
and modern concept.
Detail investigation of organic compound
indicates that all organic compound contains
covalently bonded carbon which always contains
hydrogen and sometimes other elements like O, N,
S, P, X and some metals. Hence hydrocarbons and
their derivatives are called organic compounds. For
example, carbohydrate, protein, vitamin, fat, oil,
hormone, acid, dyes, drug, explosive, rubber,
plastic, petroleum product etc.
The branch of chemistry that deals with
hydrocarbons and their derivatives is called organic
chemistry. Simply, the study of carbon compounds is
called organic chemistry.
CO, CO₂, H₂CO₃, metal carbonates, metal bicarbonates,
metal cyanides etc are inorganic compounds.

Reason for separate study of organic compounds

1. Large numbers of organic compounds


(Carbon compounds)
2. Unique physical and chemical properties
3. Unique nature of carbon
Difference between organic and inorganic compounds

Organic compounds Inorganic compounds


• They are made up of C, H and • They are made up of almost
some other elements. all elements.
• Mostly occurs in living • Mostly occurs in non-living
organism. matters.
• They are more than 10 billion. • They are less than 1 lakhs.
• They are mostly soluble in • They are mostly soluble in
organic solvents. water.
• They show covalent bond. • They show ionic bond.
• They have low melting and • They have high melting and
boiling point. boiling point.
• They show isomerism. • They do not show isomerism.
.
Organic compounds Inorganic compounds
• They are directional in nature. • They are non-directional in
nature.
• They form homologous series • They do not form any types
of same functional group. of homologous series.
• They show molecular reaction • They show ionic reaction
which is very slow. which is very fast.
• They are combustible. • They are non-combustible.
• Their solution is non- • Their solution is conductor of
conductor of electricity. electricity.
• Carbon atom can show • No any element can show
catenation property. catenation.
Source of organic compounds
1. Plants and animals: Carbohydrate, fat, protein,
vitamin, oil, resin, rubber, starch, cellulose etc.
2. Natural gas and petroleum: Cooking gas, diesel,
petrol, kerosene, methane, ethane, benzene,
toluene, anthracene etc.
3. Coal: Coke, coal-tar, starting material for dyes,
drugs, perfumes etc.
4. Fermentation: Alcohol, acid, vitamin, drugs,
antibiotics etc.
5. Synthesis: Dyes, drug, explosive, rubber, plastic,
fiber, polymer etc.
Importance of organic compounds
1. Food: Carbohydrate, protein, fat, oil, vitamin,
milk, egg, meat, cereals, fruits etc.
2. Clothes: Cotton, silk, wool, nylon, terylene,
polystyrene, cellulose etc.
3. Medicinal drugs: Antibiotics, pain killer, vitamin,
antipyretics, antiseptics, quinine etc.
4. Plastics, dyes and explosives: Polyethenes,
polystyrene, rubber, PVC, congo-red, aniline
blue, aniline yellow, azodyes, TNT, TNG, picric
acid, gun-cotton etc.
5. Fertilizers, pesticides and insecticides: NPK, DDT,
BHC etc.
6. Petroleum products: Cooking gas, gasoline,
diesel, petrol, kerosene, air fuel, lubricating oil,
gelly wax etc.
7. Cosmetics: Perfumes, face cream, hair oil, nail
polish, beauty soap, skin lotion, shampoo etc.
8. Industrial goods: Alcohol, paper, soap, detergent,
color, paint, varnishes etc. all are organic
compounds.
Unique nature of carbon
1. Terta-covalency of Carbon
Atomic number of carbon is 6 which belongs to
group IVA and second period in periodic table. Electronic
configuration of C (6) = 1s²,2s²2p²
Carbon atom has six electrons in which two are inner
electrons and rest four are valence electrons which are
distributed to 2s and 2p orbital.
In excited state, one electron from 2s orbital excites to
2p orbital and becomes four unpaired electron in valence
shell. Which accounts for tetra-covalency of carbon atom.
This carbon atom acquires octet state by sharing these
four unpaired electrons with four electrons of other atom
(same or different) during chemical bond formation. This
tendency of carbon to form four covalent bond is called
tetra-covalency.
Similarly carbon atom can form carbon to carbon single,
double and triple bond in a series of organic compounds.
For example,
2. Catenation property
Carbon is only one element in periodic table
which can form millions of carbon compound with
varying number of carbon atom. It has a unique
property of linking itself to another carbon atom to
give several open chain as well as cyclic compounds.
This property of self linking of carbon atom with
each other to form long chain compound is called
catenation property.
This property is favoured by the formation of carbon
to carbon strong covalent bond. Each carbon atom can form
single, double and triple bond and can combined with 2, 3,
4, or 5 C-atom through covalent bond to form variety of
linear, branched or cyclic compounds.

Alkyl groups
An alkyl group is formed by removing one
hydrogen atom from alkane molecule. They are
named by adding yl to ane of alkane. For example,
alkane –ane + yl = alkyl.
R-H ⟶ -R + H CH₄ ⟶ -CH₃ + H
Alkane Alkyl Methane Methyl
Types of chemical formula
There are different types of chemical formula
which are used to represent the organic compound.
1. Molecular formula
2. Empirical formula
3. Structural formula:- The formula that indicates how the
atoms are bonded in a molecule is called structural formula.
This shows the connection between atoms in the molecule.
For example,
4. Contracted formula:- The formula in which hydrogen
atoms are condensed with carbon is called contracted or
condensed formula. For example,

5. Bond line formula:- The formula in which carbon and


hydrogen are not shown and are represented by a bond line
is called bond line structural formula. Each corner and end
point represents the carbon. The hydrogen atoms are
understood to satisfy the valency of carbon. For example,
Classification of Organic Compounds
Organic compounds

[A] Open chain or [B] Cyclic chain or


Acyclic compound ring compound

(a) Alkane (a)Homocyclic (b) Heterocyclic


(b) Alkene
(c) Alkyne (i) Alicyclic (i) Heteroalicyclic
(ii)Aromatic (ii) Heteroaromatic
Classification of organic compounds
[A] Open chain or acyclic organic compounds
The compounds which consist of open chain of
carbon atom are called open chain or acyclic or
aliphatic organic compounds. The carbon chain may
be linear or branched.
(a) Alkanes:
The open chain organic compounds which
consist if carbon to carbon single bond (C-C) are
called alkanes.
(b) Alkenes
The open chain organic compounds which
consist of carbon to carbon double bond (C=C) are
called alkenes. For example,

(c) Alkynes
The open chain organic compounds which
consist of carbon to carbon triple bond (C≡C) are
called alkynes. For example,
[B] Closed chain or cyclic organic compounds
The compounds which consist of one or more
cyclic chain of carbon atom are called closed chain
or cyclic chain compounds or ring compounds.
(a) Homocyclic organic compounds
The cyclic compound in which the ring forming
atom is only carbon are called homocyclic or
carbocyclic compounds. For example,
(i) Alicyclic compounds
The cyclic organic compounds which are similar to
open chain compound in chemical behaviour are called
alicyclic or cyclic aliphatic compounds. For example,

(ii) Aromatic compounds


The cyclic organic compound which consist of at least
one benzene ring and alternate carbon to carbon single
and double bond having (4n+2) number of π electron
system are called aromatic compounds. For example,
(b) Heterocyclic organic compounds
The cyclic organic compound in which the ring
forming atom are carbon and one or more hetero
atoms (O, N, S, X etc) are called heterocyclic organic
compounds. For example, epoxyethane, THF,
pyrrole, pyridine etc.
(i) Aliphatic heterocyclic compounds
The heterocyclic compound which are similar to
aliphatic compound on their behaviour are called aliphatic
heterocyclic compound. For example,

(ii) Aromatic heterocyclic compounds


The heterocyclic compound which are similar to
aromatic compound on their behaviour are called aromatic
heterocyclic compound. For example,
Functional group
An atom or group of atoms that determines the
chemical properties (nature or behaviour) of
organic compound is called functional group. For
example, -X, -OH, -CHO, -COOH, -NH₂, -NO₂ etc.
Generally organic compound are formed by combining
two parts i.e. functional group and molecular body. The
molecular body is only hydrocarbon part that determines
physical property and functional group is reactive site that
determines chemical property.
S.N. Class of Organic Functional group
compounds Name Symbol
1 Alkanes Alkane -C-C-
2 Alkenes Alkene -C=C-
3 Alkynes Alkyne -C≡C-
4 Alkyl halides Halo -X (X=F,Cl,Br,I)
5 Alcohols Hydroxy -OH
6 Aldehydes Formyl -CHO
7 Ketones Oxo or keto >C=O
8 Carboxylic acids Carboxyl -COOH
9 Acid halides Acid halide -COX (X=F,Cl,Br,I)
10 Amides Amido -CONH₂
S.N. Class of Organic Functional group
compounds Name Symbol
11 Esters Ester -COO-
12 Acid anhydrides Acid anhydride -(CO)₂O
13 Sulphonic acids Sulphonic acid -SO₃H
14 Ethers Ether -O-
15 Thioethers Thioether -S-
16 Thiols (Mercaptides) Thiol (Mercapto) -SH
17 Nitriles (Cyanides) Nitrile (Cyanide) -CN
18 Isocyanides Isocyanide -NC
19 Nitro compounds Nitro -NO₂
20 Nitrites Nitrite -ONO
21 Amines Amine -NH₂
22 Diazo compounds Diazo -N=N-
23 Thiocyanides Thiocyanide -SCN
24 Isothiocyanides Isothiocyanide -NCS
Homologous series
The hydrocarbons and their derivatives are
called organic compounds. There are large number
of organic compounds with same functional group.
Each functional group consist of particular class of
organic compound with various members.
A regular series of organic compounds having
same functional group in the increasing order of
their molecular mass is called homologous series.
The respective members of particular series are
called homologue and the phenomenon which involves
their formation is called homology. Two regular members
are differ by a –CH₂ unit and thus their molecular mass is
differ by 14 amu. There is regular change in physical
properties of each homologue. For example,
1. Homologous series of alkane (CnH2n+2)
Series Name
CH₄ Methane
CH₃-CH₃ Ethane
CH₃-CH₂-CH₃ Propane
CH₃-CH₂-CH₂-CH₃ Butane
CH₃-CH₂-CH₂-CH₂-CH₃ Pentane
2. Homologous series of alcohol (CnH2n+1OH)
Series Name
CH₃-OH Methanol
CH₃-CH₂-OH Ethanol
CH₃-CH₂-CH₂-OH Propanol
CH₃-CH₂-CH₂-CH₂-OH Butanol
CH₃-CH₂-CH₂-CH₂-CH₂-OH Pentanol
3. Homologous series of carboxylic acid (CnH2n+1COOH)
Series Name
H-COOH Methanoic acid
CH₃-COOH Ethanoic acid
CH₃-CH₂-COOH Propanoic acid
CH₃-CH₂-CH₂-COOH Butanoic acid
CH₃-CH₂-CH₂-CH₂-COOH Pentanoic acid
General Characteristics of Homologous Series
1. All members of homologous series consist of same
functional group.
2. Each homologue possess same chemical properties
but different physical properties.
3. Each homologue can be represented by same
general formula having similar structure.
4. Each homologue can be prepared by same general
method.
5. Two regular members of homologous series differ
by a –CH₂ unit i.e. 14 amu. molecular mass.
6. The physical properties of homologue shows regular
gradation with rise in molecular mass.
7. First member of homologous series shows some
different behaviour than rest of members.
Fractional distillation of crude oil

 Source, Origin and Composition of Coal and Petroleum
 Isolation of aromatic hydrocarbons from coal
Cracking or pyrolysis
The process of decomposition of higher hydrocarbon
of petroleum fractions into lower hydrocarbons with low
boiling point on strong heating in presence or absence of
catalyst is called cracking or pyrolysis. This process involves
the breaking of C-C and C-H bond which results the
formation of lower hydrocarbons depend upon the
condition employed for it. For example,
Reforming or aromatization
The process of conversion of aliphatic and alicyclic
hydrocarbon into aromatic hydrocarbon on strong heating
in presence of suitable catalyst is called reforming or
aromatization. This process involves dehydration,
isomerisation and cyclization. For example,
Quality of gasoline (Octane number)
The term which is used to determine the
quality of fuel (Petrol or gasoline/C₆-C₁₀) is known as
octane number. The quality of fuel which is used to
indicate the anti-knocking property in internal
combustion engine of vehicles is called octane
number. For example,
Iso-octane has anti-knocking property = 100
n-heptane has anti- knocking property = 0
Generally a quality of fuel is determined by its
octane number value. For example, A fuel has
octane number 80 that means a fuel has same anti-
knocking property to that of 80% iso-octane and
20% n-heptane by volume.
A quality of fuel (octane number) of different
hydrocarbon is given as:- Straight chain alkanes <
branched chain alkanes < alkenes and alkynes <
cycloalkanes < aromatic hydrocarbons.
The gasoline that is used in motor cars has octane number
74 which is regular gasoline. (Octane number less than 74 is
third grade gasoline and more than 74 is premium gasoline)
2,2,3-trimethylbutane has highest octane number = 125
n-nonane has lowest octane number = -45
Gasoline additives (Anti-knocking agent)
The chemical compounds which are added to
gasoline (fuel oil) to improve its octane number are
called anti-knocking agent.
Tetra-ethyl lead (TEL) is the best known anti-
knocking agent which is added to gasoline that
converts straight chain hydrocarbon into branched
chain hydrocarbon and improves its octane number.
For example,
.

The lead free radical produced may damage an


engine thus it can be removed by treating with 1,2-
dibromoethane as,

 The quality of fuel can also be improved by cracking,


alkylation and isomerization.
Cetane number
The term which is used to determine the
quality of diesel fuel is known as cetane number.
The quality of diesel which is used to indicate the
ignition property in internal combustion engine of
vehicles is called cetane number. For example,
Cetane (Hexadecane) has cetane number = 100
α- methyl naphthalene has cetane number = 0

α—
The cetane number of diesel is the percentage
of cetane by volume in a mixture of cetane and α-
methyl naphthalene, which has same ignition
properties. For example, A diesel with cetane
number 75 has same ignition properties as the
mixture of 75% cetane and 25% α-methyl
naphthalene
Cetane ignites too rapidly which is assigned
the cetane number of 100 while α-methyl
naphthalene ignites too slowly due to its extremely
poor ignition properties, which is assigned the
cetane number of 0.
Some Important questions for exam (Very Short Questions)
1. Define organic compounds with examples.
2. What is vital force theory and write its limitations.
3. Write the source and importance of organic compound.
4. Why carbon atom shows tetra-covalency?
5. Differentiate structural and contracted formula.
6. What are alkyl groups? Write name of any 4 alkyl group.
7. Differentiate homocyclic & heterocyclic compounds.
8. Differentiate saturated & unsaturated compounds.
9. Define functional group. Write the functional group of
(i) Alcohol (ii) Aldehyde (iii) Carboxylic acid (iv) Amide
10. What do you mean by homologous series? Write the
name of first three members of alcohols and aldehydes.
Some Important questions for exam (Short Questions)
1. There are large number of organic and inorganic
compounds in our society and surroundings.
(a) Define organic compounds in terms of vital force theory
and modern concept.
(b) Carbon can form large number of organic compounds
which is its unique nature. Describe the unique nature
of carbon in terms of tetra-covalency and catenation
properties. [2+3]
2. (a) State and explain the concept of vital force theory for
the origin of organic compounds? Now a days this theory is
not acceptable why?
(b) How does organic compounds differ from inorganic
compounds in terms of chemical bond & solubility. [3+2]
3. There are large number of organic compounds with same
functional group. Each functional group consist of particular
class of organic compound with various members.
(a) Define functional group with example.
(b) Define homologous series, homologue and homology.
[2+3]
4. Explain why
(a) Organic compounds are combustible in nature?
(b) Organic compound have low melting and boiling point?
(c) Carbon can form large number of organic compounds?
(d) Functional group gives the identification of compound?
(e) Each homologue differ by 14 amu. molecular mass?
[1+1+1+1+1+]
5. Petroleum product are main source of organic compound
and are isolated by fractional distillation of crude oil.
(a) Define cracking or pyrolysis with example.
(b) Define reforming and aromatization with example.
(c) Why these two process are mainly used in industrial
chemistry? [2+2+1]
6. Gasoline is mainly used in internal combustion engine of
automobiles and aeroplanes for petrol engine.
(a) What is gasoline or petrol?
(b) Which term is used to indicate the quality of gasoline?
Define the term with example.
(c) How would you improve the quality of gasoline?
(d) Define gasoline additives with suitable example.
[1+2+1+1]
THANK YOU
Study well

Stay safe & stay healthy

Bheshraj Subedi
bheshraj.subedi@trinitycollege.edu.np

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