Organic Chemistry: Structure and Function
Organic Chemistry: Structure and Function
8th Edition
ISBN: 9781319079451
Author: K. Peter C. Vollhardt, Neil E. Schore
Publisher: W. H. Freeman
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Chapter 6.7, Problem 6.20E

(a)

Interpretation Introduction

Interpretation:

The anion which is more basic between OH and SH should be predicted. The relative acidities of the conjugate acids within each group should be predicted.

Concept Introduction:

Base is defined as species which can give hydroxide ion in the solution. To compare the basicity of anions, the acidity of their conjugate acids needs to be compared. In an acid, if the electronegativity of the atom attached to the acidic proton is increased, the bond between the electronegative atom and hydrogen becomes more polar, this results in increase in the acidic strength.

On increasing the size of the atom attached to the acidic proton, the acidic strength increases. The third factor that determines the acidity of a molecule is its resonance ability. If the charge can be delocalized over several atoms in the acid, it will be more acidic. This effect is enhanced by the presence of additional electronegative atoms.

Good leaving groups are conjugate bases of strong acids.

(b)

Interpretation Introduction

Interpretation:

The anion which is more basic between PH2 and SH should be predicted. The relative acidities of the conjugate acids within each group should be predicted.

Concept Introduction:

Base is defined as species which can give hydroxide ion in the solution. To compare the basicity of anions, the acidity of their conjugate acids needs to be compared. In an acid, if the electronegativity of the atom attached to the acidic proton is increased, the bond between the electronegative atom and hydrogen becomes more polar, this results in increase in the acidic strength.

On increasing the size of the atom attached to the acidic proton, the acidic strength increases. The third factor that determines the acidity of a molecule is its resonance ability. If the charge can be delocalized over several atoms in the acid, it will be more acidic. This effect is enhanced by the presence of additional electronegative atoms.

Good leaving groups are conjugate bases of strong acids.

(c)

Interpretation Introduction

Interpretation:

The anion which is more basic between I and SeH should be predicted. The relative acidities of the conjugate acids within each group should be predicted.

Concept Introduction:

Base is defined as species which can give hydroxide ion in the solution. To compare the basicity of anions, the acidity of their conjugate acids needs to be compared. In an acid, if the electronegativity of the atom attached to the acidic proton is increased, the bond between the electronegative atom and hydrogen becomes more polar, this results in increase in the acidic strength.

On increasing the size of the atom attached to the acidic proton, the acidic strength increases. The third factor that determines the acidity of a molecule is its resonance ability. If the charge can be delocalized over several atoms in the acid, it will be more acidic. This effect is enhanced by the presence of additional electronegative atoms.

Good leaving groups are conjugate bases of strong acids.

(d)

Interpretation Introduction

Interpretation:

The anion which is more basic between HOSO2 and HOSO3 should be predicted. The relative acidities of the conjugate acids within each group should be predicted.

Concept Introduction:

Base is defined as species which can give hydroxide ion in the solution. To compare the basicity of anions, the acidity of their conjugate acids needs to be compared. In an acid, if the electronegativity of the atom attached to the acidic proton is increased, the bond between the electronegative atom and hydrogen becomes more polar, this results in increase in the acidic strength.

On increasing the size of the atom attached to the acidic proton, the acidic strength increases. The third factor that determines the acidity of a molecule is its resonance ability. If the charge can be delocalized over several atoms in the acid, it will be more acidic. This effect is enhanced by the presence of additional electronegative atoms.

Good leaving groups are conjugate bases of strong acids.

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