DR. PRAVIN S. JOGI
Transcript of DR. PRAVIN S. JOGI
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DR. PRAVIN S. JOGI M.Sc., NET, Ph.D.
HEAD & ASSISTANT PROFESSOR
DEPARTMENT OF CHEMISTRY
JANATA MAHAVIDYALAYA, CHANDRAPUR
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ISOMERISM
Same MF with different chemical
structure……
Eg
C2H6O
C
H
H
H
C O
H
H
H
CH
H
H
OC
H
HH
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CLASSIFICATION OF ISOMERS
ISOMERS
STRUCTURAL OR
CONSTITUTIONAL ISOMER
• CHAIN
• POSITIONAL
• FUNCTIONAL
• METAMERS
• TAUTOMERS
STEREOISOMERS
• OPTICAL
• GEOMETRICAL
• CONFORMER
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WHY NEED TO STUDT STEREOCHEMISTRY ?
The properties of many drugs depends on
their stereochemistry:
Pt
Cl
Cl
NH3
NH3
CIS
Pt
H3N
Cl
Cl
NH3
TRAN
ANTINEOPLASTIC DRUGSNON-ANTINEOPLASTIC DRUGS
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Cl
O
NHCH3
R-KETAMINE
Cl
O
NHCH3
R-KETAMINE
ANASTHETICHALLUCINOGEN
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The difference in odor between caraway seeds and mint leaves arises
from two stereoisomers of carvone due to different arrangement of
atoms at the carbon (*)
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DIFFERENCE BETWEEN STRUCTURAL AND STEREOISOMER
C
H
H
H
C O
H
H
H C
H
H
H
C O
H
H
H STRUCTURAL
STEREOISOMERSC
COOH
CH3
OHHC
COOH
CH3
HHO
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• Tetrahedral carbon, Asymmetric carbon
C
H
HH
HBr
Cl
I
F
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C
A
B
C
DC DC
A
B
CONVERTION OF TETRAHEDRAL STRUCTURE INTO FISCHER
PROJECTION FORMULA
C
A
B
DC
OBSERVER
A
B
DC
Horizontal-near to observer
Vertical-away from observer
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C OHH
CHO
CH2OH
C
CH2OH
CHO
OHH
C
CHO
HOH2C
H
OH
CONVERTION OF 3D INTO PLANER STRU.
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CONFIGURATION
•An absolute configuration refers to the spatial arrangement of
atoms of a chiral molecular entity (or groups) and its
stereochemical description. It is determine by X- ray
crystallography.
C
CHO
CH2OHHHO
C
CHO
CH2OHHOH
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Methods of determining relative configuration.
Method-1D ,L- configuration: RELATIVE CONFIGURATION
Method-2R ,S- configuration: ABSOLUTE CONFIGURATION
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RELATIVE
CONFIGURATION
C
CH2OH
OH
CHO
H C
CH2OH
H
CHO
HO
(+)-GLYCERALDEHYDE (-)-GLYCERALDEHYDE
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D and L Assignments
CHO
H OH
CH2OH
D-(+)-glyceraldehyde
Chapter 6 16
COOH
H2N H
CH2CH2COOH
L-(+)-glutamic acid
*
Penultimate carbon is the stereocenter farthest away from the carbonyl group. If the higher priority group is on the left, then (L), if on the right then (D) sugar.
CHO
H OH
HO H
H OH
H OH
CH2OH
D-(+)-glucose
*
*
*
*
*
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What is the meaning of……
1.D-(d)-Glucose
2.L-(d)- Glucose
3.D-(l)-Glucose
4.L-(l)-Glucose
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CONFIGURATION AND THE R-S
CONVENTION
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Rule 1
The atoms directly attached to the stereogenic center are ranked according to atomic
number. The higher the atomic number, the higher the priority
Rule 2
If a decision cannot be reached with rule 1, work outward from the
stereogenic center until a decision is made. Example of ethyl and methyl
below.
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Rule 3
Multiple bonds are treated as if they were an equal number of single bonds.
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Which group has the higher priority, isopropyl or vinyl?
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Assign the configuration (R or S) to the following enantiomer of 3-methyl-hexane
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CCH
3
CH2CH
2Br
H
CH(CH3)
2
CH2
O
O
H
H
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Example: Name the following compounds.
C
H
Br
CH2CH
3
CH3
CH3Br
CH3H
CH3H3C
ClHH Br
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CLASIFICATION OF STEREOISOMERS
1.OPTICAL ISOMERS
2. GEOMETRICAL ISOMERS
3. CONFORMATIONAL
ISOMERS
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Optical activity – When a substance rotates
the plane of plane polarized light. (1815 by
Biot)
Plane polarized light – Light that has been
passed through a nicol prism or other
polarizing medium so that all of the vibrations
are in the same plane.
non-polarized polarized
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POLARIMETER – An instrument used to measure optical activity.
light source sample tube
polarizer analyzer
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DEXTROROTATORY – when the plane of polarized light
is rotated in a clockwise direction when viewed through
a polarimeter.
(+) or (d) do not confuse with D
LEVOROTATORY – when the plane of polarized light is
rotated in a counter-clockwise direction when viewed
through a polarimeter.
(-) or (l) do not confuse with L
The angle of rotation of plane polarized light by an
optically active substance is proportional to the number
of atoms in the path of the light.
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Stereoselective and stereospecific
reactions.* *
CH3CH=CHCH3 + Br2 → CH3CHCHCH3
Br Br
2-butene 2,3-dibromobutane
2 geometric isomers 3 stereoisomers
cis- and trans- (S,S)-, (R,R)-, and (R,S)-
meso-
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C C
H
CH3
H3C
H
TRAN OR E 2-BUTENE
CH3
BrH
BrH
CH3
MESO-2,3-DIBROMOBUTANE
Bromiation
Br BrCH3
HBr
HBr
CH3
A reaction in which stereochemically different molecules react differently
is called a stereospecific reaction. In this case the cis- and trans-
stereoisomers give different products.
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C C
CH3
H
H3C
H
CIS OR Z 2-BUTENE
CH3
BrH
HBr
CH3
CH3
HBr
BrH
CH3
S,S-2,3- DIBROMOBUTANE
R,R-2,3 -DIBROMOBUTANE
Bromiation
Br Br
PRODUCT IS RACEMIC MIXTURE
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HOMOTOPIC ATOMS
C C
H
H
H H
HH
C C
H
H
H Cl
HH
C C
H
H
H H
HCl
H By ClH By Cl
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ENANTIOTOPIC ATOM
C C
H3C
CH3
H H
HH
C C
H3C
CH3
H Cl
HH
C C
H3C
CH3
H H
HCl
H By ClH By Cl
R-2-CHLOROBUTANES-2-CHLOROBUTANE
n-BUTANE
PRODUCTS ARE ENANTIOMERS OF EACH OTHER
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C C
H
HH3C
H
H by ClH by Cl
C C
H
ClH3C
H
C C
Cl
HH3C
H
PRODUCTS ARE DIASTEREOMERS OF EACH OTHER
DIASTEREOTOPIC ATOM
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THANK
YOU