Organic Chemistry: A Guided Inquiry
Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN: 9780618974122
Author: Andrei Straumanis
Publisher: Cengage Learning
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Chapter 4, Problem 27E

a)

Interpretation Introduction

Interpretation: Conjugate base for each below acid should be determined. Also, rank of conjugate bases from strongest to weakest P.E. should be determined.

  Organic Chemistry: A Guided Inquiry, Chapter 4, Problem 27E , additional homework tip  1

Concept introduction: According to the Bronsted-Lowry concept, a substance that donates proton is termed as acid while that accepts or gains protons is called a base. Species formed after loss of protons from acids are known as their respective conjugate bases whereas conjugate acid is produced by the addition of protons to base. The strength of conjugate acids and conjugate bases are inversely related to strengths of their respective bases and acids.

According to Lewis's concept, a substance that donates electron pair is termed as a base while that accepts or gains electron pair is called acid. For example, BF3 is an electron-deficient compound and can easily accept electrons so it is Lewis acid. But NH3 has lone pair of electrons that it can donate easily so it acts as Lewis base.

According to the Arrhenius concept, substances that donate hydrogen ions in solutions are known as acids while bases are substances that release hydroxide ions in solutions.

b)

Interpretation Introduction

Interpretation: Type of orbital that has a lone pair of electrons in the below conjugate base should be drawn.

  Organic Chemistry: A Guided Inquiry, Chapter 4, Problem 27E , additional homework tip  2

Concept introduction: Hybridization is processed to intermix atomic orbitals in order to form new hybrid orbitals. It can be determined by the calculation of the number of hybrid orbitals (X) which is formed by atom. The number of hybrid orbitals (X) is calculated as follows:

  X = [(number of atoms bonded to the central atom)+(number of lone pairs on the central atom)]

Type of hybridization that corresponds to the different number of hybrid orbitals is described in the following table:

   Number of hybrid orbitalsHybridization2sp3sp24sp35sp3d6sp3d2

c)

Interpretation Introduction

Interpretation: Percent s character of each orbital with lone pair in below conjugate bases should be determined.

  Organic Chemistry: A Guided Inquiry, Chapter 4, Problem 27E , additional homework tip  3

Concept introduction: Hybridization is processed to intermix atomic orbitals in order to form new hybrid orbitals. It can be determined by the calculation of the number of hybrid orbitals (X) which is formed by atom. Number of hybrid orbitals (X) is calculated as follows:

  X = [(number of atoms bonded to the central atom)+(number of lone pairs on the central atom)]

Type of hybridization that corresponds to a different number of hybrid orbitals is described in the following table:

   Number of hybrid orbitalsHybridization2sp3sp24sp35sp3d6sp3d2

d)

Interpretation Introduction

Interpretation: Whether s orbital or p orbital is lower in PE should be determined.

Concept introduction: Orbitals are defined as regions around atomic nucleus where electrons are found. Atomic orbitals help to form covalent bonds. Atomic orbitals can be s , p , d and f orbitals.

e)

Interpretation Introduction

Interpretation: Reason for pattern in pKa data should be determined.

Concept introduction: pKa is defined as the negative logarithm of the dissociation constant of acid (Ka) . If conjugate acid has a high pKa value, its dissociation constant will be less. As a result, it cannot dissociate completely in solutions and acts as a weak acid. The strength of the base and its conjugate acid are inversely related to each other. So base that corresponds to weak conjugate acid will be a strong base. Higher the pKa of conjugate acid, the stronger the base and vice-versa.

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Chapter 4 Solutions

Organic Chemistry: A Guided Inquiry

Ch. 4 - Prob. 11CTQCh. 4 - Prob. 12CTQCh. 4 - Prob. 13CTQCh. 4 - Prob. 14CTQCh. 4 - Prob. 15CTQCh. 4 - Prob. 16CTQCh. 4 - Prob. 17CTQCh. 4 - Prob. 18CTQCh. 4 - Prob. 19CTQCh. 4 - Prob. 20CTQCh. 4 - Prob. 21CTQCh. 4 - Prob. 22CTQCh. 4 - (E) Label each of the following as strong acid,...Ch. 4 - Prob. 24CTQCh. 4 - Draw the structure of the conjugate base of water....Ch. 4 - Does Cl have a conjugate acid? If so, what is it?...Ch. 4 - Draw the conjugate base of CH4 (methane).Ch. 4 - For the previous four questions, label each...Ch. 4 - Prob. 29CTQCh. 4 - According to the conventions above, what is the...Ch. 4 - Draw an arrow on Figure 4.13 representing Hrxn4 ....Ch. 4 - Prob. 32CTQCh. 4 - Add a + or above each curved arrow in Figure 4.11...Ch. 4 - Prob. 34CTQCh. 4 - Prob. 35CTQCh. 4 - Prob. 36CTQCh. 4 - Prob. 37CTQCh. 4 - Prob. 38CTQCh. 4 - Prob. 39CTQCh. 4 - Prob. 40CTQCh. 4 - Prob. 41CTQCh. 4 - Prob. 42CTQCh. 4 - Prob. 43CTQCh. 4 - Prob. 44CTQCh. 4 - Prob. 45CTQCh. 4 - Prob. 46CTQCh. 4 - For NH3 (ammonia) and H2O (water)... a. Use curved...Ch. 4 - Prob. 48CTQCh. 4 - Prob. 49CTQCh. 4 - Prob. 50CTQCh. 4 - Prob. 51CTQCh. 4 - Prob. 52CTQCh. 4 - Prob. 53CTQCh. 4 - Prob. 1ECh. 4 - Prob. 2ECh. 4 - Prob. 3ECh. 4 - Prob. 4ECh. 4 - Prob. 5ECh. 4 - Prob. 6ECh. 4 - Prob. 7ECh. 4 - Prob. 8ECh. 4 - Propanal (bp 48°C) and propanol (bp 97°C), both...Ch. 4 - Rank the following molecules from lowest to...Ch. 4 - Prob. 12ECh. 4 - For each molecule below, draw the conjugate acid...Ch. 4 - For each structure you drew in the answer to the...Ch. 4 - Mark each of the following statements True or...Ch. 4 - Organic chemistry is a bit like cooking. Later in...Ch. 4 - Prob. 17ECh. 4 - Prob. 18ECh. 4 - Are endothermic reactions favorable or...Ch. 4 - Prob. 20ECh. 4 - Is bond formation endothermic or exothermic? Write...Ch. 4 - Summarize the relationship between pKa and acid...Ch. 4 - Summarize the relationship between pKa and base...Ch. 4 - Prob. 25ECh. 4 - Consider the following bases: a. For each base...Ch. 4 - Prob. 27ECh. 4 - The following are equivalent ways of asking about...Ch. 4 - Prob. 29E
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