Organic Chemistry-I

CHT1137

Stereochemistry of Organic Compounds

Dr. Hitesh Pawar

Assistant Professor
DBT-ICT-CEB, Institute of Chemical Technology
Mumbai-400 019, India
hs.pawar@ictmumbai.edu.in,

Organic Chemistry-1 Stereochemistry Institute of Chemical Technology Mumbai-400 019

 Classification of Stereoisomers

Stereoisomer
(Isomer with difference in 3D
arrangement only)

Conformational Isomer Configurational Isomer

(Isomers which are readily converted
(No rotation possible through
into each other through single bond
single bond

Eclipsed Gauche
conformation conformation Anti Geometrical Optical
conformation
Staggered
Conformation

Cis and Trans E and Z D and L Enantiomer

configuration configuration isomer and
Diastereomers
Organic Chemistry-1 Stereochemistry Institute of Chemical Technology Mumbai-400 019
 1. Geometrical isomerism
- Isomers which differ in spatial arrangement of atoms or group attached to double bonds or rings
are called as geometrical isomerism.
- The geometrical isomerism arises when atoms or groups are arranged differently in space due to
restricted rotation of a bond or bonds in a molecule.
- Geometrical isomers are not radially interconvertible

Geometrical isomer Geometrical isomer

- The C=C double bond consist of Π-bond and σ-bond which is difficult to rotate the substituents
at 180o since Π-bond must be broken for rotation which requires 264 kJ/mol of energy thus
rotaion around double bond crates hindrance.
Organic Chemistry-1 Stereochemistry Institute of Chemical Technology Mumbai-400 019
 - There are two geometrical isomers (cis & trans) possible in case of 1,4–dimethylcyclohexane

- The methyl groups are arranged differently about

or
the plane of the cyclohexane ring.
- These isomers are not inter convertible since it is
not possible to rotate the bonds in the cyclohexane
or
ring.

- The geometrical isomers often show different physical and chemical properties.
- The difference in their physical properties is more significant when there is more difference in
their polarity.
- Usually the dipole moment of cis-isomers is greater than that of trans isomers. Hence the cis
isomers usually have more solubility in polar solvents.
- In general, the trans isomers are more stable than cis isomers.

Organic Chemistry-1 Stereochemistry Institute of Chemical Technology Mumbai-400 019

  Cis and Trans isomer Nomenclature

A: Cis-isomer: (Latin: on this side)

Similar groups are on the same side of double bond, it is called as cis isomer.
B: Trans isomer: (Latin: across)
Similar groups are on the opposite side of double bond, it is called as trans isomer.

1. Compound of type ABC=CAB (two different substituents)

Cis Trans cis-2-butene trans-2-butene Malic acid Fumaric acid

2. Compound of type ABC=CAD (three different substituents)

Cis Trans Cis Trans

Cis Trans 1-chloropropane
Organic Chemistry-1
Isocrotonic Stereochemistry
acid crotonic acid 1-chloropropane
Institute of Chemical Technology Mumbai-400 019
 Examples

Trans Cis
Cis Trans Trans Cis

Trans Cis Trans Cis

Trans Cis

Trans Cis Trans Cis Trans Cis

Organic Chemistry-1 Stereochemistry Institute of Chemical Technology Mumbai-400 019