Submitted To Sir Kashif: Course Code CHEM-413 Course Tittle Organic Chemistry (Natural Products)

SUBMITTED TO
SIR KASHIF
Course Code…
CHEM-413
Course Tittle
Organic Chemistry(Natural Products)
SUBMITTED BY
Aneeda Shabir
BS Chemistry
(8th Semester)
Topic
ALKALOIDS
CONTENTS..
1. Introduction
2. Extraction
3. General Properties
4. General method for dertermining
structure
INTRODUCTION
Definition Of Alkaloids
 Originally …the name alkaloid was given to all organic basis
isolated from plants ..
 Konigs(1880)…alkaloids defined as naturally occurring organic
bases which contain a pyridine ring
 Ladenburg’s…alkaloids defined as naturally plant compounds
having a basic character and containing at least one nitrogen
atom in a heterocyclic ring
”One must admit that even today it is still difficult to define an
alkaloid”
Main Characteristics Of Alkaloids
 Alkaloids obtained from plant known as plant alkaloids
 Alkaloids are very poisonous , but are used medicinally in
very small quantities.
 Basic properties,
 Physiological action
 Plant origin..….that are the main characters which define
plant alkaloid but exception still present like purines are the
compound which possess the above characteristics but not
include under the heading of alkaloids
Extraction Of Alkaloids
 Extraction of alkaloids from plant can be take place in
four stages
 Stage 1..The plant is dried , then finely powdered and then
extracted with ethanol.
 Stage 2..The solvent is distilled off , and residue treated with dilute
inorganic acid, where upon the bases are extracted as their soluble
salts.
 Step 3..The free bases are liberated by the addition of sodium
carbonate and extracted with solvent like chloroform etc.
 Step 4.. Mixture of bases thus obtained are separated by various
method like chromatography into individual component.
General peoperties
1. Alkaloids are usually colourless but few are coloured.. (e.g berberine
is yellow)
2. Crystalline
3.Bitter taste
4.Optically active and that alkaloids are very useful for resolving
racemic acids
5.Solubility ..non-volatile solid are insoluble in water but soluble in
organic solvents ,,liquid alkaloids are soluble in water
6. Appearance …they are generally tertiary nitrogen compounds
,,most of alkaloids also contain oxygen
7. Alkaloids form insoluble precipitates,many precipitates have
crystalline shapes that may be used to identify the alkaloid
General Method For Determining
Structure
 Qualitative analysis (alkaloid contains carbon, nitrogen ,oxygen
, hydrogen )
 Quantitative analysis(empirical formula; determine molecular
weight lead to determine molecular formula)
Functional Nature of Oxygen
(a) Hydroxyl group
The presence and number of hydroxyl group can be
determine by the action of acetic anhydride,acetyl chloride
on the alkaloid
Contiued….
The nature of hydroxyl group can be determined as;

 If it is phenolic then soluble in NaOH and reprecipitated by CO2
 If it is alcoholic then readily dehydrated by H2SO4 or phosphprous
pentaoxide
(b) Carboxyl group
The solubility in aqueous sodium carbonates and
formation of esters indicate the presence od carboxyl group
(c) Oxo group
Formation of oxime,semicarbazone indicate the presence
of oxo group
(d) Hydrolysis of alkaloids also lead to examine the products

Contiued…
(e) Methoxyl Group
• Presence ana number of methoxyl group determine by Zeisel method :
 In this alkaloid is heated with conc.hydriodic acid at its boiling point ;the
methoxyl groups converted into methyl iodide ,which is absorbed by ethanolic
silver nitrate and silver iodide is weighed
(d) Methylenedioxyl Group
Formation of formaldehyde is the indication of presence of methylenedioxyl
group when alkaloid is heated with HCl or H2SO4
(e) Zerewitinoff active hydrogen determination may applied to alkaloid
Functional Nature Of Nitrogen

(a) Reaction of alkaloid with acetic anhydride,nitrous acid
and methyl iodide shoe the nature of nitrogen
(b) Distillation of alkaloids with aq. KOH lead to information
regarding nature and number of alkyl groups attached to
nitrogen
(c) The presence of N-methyl group and their nymber

determined by Herzig-Meyer method

Submitted To Sir Kashif: Course Code CHEM-413 Course Tittle Organic Chemistry (Natural Products)

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The nature of hydroxyl group can be determined as;

(d) Hydrolysis of alkaloids also lead to examine the products

(e) Zerewitinoff active hydrogen determination may applied to alkaloid

Functional Nature Of Nitrogen

(c) The presence of N-methyl group and their nymber

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