a) Interpretation: The change has to be explained when the concentration of the halide is tripled and the concentration of the ethanol is halved by adding diethyl ether as an inert solvent. Concept introduction: S N 1 reaction: The alcohol is reaction with acids like hydrochloric acid or hydrobromic acid which yield the corresponding carbocation intermediate, this carbocation intermediate undergoes substitution reaction which yields the corresponding substitution product. Tertiary alcohols undergo substitution very fast than the secondary alcohols because tertiary carbocation is more stable than the secondary carbocation than the primary carbocation. Primary alcohol is less stable therefore it won’t undergo S N 1substitution reaction.

Question

1. What effect would you expect on the rate of reaction of ethanol with 2-iodo-2-methyl-butane if the concentration of the halide is tripled? 2. Explain the difference between addition, elimination and substitutionreactions. 3. Optically active 2-butanol slowly racemizes on standing in dilute sulfuricacid. Propose a mechanism to account for this observation.

Answer 1

Question

Chapter 11.SE, Problem 44AP

Interpretation Introduction

a)

Interpretation:

The change has to be explained when the concentration of the halide is tripled and the concentration of the ethanol is halved by adding diethyl ether as an inert solvent.

Concept introduction:

S_N1 reaction:

The alcohol is reaction with acids like hydrochloric acid or hydrobromic acid which yield the corresponding carbocation intermediate, this carbocation intermediate undergoes substitution reaction which yields the corresponding substitution product.

Tertiary alcohols undergo substitution very fast than the secondary alcohols because tertiary carbocation is more stable than the secondary carbocation than the primary carbocation.

Primary alcohol is less stable therefore it won’t undergo S_N1substitution reaction.

Interpretation Introduction

b)

Interpretation:

The change has to be explained when the concentration of the halide is tripled and the concentration of the ethanol is halved by adding diethyl ether as an inert solvent.

Concept introduction:

S_N1 reaction:

The alcohol is reaction with acids like hydrochloric acid or hydrobromic acid which yield the corresponding carbocation intermediate, this carbocation intermediate undergoes substitution reaction which yields the corresponding substitution product.

Tertiary alcohols undergo substitution very fast than the secondary alcohols because tertiary carbocation is more stable than the secondary carbocation than the primary carbocation.

Primary alcohol is less stable therefore it won’t undergo S_N1substitution reaction.

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