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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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.) a. Br b CH2CH3 c. C=OCH3 d. NHCH3 e. OCH3 f. +N(CH3)3

TRUE OR FALSE. Write T if True, F if False. 1. In numbering the longest chain, the first substituent should have the higher number. 2. Alphabetize the names of the substituents, ignoring all prefixes except iso, as in isopropyl and isobutyl. 3. A number is always designated to indicate the location of a single substituent in cyclohexane. 4. For rings with two different substituents, number the ring to assign the lower number to the substituents alphabetically. 5. In naming alkenes, the longest carbon chain is always used as the parent name. 6. Toluene is an IUPAC name. 7. A benzyl group differs from a phenyl group only by an extra CH2 group. 8. Naming of branched molecules depend on the type of C atom removed from the parent chain. 9. An unbranched alkane with a chain of 50 carbons is called pentacontane. 10. Heterocyclic amines still…

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.

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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

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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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