Fundamentals of General, Organic, and Biological Chemistry, Books a la Carte Plus Mastering Chemistry with Pearson eText -- Access Card Package (8th Edition)
Fundamentals of General, Organic, and Biological Chemistry, Books a la Carte Plus Mastering Chemistry with Pearson eText -- Access Card Package (8th Edition)
8th Edition
ISBN: 9780134261256
Author: John McMurray, David S. Ballantine, Carl A. Hoeger, Virginia E. Peterson
Publisher: PEARSON
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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 NH2, NHR' or NR'2 group is attached to the carbonyl carbon atom of the compound. It is represented as RCONR'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 NH2, NHR' or NR'2 group is attached to the carbonyl carbon atom of the compound. It is represented as RCONR'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.

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Chapter 17 Solutions

Fundamentals of General, Organic, and Biological Chemistry, Books a la Carte Plus Mastering Chemistry with Pearson eText -- Access Card Package (8th Edition)

Ch. 17.1 - Prob. 17.11PCh. 17.1 - Prob. 17.12PCh. 17.1 - Prob. 17.13KCPCh. 17.2 - Salsalate, which is an ester formed by the...Ch. 17.2 - Prob. 17.2CIAPCh. 17.2 - Prob. 17.3CIAPCh. 17.2 - Prob. 17.14PCh. 17.2 - Prob. 17.15PCh. 17.2 - Prob. 17.16PCh. 17.3 - Prob. 17.17PCh. 17.3 - Raspberry oil contains an ester that is made by...Ch. 17.3 - Prob. 17.19PCh. 17.3 - Prob. 17.20PCh. 17.3 - Prob. 17.21PCh. 17.4 - If a bottle of aspirin tablets has the aroma of...Ch. 17.4 - Prob. 17.23PCh. 17.4 - What carboxylic acids and amines result from...Ch. 17.5 - Prob. 17.25PCh. 17.5 - Prob. 17.26KCPCh. 17.6 - Prob. 17.27PCh. 17.6 - Prob. 17.28PCh. 17.6 - Prob. 17.4CIAPCh. 17.6 - Prob. 17.5CIAPCh. 17.6 - Prob. 17.29PCh. 17 - Prob. 17.30UKCCh. 17 - Prob. 17.31UKCCh. 17 - One phosphorylated form of glycerate is...Ch. 17 - Prob. 17.33UKCCh. 17 - Prob. 17.34UKCCh. 17 - Prob. 17.35UKCCh. 17 - Prob. 17.36UKCCh. 17 - For the following compounds, give the systematic...Ch. 17 - Write the equation for the ionization of hexanoic...Ch. 17 - Prob. 17.39APCh. 17 - Prob. 17.40APCh. 17 - Prob. 17.41APCh. 17 - Give systematic names for the following carboxylic...Ch. 17 - Give systematic names for the following carboxylic...Ch. 17 - Prob. 17.44APCh. 17 - Prob. 17.45APCh. 17 - Draw structures corresponding to the following...Ch. 17 - Draw structures corresponding to the following...Ch. 17 - Malic acid, a dicarboxylic acid found in apples,...Ch. 17 - Prob. 17.49APCh. 17 - Prob. 17.50APCh. 17 - Prob. 17.51APCh. 17 - Prob. 17.52APCh. 17 - Prob. 17.53APCh. 17 - Give systematic names for the following structures...Ch. 17 - Give systematic names for the following structures...Ch. 17 - Prob. 17.56APCh. 17 - Prob. 17.57APCh. 17 - Give systematic names for the following structures...Ch. 17 - Give systematic names for the following structures...Ch. 17 - Prob. 17.60APCh. 17 - What compounds are produced from hydrolysis of...Ch. 17 - Procaine, a local anesthetic whose hydrochloride...Ch. 17 - Prob. 17.63APCh. 17 - Lactones are cyclic esters in which the carboxylic...Ch. 17 - When both the carboxylic acid and the amine are in...Ch. 17 - LSD (lysergic acid diethylamide), a semisynthetic...Ch. 17 - Prob. 17.67APCh. 17 - Prob. 17.68APCh. 17 - Prob. 17.69APCh. 17 - Prob. 17.70APCh. 17 - Prob. 17.71APCh. 17 - Prob. 17.72APCh. 17 - Prob. 17.73APCh. 17 - Prob. 17.74APCh. 17 - Prob. 17.75APCh. 17 - Three amide isomers, N,N-dimethylformamide,...Ch. 17 - Prob. 17.77CPCh. 17 - Prob. 17.78CPCh. 17 - Mention at least two simple chemical tests by...Ch. 17 - Prob. 17.80CPCh. 17 - Name the following compounds.Ch. 17 - Each of the following materials has an ester that...Ch. 17 - Prob. 17.83GPCh. 17 - Prob. 17.84GP
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