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APPROCH
TO
ORGANIC SYNTHESIS
FUNCTIONAL GROUP
INTERCONVERSION
Addition
Elimination
Oxidation
Reduction
Why FGI is needed?
A TM containing more than
one functional group, one
functional group may interfere
with desired reaction on
second functional group during
a synthesis.
Why FGI is needed?
This problem can be solved
into ways
a) Use of protecting group
Ph Ph
TM
First step in the retrosynthetic
analysis of TM could be functional
group interconversion to an alcohol
But which alcohol ?
Importance of FGIs
FGI O OH
i Ph Ph
O
Ph Ph
TM FGI O
ii Ph Ph
OH
RETROSYNTESIS
O
FGI O OH
Ph Ph
i Ph Ph
TM
Matched Latent Polarity
O O
(Consonant)
_
Ph Ph
+
O
OH
+ H Ph
Ph
RETROSYNTESIS
O O
FGI
Ph Ph Ph Ph
ii
OH
Mismatched Latent Polarity
(Dissonant)
Functional group
containing heteroatoms
For convenience these
functional groups will be
initially divided into three
major classes depending
upon their oxidation level
a) Carboxylic acid and their
derivatives
Compounds in this class are the highest
oxidation level of organic compounds
It includes
Carboxylic acid (RCO2H)
Esters/lactone (RCOO2R)
Amide/lactam (RCONHR)
They may be interconverted by a series
of simple reactions
Transformations of
carboxylic acid derivatives
O O O H2O
R C N
R O R' R OH
Ketones (RR’C=O)
Imines (RR’C=NR”)
Hydrazones (RR’C=NNHR”)
Oximes (RR’C=NOH)
Transformations of
aldehydes
R'O OR' O
2R’OH/H + HS(CH2)3SH/H+
R H S S
R H
aldehyde H H
H2O R’NH2
Thiols (RSH)
Disulphides (RSSR)
Ethers (ROR)
SOCl2 or
HBr PCl5
R Br R OH R Cl
HO- HO-
Use of a sulphonic ester
as a leaving group
R’SO2Cl
R OH R OSO2R'
Nu-
R Nu + R’SO3-
Interconversions between
the three oxidation levels
a,b & c above
To move between groups
classified in the previous section,
it is necessary to perform a
reduction or oxidation at some
stage.
Oxidation
Nitriles 1 eq.
DIBAL-H O
LiAlH4
R NH2 R CN
Low temp. R H
Unsaturated
Hydrocarbons
OH
HO OH
H2,Pd/C
BH3,NaOH/
H2O2 OsO4
RCO3H O3
H O H
HBr
Br CHO
CHO
Removal of Functional Group
Alcohol to corresponding hydrocarbon
Alcohol
Dehydration
Alkene
Hydrogenation
Alkane
Removal of Functional Group
Aldehydes/ ketones to hydrocarbons
Clemmensen
O Zn,HCl H H
R R'(H)
R R'(H) NH2NH2,KOH
Wolf-Kishner