GENERAL INTRODUCTION

1. Organic compounds appear in materials like

clothing, fuels, polymers dyes and medicines, protein,
carbohydrate, etc.,
2. F. Wohler synthesised an organic compound, urea
from an inorganic compound, ammonium cyanate
rejecting the ‘vital force’ proposed by Berzilius
 Tetravalence of Carbon
•Makes sp3 hybridized orbitals of Tetrahedral shape
•sp2 hybridized orbitals of Trigonal planar shape
• sp hybridized orbitals of Linear shape
•It also makes sigma(σ ) and (π ) bonds in the
molecules
First 10 members of hydrocarbon
STRUCTURAL REPRESENTATIONS OF
ORGANIC COMPOUNDS
Complete, condensed and bond line structural
formulas.

1. The Lewis structure or dot structure

2. The Lewis structures, however, can be simplified

by representing the two-electron covalent bond by a
dash (–).

°° °°
°°
COMPLETE STRUCTURAL FORMULA uses lines to show
the bonds between the atoms.
H H
C C H C C H
H C C H
H H
E thyne
H H Ethene

Ethane

CONDENSED STRUCTURAL FORMULA omits lines

between the atoms.

HC
Ethan Ethen Ethyne
e e
BOND LINE STRUCURAL FORMULA
uses only lines, carbon and hydrogen atoms are not shown
and the lines representing carbon-carbon bonds are drawn in
a zig-zag fashion. The only atoms specifically written are oxygen,
chlorine, nitrogen etc.
The terminals denote methyl (–CH3) groups (unless indicated
otherwise by a functional group), while the line junctions denote
carbon atoms bonded to appropriate number of hydrogens
required to satisfy the valency of the carbon atoms
For example: 3-Methyloctane can be represented in various
forms as:
a) CH3CH2CHCH2CH2CH2CH2CH3
|
CH3
Expand each of the following condensed formulas into their complete
structural formulas.
For each of the following compounds, write a condensed formula and
also their bond-line formula.
 Three-Dimensional
Representation of Organic
Molecules
The three-dimensional (3-D) structure of organic molecules can be
represented on paper by using certain conventions. For example,
by using solid and dashed wedge formula, the 3-D image of
a molecule from a two- dimensional picture can be perceived.

solid-wedge is used to indicate a bond projecting out of

the plane of paper, towards the observer.

The dashed-wedge is used to depict the bond

projecting out of the plane of the paper and away from
the observer.
The bonds lying in plane of the paper
are depicted by using a normal line (—).
Other Molecular Models

both the atoms and the bonds

only the bonds connecting
are shown
the atoms

relative size of each atom

 CLASSIFICATION OF ORGANIC COMPOUNDS COMPOUNDS

i)On the basis of structure

Acyclic or open chain compounds
These compounds are also called as aliphatic compounds and
consist of straight or branched chain compounds, for example:
 Alicyclic or closed chain or ring compounds
Alicyclic (aliphatic cyclic) compounds contain carbon atoms joined
in the form of a ring (homocyclic). Sometimes atoms other than
carbon are also present in the ring (heterocylic).
For example:
 Aromatic compounds
.These include benzene and other related ring compounds.
ii) On the basis of Functional groups
•Functional groups - An atom or a group of atoms
present in a molecule which largely determines the
chemical properties.

•Example – Hydroxyl (- OH)

•Aldehyde ( -CHO )
•Carboxylic acid (- COOH) ,etc.,
 Homologoues series
It is a family or group of structurally similar
organic compounds all members of which contain
the same functional group.

It shows a gradation in physical and similarity in

chemical properties.

Any two adjacent members of which differ by -

CH2 group.
.
 Check your understanding
• Question 1. What are hybridisation states of each carbon
atom in the following compounds? CH2=C=O,
CH3CH=CH2, (CH3)2CO, CH2=CHCN, C6H6.
• Question 2. Write bond line formulas for: Isopropyl
alcohol, 2,3-Dimethyl butanal, Heptan-4-one
• Question 3. Indicate the σ and π bonds in the following
molecules: C6 H6 , C6 H12 , CH2Cl2, HCONHCH3.
NOMENCLATURE OF ORGANIC COMPOUNDS

COMMON IUPAC
OR TRIVIAL
IUPAC (International Union of Pure and
Applied Chemistry)
• Systematic method of naming
• The reader or listener can deduce the structure
from the name.
The Traditional names - Trivial or Common
names.
Hydrocarbons Compounds containing carbon and
: hydrogen only are called
hydrocarbons.
I) (Straight chain)

word root (name of number of carbon

atoms in chain) + ane
 ii) Branched chain Hydrocarbons

Parentchain/Alkane/
ene/yne
Small chain/
branch/alkyl

Prefix (alkyl) + word root + suffix

-H
Alkane → Alkyl
Methane → Methyl

Names of branched alkyl group

 Nomenclature of branched chain alkanes

Rule 1: First of all, the longest carbon chain in the

molecule is identified.
Example

Rule 2 : The numbering is done in such a way that

the branched carbon atoms get the lowest

possible numbers.
Rule 3. If different alkyl groups are present, they are
listed in alphabetical order. Thus, name for the
compound shown above is: 6-ethyl-2-methylnonane.

[Note: the numbers are separated from the groups

by hyphens and there is no break between methyl
and nonane.]

6-ethyl-2-methylnonane
Rule 4. Name the identical alkyl groups at different
positions of the carbon chain using the prefixes
di,tri,tetra, etc.,

Rule 5 : When two substituents are in equivalent

positions, the lower number is given to the one coming
first in the alphabetical listing.
Rule 6 : The branched alkyl groups can be named by
following the above mentioned procedures. carbon
atom of the branch that attaches to the root alkane is
numbered 1 as exemplified below:
While writing the trivial names of substituents’
in alphabetical order, the prefixes iso- and
neo- are considered to be the part of the
fundamental name of alkyl group. The
prefixes sec- and tert- are not considered to be
the part of the fundamental name. iso and neo
names are used in IUPAC as long as these are
not further substituted.
If there happens to be two chains of equal size, then
that chain is to be selected which contains more number
of side chains.
After selection of the chain, numbering is to be done
from the end closer to the substituent.
5, 5 Dimethyl 1-Hexene
1, 4 Hexadiene
3-Penten-1-yne

1,3 Hexadie-5yne

1, 4,4 Trimethyl Cyclobutene

 CYCLIC COMPOUNDS
For a saturated
monocyclic
compound: ‘cyclo’+
straight chain alkane
If side chains are
present, then the
rules used for naming
branched chain
alkanes are applied.
Functional Groups: A functional group is defined as an atom or group of
atoms within a molecule that has similar chemical properties whenever
it appears in various compounds.

https://www.organicchemistrytutor.com/lessons/functional-groups/
Example: http://www.chem.uiuc.edu/flashcards/functional/index.html
Example 2:
Assignment: Flashcards of
Functional groups
1.The longest chain of 2.Priority order for
carbon atoms containing
the functional group is polyfunctional group :
identified and numbered -COOH,-SO3H,-COOR,
to get the carbon with
functional group gets the -COCl, -CONH2, -CN,
lowest number.
-HC=O, =C=O, -OH,
-NH2, =C=C=,-CΞ C-.
.
Priority order for polyfunctional group

https://youtu.be/lRNLo0loqm0
Trick-May help you catch up FGs!!
Carboxylic = carboxylic acid
Stop = sulphonic acid
Asking = anhydride
Ester= Ester
Anything = Acid halide
About = amide
Cyanide = cyanide
I = Iso cyanide
Already = aldehyde
Know = ketone
All = alcohol
Things = thio alcohol
Example :

Hexane-2,4-dione
 Your Turn:
1. 2- Methylbutanoic
acid
2. 3-Bromobutanal
3. 3-Chloro-2-methyl
buatan-1-oic acid
4. Ethyl-2-bromobut
ane-1-oate
For IUPAC nomenclature of substituted benzene compounds,
the substituent is placed as prefix to the word benzene as
shown in the following examples. However, common names
(written in bracket below) of many substituted benzene
compounds are also universally used.
For disubstituted benzene compounds, lower numbers should
go to carbon containing substituents such that the
substituents
are located at the lowest numbers possible.

In the trivial system , the terms ortho (o), meta

(m) and para (p) are used as prefixes to indicate the relative
positions 1,2- ;1,3- and 1,4- respectively.
Naming of Trisubstituted Benzene
• Derivative of the compound with the
principal functional group fixed as
number 1
• Lowest locant rule is followed while
numbering carbon atoms of benzene.
• Alphabetical order is followed while
writing name.
Higher substituted benzene derivatives, these prefixes cannot be
used and the compounds are named by identifying substituent
positions on the ring by following the lowest locant rule. In
some cases, common name of benzene derivatives is taken as
the base compound.
Substituent of the base compound is assigned number1 and
then the direction of numbering is chosen such that the next
substituent gets the lowest number. The substituents appear in
the name in alphabetical order. Some examples are given
For reference
When benzene is linked to an alkane with the
functional group then benzene ring is treated a
substituent.

2-Phenylethanol
Write the structural formula of:
(a) o-Ethylanisole, (b) p-Nitroaniline,
(c) 2,3 - Dibromo -1 - phenylpentane,
(d) 4-Ethyl-1-fluoro-2-nitrobenzene.
 ISOMERISM-not included

same molecular formula but different properties

TYPES
 Structural Isomerism
(i) Chain isomerism: When two or more
compounds have similar molecular formula
but different carbon skeletons (isomers)
(ii) Position

isomerism: differ in
the position of
substituent atom or
functional group on
the carbon skeleton
(iii) Functional group
isomerism: different
functional groups.
(iv) Metamerism - different alkyl chains on
either side of the functional group in the
molecule.

Streoisomerism
same constitution and sequence of covalent
bonds but differ in relative positions of their
atoms or groups in space
Check your Understanding
Question 1. Give the IUPAC names following compounds:

Question 2.
Name the type of isomerism shown by the given pair of formulae.
 OUTLINE
• REVIEW OF PREVIOUS SESSION
• REACTION MECHANISM
• ELECTRON MOVEMENT IN ORGANIC REACTION
• FISSION OF A COVALENT BOND
• TYPES OF ATTACKING REAGENTS
• ELECTRON DISPLACEMENTS IN COVALENT BONDS
• METHODOF PURIFICATION OF ORGANIC
COMPOUNDS
 REVIEW OF PREVIOUS SESSION
• General Introduction
• Tetravalence of Carbon – Shapes of Compounds
and Types Of Bonds.
• Strucural Representation Of Organic Compounds –
Complete, Condensed and Bond Line
• Classification Of Organic Compounds – Aliphatic,
Aromatic and Cyclic Compounds
• Rules Of IUPAC Nomenclature Of Organic
Compounds
• Isomerism - Chain, Functional Group, Position,
Metamerism and Streoisomerism.
Can you describe the given process?
What is reaction mechanism?
The general reaction is depicted as follows :

Supplies carbon to
new bond
REACTION MECHANISM

Details of electron movement

A sequential account of
each step

Energetics during bond cleavage and

bond formation

Rate of transformation of reactants

into products
Electron Movement in Organic Reactions
Presentation of shifting
of electron pair by
curved arrow notation

Shifting of single electron

is shown by a single
barbed ‘fish hooks’ (i.e.
half headed curved arrow)
 Fission of a Covalent Bond

Heterolytic cleavage Homolytic cleavage

•Shared pair of Each fragment gets
electrons remains an electron from bond
with one of the pair
fragments.

Octet
Sextet electrons with ̶
electrons with charge
+ charge
Examples
• Product of heterolytic •Product of homolytic
fission is (a)
Carbocation (or) fission is free radicals.
Carbonium ion and
carbanions.
• Order of stability of
carbocation
Homolytic Heterolytic
Attacking Reagents
The attacking reagents are
those species which brings about
a change in a chemical reaction.
 Types of Attacking Reagents
Nucleophile ( ̶ ) Electrophile ( + )
• Brings an electron pair • Takes away an electron pair

• Nucleus seeking (Nu: ) • Electron seeking(E + )

• Attacks electrophilic • Attacks nucleophilic centre

centre (electron deficient) (electron rich centre)

• Reaction is nucleophilic • Reaction is electrophilic

• Ex. OH ̅ , CN ̅ , H2O , • Ex. Br + , Cl +, CH3 + ,AlCl3

NH3
Electron Displacement Effects in
Covalent Bonds
Permanent Polarization of
the bond Temporary Polarization of
the bond
• Under the influence of
• When a reagent
an atom or substituent
approaches to attack it.
in the molecule.
Example:
Example
Electromeric Effect or
1) Inductive Effect
Polarisability Effect
2) Resonance Effect
Inductive Effect – Polarization of σ bond
by polarisation of adjacent σ bond

̶ I Effect + I Effect
• Electron moves from • Electron moves form
the system to substituent (electron
substituent (electron releasing group ) to the
withdrawing group). system.

• Ex. - Cl, - NO2, - CN • EX.(CH3)2CH+

 What is resonance?

In Chemistry, resonance
describes the fact
that electrons are
delocalized, or flow freely
through the molecule,
which allows multiple
structures to be possible for
a given molecule.
Resonance Effect Or Mesomeric Effect
The resonance effect can be defined as a chemical phenomenon that is
observed in the characteristic compounds having double bonds in the
organic compounds. The organic compounds contain these double bonds in
the structures and usually have the overlapping of the p-orbitals on the two
adjacent sides of carbon atoms.
It is attributed to a particular substituent through the delocalization of π or
pi-electrons that can be seen by drawing various canonical structures is
called a resonance effect or mesomeric effect. M or R symbols are used to
represent the resonance effect.
Types:
̶ R Effect + R Effect
• Transfer of electrons • Transfer of electrons away

towards the substituent from the substituent attached

attached to the conjugated to the conjugated system.
system.
Hyperconjugation
effect operating in
Electromeric Effect (E Effect ) –
Temporary effect due to attacking reagent

+ E Effect ̶ E Effect
Π - electrons of multiple Π - electrons of multiple
bond transfer to the atom bond transfer to the atom to
to which the reagent gets which the reagent does not
attached. get attached.
What’s difference between inductive &
electromeric effect
Organic reactions:
 METHODS OF PURIFICATION
OF ORGANIC COMPOUNDS
Method of selection of purification of organic
compounds is based on the nature of the
compound and the impurity present in it.
(i) Sublimation (ii) Crystallization
(ii) Distillation
(iii) Differential extraction and
(iv) Chromatography
SUBLIMATION:
∆
Crystallization
Crystallization
•Principle : Difference in the solubilities of the
compound and the impurities in a suitable
solvent.
•Steps : 1. Dissolution of impure compound to
prepare saturated solution.
•2. Concentration by heating 3. Crystallization by
cooling 4. Filtration 5. Repeated crystallisation.
•Ex. Purification of benzoic acid
 Distillation

• Separate volatile liquids from

non-volatile impurities
• The liquids should have
sufficient difference in their
boiling points.
• Ex. Chloroform (B.P 334K)
and Aniline (B.P 457K)
 Types of Distillation
i) Fractional distillation:
• Separate a mixture of two or more miscible
liquids having boiling points close to each
other.
• Fractionating column is used.
• Ex. A mixture of acetone ( B.P 330K ) and
Methyl alcohol ( B.P 338 K )
Fractional Distillation

Application: Crude oil in petroleum industry

ii) Distillation Under Reduced
Pressure
• Liquids having very high boiling points are purified

• They decompose at their boiling point

• So , their boiling point is reduced by reducing the
pressure on its surface.

• Vacumn pump is used to reduce the pressure

• Ex. Glycerol is separated from spent lye in soap

industry
A liquid boils at a temperature below its vapour
pressure by reducing the pressure

Distillation under reduced pressure

iii) Steam Distillation
• To separate substances
which are steam volatile
and are immiscible with
water.
• Aniline is separated by this
technique from aniline – water
mixture

Ex. Separation of Aniline and water mixture

 Chromatography

Mobile phase made Stationary phase is

up of mixture of fixed
components
(Adsorbent)
(Adsorbate)
TYPES OF
CHROMATOGRAPHY
Adsorption Partition
Different compounds Continuous differential
adsorbed on an partitioning of
adsorbent to different component of a mixture
degrees. between stationary and
Common adsorbents are mobile phase.
silica gel and alumina.
Adsorption Chromatography
Column Thin Layer (TLC)
Separation of a mixture over separation of substances of a

a column of adsorbent mixture over a thin layer of

packed in a glass tube. an adsorbent coated on glass

plate.
RETARDATION FACTOR
The relative adsorption of each component of
the mixture is Rf.
 Check your Understandig
• Question 1.
Name a suitable technique of separation of the
components from a mixture of calcium sulphate and
camphor.
• Question 2.
What are electrophiles and nucleophiles? Explain with
examples.
• Question 3.
Explain why alkyl groups act as electron donors when
attached to a π system.
 REVIEW OF PREVIOUS SESSION
• Reaction Mechanism
• Electron Movement In Organic Reaction
• Homolytic and Heterolytic Fission of a Covalent Bond
• Types of Attacking Reagents – Nucleophile and
Electrophile
• Electron Displacements in Covalent Bonds – Inductive ,
Resonance,Hyperconjugation and Electromeric Effects
• Methodof Purification of Organic Compounds –
Sublimation,Crystallisation,Types of Distillation and
Chromatography.
QUALITATIVE ANALYSIS OF
ORGANIC COMPOUNDS
Not included for half yearly, will cover with
practical for next term
The elements present in organic compounds are carbon and
hydrogen. In addition to these oxygen, nitrogen, sulphur, halogens
and phosphorus.
Detection of Carbon and Hydrogen
Carbon and hydrogen are detected by heating the compound
with copper(II) oxide.
Carbon present in the compound is oxidised to carbon dioxide (tested
with lime-water, which develops turbidity)
Hydrogen to water (tested with anhydrous
copper sulphate, which turns blue).
Detection of other Elements
(N,S,X & P) – Lassaigne’s Test
•Preparation of Lassaigne’s Extract
(Sodium fusion Extract):
Heat a small piece of small amount
Na in a fusion tube to of organic
+
red hot compound ∆
Plunge this hot mixture in
distilled water, boil and
filter. Filtrate is
Lassaigne’s Extract.
 A) Test for Nitrogen
Sodium Fusion Boil Prussian
Iron
Extract + (II)Sulphate
→ Blue
Add Solution
Conc.H2SO4
Confirms the presence
of Nitrogen

H2SO4 Oxidises
Some Fe 2+ into
Fe 3+
iron(III) hexacyanidoferrate(II)
(ferriferrocyanide)
 B) Test for Sulphur
i)
Sodium Black
Acetic Lead
+ + Acetate
→
Fusion Extract Acid precipitate
Confirms the
presence of Sulphur

ii)
Sodium Violet
+ Sodium →
Fusion Extract nitroprusside Colour
Confirms the
presence of Sulphur
 C) Test for Nitrogen &
Sulphur
i)
Sodium
+ Ferric Blood Red Colour
Fusion Extract Chloride → Solution
having both N solution
Confirms the
& S in O.C presence of Nitrogen
& Sulphur
Sodium Cyanide
Decompose (for N)
Fusion Extract Excess
+ Sodium
→ Sodium → +
having both N thiocyanate
Sulphide
& S in O.C ( for S )
 d) Test for Halogens (X)
Sodium
Nitric Silver
Fusion Extract + Acid + Nitrate

Yellow PPT sparingly

White PPT
soluble in NH4OH
soluble in

→
NH4OH Br2 Confirmed
Yellow PPT
→

insoluble in → I2 Confirmed
Cl 2 Confirmed
NH4OH
 e) Test for Phosphorous
Organic
Sodium ∆ Phosphate
Boil
compound
+ Peroxide → solution
→ Yellow PPT
HNO3 +
Ammonium Confirms the
Molybdate presence of
Phosphorous
 QUANTITATIVE ANALYSIS

Mass of Mass of
Element in × compound × 100
Percentage Compound formed (m) g
=
of Element Molecular Mass Mass of
of compound × Organic
compound
taken (w) g
Estimation of Carbon and
Hydrogen

Mass of Mass of CO2 Mass of H2O

O.C (W) g formed (m1) g formed (m2) g
 The increase in masses of U – tubes containing CaCl2 and KOH
gives the amounts of H2O and CO2 from which the % of C and
H are calculated.
Mass of C in Mass of CO2
CO2
× formed (m1) g ×
100
Percentage of C =
Mass of Organic
Molecular Mass of
CO2
× compound taken
(w) g

Mass of H in Mass of H2O

H2O
× formed (m2) g × 100
Percentage of H =
Molecular Mass of Mass of Organic
H2O × compound taken
(w) g
 Estimation of Nitrogen

Mass of Mass of CO2 Mass of H2O

O.C (W) g formed (m1) g formed (m2) g
 i) Dumas Method Volume of
N2 = V1 ml

Mass of O.C
=mg

Volume of
N2 = V1 ml
ii) Kjeldahl’s Method

Not applicable for compounds containing nitrogen in

nitro and azo and nitrogen in ring.
 Estimation of Halogens
CARIUS
METHOD

Mass of
O.C = m g

X ͞ + Ag + → AgX (mass of AgX = m1 g )

C + O 2 → CO2, H2 + O2 → H2O
 Estimation of Sulphur

Mass of
O.C = m g

S 2- + HNO3 → H2SO4
H2SO4 + BaCl2 → BaSO4(mass of BaSO4 = m1 g )
Let the mass of the organic compound
taken = m g
Mass of BaSO4 formed = m1 g

% of Sulphur = 32 x m1 x 100
233 x m

Atomic mass of
S in BaSO4
Molar mass of
BaSO4
Estimation of Phosporous

Mass of
O.C = m g

P + HNO3 → H3PO4
(Mass of
Molybdate= m1 g)
% of Phosphorous = 31 x m1 x 100
1877 x m

Atomic mass of
P in Molybdate
Molar mass of
Ammonium Phospho
Molybdate
 ESTIMATION OF OXYGEN
Heat
Compound O2 Other Gaseous
Products
Mass of
In the atmosphere
of CO2
+ Mass of CO2
O.C = m (g) = m (g)
1373K
[2C + O2 2CO ] × 5
[ I2O5 + 5CO I2 + 5CO2 ] × 2
One mole of O2 used to produce 2 mole of CO2

∴ Percentage of oxygen
Percentage of oxygen can also be
determined in terms of Iodine also.
 CHN Elemental Analyzer

The Estimation of Elements in an O.C is carried out by

using microquantities of substances and automatic
experimental techniques.
 Check your Understandig
• Question 1.
Explain the reason for the fusion of an organic compound
with metallic sodium for testing nitrogen, sulphur and
halogens.

• Question 2.
0 .3780 g of an organic chloro compound gave 0.5740 g
of silver chloride in Carius estimation. Calculate the
percentage of chlorine present in the compound.