Pearson eText Fundamentals of General, Organic, and Biological Chemistry -- Instant Access (Pearson+)
Pearson eText Fundamentals of General, Organic, and Biological Chemistry -- Instant Access (Pearson+)
8th Edition
ISBN: 9780135213759
Author: John McMurry, David Ballantine
Publisher: PEARSON+
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Chapter 16, Problem 16.23UKC

Chapter 16, Problem 16.23UKC, (a) For the compound above, identify each nitrogen as either a primary, secondary, tertiary,

  1. (a) For the compound above, identify each nitrogen as either a primary, secondary, tertiary, quaternary, or aromatic amine.
  2. (b) Which amine group(s) would be able to provide a hydrogen bond? Which could accept a hydrogen bond?

(a)

Expert Solution
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Interpretation Introduction

Interpretation:

It should be identified that the each nitrogen in the given compound either as a primary, secondary, tertiary amine, or aromatic amine.

Concept introduction:

Amines are the derivatives of ammonia (NH3) with one or more of the hydrogens replaced with a substituent such as an alkyl group.

Depending on the number of carbon side chain of the nitrogen, different types of amines can form.

Pearson eText Fundamentals of General, Organic, and Biological Chemistry -- Instant Access (Pearson+), Chapter 16, Problem 16.23UKC , additional homework tip  1

In a quaternary ammonium ion a nitrogen atom with four attached groups is positively charged. And their compounds are known as quaternary ammonium salt.

Example: Tetramethylammonium ion

Aniline is an aromatic amine compound and its structure is,

Pearson eText Fundamentals of General, Organic, and Biological Chemistry -- Instant Access (Pearson+), Chapter 16, Problem 16.23UKC , additional homework tip  2

Answer to Problem 16.23UKC

Pearson eText Fundamentals of General, Organic, and Biological Chemistry -- Instant Access (Pearson+), Chapter 16, Problem 16.23UKC , additional homework tip  3

Explanation of Solution

Structure of the given compound is,

Pearson eText Fundamentals of General, Organic, and Biological Chemistry -- Instant Access (Pearson+), Chapter 16, Problem 16.23UKC , additional homework tip  4

As per the concepts above mentioned,

Each nitrogen atoms in the given compound can be identified either as a primary, secondary, tertiary amine or aromatic amine as follows,

Pearson eText Fundamentals of General, Organic, and Biological Chemistry -- Instant Access (Pearson+), Chapter 16, Problem 16.23UKC , additional homework tip  5

(b)

Expert Solution
Check Mark
Interpretation Introduction

Interpretation:

The amine group which would be able to provide a hydrogen bond and accept a hydrogen bond in the given compound has to be identified.

Concept introduction:

Amines are the derivatives of ammonia (NH3) with one or more of the hydrogens replaced with a substituent such as an alkyl group.

Depending on the number of carbon side chain of the nitrogen, different types of amines can form.

Pearson eText Fundamentals of General, Organic, and Biological Chemistry -- Instant Access (Pearson+), Chapter 16, Problem 16.23UKC , additional homework tip  6

Hydrogen bond is an attractive force established between hydrogen atom attached to a highly electronegative element and another highly electronegative element of the same or different molecule.

Answer to Problem 16.23UKC

Pearson eText Fundamentals of General, Organic, and Biological Chemistry -- Instant Access (Pearson+), Chapter 16, Problem 16.23UKC , additional homework tip  7

Explanation of Solution

Structure of the given compound is,

Pearson eText Fundamentals of General, Organic, and Biological Chemistry -- Instant Access (Pearson+), Chapter 16, Problem 16.23UKC , additional homework tip  8

In a hydrogen bond strong partial positive charge on hydrogen attracts lone electron pair on oxygen or nitrogen.

Here in the given molecule, an amine group which was able to provide a hydrogen bond and accept a hydrogen bond and those amines can be identified as follows,

Pearson eText Fundamentals of General, Organic, and Biological Chemistry -- Instant Access (Pearson+), Chapter 16, Problem 16.23UKC , additional homework tip  9

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Chapter 16 Solutions

Pearson eText Fundamentals of General, Organic, and Biological Chemistry -- Instant Access (Pearson+)

Ch. 16.4 - Prob. 16.11PCh. 16.5 - Write an equation for the acid-base equilibrium...Ch. 16.5 - Prob. 16.13PCh. 16.5 - Prob. 16.14PCh. 16.5 - Prob. 16.15PCh. 16.5 - Prob. 16.16PCh. 16.6 - Prob. 16.17PCh. 16.6 - Prob. 16.18PCh. 16.6 - Prob. 16.19PCh. 16.6 - Prob. 16.20PCh. 16.6 - Prob. 16.21PCh. 16.6 - Prob. 16.22PCh. 16.7 - Prob. 16.1CIAPCh. 16.7 - Prob. 16.2CIAPCh. 16.7 - Prob. 16.3CIAPCh. 16 - (a) For the compound above, identify each nitrogen...Ch. 16 - The structure of the amino acid lysine (in its...Ch. 16 - Prob. 16.25UKCCh. 16 - Prob. 16.26UKCCh. 16 - Prob. 16.27UKCCh. 16 - Complete the following equations: (a) (b)...Ch. 16 - Prob. 16.29APCh. 16 - Draw the structures corresponding to the following...Ch. 16 - Name the following amines, and classify them as...Ch. 16 - Name the following amines, and identify them as...Ch. 16 - Prob. 16.33APCh. 16 - Which is a stronger base, diethyl ether or...Ch. 16 - Prob. 16.35APCh. 16 - Prob. 16.36APCh. 16 - The compound lidocaine is used medically as a...Ch. 16 - Prob. 16.38APCh. 16 - Draw the structures of the ammonium ions formed...Ch. 16 - Prob. 16.40APCh. 16 - Prob. 16.41APCh. 16 - Prob. 16.42APCh. 16 - Prob. 16.43APCh. 16 - Prob. 16.44APCh. 16 - Prob. 16.45CPCh. 16 - Prob. 16.46CPCh. 16 - Prob. 16.47CPCh. 16 - Prob. 16.48CPCh. 16 - How do amines differ from analogous alcohols in...Ch. 16 - Name at least two undesirable characteristics are...Ch. 16 - Prob. 16.52CPCh. 16 - Complete the following equations (Hint: Answers...Ch. 16 - Prob. 16.54CPCh. 16 - Prob. 16.55CPCh. 16 - Why is cyclohexylamine not considered to be a...Ch. 16 - Prob. 16.57CPCh. 16 - Prob. 16.58GPCh. 16 - 1-Propylamine, 1-propanol, acetic acid, and butane...Ch. 16 - Prob. 16.60GPCh. 16 - Lemon juice, which contains citric acid, is...
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