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15 Isomerism Formula Sheets Quizrr

The document discusses different types of isomerism: 1. Structural isomerism includes chain, positional, functional, ring-chain, and metamerism isomers arising from differences in molecular structure and atom connectivity. 2. Stereoisomerism includes cis-trans and optical isomers arising from non-superimposable 3D structures. 3. Tautomerism is a special type of functional isomerism where structural isomers interconvert through hydrogen atom migration between atoms, such as keto-enol tautomerism between carbonyl and enol forms.

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83 views5 pages

15 Isomerism Formula Sheets Quizrr

The document discusses different types of isomerism: 1. Structural isomerism includes chain, positional, functional, ring-chain, and metamerism isomers arising from differences in molecular structure and atom connectivity. 2. Stereoisomerism includes cis-trans and optical isomers arising from non-superimposable 3D structures. 3. Tautomerism is a special type of functional isomerism where structural isomers interconvert through hydrogen atom migration between atoms, such as keto-enol tautomerism between carbonyl and enol forms.

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ISOMERISM
Definition:
The different organic compounds having same molecular formula but different physical or chemical or both the
properties are called isomers and the phenomenon is called Isomerism.
Isomerism

Structural Stereo isomerism


isomerism or space isomerism

Chain isomerism
Configurational Conformational
Positional
Functional
Metamerism Geometrical Optical
Ringchain or
Tautomerism Cis-trans isomerism

A. STRUCTURAL ISOMERISM
Arises due to the difference in the manner of linkage of atom to atom.
1. Chain isomerism/Skeleton/Nuclear :
The structural isomerism which arises due to the difference in the length of C-chain is called chain isomerism.
(a) H3C – CH2 – CH2 – CH3 & CH3 – CH – CH3
n-Butane
CH3
iso-Butane

CH3

(b) CH3CH2CH2 CH2CH3, CH3– CH– CH2CH3 & CH3 – C – CH3


n -Pentane
CH3 CH3
iso-Pentane neo-Pentane

2. Positional Isomerism :
The structural isomerism which arises due to the difference in the position of
(a) Double bond (b) Triple bond
(c) Same functional groups

 CH3  CH  CH  CH 3 , CH3  CH  CH  CH 2
e.g. But  2  ene But  1  ene

 CH3  CH 2  CH 2OH, CH3  CH  CH3


1  Pr opanol
OH
2  Pr opanol
1
6 2 1,2/1,6 = ortho
1,5/1,3 = meta
5 3 1,4 = para
4 X
X X
Y

Y
ortho meta Y
para
3. Functional Isomerism :
The isomerism which arises due to the difference in their functional group is called as functional isomerism.
General Formula Homologous Series Homologous Series
CnH2n+2O Alcohol Ether
CnH2n+2 Aldehyde Ketone
CnH2nO Acid Ester
Cn+1H2n+1N Cyanide Isocyanide (carbylamine)

(i)  CH3CH 2CH 2CH 2OH & CH3  CH 2  O  CH 2  CH3


Butylalcohol Diethylether

(ii) C2 H5OH & CH3  O  CH3


Ethylalcohol Dimethylether

4. Metamerism :
- The structural isomerism which arises due to the difference in the distribution of C-atom on the either or both
sides of same functional group.
- Metamers can also be chain and position isomers.
Some examples of Metamerism

(i) CH3  O  CH3  CH 2  CH3 , CH3  CH 2  O  CH 2  CH3  CH3  O  CH  CH3


|
CH 3
O O
(ii) CH3 – C – CH2 – CH2 – CH3 and CH3 – CH2 – C – CH2 – CH3
2-Pentanone 3-Pentanone
5. Ring Chain Isomerism
Shown by unsaturated hydrocarbons and alicyclic compounds.
e.g. CH3CH2CH = CH2
CH3CH2–CH = CH2 &
But-1-ene Cyclobutane
* Ring chain isomers are actually a type of functional isomers.
6. Tautomerism :
- It is special type of functional isomerism in which two functional isomers interconvert due to the movement of an
acidic H-atom between two poly valent atoms. Here two isomers exist in dynamic equilibrium and hence it is also
known as desmotropism/kryptomerism/Alleotropism.

O O H

Shown by the compounds having  C , –N = O,  N  O, – CN groups attached with  C group.

- Tautomerism arises due to shift of an atom from one site in the molecule to another equivalent site in the same
molecule.

SOME EXAMPLES OF TAUTOMERISM :


(i) Keto-enol tautamerism :
O

- Aldehydes and ketones containing  C CH  group shows tautomerism.


2

OH

- Enol containing  C  C  group shows tautomerism.

O H OH H
|| | | |
 C C   C  C
|
H enol form

H OH
O | |
H  C C  C H
CH3  C  CH3 | |
H H
Keto.form
enolform
99%
(1%)

-  -diketones have more enolic content due to theformationof chelation.


O H O O OH
|| | ||
CH3  C C H  C CH3 CH3 – C – CH = C – CH3
enol form

O------HO

CH3 – C C – CH3
CH

Order of enol-content of some molecule :


O O O O O
|| || || || ||
CH3  C CH 2  C  CH3  CH3  C  CH 2  C H  CH3  C  CH3  CH3CHO

H
H
(ii) Nitro-aci tautomerism : H – C – N = O C = N – OH
H
H O O
Nitro form aci form

H
H
(iii) Nitroso-oximino form : H – C – N = O C=N–O–H
H
H
Nitroso form Oximino-form

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