Overview of Syllabus
Fundamental of Chemistry(II)
Course No./Subject Code: CHE 322 Semester: II
Nature of Course: Theory Credit: 1
Objective/Aim of this course: To acquire basic knowledge of organic stereochemistry and aliphatic
substitution reactions.
UNIT V: Stereochemistry:
Introduction, Structural Isomers and stereoisomers; Stereoisomerism; Optical activity;
Polarimeter; Specific rotation; Enantiomerism and Optical activity; Chirality; Chiral
centre; Enantiomers and Racemic modification; Configuration; Absolute
configuration(R&S); Sequence rules; Diastereomers; Meso compounds; Reaction
involving stereoisomers; Generation of a chiral certre (only one chiral certre).
UNIT VI: Alkyl halides (Nucleophilic Substitution):
Homolytic and heterolytic bond fission; Structure (the functional group); Classification
and nomenclature of alkyl halides; Physical properties; Preparation; Nucleophilic
aliphatic substitution reactions; Nucleophiles and leaving groups; Rate of reaction (effect
of concentration); The SN2 reaction (mechanism, kinetics, stereochemistry, inversion of
configuration); The SN1 reaction (mechanism, kinetics and stetreochemistry);
Carbocations (structure and relative stability); Rearrangement of carbocations; S N1 vs.
SN2 reactions.
UNIT V: Stereochemistry:
Introduction: Isomerism is the characteristic property of organic compounds. Due to this
unique property there is a possibility of more than one structure for a given molecular formula.
The chemical entities which have the same molecular formula (same number of atoms) but may
differ in structure and are separated by energy barriers are known as isomers. The isomers have
at least one different physical property (melting point, boiling point, solubility, etc) and/or
chemical property. The phenomenon of existence of isomers is called isomerism. The study of
chemistry with reference to three dimensionality (arrangement of atoms and groups related to
one another in three dimensional space also called spatial arrangement of atom and groups) of
the chemical units is Stereochemistry. The structure of a chemical entity is a description of the
sequential bond connectivity of the constituent atoms or groups of the entity including their
orientation in space while constitution of an entity refers to the sequential bond connectivity of
the constituent atom or groups regardless of their direction in the space. Thus, isomers are
broadly classified into two categories:
I. Stereoisomers (Configurational Isomers, and Conformational isomers)
II. Constitutional Isomers (Structural isomers)
Historical Resume:
Isomerism was first recognized in 1827 by Friedrich Wohler when he prepared silver cyanate
and noted that, although its elemental composition was identical to liver fulminate (prepared
by Justus von Leibig the previous year), its properties were quite different. The term isomerism
was coined by J. J. Berzelius in 1830. The term stereochemistry was coined by Victor Meyer of
the University of Heidelberg in 1878 from the Greek word ‘stereo’ meaning three-dimensional.
Stereochemistry is the study of static and dynamic aspects of three dimensional arrangements
of atoms or groups in molecules
Structural Isomers are classified into following types:
Chain Isomers (Nuclear Isomers)
Positional Isomers
Functional Isomers
Metamers
Tautomers (They are in rapid equilibrium unlike other types of structural isomers. They
are inter-convertible by the migration of labile hydrogen and the π bond.)
