Chapter 23, Problem 55A

(a)

Interpretation Introduction

Interpretation: Structure of the expected product for the given reaction should be written.

CH_3-CH₂-COO-CH₂-CH₃ + NaOH(

Concept Introduction: A compound derived from an Oxoacid in which at least one Hydroxyl group (-OH) is replaced by an Alkoxy group (-O-R) is an Ester.

Answer to Problem 55A

Structure of the expected product is

CH_3-CH₂-COO-Na + CH₃- CH₂-OH

Explanation of Solution

An Ester reacts with Sodium Hydroxide:

CH_3-CH₂-COO-CH2-CH3 + NaOH( CH_3-CH₂-COO-Na + CH₃- CH₂-OH

It is a Saponification reaction, that is, used to synthesize soap. In this reaction, an ester reacts with Sodium Hydroxide yielding Carboxylate salt and Alcohol.

(b)

Interpretation Introduction

Interpretation: Structure of the expected product for the given reaction should be written.

CH₃-COO-C₆H₅+KOH(

Concept Introduction: A compound derived from an Oxoacid in which at least one Hydroxyl group (-OH) is replaced by an Alkoxy group (-O-R) is an Ester.

Answer to Problem 55A

Structure of the expected product is

CH₃-COO-C₆H₅+KOH( C₆H₅-COOK+ CH₃OH

Explanation of Solution

An Ester reacts with Potassium Hydroxide:

CH₃-COO-C₆H₅+KOH( C₆H₅-COOK+ CH₃OH

In this reaction of basic Hydrolysis, the molecule of the base splits the linkage of an Ester. Acid portion of an Ester ends up as the Potassium salt and the Alcohol portion ends up as the free Alcohol.

(c)

Interpretation Introduction

Interpretation: The structure of the expected product for the given reaction should be written.

  ${\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}{\text{COOCH}}_{\text{2}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{3}}+{\text{ H}}_{\text{2}}\text{O}\stackrel{H^{+}}{\to }$

Concept Introduction: A compound derived from an Oxoacid in which at least one Hydroxyl group (-OH) is replaced by an Alkoxy group (-O-R) is an Ester.

Answer to Problem 55A

Structure of the expected product is

  ${\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}{\text{COOCH}}_{\text{2}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{3}}+{\text{ H}}_{\text{2}}\text{O}\stackrel{H^{+}}{\to }{\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}\text{COOH}+{\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{2}}\text{OH}$

Explanation of Solution

Acidic Hydrolysis of an Ester.

  ${\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}{\text{COOCH}}_{\text{2}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{3}}+{\text{ H}}_{\text{2}}\text{O}\stackrel{H^{+}}{\to }{\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}\text{COOH}+{\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{2}}\text{OH}$

In this reaction of Acidic Hydrolysis, water splits an ester bond. Hydrogen of H₂O joins to the Oxygen atom in the (OR) part of the original Ester and the (OH) of H₂O joins to the Carbonyl Carbon atom.

(d)

Interpretation Introduction

Interpretation: The structure of the expected product for the given reaction should be written.

  ${\text{CH}}_{\text{3}}-{\text{CH}}_{\text{2}}-\text{COO}-{\text{CH}}_{\text{2}}-\text{CH}\left({\text{CH}}_{\text{3}}\right)-{\text{ CH}}_{\text{3}}+{\text{ H}}_{\text{2}}\text{O}\stackrel{\text{HCl}}{\to }$

Concept Introduction: A compound derived from an Oxoacid in which at least one Hydroxyl group (-OH) is replaced by an Alkoxy group (-O-R) is an Ester.

Answer to Problem 55A

Structure of the expected product is

  ${\text{CH}}_{\text{3}}-{\text{CH}}_{\text{2}}-\text{COOH }+{\text{ CH}}_{\text{3}}-\text{CH}\left({\text{CH}}_3\right)-\text{OH}$

Explanation of Solution

Acidic Hydrolysis of an Ester.

  ${\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}{\text{COOCH}}_{\text{2}}-\text{CH}\left({\text{CH}}_{\text{3}}\right)-{\text{CH}}_{\text{3}}+{\text{ H}}_{\text{2}}\text{O}\stackrel{\text{HCl}}{\to }{\text{CH}}_{\text{3}}-{\text{CH}}_{\text{2}}-\text{COOH }+{\text{ CH}}_{\text{3}}-\text{CH}\left({\text{CH}}_3\right)-\text{OH}$

In this reaction of Acidic Hydrolysis, an Ester reacts with water to produce an Acid and an Alcohol. In order to have major Hydrolysis, excess water can be used. HCl provides the formation of both an Acid catalyst and water.