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.

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Answer 1

Question

Chapter 8.10, Problem 20P

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.

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Which group is of lower priority than –CH=CH2 according to Cahn-Ingold-Prelog rules. –CH=C(CH3)2 –C(CH3)3 –CH(CH3)2 –CH=CHCl a b c d

For each of the following substituents, indicate whether it withdraws electrons inductively, donates electrons by hyperconjugation, withdraws electrons by resonance, or donates electrons by resonance. (Effects should be compared with that of a hydrogen; remember that many substituents can be characterized in more than one way.)

The central carbon atom of an allene is a member of two double bonds, and ithas an interesting orbital arrangement that holds the two ends of the molecule at rightangles to each other.(a) Draw an orbital diagram of allene, showing why the two ends are perpendicular.(b) Draw the two enantiomers of penta-2,3-diene. A model may be helpful

Answer 2

Question

Chapter 8.10, Problem 20P

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.

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Answer 3

Question

Chapter 8.10, Problem 20P

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.

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Answer 4

Question

Chapter 8.10, Problem 20P

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.

Expert Solution & Answer

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Answer 5

Chapter 8.10, Problem 20P

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.

Answer 6

Chapter 8.10, Problem 20P

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.

Answer 7

Chapter 8.10, Problem 20P

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.

Answer 8

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.

Answer 9

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.

Answer 10

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.

Answer 11

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.

Answer 12

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.

Answer 13

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.

Answer 14

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.

Answer 15

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.

Answer 16

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.

Answer 17

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.

Answer 18

Expert Solution & Answer

Answer 19

Expert Solution & Answer

Answer 20

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Answer 21

Ch. 8.1 - Prob. 1P Ch. 8.1 - Prob. 2P Ch. 8.4 - Prob. 3P Ch. 8.5 - Prob. 4P Ch. 8.5 - Prob. 6P Ch. 8.6 - a. Predict the relative bond lengths of the three...Ch. 8.6 - Prob. 8P Ch. 8.6 - Prob. 9P Ch. 8.6 - Prob. 10P Ch. 8.7 - Prob. 11P

Solution Summary: The author explains that electron donating groups decrease acidity by inductive effect. Electron withdrawal increases acid; ethyl substituents donate electron by hyper conjugation.

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