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Conformational Isomers 2 Sep Offline

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11 views4 pages

Conformational Isomers 2 Sep Offline

Goc

Uploaded by

Amandeep Kaur
Copyright
© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
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ARORA CLASSES CONFORMATIONAL ISOMERISM BY KAJAL MAM

CONFORMATIONAL ISOMERS
Isomerism are of two types
Stereoisomers are further classified into three type:
1. Conformational isomerism
2. Optical isomerism
3. Geometrical isomerism
CONFORMATIONAL ISOMERISM
The different arrangements of atoms in space that result from the free rotation of groups about C –C (single) bond axis are callled
conformation or conformational isomers or rotational isomers and the phenomenon is known as conformational isomerism.
This type of isomerism is found in alkanes, cycloalkanes and their derivatives. Representation of conformers
(i) Sawhorse formula
In this representation, molecule is viewed slightly from above and from right side
of one carbon atom Carbon – carbon bond is drawn diagonally and slightly elongated and remaining
six bonds attached to each carbon atom are represented as straight line

(ii) Newman projection formula


In this representation, the molecule is viewed along the carbon – carbon single bond
The front carbon atom is represented by a point and groups attached to it are
represented by equally spaced radii. Whereas rear carbon atom is represented by
circle and groups attached to it are represented by three equally spaced radial extensions

Conformations of ethane ( CH3 – CH3 )


Two extreme conformation are important, staggered and eclipsed. There can be
number of arrangements between staggered and eclipsed forms and these
arrangements are called skew forms.
(i) Eclipsed conformation
In this conformation rotation about C – C single bond is such that hydrogen atoms
of front carbon atom completely cover or eclipse the hydrogen atom of rear
carbon atom.
In this conformation, hydrogen atoms of two carbon atoms are at minimum
distance which makes conformation unstable
(ii) Staggered conformation
In this confirmation rotation about C – C bond is by an angle of 60O so that hydrogen atoms of two carbon atoms are at maximum
distance from each other making it stable.
In staggered conformation, all the six hydrogen atoms are visible
(iii) Skew conformation
In this conformations, hydrogen atoms are closer than in staggered but way than in eclipsed conformation
The relative stabilities of the various conformation of ethane are in the following order
Staggered > Skew > eclipsed
Ethane is mostly in staggered form.

The order of stability of n-Butane conformations is


Anti > gauche = gauche > partially eclipsed = partially eclipsed > fully eclipsed
Trick- Ag pet full
Factors affecting stability of conformations
(i) Torsional strain
Torsional strain arise due to repulsive interaction between bonds on
adjacent atoms
As the repulsive interaction between electronic cloud increases, torsional
strain increases and thus stability decreases.
(ii) Steric strain
Steric strain arises due to crowding around central atom more the bulky
groups present around the central more will be steric strain and thus less
will be stability.
For example, gauche conformation of n-Butane is less stable than anticonformation
Baeyer’s strain theory
Amount of deviation (d) = ( 109O28’ – Bond angle of the ring)
Cyclohexane is free from angle strain and hence is quite stable and unreactive.
Therefore, cyclohexane adopts a non-planar structure.
Intramolecular hydrogen bonding also influences the relative stability of conformations of a molecule

For example in ethylene glycol gauche conformations are more stable than anti form due to intramolecular hydrogen bonding.
QUESTION
IN CASE OF ETHYLENE GLYCOL WHICH IS MOST STABLE?
Conformations of cyclohexane

Order of relative stabilities of various conformations of cyclohexane is :


chair > twist boat > boat > half chair
PYQ- Which is stable conformation of cyclohexane
a. chair b. twist boat c. boat d. half chair
Chair conformations
It is most stable conformation of cyclohexane as it is free angle and torsional
strain as all groups are staggered and bond angles are tetrahedral.
Axial and equatorial bond in cyclohexane
Hydrogen atoms are perpendicular to the ring are called axial hydrogen atoms
and hydrogen atom lying in the plane of ring are called equatorial hydrogen
atom.
Boat conformation- twist boat

If in the boat conformation of cyclohexane bond along C2 – C3 and C5 – C6


Is twisted in such a way that flagpole hydrogens move away.
Torsional strain in this conformation is less, making it more stable than boat conformation
Half chair conformation
It transition state conformation chair and twist boat conformation

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