(a) Interpretation: Whether the given substituent exhibits an electron-withdrawing or an electron-donating inductive effect is to be identified. Concept introduction: The atoms which are more electronegative than carbon pull charge density away from carbon and exhibit an electron-withdrawing inductive effect. Alkyl groups donate electron density, thus exhibit an electron donation inductive effect.

Question

Using the data in Appendix C, determine which of the following bases is strong enough to deprotonate acetonitrile (CH3CN), so that equilibrium favors the products: (a) NaH; (b) Na2CO3; (c) NaOH; (d) NaNH2; (e) NaHCO3.

Answer 1

Question

Chapter 16.6, Problem 14P

Interpretation Introduction

(a)

Interpretation: Whether the given substituent exhibits an electron-withdrawing or an electron-donating inductive effect is to be identified.

Concept introduction: The atoms which are more electronegative than carbon pull charge density away from carbon and exhibit an electron-withdrawing inductive effect. Alkyl groups donate electron density, thus exhibit an electron donation inductive effect.

Interpretation Introduction

(b)

Interpretation: Whether the given substituent exhibits an electron-withdrawing or an electron-donating inductive effect is to be identified.

Concept introduction: The atoms which are more electronegative than carbon pull charge density away from carbon and exhibit an electron-withdrawing inductive effect. Alkyl groups donate electron density, thus exhibit an electron donation inductive effect.

Interpretation Introduction

(c)

Interpretation: Whether the given substituent exhibits an electron-withdrawing or an electron-donating inductive effect is to be identified.

Concept introduction: The atoms which are more electronegative than carbon pull charge density away from carbon and exhibit an electron-withdrawing inductive effect. Alkyl groups donate electron density, thus exhibit an electron donation inductive effect.

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Using the data in Appendix C, determine which of the following bases is strong enough to deprotonate acetonitrile (CH3CN), so that equilibrium favors the products: (a) NaH; (b) Na2CO3; (c) NaOH; (d) NaNH2; (e) NaHCO3.

Complete each acid-base reaction and predict whether the position of equilibrium lies toward the left or toward the right.

Predict the products of the following acid-base reactions. If the equilibrium would not result in the formation of appreciable amounts of products, you should so indicate. In each case label the stronger acid, the stronger base, the weaker acid, and the weaker base: (a) CH3CH=CH2 + NANH2 (d) CH3C=C: + CH;CH2OH → (e) CH3C=C:- + NH¾CI – | (b) CH;C=CH + NaNH2 (c) CH3CH2CH3 + NANH2 → | HAS

Answer 2

Question

Chapter 16.6, Problem 14P

Interpretation Introduction

(a)

Interpretation: Whether the given substituent exhibits an electron-withdrawing or an electron-donating inductive effect is to be identified.

Concept introduction: The atoms which are more electronegative than carbon pull charge density away from carbon and exhibit an electron-withdrawing inductive effect. Alkyl groups donate electron density, thus exhibit an electron donation inductive effect.

Interpretation Introduction

(b)

Interpretation: Whether the given substituent exhibits an electron-withdrawing or an electron-donating inductive effect is to be identified.

Concept introduction: The atoms which are more electronegative than carbon pull charge density away from carbon and exhibit an electron-withdrawing inductive effect. Alkyl groups donate electron density, thus exhibit an electron donation inductive effect.

Interpretation Introduction

(c)

Interpretation: Whether the given substituent exhibits an electron-withdrawing or an electron-donating inductive effect is to be identified.

Concept introduction: The atoms which are more electronegative than carbon pull charge density away from carbon and exhibit an electron-withdrawing inductive effect. Alkyl groups donate electron density, thus exhibit an electron donation inductive effect.

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Answer 3

Question

Chapter 16.6, Problem 14P

Interpretation Introduction

(a)

Interpretation: Whether the given substituent exhibits an electron-withdrawing or an electron-donating inductive effect is to be identified.

Concept introduction: The atoms which are more electronegative than carbon pull charge density away from carbon and exhibit an electron-withdrawing inductive effect. Alkyl groups donate electron density, thus exhibit an electron donation inductive effect.

Interpretation Introduction

(b)

Interpretation: Whether the given substituent exhibits an electron-withdrawing or an electron-donating inductive effect is to be identified.

Concept introduction: The atoms which are more electronegative than carbon pull charge density away from carbon and exhibit an electron-withdrawing inductive effect. Alkyl groups donate electron density, thus exhibit an electron donation inductive effect.

Interpretation Introduction

(c)

Interpretation: Whether the given substituent exhibits an electron-withdrawing or an electron-donating inductive effect is to be identified.

Concept introduction: The atoms which are more electronegative than carbon pull charge density away from carbon and exhibit an electron-withdrawing inductive effect. Alkyl groups donate electron density, thus exhibit an electron donation inductive effect.

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Answer 4

Question

Chapter 16.6, Problem 14P

Interpretation Introduction

(a)

Interpretation: Whether the given substituent exhibits an electron-withdrawing or an electron-donating inductive effect is to be identified.

Concept introduction: The atoms which are more electronegative than carbon pull charge density away from carbon and exhibit an electron-withdrawing inductive effect. Alkyl groups donate electron density, thus exhibit an electron donation inductive effect.

Interpretation Introduction

(b)

Interpretation: Whether the given substituent exhibits an electron-withdrawing or an electron-donating inductive effect is to be identified.

Concept introduction: The atoms which are more electronegative than carbon pull charge density away from carbon and exhibit an electron-withdrawing inductive effect. Alkyl groups donate electron density, thus exhibit an electron donation inductive effect.

Interpretation Introduction

(c)

Interpretation: Whether the given substituent exhibits an electron-withdrawing or an electron-donating inductive effect is to be identified.

Concept introduction: The atoms which are more electronegative than carbon pull charge density away from carbon and exhibit an electron-withdrawing inductive effect. Alkyl groups donate electron density, thus exhibit an electron donation inductive effect.

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Answer 5

Chapter 16.6, Problem 14P

Interpretation Introduction

(a)

Interpretation: Whether the given substituent exhibits an electron-withdrawing or an electron-donating inductive effect is to be identified.

Concept introduction: The atoms which are more electronegative than carbon pull charge density away from carbon and exhibit an electron-withdrawing inductive effect. Alkyl groups donate electron density, thus exhibit an electron donation inductive effect.

Interpretation Introduction

(b)

Interpretation: Whether the given substituent exhibits an electron-withdrawing or an electron-donating inductive effect is to be identified.

Concept introduction: The atoms which are more electronegative than carbon pull charge density away from carbon and exhibit an electron-withdrawing inductive effect. Alkyl groups donate electron density, thus exhibit an electron donation inductive effect.

Interpretation Introduction

(c)

Interpretation: Whether the given substituent exhibits an electron-withdrawing or an electron-donating inductive effect is to be identified.

Concept introduction: The atoms which are more electronegative than carbon pull charge density away from carbon and exhibit an electron-withdrawing inductive effect. Alkyl groups donate electron density, thus exhibit an electron donation inductive effect.

Answer 6

Chapter 16.6, Problem 14P

Interpretation Introduction

(a)

Interpretation: Whether the given substituent exhibits an electron-withdrawing or an electron-donating inductive effect is to be identified.

Concept introduction: The atoms which are more electronegative than carbon pull charge density away from carbon and exhibit an electron-withdrawing inductive effect. Alkyl groups donate electron density, thus exhibit an electron donation inductive effect.

Answer 7

Chapter 16.6, Problem 14P

Interpretation Introduction

(a)

Interpretation: Whether the given substituent exhibits an electron-withdrawing or an electron-donating inductive effect is to be identified.

Concept introduction: The atoms which are more electronegative than carbon pull charge density away from carbon and exhibit an electron-withdrawing inductive effect. Alkyl groups donate electron density, thus exhibit an electron donation inductive effect.

Answer 8

Interpretation Introduction

(b)

Interpretation: Whether the given substituent exhibits an electron-withdrawing or an electron-donating inductive effect is to be identified.

Concept introduction: The atoms which are more electronegative than carbon pull charge density away from carbon and exhibit an electron-withdrawing inductive effect. Alkyl groups donate electron density, thus exhibit an electron donation inductive effect.

Answer 9

Interpretation Introduction

(b)

Interpretation: Whether the given substituent exhibits an electron-withdrawing or an electron-donating inductive effect is to be identified.

Concept introduction: The atoms which are more electronegative than carbon pull charge density away from carbon and exhibit an electron-withdrawing inductive effect. Alkyl groups donate electron density, thus exhibit an electron donation inductive effect.

Answer 10

Interpretation Introduction

(c)

Interpretation: Whether the given substituent exhibits an electron-withdrawing or an electron-donating inductive effect is to be identified.

Concept introduction: The atoms which are more electronegative than carbon pull charge density away from carbon and exhibit an electron-withdrawing inductive effect. Alkyl groups donate electron density, thus exhibit an electron donation inductive effect.

Answer 11

Interpretation Introduction

(c)

Interpretation: Whether the given substituent exhibits an electron-withdrawing or an electron-donating inductive effect is to be identified.

Concept introduction: The atoms which are more electronegative than carbon pull charge density away from carbon and exhibit an electron-withdrawing inductive effect. Alkyl groups donate electron density, thus exhibit an electron donation inductive effect.

Answer 12

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Answer 13

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Answer 23

Ch. 16.1 - Prob. 1P Ch. 16.2 - Prob. 2P Ch. 16.3 - Prob. 3P Ch. 16.4 - Prob. 4P Ch. 16.5 - Prob. 5P Ch. 16.5 - Prob. 6P Ch. 16.5 - Prob. 9P Ch. 16.5 - Problem 18.9 Draw the product of each reaction a....Ch. 16.5 - Prob. 11P Ch. 16.5 - Prob. 12P

Solution Summary: The author analyzes whether a given substituent exhibits an electron-withdrawing or donating inductive effect. The atoms which are more electronegative than carbon pull charge density away from carbon.

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