Two or more than two organic compounds having the same
molecular formula and molecular weight but different physical or chemical or both properties are called isomers and the phenomenon is called isomerism.
Propanoic acid Methyl ethanoate
O CH3–CH2–COOH CH3–C–O–CH3
Water soluble Water insoluble
ISOMERISM
Structural Isomerism Stereoisomerism
ISOMERISM
Structural Isomerism Stereoisomerism
Chain Conformational
Position Configurational
Ring Chain Geometrical
Functional Optical Metamerism Tautomerism The compounds which have same molecular formula, same functional group, same position of functional group or multiple bond or substituent but different arrangement of carbon chain (main chain or side chain) shows chain isomerism
CH3 — CH — CH3 1. CH3 — CH2 — CH2 — CH3 CH3
Butane(4C) 2-Methyl propane (3C)
The compounds which have same molecular formula, same functional group, same parent carbon chain but different position of functional group or multiple bond or substituents, are position isomers.
N TE
Chain and position isomer can not be present, simultaneously as
for Position isomer carbon chain length must be same. EXAMPLE
1-Chlorobutane | Cl 2-Chlorobutane Same molecular formula but different mode of linking (open chain or closed chain) of carbon atoms.
CH3 — CH = CH2 [open chain]
C3H6 CH2 / \ CH2 — CH2 [closed chain or ring]
They have same molecular formula so they are Ring chain isomers. Compounds having same molecular formula, but different functional groups are called functional Isomer.
(i) Alcohol and ether
CH3 — CH2 — OH and CH3 — O — CH3
(ii) Alcoholic and phenolic compounds
OH CH2OH CH3 and
(iii)Aldehydes and ketones
CH3 — CH2 — C — H and CH3 — C — CH3
|| || O O (iv) Acids and ester
CH3 — CH2 — C — OH and CH3 — C — O — CH3
|| || O O
(v) Cyanide and isocyanide
CH3 − CH2 − CH2 − CN and CH3 − CH2 − CH2 − NC
(vi) Nitro and Nitrite
O CH3 − CH2 − N and CH3 − CH2 − O − N = O O
(vii) Amide and Oxime
CH3 − C − NH2 and CH3 − CH = NOH and CH3CH2 − N = O
O O O || || || MeCH2CH2 − C − NH2 , MeCH2 − C − NH − Me , Me − C − N − Me | Me
10, 20, 30 amides are different functional group.
It arises due to different alkyl chains on either side of the functional group in the molecule. Polyvalent Functional group [More than one valency] are : 1. O
2. S
3. C
O O
4. C O C
O Polyvalent Functional group [More than one valency] are :
5. C NH 9. C O
O O
6. C N
7. NH
8 N EXAMPLE Check whether the given molecules are metamers of each other
1. CH3 − O − CH2 − CH2 − CH3 CH3 − CH2 − O − CH2 − CH3
(3) CH3 − C − CH2 − CH2 − CH2 − CH3 & CH3 − CH2 − C − CH2 − CH2 − CH3 || || O O
(4) CH3 − C − O − CH2 − CH2 − CH3 & CH3− O− C − CH − CH3
|| || | O O C H3 Priority order of Structure isomerism
R>T>F>M>C>P EXAMPLE Relationship between molecules :–
(i) &
Solution
Ans. No Isomer EXAMPLE [JEE (Main) 2021] Which one of the following pairs of isomers is an example of metamerism ? CH3 O (1) CH3CH2CH2CH2CH3 and H3C–C–CH3 (2) C6H5 and H5C6 H CH3 O OH O O (4) (3) OH and H5C6 and H5O6
