Chapter 19.14, Problem 15P

a)

Interpretation Introduction

Interpretation:

• The given substituents has to be predicted.

Concept Introduction:

Electronic effect:

Electron donating groups decreases acidity by inductive effect (withdrawal of electrons through a sigma bond).  Electron withdrawal increases acidity.  Electron-donating substituents destabilize a base, and decrease the strength of its conjugate acid; electron-withdrawing substituents stabilize a base, which increase the strength of its conjugate base.

Rule: The strength of a base depends on the stability of its conjugate acid.

b)

Interpretation Introduction

Interpretation:

The given substituents to be predicted

Concept Introduction:

Electronic effect:

Electron donating groups decreases acidity by inductive effect (withdrawal of electrons through a sigma bond).  Electron withdrawal increases acidity.  Electron-donating substituents destabilize a base, and decrease the strength of its conjugate acid; electron-withdrawing substituents stabilize a base, which increase the strength of its conjugate base.

Rule: The strength of a base depends on the stability of its conjugate acid.

c)

Interpretation Introduction

Interpretation:

• The following substituents to be predicted.

Concept Introduction:

Electronic effect:

Electron donating groups decreases acidity by inductive effect (withdrawal of electrons through a sigma bond).  Electron withdrawal increases acidity.  Electron-donating substituents destabilize a base, and decrease the strength of its conjugate acid; electron-withdrawing substituents stabilize a base, which increase the strength of its conjugate base.

Rule: The strength of a base depends on the stability of its conjugate acid.

d)

Interpretation Introduction

Interpretation:

• The following substituents to be predicted.

Concept Introduction:

Electronic effect:

Electron donating groups decreases acidity by inductive effect (withdrawal of electrons through a sigma bond).  Electron withdrawal increases acidity.  Electron-donating substituents destabilize a base, and decrease the strength of its conjugate acid; electron-withdrawing substituents stabilize a base, which increase the strength of its conjugate base.

Rule: The strength of a base depends on the stability of its conjugate acid.

e)

Interpretation Introduction

Interpretation:

• The following substituents to be predicted.

Concept Introduction:

Electronic effect:

Electron donating groups decreases acidity by inductive effect (withdrawal of electrons through a sigma bond).  Electron withdrawal increases acidity.  Electron-donating substituents destabilize a base, and decrease the strength of its conjugate acid; electron-withdrawing substituents stabilize a base, which increase the strength of its conjugate base.

Rule: The strength of a base depends on the stability of its conjugate acid.

f)

Interpretation Introduction

Interpretation:

• The following substituents to be predicted.

Concept Introduction:

Electronic effect:

Electron donating groups decreases acidity by inductive effect (withdrawal of electrons through a sigma bond).  Electron withdrawal increases acidity.  Electron-donating substituents destabilize a base, and decrease the strength of its conjugate acid; electron-withdrawing substituents stabilize a base, which increase the strength of its conjugate base.

Rule: The strength of a base depends on the stability of its conjugate acid.