Paaras Thakur

Organic Chemistry

SN1 and SN2

Reactions - 1
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Example For each pair, predict the stronger nucleophile
 Solvent Effects on Nucleophilicity

A protic solvent is one that has acidic protons and can solvate both cations
and anions.

Small anions are solvated more strongly than large anions in a protic solvent
and this reduces their nucleophilicity.
Solvent Effects on Nucleophilicity
 Solvent Effects on Nucleophilicity

Polar aprotic solvents have strong dipole moments to enhance solubility, yet
they have no H capable of forming hydrogen bonds with anions. These can only
solvate cations.
Example
Example
Example
Example
Example
 Nucleophilic Substitution

Nucleophilic substitution reactions are among the most fundamental types of

organic reactions. In a nucleophilic substitution reaction a nucleophile (NuC)
displaces a leaving group (LG) in the molecule that undergoes the substitution
(the substrate).

When does the bond between the leaving group and the carbon break?
 Bimolecular Nucleophilic Substitution - SN2

General Reaction:

Order of Reaction:
Bimolecular Nucleophilic Substitution - SN2
 Bimolecular Nucleophilic Substitution - SN2

Single step reaction. No intermediates, no

rearrangements.

Complete Inversion - Walden Inversion

Bimolecular Nucleophilic Substitution - SN2
Bimolecular Nucleophilic Substitution - SN2
 Factors affecting Rate of SN2 reaction

Effect of substrate

Sn2 reactions are faster in less hindered environment

Example Rank the following alkyl bromides in order of decreasing reactivity (from
fastest to slowest) as a substrate in an SN2 reaction.
 Factors affecting Rate of SN2 reaction

Concentration and Reactivity of Nucleophile

Strong Nucleophile required

 Factors affecting Rate of SN2 reaction

Nature of Solvent

Favored in Polar Aprotic Solvent

 Factors affecting Rate of SN2 reaction

Leaving Group

Good leaving group helps the reaction go faster.

Example Which alkyl halide would you expect to react more rapidly by an SN2
mechanism? Explain your answer.
Example Which SN2 reaction of each pair would you expect to take place more
rapidly in a protic solvent?
Example Which SN2 reaction of each pair would you expect to take place more
rapidly in a protic solvent?
Example
Example
Example
Nucleophilic Substitution
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