Isomerism in Organic Compound

DR. Marham Sitorus, M.Si

Isomerism
Same FM difrent Structure
(different properties)
 Types of isomerism

Isomerism

Structural Stereoisomerism
isomerism
Fungtional
Isomerism Geometric Optical
isomerism isomerism
 Structure Isomerism

Difrent structure same molecular formula

Ex: 1. n- pentane – iso-pentane and
neo-pentane
2. n-propanol and 2- propanol
3. 2- hexanone and 3 – hexanone
4. 1- fluoro prapane and 2- fluoro
propana
Ect
 Functional Group Isomerism

Difrent functional group same MF

• Alkhohol and Ether
Ethanol and dimethyl ether
• Aldehide and Ketone
Propanaldehide and Acetone
• Carboxilic acid and Esther
Buthanoic acid and Ethyl acetate
 Newman Conformational
• More in 5 and 6 carbon (Bayer Theory)
cycloprpane : amplope conformational
cylohexane : boat and chair conformational
• Alifatic compound Conformational:
eclips and staggered
 Geometries Isomers
Difrent geometries same MF
• Alkene (Sp2) hybrid
• C(Cis) – t(Trans)
• Z (Zusamen) – E(Engegen)
 Build these models

trans but-2-ene
Cis but-2-ene
Two isomers are not interchangeable.

• Carbon 2 & 3 joined by

double bond.
• No free rotation.
• Bonds would have to be
broken and reformed.
• +270 kJ mol-1 energy needed
to break this bond.
• Insufficient energy available
at room temperature.
 cis...
• Different names
needed to identify
isomers.
• Substituent groups
on the same side of
double bond.
Cis but-2-ene
• Cis but-2-ene
 ...and trans.
• “trans” means other
side or cross over
e.g. trans Atlantic,
transplant, trans…..!
• Substituents on
trans but-2-ene
opposite sides of
double bond.
Different compounds- different properties.
Time to think and apply what we have
learned!
• How are the structures of
nerol and geraniol related?

• How many moles of H2

would be needed to
saturate one mole of
geraniol?
• How are nerol and geraniol
related to citronellol?
• How are the structures of
nerol and geraniol related
to linalool?
 Geometries Isomers in Fat & Oils
• Linoleic : 18 : 2(9,12) or omega-6
• Linolenic : 18 : 3 (9,11,15) or omega-3
• Ricinoleic: 18 : 1 (9), (12-OH)
• CLA (Conjugated Linoleic Acid) : 18:2 (9c,11t).
if not mention geometry is cis (c)
 Fischer Projection

a
b d
d Carbon atom