DEPARTMENT OF CHEMISTRY

MINOR ORGANIC ASSIGNMENT

Topic Name:
Woodward Fieser Rule
Submitted To:
Sir Rizwan Paracha
Submitted By:
Tehmina Hanif
Student ID:
MCHF19BM008

UNIVERSITY OF SARGODHA SUB CAMPUS BHAKKAR

Problem#01

β
α

Woodward Component Contribution Contribution

Core:Cyclohexenone 215nm
Substituents:
Substituents at β-position: 2-alkyle 2×12=24nm
Other effects:Exocyclic 1×5=5nm
Calculated λmax: 244nm

Problem#02

δ
β
α γ

Woodward Component Contribution: Contribution

Core:Cyclohexenone 215nm
Substituents:
Substituents at β-position: alkyle 1×12=12nm
Substituents at γ-position: alkyle 1×18=18nm
Substituents at δ-position: alkyle 1×18=18nm
Other effects:Exocyclic Bond 1 5nm
Extended conjugation 1 30nm
Calculated λmax: 298nm
Problem#03 ζ
ε

β δ
α γ

Woodward Component Contribution

Contribution:
Core:Cyclohexenone 215nm
Substituents:
Substituents at β-position: akyle 12nm
Substituents at γ-position: alkyle 18nm
Substituents at ζ-position: alkyle 18nm
Other effects:Exocyclic 5nm
Extended conjugation 2 2×30=60nm
Homoannular diene 39nm
Calculated λmax: 367nm

Problem#04

δ α
β

Woodward Component Contribution: Contribution

Core:Cyclohexenone 215nm
Substituents:
Substituents at β-position: 1-alkyle 1×12=12nm
Substituents at γ-position: 1-alkyle 1×18=18nm
Substituents at δ-position:2-alkyle 2×18=36nm
Other effects:Exocyclic Bonds 3 3×5=15nm
Extended conjugation 30nm
Calculated λmax: 326nm
Problem#05
γ α
δ β

Woodward Component Contribution: Contribution

Core:Cyclohexenone 215nm
Substituents:
Substituents at γ-position: 18nm
Substituents at δ-position: 18nm
Other effects: 1-Exocyclic Bonds 1×5=5nm
Extended conjugation 1 30nm

Calculated λmax: 326nm

Problem#06 δ

α
γ
β

Woodward Component Contribution: Contribution

Core:Cyclohexenone 215nm
Substituents:
Substituents at α-position: alkoxy 35nm
Substituents at γ-position: akyle 18nm
Substituents at δ-position: 2-alkyl 2×18=36nm
Other effects:Extended conjugation 30nm
Homoannular diene 39nm

Calculated λmax: 373nm

Problem#07 β

Woodward Component Contribution: Contribution

Core:Cyclohexenone 215nm
Substituents:
Substituents at α-position: 10nm
Substituents at β-position: 2×12=24nm
Other effects: 0
Calculated λmax: 249nm

Problem#08 δ
γ

β
α

Woodward Component Contribution: Contribution

Core:Cyclohexenone 215nm
Substituents:
Substituents at β-position: 1-alkyle 12nm
Substituents at γ-position: 1-alkyle 18nm
Substituents at δ-position: 1-alkyle 18nm
Other effects:Exocyclic Bonds 2 2×5nm=10nm
Extended conjugations 1 30nm
Calculated λmax: 303nm
 α

Problem#09
β

Woodward Component Contribution: Contribution

Core:Cyclohexenone 215nm
Substituents:
Substituents at α-position:1-alkyl 10nm
Substituents at β-position:2-alkyle 2×12=24nm
Other effects: 0
Calculated λmax: 249nm

Problem#10 R
C10
C2
C1
C3 C9

C4 C6 C8

C5 C7

Woodward Component Contribution: Contribution

Core:Homoannular 253nm

Ring Residue:
Alkyl residue at C2,C6,C10 3×5=15nm
RS-substitution at C4 30nm
Other effects:Exocyclic Bonds 2 2×5=10nm
Extended conjugation 3 3×30=90nm
Calculated λmax: 398nm
Problem#11
ζ α
β

ε γ
δ

Woodward Component Contribution: Contribution

Core:Cyclohexenone 215nm
Substituents:
Substituents at β-position: alkyle 12nm
Substituents at ε-position:alkyle 18nm
Substituents at ζ-position:2-alkyle 2×18nm=36

Other effects:exocyclic bonds 1 5nm

Extended conjugation 2 2×30nm=60nm
Homoannular diene 39nm
Calculated λmax: 385nm

Problem#12 ζ
ε

δ
β
γ α

Woodward Component Contribution: Contribution

Core:Cyclohexenone 215nm
Substituents:
Substituents at β-position: alkyle 12nm
Substituents at δ-position: N(CH3)2 0nm
Substituents at ε-position: alkyle 18nm
Substituents at ζ-position:alkyle 18nm
Other effects:Exocyclic bonds 1 5nm
Extended conjugation 2 2×30=60nm
Homoannular diene 39nm
Calculated λmax: 367nm
Problem#13
α
γ
β δ

Woodward Component Contribution: Contribution

Core:Cyclohexenone 215nm
Substituents:
Substituents at α-position: alkyle 10nm
Substituents at β-position: alkyle 12nm
Substituents at γ-position: alkyle 18nm
Substituents at δ-position: alkyle 18nm
Other effects:exocyclic bonds 1 5nm
Extended conjugation 1 30nm

Calculated λmax: 308nm

Problem#14 γ
β
δ

Woodward Component Contribution: Contribution

Core:Cyclohexenone 215nm
Substituents:
Substituents at α-position: alkyle 10nm
Substituents at β-position: alkyle 12nm
Substituents at γ-position:alkyle 18nm
Substituents at δ-position: 2-alkyle 2×18nm=36
Other effects:
Extended conjugation 1 30nm

Calculated λmax: 321nm

Problem#15 γ δ ζ
ε

α β

Woodward Component Contribution: Contribution

Core:Cyclohexenone 215nm
Substituents:
Substituents at α-position: N(CH3)2 0nm
Substituents at β-position: alkyle 12nm
Substituents at γ-position: alkyle 18nm
Substituents at δ-position: alkyle 18nm
Substituents at ε-position: alkyle 18nm
Substituents at ζ-position:2-alkyle 2×18=36nm
Other effects:Exocyclic bonds 4 4×5=20nm
Extended conjugation 2 2×30=60nm
Calculated λmax: 397nm

Problem#16

α γ
β δ

ε
ζ
Woodward Component Contribution: Contribution

Core:Cyclohexenone 215nm
Substituents:
Substituents at β-position: alkyle 12nm
Substituents at γ-position: chloro 0nm
Substituents at δ-position: alkyle 18nm
Substituents at ε-position: alkyle 18nm
Substituents at ζ-position:alkyle 18nm
Other effects:Exocyclic bonds 3 3×5=15nm
Extended conjugation 2 2×30=60nm
Calculated λmax: 356nm
Problem#17 C10 C14 C2
C9 C1
C11 C3

C4
C12
C8 C6
C13 C7 C5

Woodward Component Contribution: Contribution

Core:acyclic conjugated diene\Heteroannular diene 214nm

Substituents:
Alkyle residue at C1,C4,2-alkyle at C6 4×5=20nm
Other effects:Exocyclic Bond 1 5nm
Extended conjugation 1 30
Calculated λmax: 269nmnm

Problem#18
ζ
ε

β δ
α γ

Woodward Component Contribution: Contribution

Core:Cyclohexenone 215nm
Substituents:
Substituents at β-position: alkyle 12nm
Substituents at γ-position: methoxy 0nm
Substituents at δ-position: alkyle 18nm
Substituents at ε-position: alkyle 18nm
Substituents at ζ-position: alkyle 18nm
Other effects:Exocyclic Bonds 3 3×5=15nm
Extended conjugations 2 2×30nm=60nm
Calculated λmax: 356nm
Problem#19
ζ
α ε
ζ'

ζ'’
β γ δ

Woodward Component Contribution: Contribution

Core:Cyclohexenone 215nm
Substituents:
Substituents at α-position:alkyle 10nm
Substituents at β-position: alkyle 12nm
Substituents at γ-position: methoxy 0nm
Substituents at δ-position: alkyle 18nm
Substituents at ε-position: alkyle 18nm
Substituents at ζ’’-position: alkyle 18nm
Other effects:Exocyclic Bonds 2 2×5=10nm
Extended conjugations 3 3×30nm=90nm
Homoannualr diene 39nm
Calculated λmax: 430nm