WAGNER MEERWIN

REARRANGEMENT
INTRODUCTION
DEFINITION
REACTION CONDITIONS
MECHANISM
EXAMPLE
APPLICATIONS
PROBLEMS
INTRODUCTION
• The reaction was first reported by Wagner in 1899 and this was further
extended by Meerwin in 1914. Thus it was named as Wagner Meerwin
rearrangement .
• The reaction was named by Georg Wagner and Hans Meerwein.
This rearrangement discovered the close relationship of
CARBOCATION as INTERMEDIATE
• The rearrangement was first discovered in bicyclic terpenes.For
example ,the conversion of isoborneol to camphene.

(Hanson, J. R. (1991). "Wagner–Meerwein Rearrangements". Compr.)

 DEFINITION
• The Wagner-Meerwein rearrangement is an organic reaction used to convert
an alcohol to an olefin using an acid catalyst.

• A Wagner–Meerwein rearrangement is a class of carbocation

1,2rearrangement reactions in which a hydrogen, alkyl or aryl group
migrates from one carbon to a neighboring carbon atom.
• This reaction occur in highly branched neopentyl type of compounds
thus it is also known as NEOPENTYL REARRANGEMENT .

CONDITIONS
• ACIDIC CONDITION . i.e.
sulphuric acid, proton, acetic
acid
WAGNER MEERWIN REARRANGEMENT

REACTANT PRODUCTS
• Reactant may be cyclic or non • Firstly it forms carbocation
cyclic compound • It also form alkene
• Usually ALCOHOL OR ALKYL
HALIDES
IMPORTANT POINTS

• It involves the 1,2 shift of migrating groups

• It is an intramolecular rearrangement
• The driving force is the formation of more stable carbonium ions
MECHANISM
• The 1st step is in the presence of proton(H+ ion, X group) takes the
bonding pair of electron and leaves as HX forming carbonium ions.
• STEP 2 .
This carbonuim ion undergoes rearrangement to produce more
stable TERTIARY carbonuim ion by transfer of one R group to
neighboring carbon atom (1,2 SHIFT)
Step 3
In this step NUCLEOPHILE attacks on carbonuim ion .
There are TWO possibilities for nucleophile to attack on ion .
1. IF attacking nucleophile is same group which left in 1st step then
rearranged product is obtained .

2. IF molecule get deprotonated (removal of proton the H+ ions from

neighboring carbon leaves forming a double bond .
EXAMPLE
APPLICATIONS

• In cracking of petroleum products.

• Dehydration of neopentyl alcohol.
• Hydrolysis of neopentyl bromide