Paaras Thakur

Organic Chemistry

SN1 and SN2

Reactions - 4
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JEELIVE
Dehydrohalogenation
 Elimination Bimolecular E2 Reaction

General Reaction

Mechanism
Elimination Bimolecular E2 Reaction
 Orientation of Elimination

In most eliminations with two or more possible products, the product with the
most substituted double bond predominates. This principle is called Zaitsev’s
rule, and the most highly substituted product is called the Zaitsev product.
 Elimination Bimolecular E2 Reaction

Stereochemistry
 Elimination Bimolecular E2 Reaction

Stereochemistry
 Elimination Bimolecular E2 Reaction

Energy Profile
 Factors affecting Rate of E2 reaction

Effect of substrate

Concentration and Strength of Base

 Factors affecting Rate of E2 reaction

Nature of Solvent

Solvent polarity is not so important

 Elimination Unimolecular E1 Reaction

General Reaction

Mechanism
Elimination Bimolecular E2 Reaction
Competition with SN1 Reaction
Energy Profile for E1 Reaction
Example When the following compound is heated in methanol, several different products
are formed. Propose mechanisms to account for the four products shown.
Example Predict the mechanisms and products of the following reactions.
Example Solvolysis of bromomethylcyclopentane in methanol gives a complex product
mixture of the following five compounds. Propose mechanisms to account for
these products.
Example The major product of the following reaction is IIT
2008
 Factors affecting Rate of E1 reaction

Effect of substrate

Concentration and Strength of Base

 Factors affecting Rate of E1 reaction

Nature of Solvent
 Comparison of E1 and E2

E1 E2

Weak base required Strong Base required

Good ionizing solvent req. Solvent polarity not important

Substrate: 3°> 2° >> 1° 3°> 2° > 1°

Rate= k[RX] Rate= k[RX][Base]

No particular geometry required Anti-coplanar geometry preferred

Rearrangements are common No rearrangements

Multi-step reaction mechanism Single step mechanism

Not stereospecific Stereospecific

Stereoselective Stereoselective
Predicting Substitution Vs Elimination
Example The final product is
Example Which will give white ppt. with AgNO3 + NH4OH?
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