EBK ORGANIC CHEMISTRY-STUD.SOLNS.MAN+SG
EBK ORGANIC CHEMISTRY-STUD.SOLNS.MAN+SG
4th Edition
ISBN: 9781119659525
Author: Klein
Publisher: WILEY CONS
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Chapter 16.11, Problem 5LTS
Interpretation Introduction

Interpretation:

The expected value for λmax of the given compound should be determined.

Concept introduction:

  • The π-systems of conjugated dienes absorb UV or visible light (200nm – 800nm).
  • The wavelength of maximum absorption of a compound is called λmax .
  • The value of λmax is highly depending on the extent of conjugation (number of conjugated double bonds).                                                                                                       Conjugated double bonds are the C=C bonds, which are separated by one σ-bond.
  • According to Woodward-Fieser rule, the portion of the molecule which absorbs UV-visible light is called chromophore and the groups attached to the chromophore are auxochromes. Woodward-Fieser rule gives the estimate value for λmax .
  • The estimate value for λmax are given in below table,
FEATURES λmax - value Example Calculation
Conjugated- diene

  Base value

    = 217

  EBK ORGANIC CHEMISTRY-STUD.SOLNS.MAN+SG, Chapter 16.11, Problem 5LTS , additional homework tip  1    217 nm
Each additional double bond

     +30

EBK ORGANIC CHEMISTRY-STUD.SOLNS.MAN+SG, Chapter 16.11, Problem 5LTS , additional homework tip  2

Base: 217

+2×30

Each auxochromic alkyl group

      +5

           EBK ORGANIC CHEMISTRY-STUD.SOLNS.MAN+SG, Chapter 16.11, Problem 5LTS , additional homework tip  3

 Base: 217                   +3×5

Each exocyclic double bond

      +5

                      EBK ORGANIC CHEMISTRY-STUD.SOLNS.MAN+SG, Chapter 16.11, Problem 5LTS , additional homework tip  4

Base: 217

     + 5

Homoannular diene (both double bonds are situated in a ring)

    + 39

            EBK ORGANIC CHEMISTRY-STUD.SOLNS.MAN+SG, Chapter 16.11, Problem 5LTS , additional homework tip  5

Base: 217

    +39

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