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Pyrones

The document summarizes key information about pyrones, including their structure as a six-membered heterocyclic compound containing one oxygen atom and a ketone functional group. It discusses the physical properties of pyrones such as their molecular weight, boiling point, melting point, solubility, and density. The document also outlines common synthetic methods for producing pyrones and describes their chemical properties including electrophilic substitution reactions like halogenation and acetylation.

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SANIA FAJAR KHAN
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656 views17 pages

Pyrones

The document summarizes key information about pyrones, including their structure as a six-membered heterocyclic compound containing one oxygen atom and a ketone functional group. It discusses the physical properties of pyrones such as their molecular weight, boiling point, melting point, solubility, and density. The document also outlines common synthetic methods for producing pyrones and describes their chemical properties including electrophilic substitution reactions like halogenation and acetylation.

Uploaded by

SANIA FAJAR KHAN
Copyright
© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
Available Formats
Download as PDF, TXT or read online on Scribd

HETEROCYCLIC

CHEMISTRY
Pyrones
α - And γ - Pyrones
Presented By: Sania Fajar Khan
Roll No. 1922107038
Class: Bs Chemistry
Semester-8

Govt. Graduate College For Women Gulberg ,


Lahore.
Contents
INTRODUCTION
PHYSICAL PROPERTIES OF PYRONES
SYNTHETIC METHODS OF PYRONES
Synthesis of Alpha Pyrone
CHEMICAL PROPERTIES OF PYRONE
ELECTROPHILIC SUBSTITUTION
Halogenation
Acetylation
REFERENCES
Pyrones
Pyrones/pyranones are a type of heterocyclic
chemical compound
They have an unsaturated six-membered ring
with one oxygen atom and a ketone functional
group
Two isomers exist: 2-pyrone and 4-pyrone
2-pyrone is found in nature as part of the
coumarin ring system
Physical Properties
1. Pyrone has a molecular weight of
96.08 g/mol.
2. It has a boiling point of 224-226°C
and a melting point of 67-68°C.
3. Pyrone is a colorless to pale yellow
liquid or solid with a sweet, floral odor.
Structure of Pyrone
4. It is soluble in water, ethanol, ether,
and chloroform but is insoluble in
nonpolar solvents such as hexane.
5. Pyrone is relatively stable under
normal conditions but can react with
strong oxidizing agents or acids.
6. It has a density of 1.23 g/mL.
α-Pyrone γ-Pyrone
Synthetic methods of Pyrones
Synthesis of Pyrone
SYNTHESIS SYNTHESIS OF
SUBSITUTED PYRONE
Substituted pyrone can be obtain by ethyl
diazoacetate with an ester to give intermediate.
this form the 2, 4-disubsituted α - Pyrone.
Chemical
Properties
Both α - And γ - Pyrones
are aromatic but latter
more stable than the
former
α - pyrone itself polyrizes
slowly
γ - Pyrones are quite stable
crystaline substances
Electrophilic
substitution
of Pyrones
Both α - And γ - Pyrones
undergo substitution at 3 or
5 position.

Halogenation
Bromination
Acetylation
Halogenation of Pyrones
Bromination: α pyrone is brominated at 3
position via an addition elimination reaction
Halogenation of Pyrones
Bromination: Bromination of γ pyrone yield
mixture of mono and di-bromo γ pyrones via
perbromide formation.
Halogenation of Pyrones
Nitration: Reaction of α pyrone with nitronium
tetrafluoroborate, reversibly form a ortho nitro
salth which is converted to 5-nitro-α-pyrone.
Acetylation of γ-pyrone
Acetylation of γ-pyrone give 3 or 5 substituted
product.
Methyl group at 2 postion in alpha pyrones
are activated, and resulting anion reacts with
carbonyl compound to yield alcohols
Reference
Raj K. Bansal. (1990).
Textbook: Heterocyclic
Chemistry (5th Edition). New
Age international Private
Limited.
Thank You!

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