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Conformations and Their Representations: Conformational Isomers

This document discusses conformational isomerism, which results from different three-dimensional arrangements of a molecule from rotation around a single carbon-carbon bond. It defines terms like conformers, dihedral angle, and classifications of conformations like eclipsed, staggered, and skewed. It also describes how to represent conformations using Newman projections and discusses torsional and steric strain that can result from different conformations.

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15 views14 pages

Conformations and Their Representations: Conformational Isomers

This document discusses conformational isomerism, which results from different three-dimensional arrangements of a molecule from rotation around a single carbon-carbon bond. It defines terms like conformers, dihedral angle, and classifications of conformations like eclipsed, staggered, and skewed. It also describes how to represent conformations using Newman projections and discusses torsional and steric strain that can result from different conformations.

Uploaded by

arya1234
Copyright
© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
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Download as DOCX, PDF, TXT or read online on Scribd
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I-1: Conformational Isomerism |1

 Conformations and their representations


 Dihedral angle, Eclipsed, Staggered & Skewed conformation
 Torsional and Steric Strains
 Drawing most stable and least stable conformations
 Conformational analysis of some molecules
 Conformations of Cyclohexane
 Relative stability of substituted cyclohexane

Conformations and their representations


Conformational Isomers: Different 3D arrangements of a molecule resulting from rotation around a
single C- C bond (σ-bond) are called conformational isomers.

Note the following:


(1) Term rotamer and Conformer are interchangeably used for conformational isomer.
(2) Due to axial (head-on) overlap in σ-bond rotation is possible while due to lateral (side-on) overlap
rotation is not possible around a double or triple bond. So, Alkenes and Alkynes do not exibit
conformational isomerism.
(3) Relation of two groups changes every second. Actauly, the energy possessed by the molecule also
changes every second.
(4) There are infinite number of conformations corresponding to each orientation about single bond
in contrast to other type of isomers where we do have finite number of isomers.
(5) Difference between Conformation and Configuration isomers: To get from one conformation to
another, we can rotate about single bond(s). We do not need to break any bond to get a different
conformer only thing we need to do is the rotation about single bond. But in case we want to
convert one configurational isomer to another we need to break the bonds and rearrange the
atoms in space.

Study of conformations: All conformations of a molecule are not equally stable. So, different
conformers are studied to asses their relative stability or relative potential energy.

Conformational analysis: Study of the change of molecular structures and molecular energy w.r.t.
rotation around σ-bond is called as conformational analysis.

Representation of conformers: Conformations can be shown by Bond-line, Sawhorse or Newman


projections:

Newman projection: Newman projection is frequently used to draw the different conformations of a
molecule. Following steps are followed to draw the Newman projection:
(1) Convert problem into a Bond-line structure
I-1: Conformational Isomerism |2

(2) Highlight the bond of interest. Label the carbon atoms with numbers for convenience

(3) Draw or imagine the eyeball glaring along the highlighted bond

(4) Surround only the bond of interest with all implied hydrogens

(5) Draw front carbon with 3 groups in the front, and back carbon with 3 groups in the back

Note that Newman projection is dependent on perspective direction:


I-1: Conformational Isomerism |3

Example-1: Draw the Newman projection of following molecule:

Solution: We need to draw the newman projection along C2-C3. C2 is front carbon; C3 is back
carbon. Newman projection is as follows:

Example-2: Draw the Newman projection of following molecule:

Solution: Newman projection is as follows:


I-1: Conformational Isomerism |4

Exercise:
Draw the Newman projections of following molecules as per perspective mentioned:
(1)

(2)

(3)

(4)

(5)

(6)
I-1: Conformational Isomerism |5

(7)

(8)

(9)

(10)

Converting Newman projection to Bond-line structure:


I-1: Conformational Isomerism |6

Example-1: Convert the following Newman projection to Bond-line structure:

Solution: Numbering the Carbon atoms and converting step-by-step:

Example-2: Convert the following Newman projection to Bond-line structure and write down its
IUPAC name:

Solution: Numbering the Carbon atoms and converting step-by-step:

Hence, the compound is 2.3-dimethylheptane

Exercise:
Draw the Newman projections of following molecules as per perspective mentioned:
(1)

(2)
I-1: Conformational Isomerism |7

Dihedral angle, Eclipsed, Staggered & Skewed conformation

Dihedral angle: A dihedral angle or torsional angle (symbol: θ) is the angle between two bonds
originating from different atoms in a Newman projection. Note that Bond angle is not the Dihedral
angle. So, Dihedral angle has nothing to do with angle between two substituents of same carbon
atom:

Eclipsed conformation: If all the groups on the back carbon are exactly behind ones on the front
carbon. They are aligned. This is called the Eclipsed conformation. Dihedral angle in eclipsed
conformation is 0 0.

Eclipsed conformation is divided into two categories: Partially eclipsed and Fully eclipsed.
 In fully eclipsed conformation two large groups are able to fully eclipse each other.
 In partially eclipsed conformation groups are not able to fully eclipse each other.

Staggered conformation: If bonds on front carbon are as far as possible from the bond of back
carbon then this conformation is called as staggered conformation. Dihedral angle in staggered
conform tion is 60 0.
I-1: Conformational Isomerism |8

Staggered conformation is divided into two categories: Anti and Gauche.


 In Gauche conformation Dihedral angle between two larger group is 60 0 or the groups are
next to each other.
 In Anti conformation Dihedral angle between two larger group is 180 0 or the groups are
opposite to each other.

Skewed conformation: Anything else between eclipsed and staggered is called skewed
conformation. So, there can be infinite skewed conformations between eclipsed and staggered
conformations.

Summary of the above classification is as follows:


I-1: Conformational Isomerism |9

Torsional and Steric Strains

Present in Eclipsed conformation only.


Acts 3 atoms apart.
Repulsion between bonds or bond electrons
Also known as Bond Eclipsed Strain

Steric Strain
Can be in Stageered as well as Eclipsed conformation
Vanderwall intercation
Acts more than 3 atoms apart.
Repulsion between electron clouds of bulky groups
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I - 1 : C o n f o r m a t i o n a l I s o m e r i s m | 11
I - 1 : C o n f o r m a t i o n a l I s o m e r i s m | 12
I - 1 : C o n f o r m a t i o n a l I s o m e r i s m | 13
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