Organic Chemistry, Binder Ready Version
Organic Chemistry, Binder Ready Version
2nd Edition
ISBN: 9781118454312
Author: David R. Klein
Publisher: WILEY
Question
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Chapter 17, Problem 60IP

 (a)

Interpretation Introduction

Interpretation:

For the given data’s of α-terpinene , the number of double bonds presented, the structure and the value of λmax are needed to be determined.

Concept introduction:

  • The Hydrogen Deficiency Index (HDI): It is used to measure the number of degrees of unsaturation (double and triple bonds or ring) present in a given molecule. It is determined by using the formula. HDI=12[(2×No. of Carbon atoms)+2+(No. of Nitrogen atoms)              - (No. of Hydrogen atoms)-(No. of halogens)]
  • Ozonolysis Reaction: It is an oxidative reaction which is used to oxidize the C=C bonds to 2C=O bonds .
  • The π-systems of conjugated dienes absorb UV or visible light (200nm – 800nm).
  • The wavelength of maximum absorption of a compound is called λmax .
  • 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

  Organic Chemistry, Binder Ready Version, Chapter 17, Problem 60IP , additional homework tip  1    217 nm
Each additional double bond

     +30

Organic Chemistry, Binder Ready Version, Chapter 17, Problem 60IP , additional homework tip  2

Base: 217

+2×30

Each auxochromic alkyl group

      +5

           Organic Chemistry, Binder Ready Version, Chapter 17, Problem 60IP , additional homework tip  3

 Base: 217                   +3×5

Each exocyclic double bond

      +5

                      Organic Chemistry, Binder Ready Version, Chapter 17, Problem 60IP , additional homework tip  4

Base: 217

     + 5

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

    + 39

            Organic Chemistry, Binder Ready Version, Chapter 17, Problem 60IP , additional homework tip  5

Base: 217

    +39

(b)

Interpretation Introduction

Interpretation:

For the given data’s of α-terpinene , the number of double bonds presented, the structure and the value of λmax are needed to be determined.

Concept introduction:

  • The Hydrogen Deficiency Index (HDI): It is used to measure the number of degrees of unsaturation (double and triple bonds or ring) present in a given molecule. It is determined by using the formula. HDI=12[(2×No. of Carbon atoms)+2+(No. of Nitrogen atoms)              - (No. of Hydrogen atoms)-(No. of halogens)]
  • Ozonolysis Reaction: It is an oxidative reaction which is used to oxidize the C=C bonds to 2C=O bonds .
  • The π-systems of conjugated dienes absorb UV or visible light (200nm – 800nm).
  • The wavelength of maximum absorption of a compound is called λmax .
  • 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

  Organic Chemistry, Binder Ready Version, Chapter 17, Problem 60IP , additional homework tip  6    217 nm
Each additional double bond

     +30

Organic Chemistry, Binder Ready Version, Chapter 17, Problem 60IP , additional homework tip  7

Base: 217

+2×30

Each auxochromic alkyl group

      +5

           Organic Chemistry, Binder Ready Version, Chapter 17, Problem 60IP , additional homework tip  8

 Base: 217                   +3×5

Each exocyclic double bond

      +5

                      Organic Chemistry, Binder Ready Version, Chapter 17, Problem 60IP , additional homework tip  9

Base: 217

     + 5

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

    + 39

            Organic Chemistry, Binder Ready Version, Chapter 17, Problem 60IP , additional homework tip  10

Base: 217

    +39

(c)

Interpretation Introduction

Interpretation:

For the given data’s of α-terpinene , the number of double bonds presented, the structure and the value of λmax are needed to be determined.

Concept introduction:

  • The Hydrogen Deficiency Index (HDI): It is used to measure the number of degrees of unsaturation (double and triple bonds or ring) present in a given molecule. It is determined by using the formula. HDI=12[(2×No. of Carbon atoms)+2+(No. of Nitrogen atoms)              - (No. of Hydrogen atoms)-(No. of halogens)]
  • Ozonolysis Reaction: It is an oxidative reaction which is used to oxidize the C=C bonds to 2C=O bonds .
  • The π-systems of conjugated dienes absorb UV or visible light (200nm – 800nm).
  • The wavelength of maximum absorption of a compound is called λmax .
  • 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

  Organic Chemistry, Binder Ready Version, Chapter 17, Problem 60IP , additional homework tip  11    217 nm
Each additional double bond

     +30

Organic Chemistry, Binder Ready Version, Chapter 17, Problem 60IP , additional homework tip  12

Base: 217

+2×30

Each auxochromic alkyl group

      +5

           Organic Chemistry, Binder Ready Version, Chapter 17, Problem 60IP , additional homework tip  13

 Base: 217                   +3×5

Each exocyclic double bond

      +5

                      Organic Chemistry, Binder Ready Version, Chapter 17, Problem 60IP , additional homework tip  14

Base: 217

     + 5

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

    + 39

            Organic Chemistry, Binder Ready Version, Chapter 17, Problem 60IP , additional homework tip  15

Base: 217

    +39

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