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SN1 and SN2

Reactions

An organic chemistry workshop for the ARC

This workshop will address:

The SN2 Reaction

Substrate

Nucleophile Leaving Group

Product

The SN2 Reaction

Substitution

Nucleophilic

Bimolecular

The SN2 Reaction

Substitution: this reaction involves a

substitution of players two reactants produce two products, in which some things have been switched around:

AB + C AC + B

reactions mixed up with substitution (SN1 and SN2) reactions.

The SN2 Reaction

Nucleophilic: these reactions involve a

nucleophile (Nuc:-) replacing a leaving group. electron pair to the new bond, and replacing the leaving group (a substitution). roots: Nucleo-(nucleus)-phile-(lover) it is attracted to the nucleus, which is positively charged! Nucleophiles are therefore negatively charged or strongly į-.

The SN2 Reaction

Bimolecular: A bimolecular reaction is one

whose rate depends on the concentrations of two of its reactants. nucleophile attacks the substrate as the leaving group leaves the substrate. slowest step. In bimolecular reactions, therefore, the slow step involves two reactants. For SN2 reactions, there are only two reactants; this means that the slow step is the only step.

The SN2 Reaction

Transition State

SN2 summary:

(1) Nucleophile back-side attacks the į+ carbon center.

(2) Transition state forms in which nucleophile is forming bond with carbon while leaving group is breaking its bond.

(3) The leaving group leaves, forming the final product. (1) (2) (1) (3)

The SN2 Reaction

Notes:

The SN1 Reaction

Carbocation

Intermediate

Substrate

Products

The SN1 Reaction

Substitution

Nucleophilic

Unimolecular

The SN1 Reaction

SN1 reactions are nucleophilic substitutions, involving a nucleophile replacing a leaving group (just like SN2).

However: SN1 reactions are unimolecular: the rate

of this reaction depends only on the concentration of one reactant.

1. The leaving group leaves, and the substrate forms a

carbocation intermediate.

2. The nucleophile attacks the carbocation, forming the

product.

The SN1 Reaction

1. The Slow Step:

First step of the SN1 reaction:

The leaving group leaves, and the substrate carbon now only has three substituents, taking on a positive charge. This is called a carbocation.

3º > 2º >> 1º

The SN1 Reaction

2. The Fast Step:

Second step of the SN1 reaction:

The nucleophile attacks the carbocation intermediate, bringing its electron pair to resolve the positive charge.

SN1 vs SN2 Reactions

Resources

All images used with permission under creative commonsquotesdbs_dbs9.pdfusesText_15