organic chemistry

1. PERKIN
REACTION
PRESENTED TO :
MA’AM MARYAM
PRESENTED BY:
GROUP “C”

2. GROUP
MEMBERS
UROOJ UMER
SAMAWIA
IQBAL
ASWA NASIR
SAIRA ABID
NIMRA JAVED

3. CONTENTS
 INTRODUCTION
 DEFINITION
 MECHANISM OF PERKIN
REACTION
 STEPS OF MECHANISM
 EXAMPLES OF PERKIN
REACTION
 APPLICATIONS AND USES

4. ENGLISH CHEMIST :
WILLIAM HENRY PERKIN
DISCOVERY:
19th CENTURY
INTRODUCTION

5. DEFINITION
 THE PERKIN REACTION IS AN
ALDOL CONDENSATION
REACTION THAT IS USED TO
MAKE CINNAMIC ACID.
 IT IS AN ORGANIC REACTION
WHICH IS USED TO CONVERT
AN AROMATIC ALDEHYDE AND
AN ACID ANHYDRIDE TO ALPHA
BETA UNSATURATED

6. CINNAMIC ACIDS
THEY ARE CARBOXYLIC ACIDS THAT OCCUR
NATURALLY.
FOUND IN :CINNAMON AND SHEA BUTTER.

7. CINNAMON SHEA BUTTER

8. ALDOL
ABBREVIATION OF ALDEHYDE AND ALCOHOL
ALDEHYDE ALCOHOL

9. GENERAL REACTION:
REGENTS : AROMATIC ALDEHYDE, ACETIC ANHYDRIDE
CATALYST :CARBON MONOXIDE GAS ,DICOBALT
OCTACARBONYL
PRODUCTS: CINNAMIC ACID

10. MECHANISM OF
PERKIN REACTION
ABSTRACTION OF ALPHA
HYDROGEN OF ACID
ANHYDRIDE BY BASE
ATTACK OF CARBANION ON
CARBONYI CARBON OF
BENZALDEHYDE
INTRAMOLECULAR ACETYL
SHIFT
LOSS OF ACETATE ION FROM
BETA CARBON

11. STEPS OF PERKIN REACTION
STEP 1
ABSTRACTION OF ALPHA HYDROGEN OF ACID ANHYDRIDE BY BASE
THE ANION OF ACID ACTS AS A BASE AND REMOVES ALPHA
HYDROGEN FROM THE ANHYDRIDE.

12. STEP 2
ATTACK OF CARBANION ON CARBONYI CARBON OF
BENZALDEHYDE.
STEP 3
 INTRAMOLECULAR ACETYL SHIFT
 THE MIGRATION OF ACETYL GROUP OCCURS VIA A CYCLIC INTERMMEDIATE
TO ALKOXY OXYGEN

13. STEP 4
 LOSS OF ACETATE ION FROM BETA CARBON
 IN THE PRSENCE OF A BASE , ALPHA HYDROGEN IS ABSTRACTED
WHICH INTURN CAUSES THE REMOVAL OF GOOD LEAVING GROUP
ACETATE ION TO FORM ALPHA BETA UNSATURATED CARBOXYLIC
ACID.

14. EXAMPLE OF PERKIN
REACTION
 FORMATION OF ALPHA BETA UNSATURATED ACID

15.  FORMATION OF METHYL CINNAMIC ACID

16. APPLICATIONS OF PERKIN REACTION
3-POLYFLUOROALKYL –CINNAMIC ACIDS BEING VERY USEFUL
BUILDING BLOCKS WERE OBTAINED BY A SIMPLE AND
CONVENIENT ONE STEP PROCEDURE .
Fluro acyl substituted arenes
 PERKIN REACTION IS USED IN THE LABORATORY SYNTHESIS
OF PHYTOESTROGEN
 IT IS ALSO INVOLVED IN SYNTHESIS OF STILBENE
 IT IS ALSO INVOLVED IN SYNTHESIS OF RESVERATROL.

17. CINNAMIC ACID THAT IS THE PRODUCT OF PERKIN
REACTION ACT AS AN ANTI MICROBIAL ( ANTI FUNGAL ,
ANTIVIRAL ,ANTI BACTERIAL) AND ANDOXIADNTS
PROPERTIES. THEY ALL ARE ISOLATED FROM PLANT
MATERIAL.
CINNAMIC ACID IS ALSO USED TO MAKE ETHYL , METHYL
AND BENZYL ESTERS USED IN PERFUME INDUSTRY
IT IS ALSO USED IN PREPARATION OF WARFARIN

18. REFRENCES
• HTTPS://WWW.SLIDESHARE.NET/PREMPRAKASH131/PERKI
N-PPT
• HTTPS://WWW.SLIDESHARE.NET/PREMPRAKASH131/PERKI
N-PPT
• HTTPS://EN.WIKIPEDIA.ORG/WIKI/PERKIN_REACTION
• PERKIN, W. H. (1868). "ON THE ARTIFICIAL PRODUCTION
OF COUMARIN AND FORMATION OF ITS HOMOLOGUE