Organic Chemistry Notes

OUTLINE
•GENERAL INTRODUCTION
•TETRAVALENCE OF CARBON
•STRUCURAL REPRESENTATION OF ORGANIC
COMPOUNDS
•CLASSIFICATION OF ORGANIC COMPOUNDS
•NOMENCLATURE OF ORGANIC COMPOUNDS
•ISOMERISM
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
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 E thene
E thane
CONDENSED STRUCTURAL FORMULA omits lines

between the atoms
CH3 CH3 H2C H2C HCHC

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.
For example
3-Methyloctane can be represented in

various forms as:
a) CH3CH2CHCH2CH2CH2CH2CH3
|
CH3
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 (—).
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).
Forexample:
. 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.
N O M E N C LAT U R E
OF ORGANIC COM
P OUNDS
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
: are called hydrogen
only
hydrocarbons.
I) (Straight chain)
word root (name of number of carbon

atoms in chain) + ane
ii) Branched chain Hydrocarbons
Parent chain
Small chain/
branch/alkyl
Prefix (alkyl) + word root + suffix

Names of branched alkyl group
-H
Alkane → Alkyl
Methane → Methyl
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.
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.
1.The longest chain of 2.Priority order for
carbon atoms polyfunctional group :
containing the
functional group is -COOH,-SO3H,-COOR,
identified and -COCl, -CONH2, -CN,
numbered to get the
carbon with functional -HC=O, =C=O, -OH,
group gets the lowest -NH2, =C=C=,-CΞ C-.
number.
.
Example
:
Hexane-2,4-dione
Name of substituent is placed as prefix to the
word benzene . Example
For disubstituted benzene compounds, lower
numbers should go to carbon containing
substituents.
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-
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.
• Albhabetical order is followed while
writing name.
When benzene is linked to an alkane with
the functional group then benzene ring is
treated a substituent.
2-Phenylethanol
ISOMERIS
M
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.
NAVODAYA VIDYALAYA SAMITI, NOIDA
E-CONTENT FOR CLASS XI CHEMISTRY
UNIT – 12, PART - II

ORGANIC CHEMISTRY – SOME BASIC PRINCIPLES AND
TECHNIQUES
PREPARED BY:
B.BETHANASAMY, PGT CHEMISTRY
JNV, PUDUCHERRY.
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.
The general reaction is depicted as
follows :
Supplies carbon
to new bond
REACTION MECHANISM
A sequential account Details of electron
of each step movement
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
with one of the bond pair
fragments.
Sextet Octet
electrons electrons
with + with ̶
charge charge
• Product of heterolytic •Product of
fission is (a)
Carbocation (or) homolytic fission
Carbonium ion and
carbanions.
is free radicals.
• Order of stability of
carbocation
Types of Attacking Reagents
Nucleophile ( ̶ ) Electrophile ( + )
• Brings an electron pair • Takes away an electron pair
• Nucleus seeking (Nu: ) • Electron seeking(E + )
• Attacks electrophilic centre • Attacks nucleophilic centre

(electron deficient) (electron rich centre)
• Reaction is nucleophilic • Reaction is electrophilic
• Ex. OH ̅ , CN ̅ , H2O , NH3 • Ex. Br + , Cl +, CH3 + ,AlCl3

Electron Displacement Effects in
Covalent Bonds
Permanent Polarization of Temporary Polarization of
the bond the bond
• Under the influence of an • When a reagent
atom or a substituent in approaches to attack it.
the molecule. Example:
Example Electromeric Effect or
1) Inductive Effect Polarisability Effect
2) Resonance Effect
1) 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
withdrawing group). the system.
• Ex. - Cl, - NO2, - CN • EX.(CH3)2CH+

Resonance Effect ( R or M ) Effect –
Polarization due to transfer of electrons between two
pi bonds or from a lone pair to a pi bond in
conjugation.
̶ R Effect + R Effect
• Transfer of electrons • Transfer of electrons away
towards the substituent from the substituent
attached to the attached to the conjugated
conjugated system. system.
Hyperconjugation
A general stabilising interaction. Permanent
effect
It involves delocalisation of σ electrons of C—H
bond of an alkyl group directly attached to an
atom of unsaturated system or to an atom with
an unshared p orbital.
Example
σ bond
Methyl
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 which the reagent gets to which the reagent does
attached. not get attached.
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 :
∆
❑ Solid → Vapor
Sublimable compound + Nonsublimable
impurities
Ex. Naphthalene, Benzoic acid
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

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What are the different types of structural representations of organic compounds?

What are the different types of structural representations of organic compounds?

What are the different classification methods of organic compounds?

What are the different classification methods of organic compounds?

OUTLINE

1. The Lewis structure or dot structure

2. The Lewis structures, however, can

CONDENSED STRUCTURAL FORMULA omits lines

CH3 CH3 H2C H2C HCHC

and the lines representing carbon-carbon bonds are

3-Methyloctane can be represented in

solid-wedge is used to indicate a bond

The dashed-wedge is used to depict the

•Example – Hydroxyl (- OH)

It shows a gradation in physical and

Any two adjacent members of which differ

• Question 2. Write bond line formulas for: Isopropyl

• Question 3. Indicate the σ and π bonds in the following

word root (name of number of carbon

Prefix (alkyl) + word root + suffix

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

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

the branched carbon atoms get the lowest

[Note: the numbers are separated from the

Rule 5 : When two substituents are in equivalent

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

UNIT – 12, PART - II

Energetics during bond

Shifting of single electron

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

• Attacks electrophilic centre • Attacks nucleophilic centre

• Reaction is nucleophilic • Reaction is electrophilic

• Ex. OH ̅ , CN ̅ , H2O , NH3 • Ex. Br + , Cl +, CH3 + ,AlCl3

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

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