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PROBLEM 7.33

Expert-verified
Organic Chemistry
Found in: Page 281

Short Answer

Question: Which solvents favor SN1 reactions and which favor SN2 reactions?

a.

b. CH3CN

c.

d.

Answer

a.This solvent favors the SN1 mechanism.

b.This solvent favors the SN2 mechanism.

c.This solvent favors the SN1 mechanism.

d.This solvent favors the SN2 mechanism

See the step by step solution

Step by Step Solution

SN1 reactions

This is a two-step reaction.

In these reactions, the leaving group leaves first, forming a carbocation. The carbocation is then attacked by the nucleophile.

The rate of the reaction depends upon the leaving group and the nature of the nucleophile.

The polar protic solvents favors the SN1 mechanism.

SN2 Reations

These reactions do not involve the formation of the carbocation.

In this reaction, one bond is broken, and another bond is formed simultaneously.

The polar aprotic solutions undergo the SN2 mechanism.

Comparison of the following compounds

a. CH3CH2OH is a polar protic solution. It contains a -OH group and hence forms an H-bond. Therefore, this favors the SN1 mechanism.

b.CH3CN is a polar aprotic solution as no hydrogen atom is bonded directly to the highly electronegative atom. Hence, this favors the SN2 mechanism.

c. CH3COOH is a polar protic solution. Hence, it favors the SN1 mechanism.

d.CH3CH2OCH2CH3 is a polar aprotic solution as no hydrogen atom is bonded directly to the highly electronegative atom, i.e., no O-H bonds are present. Hence, this favors the SN2 mechanism.

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