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5 Woodward Rule - Pps

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104 views37 pages

5 Woodward Rule - Pps

Uploaded by

al yasa
Copyright
© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
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Spectroscopy

Structural Analysis
(Application of Woodward-Fieser Rules)
U.A. Deokate

Copyright © by U. A. Deokate, all rights reserved.


Woodward-Fieser Rules
 It is used for finding absorption maxima
position (λMax)
 This differs from observed values by 5-6%.
 Effect of substituent groups can be reliably
quantified by use Woodward –Fieser Rule
 Separate values for conjugated dienes
and trines and α-β-unsaturated ketnones
are available
Woodward-Fieser Rules
 Woodward and the Fiesers performed extensive studies of
terpene and steroidal alkenes and noted similar substituents
and structural features would predictably lead to an
empirical prediction of the wavelength for the lowest energy
p p* electronic transition

 This work was distilled by Scott in 1964 into an extensive


treatise on the Woodward-Fieser rules in combination with
comprehensive tables and examples – (A.I. Scott,
Interpretation of the Ultraviolet Spectra of Natural Products,
Pergamon, NY, 1964)

 A more modern interpretation was compiled by Rao in 1975


– (C.N.R. Rao, Ultraviolet and Visible Spectroscopy, 3rd
Ed., Butterworths, London, 1975)
Terminology
 Alkenes are named by dropping the -ane ending
of the parent and adding -ene.
 Conjugated :organic compound; containing two
or more double bonds each separated from the
other by a single bond
 Dienes: One of a class of organic compounds
containing two ethylenic linkages (carbon-to-
carbon double bonds) in the molecules. Also
known as alkadiene; diolefin.
Terminology
 Endocyclic double bonds have both
carbons in the ring and exocyclic double
bonds have only one carbon as part of the
ring.
 Cyclopentene is an example of an endocyclic
double bond.
 Methylenecylopentane is an example of an
exocyclic double bond.
Woodward
Fieser
Rule
for
Dienes
&
Polyenes
Problem Illustration -1
Problem Illustration -2
Problem Illustration -3
Problem Illustration -4
Woodward
Fieser rule for
undsaturated
carbonyl
compound
Problem Illustration - 5
Problem Illustration - 6
Problem Illustration - 1
Problem Illustration - 2
Worked Problem - 1
Worked Problem - 2
Worked
Problem -
3
Worked Problem - 4
Worked Problem - 5
Worked Problem - 6
Worked Problem - 7
Worked Problem - 8
EMPIRICAL
RULES FOR
BENZOYL
DERIVATIV
ES
Problem - 1
Problem - 2
Problem -
3
Problem -
4
Problem
-5
Fieser Rules
 If more than four double bonds are present the
Woodward rule is not applicable
 The plant pigments contains double bonds up to
11 for this Fieser Rules is used.
 λMax= 114 + 5(M) +n(48-1.7n)- 16.5Rendo-10 Rexo
 n=no of conjugated double bonds
 M= no of alkyl or alkyl like Substituents
 Rendo= No of endocyclic double bonds
 Rexo = No of exocyclic double bonds
Fisher Problem-1

λMax= 114 + 5(M) +n(48-1.7n)- 16.5Rendo-10 Rexo


= 114 + 5 (8) + 11(48-1.7x 11) –0 -0 = 476
Fisher formula
Fisher Problem-2

λMax= 114 + 5(M) +n(48-1.7n)- 16.5Rendo-10 Rexo


= 114 + 5 (8) + 11(48-1.7x 11) –0 -0 = 476
Fisher formula
Fisher Problem-3

λMax= 114 + 5(M) +n(48-1.7n)- 16.5Rendo-10 Rexo


= 114 + 5 (8) + 18(48-1.7x 18) –0 -0 =
Fisher formula

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