(a) Interpretation: The stepwise mechanism to explain the given result is to be drawn. Concept introduction: Carbonyl compounds in presence of base, loses its alpha hydrogen to form enolate. Enolates have negatively charged oxygen with adjacent carbon-carbon double bond. Enolates are resonance stabilized species.

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Answer 1

Question

Chapter 23, Problem 23.74P

Interpretation Introduction

(a)

Interpretation: The stepwise mechanism to explain the given result is to be drawn.

Concept introduction: Carbonyl compounds in presence of base, loses its alpha hydrogen to form enolate. Enolates have negatively charged oxygen with adjacent carbon-carbon double bond. Enolates are resonance stabilized species.

Interpretation Introduction

(b)

Interpretation: The validation of the fact that optically pure isomer is obtained regardless of the amount of base used in litorene is to be stated with an explanation.

Concept introduction: Carbonyl compounds in presence of base, loses its alpha hydrogen to form enolate. Enolates have negatively charged oxygen with adjacent carbon-carbon double bond. Enolates are resonance stabilized species.

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Arrange each group of compounds in order of increasing basicity.(a) CH3COO-, ClCH2COO-, and PhO- (b) sodium acetylide, sodium amide, and sodium acetate(c) sodium benzoate, sodium ethoxide, and sodium phenoxide (d) pyridine, sodium ethoxide, and sodium acetate

(−)-Hyoscyamine, an optically active drug used to treat gastrointestinal disorders, is isolated from Atropa belladonna, the deadly nightshade plant, by a basic aqueous extraction procedure. If too much base is used during isolation, optically inactive material is isolated. (a) Explain this result by drawing a stepwise mechanism. (b) Explain why littorine, an isomer isolated from the tailflower plant in Australia, can be obtained optically pure regardless of the amount of base used during isolation.

Answer 2

Question

Chapter 23, Problem 23.74P

Interpretation Introduction

(a)

Interpretation: The stepwise mechanism to explain the given result is to be drawn.

Concept introduction: Carbonyl compounds in presence of base, loses its alpha hydrogen to form enolate. Enolates have negatively charged oxygen with adjacent carbon-carbon double bond. Enolates are resonance stabilized species.

Interpretation Introduction

(b)

Interpretation: The validation of the fact that optically pure isomer is obtained regardless of the amount of base used in litorene is to be stated with an explanation.

Concept introduction: Carbonyl compounds in presence of base, loses its alpha hydrogen to form enolate. Enolates have negatively charged oxygen with adjacent carbon-carbon double bond. Enolates are resonance stabilized species.

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Answer 3

Question

Chapter 23, Problem 23.74P

Interpretation Introduction

(a)

Interpretation: The stepwise mechanism to explain the given result is to be drawn.

Concept introduction: Carbonyl compounds in presence of base, loses its alpha hydrogen to form enolate. Enolates have negatively charged oxygen with adjacent carbon-carbon double bond. Enolates are resonance stabilized species.

Interpretation Introduction

(b)

Interpretation: The validation of the fact that optically pure isomer is obtained regardless of the amount of base used in litorene is to be stated with an explanation.

Concept introduction: Carbonyl compounds in presence of base, loses its alpha hydrogen to form enolate. Enolates have negatively charged oxygen with adjacent carbon-carbon double bond. Enolates are resonance stabilized species.

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Answer 4

Question

Chapter 23, Problem 23.74P

Interpretation Introduction

(a)

Interpretation: The stepwise mechanism to explain the given result is to be drawn.

Concept introduction: Carbonyl compounds in presence of base, loses its alpha hydrogen to form enolate. Enolates have negatively charged oxygen with adjacent carbon-carbon double bond. Enolates are resonance stabilized species.

Interpretation Introduction

(b)

Interpretation: The validation of the fact that optically pure isomer is obtained regardless of the amount of base used in litorene is to be stated with an explanation.

Concept introduction: Carbonyl compounds in presence of base, loses its alpha hydrogen to form enolate. Enolates have negatively charged oxygen with adjacent carbon-carbon double bond. Enolates are resonance stabilized species.

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Answer 5

Chapter 23, Problem 23.74P

Interpretation Introduction

(a)

Interpretation: The stepwise mechanism to explain the given result is to be drawn.

Concept introduction: Carbonyl compounds in presence of base, loses its alpha hydrogen to form enolate. Enolates have negatively charged oxygen with adjacent carbon-carbon double bond. Enolates are resonance stabilized species.

Interpretation Introduction

(b)

Interpretation: The validation of the fact that optically pure isomer is obtained regardless of the amount of base used in litorene is to be stated with an explanation.

Concept introduction: Carbonyl compounds in presence of base, loses its alpha hydrogen to form enolate. Enolates have negatively charged oxygen with adjacent carbon-carbon double bond. Enolates are resonance stabilized species.

Answer 6

Chapter 23, Problem 23.74P

Interpretation Introduction

(a)

Interpretation: The stepwise mechanism to explain the given result is to be drawn.

Concept introduction: Carbonyl compounds in presence of base, loses its alpha hydrogen to form enolate. Enolates have negatively charged oxygen with adjacent carbon-carbon double bond. Enolates are resonance stabilized species.

Answer 7

Chapter 23, Problem 23.74P

Interpretation Introduction

(a)

Interpretation: The stepwise mechanism to explain the given result is to be drawn.

Concept introduction: Carbonyl compounds in presence of base, loses its alpha hydrogen to form enolate. Enolates have negatively charged oxygen with adjacent carbon-carbon double bond. Enolates are resonance stabilized species.

Answer 8

Interpretation Introduction

(b)

Interpretation: The validation of the fact that optically pure isomer is obtained regardless of the amount of base used in litorene is to be stated with an explanation.

Concept introduction: Carbonyl compounds in presence of base, loses its alpha hydrogen to form enolate. Enolates have negatively charged oxygen with adjacent carbon-carbon double bond. Enolates are resonance stabilized species.

Answer 9

Interpretation Introduction

(b)

Interpretation: The validation of the fact that optically pure isomer is obtained regardless of the amount of base used in litorene is to be stated with an explanation.

Concept introduction: Carbonyl compounds in presence of base, loses its alpha hydrogen to form enolate. Enolates have negatively charged oxygen with adjacent carbon-carbon double bond. Enolates are resonance stabilized species.

Answer 10

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Answer 11

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Answer 12

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Answer 13

Ch. 23 - Problem 23.1 Draw the enol or keto tautomer(s) of...Ch. 23 - Prob. 23.2P Ch. 23 - Problem 23.3 When phenylacetaldehyde is dissolved...Ch. 23 - Prob. 23.4P Ch. 23 - Problem 23.5 Which bonds in the following...Ch. 23 - Prob. 23.6P Ch. 23 - Prob. 23.7P Ch. 23 - Prob. 23.8P Ch. 23 - Prob. 23.9P Ch. 23 - Prob. 23.10P

Solution Summary: The author explains the stepwise mechanism to explain the given result. Carbonyl compounds in presence of base, lose their alpha hydrogen to form enolate.

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Chapter 23 Solutions