Paaras Thakur

Stereochemistry

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Stereochemistry
 Introduction

• Stereochemistry is the three-dimensional structure of a molecule but

How important is stereochemistry?
• Starch and cellulose are two polymers that belong to the family of biomolecules
called carbohydrates.

• Cellulose and starch are both composed of the same repeating unit.

• Starch and cellulose are isomers because they are different compounds with
the same molecular formula (C6H10O5)n. They are stereoisomers because only
the three-dimensional arrangement of atoms is different.
The Two Major Classes of Isomers

Constitutional Isomers

• Differ in the way the atoms are connected to each other

• Have different IUPAC names

• Have same or different functional groups

• Have different physical properties, so they are separable by physical

techniques such as distillation

• Have different chemical properties.

The Two Major Classes of Isomers

Constitutional Isomers
The Two Major Classes of Isomers

Stereoisomers

• Differ only in the way atoms are oriented in space

• Stereoisomers have identical IUPAC names (except for a prefix like cis or
trans), same physical properties.
• Because they differ only in the 3D arrangement of atoms, stereoisomers
always have the same functional group(s).
Example Classify each pair of compounds as constitutional isomers or stereoisomers.
Subdivision of Isomers
Configuration and Conformation
Configuration and Conformation
 Configuration and Conformation

Structures that can be interconverted simply by rotation about single bonds

are conformations of the same molecule.

Structures that can be interconverted only by breaking one or more bonds

have different configurations, and are stereoisomers
 Geometrical isomerism

These isomers result from restricted rotation. Restricted rotation can be caused
by either a cyclic structure or a double bond.
 Geometrical isomerism

These isomers result from restricted rotation. Restricted rotation can be caused
by either a cyclic structure or a double bond.

Conditions of geometrical isomerism

(I) Geometrical isomerism arises due to the presence of a double bond or a

ring structure
 Geometrical isomerism

(II) Different groups should be attached at each doubly bonded atom.

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