Chapter 17, Problem 17.31UKC

(a)

Interpretation Introduction

Interpretation:

The chemical conditions to remove the acetyl group from N-Acetylglucosamide 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 structure of products formed during the acid hydrolysis of N-Acetylglucosamide has to be drawn.

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.