Nicotine

1 Nicotine
2 Structure
3 Herzig and Meyer Method
4 Pinner Method (1892)
5 Method Via Addition

1. Govt: Post Graduate College Mardan 23200 KP Pakistan

[email protected] https://www.slideshare.net/amirhassan27


Name Amir Hassan
Department BS- Chemistry
Institute GPGC–Mardan KP Pakistan.
Subject Natural Product
Topic Nicotine


Contents Study
1 Nicotine
2 Structure
3 Herzig and Meyer Method
4 Pinner Method (1892)
5 Method Via Addition

2. Structure Elucidation Of Nicotine
1
Written By: Amir Hassan BS – CHEMISTRY DEPTT GPGC – MARDAN.

Nicotine :
Nicotine is the chief alkaloid of tobacco plant (Nicotina tabacum). It occurs in the
plants leaves as salt of malic acid and citric acid to the extent of 4 to5 percent. The alkaloid was
named after the Frenchman Nicot who introduced in France in 1560.

Structure :
The elemental analysis and molecular weight determination leads to the molecular
formula C10H14N2 for nicotine.
From a consideration the structural formula of nicotine may be written as

















(Structure Of Nicotine)
The given structure of Nicotine is elucidated and confirmed via the following chemical reaction
as follows

1) HERZIG AND MEYER METHOD

 The alkaliod form an addition compound with zinc chloride, which when heated
with lime yields pyridine, pyrrole, and methylamine.
 This suggest that a side chain C5H10N, is a pyrrole derivatious.

3. Structure Elucidation Of Nicotine
2
Written By: Amir Hassan BS – CHEMISTRY DEPTT GPGC – MARDAN.











 Nicotine hydriodide when treated with CH3I, form nicotinic isomethiodide which on
oxidation with potassium ferricyanide yield nicotine. This on further oxidation with
chromium trioxide produces hygrinic acid.
 The formation of hygrinic acid proves beyond doubt that the side chain N –
methylpyrrolodine, is attached with pyridine nucleus at C2 Position.

4. Structure Elucidation Of Nicotine
3
Written By: Amir Hassan BS – CHEMISTRY DEPTT GPGC – MARDAN.


2) PINNER METHOD (1892).

 The nicotince structure is further confirmed and explain by the followinf reaction.
 Nicotine when treated with bromine in acetic acid followed by aqueous sulfurous
acid gives dibromonicotine, C10H10ON2. This upon oxidation with amixture of
sulfurous acid and sulphuric acid at 130
0
– 140
0
C, yields 3 –acetylpyridine,
oxalic acid and methylamine.



















3) PINNER METHOD CONT…..


 Nicotine on reaction with bromine in hydrobromic acid give dibromonicotine which
when heated with barium hydroxide solution at 100
0
C, yields nicotinic acid, malonic acid
and maethylamine.
 The chemical reaction are as follows

5. Structure Elucidation Of Nicotine
4
Written By: Amir Hassan BS – CHEMISTRY DEPTT GPGC – MARDAN.



4) Method Via Addition
 Also, Nicotine add six hydrogen atom and forms nicotine hexahydride.
 Also, known that pyridine ring is unsaturted and can accept six hydrgen atoms.
Nicotine is accepting only Six Hydrogen atoms that mean the side cahin is
staurated.







Comments To
Email: [email protected]
BS Organic Chemistry Department
GPGC MARDAN 23200 KP.
The End!!!