Organic Chemistry
Organic Chemistry
3rd Edition
ISBN: 9781119316152
Author: Klein, David R.
Publisher: WILEY
Question
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Chapter 16, 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, Chapter 16, Problem 60IP , additional homework tip  1    217 nm
Each additional double bond

     +30

Organic Chemistry, Chapter 16, Problem 60IP , additional homework tip  2

Base: 217

+2×30

Each auxochromic alkyl group

      +5

           Organic Chemistry, Chapter 16, Problem 60IP , additional homework tip  3

 Base: 217                   +3×5

Each exocyclic double bond

      +5

                      Organic Chemistry, Chapter 16, Problem 60IP , additional homework tip  4

Base: 217

     + 5

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

    + 39

            Organic Chemistry, Chapter 16, 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, Chapter 16, Problem 60IP , additional homework tip  6    217 nm
Each additional double bond

     +30

Organic Chemistry, Chapter 16, Problem 60IP , additional homework tip  7

Base: 217

+2×30

Each auxochromic alkyl group

      +5

           Organic Chemistry, Chapter 16, Problem 60IP , additional homework tip  8

 Base: 217                   +3×5

Each exocyclic double bond

      +5

                      Organic Chemistry, Chapter 16, Problem 60IP , additional homework tip  9

Base: 217

     + 5

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

    + 39

            Organic Chemistry, Chapter 16, 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, Chapter 16, Problem 60IP , additional homework tip  11    217 nm
Each additional double bond

     +30

Organic Chemistry, Chapter 16, Problem 60IP , additional homework tip  12

Base: 217

+2×30

Each auxochromic alkyl group

      +5

           Organic Chemistry, Chapter 16, Problem 60IP , additional homework tip  13

 Base: 217                   +3×5

Each exocyclic double bond

      +5

                      Organic Chemistry, Chapter 16, Problem 60IP , additional homework tip  14

Base: 217

     + 5

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

    + 39

            Organic Chemistry, Chapter 16, Problem 60IP , additional homework tip  15

Base: 217

    +39

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Chapter 16 Solutions

Organic Chemistry

Ch. 16.5 - Prob. 9PTSCh. 16.5 - Prob. 10PTSCh. 16.5 - Prob. 11ATSCh. 16.5 - Prob. 12CCCh. 16.7 - Prob. 3LTSCh. 16.7 - Prob. 13PTSCh. 16.7 - Prob. 14ATSCh. 16.7 - Prob. 15CCCh. 16.7 - Prob. 16CCCh. 16.7 - Prob. 17CCCh. 16.7 - Predict the regiochemical outcome (major product)...Ch. 16.8 - Prob. 19CCCh. 16.9 - Prob. 20CCCh. 16.9 - Prob. 4LTSCh. 16.9 - Prob. 21PTSCh. 16.9 - Prob. 22ATSCh. 16.10 - Prob. 23CCCh. 16.10 - Prob. 24CCCh. 16.10 - Prob. 25CCCh. 16.10 - Prob. 26CCCh. 16.11 - Prob. 5LTSCh. 16.11 - Prob. 27PTSCh. 16.11 - Prob. 28ATSCh. 16.12 - Prob. 29CCCh. 16 - Prob. 30PPCh. 16 - Prob. 31PPCh. 16 - Prob. 32PPCh. 16 - Prob. 33PPCh. 16 - Prob. 34PPCh. 16 - Prob. 35PPCh. 16 - Prob. 36PPCh. 16 - Prob. 37PPCh. 16 - Prob. 38PPCh. 16 - Prob. 39PPCh. 16 - Prob. 40PPCh. 16 - Prob. 41PPCh. 16 - Prob. 42PPCh. 16 - Prob. 43PPCh. 16 - Prob. 44PPCh. 16 - Prob. 45PPCh. 16 - Prob. 46PPCh. 16 - Prob. 47PPCh. 16 - Prob. 48PPCh. 16 - Prob. 49PPCh. 16 - Prob. 50PPCh. 16 - Prob. 51PPCh. 16 - Prob. 52PPCh. 16 - Prob. 53PPCh. 16 - Prob. 54PPCh. 16 - Prob. 55PPCh. 16 - Prob. 56PPCh. 16 - Prob. 57PPCh. 16 - Prob. 58PPCh. 16 - Prob. 59PPCh. 16 - Prob. 60IPCh. 16 - Prob. 61IPCh. 16 - Prob. 62IPCh. 16 - Prob. 63IPCh. 16 - Prob. 64IPCh. 16 - Prob. 65IPCh. 16 - Prob. 66IPCh. 16 - Prob. 67IPCh. 16 - Prob. 68IPCh. 16 - Prob. 69IPCh. 16 - Prob. 70IPCh. 16 - Prob. 71IPCh. 16 - Prob. 72IPCh. 16 - Prob. 73IPCh. 16 - Prob. 74IPCh. 16 - Prob. 76IPCh. 16 - Prob. 77CPCh. 16 - Prob. 78CPCh. 16 - Prob. 79CPCh. 16 - Prob. 80CPCh. 16 - Prob. 81CP
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