Chapter 17.6, Problem 17.28P

(a)

Interpretation Introduction

Interpretation:

The functional group of the given compound has to be identified. Also the products formed during the hydrolysis of the given compound have to be determined.

Concept introduction:

Carboxylic acid: One $-OH$ group is attached to the carbonyl carbon atom of the compound. It is represented as $RCOOH$

Amide: One $-N{H}_2$, $-NHR\text{'}$ or $-NR{\text{'}}_2$ group is attached to the carbonyl carbon atom of the compound. It is represented as $RCONR{\text{'}}_2$.

Amide Formation: Amide is formed when a carboxylic acid reacts with an amine or ammonia.

• Primary amide is produce when a carboxylic acid reacts with ammonia.
• Secondary and tertiary amide is produce when a carboxylic acid reacts with primary and secondary amine respectively.
• Ammonium salt is formed when tertiary amine and a carboxylic acid reacts forming an ionic compound with a carboxylate acid anion and a trialkyl ammonium cation since there is no hydrogen atom in trialkyl amine

Amide Hydrolysis: In presence of base or acid with continuous heating, amide reacts with water to form the corresponding amine and carboxylic acid.

• Carboxylic acid and amine salt are obtained when amide hydrolysis takes place in presence of acid.
• Carboxylate anion and amine are obtained when amide hydrolysis takes place in presence of base.

(b)

Interpretation Introduction

Interpretation:

The functional group of the given compound has to be identified. Also the products formed during the hydrolysis of the given compound have to be determined.

Concept introduction:

Phosphoric Acid: It is an inorganic acid having similarities with a carboxylic acid. There are three different acidic hydrogens which causes it to form three anions.

Phosphate Ester: Phosphate esters are prepared by the reaction of a phosphoric acid and an alcohol molecule with the elimination of water molecule.

• Alcohol can react with one $-OH$ group forming Phosphate monoester.
• Alcohol can react with two $-OH$ groups of phosphoric acid forming Phosphate diester.
• Alcohol can react with three $-OH$ groups of phosphoric acid forming Phosphate triester.

Phosphate Ester Hydrolysis: Phosphate ester reacts with water to form the corresponding alcohol and phosphoric acid.

(c)

Interpretation Introduction

Interpretation: The products formed during the acid-catalyzed hydrolysis of the given ester have to be determined.

Concept introduction:

Carboxylic acid: One $-OH$ group is attached to the carbonyl carbon atom of the compound. It is represented as $RCOOH$

Ester: One $-OR\text{'}$ group is attached to the carbonyl carbon atom of the compound. It is represented as $RCOOR\text{'}$. The hydrogen atom of $-COOH$ is replaced by an alkyl group.

Ester Hydrolysis: Ester hydrolysis can be caused by acid and base.

• Acid-catalyzed hydrolysis: In presence of strong acid such as ${\text{H}}_{\text{2}}{\text{SO}}_{\text{4}}$, ester reacts wither water to form the corresponding alcohol and carboxylic acid. T s the reverse of esterification.
• Saponification: Ester hydrolysis taking place in presence of base such as $NaOH$ or $KOH$ is known as saponification. Ester reacts with hydroxide ion forming carboxylic acid which again reacts with base resulting in the formation of a caboxylate anion.