STRUCTURE ELUCIDATION
OF MORPHINE
By smit vaniya
23MSCC22
Structure Elucidation of Morphine
1. Determination of molecular formula : By qualitative
and quantitative analysis and by molecular weight
determination molecular formula of the morphine is
C17H19O3N
2. Detection of unsaturation : Presence of a double
bond Upon catalytic hydrogenation it gives dihydromorphine
indicates presence of a double bond.
C17H19O3N + H2 Pd C17H21O3N
morphine di hydro
morphine
Structure Elucidation of Morphine
IV) The third oxygen atom is must be present in ether
form.
3. Nature of oxygen atoms
I) Upon acetylation morphine forms diacetyl derivative
which indicates presence of two - OH groups.
II) It forms monosodium salt with NaOH and gives
violet colour with FeCl3 solution indicates presence of a
phenolic -OH group.
III) The another -OH group is secondary alcoholic
group, as morphine when treated with halo acid-OH
group is replaced by halogen atom.
Structure Elucidation of Morphine
4. Nature of nitrogen atom
I) For exhaustive methylation, morphine requires one
molecule of methyl iodide to form quaternary ammonium
salt which indicates 'N' atom is tertiary in nature.
C17H19O3N + CH3I C18H22O3
Morphine Morphine Quaternary salt
II) In Herzig Meyer method, morphine release one CH3NH2
indicates presence of one 'N-methyl' group.
C17H19O3N CH3NH2
Morphine Methyl amine
Sodalime
distillation
Structure Elucidation of Morphine
5. Degradation studies
I) Zn distillation - Morphine upon Zn distillation gives
phenanthrene which indicates morphine contains fused
carbocycle like phenanthrene.
C17H19O3N Zn
distillation
Morphine
phenanthrene.
Structure Elucidation of Morphine
II) Hoffman degradation of Morphine
Morphine Heroin
Acetylatio
n
Ac₂O
CH3I
CH3
+
𝐈−
Heroin methiodide
Hoffman
degradation
O
H
O
H
Dihydroxy phenanthrene
(Morphol)
The structure of
morpho is
confirmed by
synthesis
THANK YOU

structure elucidation of Morphine ppt.pptx

  • 1.
  • 2.
    Structure Elucidation ofMorphine 1. Determination of molecular formula : By qualitative and quantitative analysis and by molecular weight determination molecular formula of the morphine is C17H19O3N 2. Detection of unsaturation : Presence of a double bond Upon catalytic hydrogenation it gives dihydromorphine indicates presence of a double bond. C17H19O3N + H2 Pd C17H21O3N morphine di hydro morphine
  • 3.
    Structure Elucidation ofMorphine IV) The third oxygen atom is must be present in ether form. 3. Nature of oxygen atoms I) Upon acetylation morphine forms diacetyl derivative which indicates presence of two - OH groups. II) It forms monosodium salt with NaOH and gives violet colour with FeCl3 solution indicates presence of a phenolic -OH group. III) The another -OH group is secondary alcoholic group, as morphine when treated with halo acid-OH group is replaced by halogen atom.
  • 4.
    Structure Elucidation ofMorphine 4. Nature of nitrogen atom I) For exhaustive methylation, morphine requires one molecule of methyl iodide to form quaternary ammonium salt which indicates 'N' atom is tertiary in nature. C17H19O3N + CH3I C18H22O3 Morphine Morphine Quaternary salt II) In Herzig Meyer method, morphine release one CH3NH2 indicates presence of one 'N-methyl' group. C17H19O3N CH3NH2 Morphine Methyl amine Sodalime distillation
  • 5.
    Structure Elucidation ofMorphine 5. Degradation studies I) Zn distillation - Morphine upon Zn distillation gives phenanthrene which indicates morphine contains fused carbocycle like phenanthrene. C17H19O3N Zn distillation Morphine phenanthrene.
  • 6.
    Structure Elucidation ofMorphine II) Hoffman degradation of Morphine Morphine Heroin Acetylatio n Ac₂O CH3I CH3 + 𝐈− Heroin methiodide Hoffman degradation O H O H Dihydroxy phenanthrene (Morphol) The structure of morpho is confirmed by synthesis
  • 7.