Mechanism for the given reaction should be identified. Concept introduction: Carbonyl compound when treated with LDA (Lithium diisopropylamide) undergoes deprotonation at the α carbon to form enolate. The resulting enolate ion is resonance stabilized by carbon and oxygen atom. The resonance stabilized intermediate undergoes reaction with other molecule of carbonyl (same or different) to form the respective products. If LDA is used as a base the less substituted α carbon is deprotonated due to steric hindrance. Deprotonation of α carbon to form enolate Nucleophilic attach of enolate Protonation of α carbon to final product

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Answer 1

Question

Chapter 21, Problem 82PP

Interpretation Introduction

Interpretation:

Mechanism for the given reaction should be identified.

Concept introduction:

Carbonyl compound when treated with LDA (Lithium diisopropylamide) undergoes deprotonation at the α carbon to form enolate. The resulting enolate ion is resonance stabilized by carbon and oxygen atom. The resonance stabilized intermediate undergoes reaction with other molecule of carbonyl (same or different) to form the respective products. If LDA is used as a base the less substituted α carbon is deprotonated due to steric hindrance.

Deprotonation of α carbon to form enolate

Nucleophilic attach of enolate

Protonation of α carbon to final product

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Where are the chiral centers in this molecule? Also is this compound meso yes or no?

Answer 2

Question

Chapter 21, Problem 82PP

Interpretation Introduction

Interpretation:

Mechanism for the given reaction should be identified.

Concept introduction:

Carbonyl compound when treated with LDA (Lithium diisopropylamide) undergoes deprotonation at the α carbon to form enolate. The resulting enolate ion is resonance stabilized by carbon and oxygen atom. The resonance stabilized intermediate undergoes reaction with other molecule of carbonyl (same or different) to form the respective products. If LDA is used as a base the less substituted α carbon is deprotonated due to steric hindrance.

Deprotonation of α carbon to form enolate

Nucleophilic attach of enolate

Protonation of α carbon to final product

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Answer 3

Question

Chapter 21, Problem 82PP

Interpretation Introduction

Interpretation:

Mechanism for the given reaction should be identified.

Concept introduction:

Carbonyl compound when treated with LDA (Lithium diisopropylamide) undergoes deprotonation at the α carbon to form enolate. The resulting enolate ion is resonance stabilized by carbon and oxygen atom. The resonance stabilized intermediate undergoes reaction with other molecule of carbonyl (same or different) to form the respective products. If LDA is used as a base the less substituted α carbon is deprotonated due to steric hindrance.

Deprotonation of α carbon to form enolate

Nucleophilic attach of enolate

Protonation of α carbon to final product

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Answer 4

Question

Chapter 21, Problem 82PP

Interpretation Introduction

Interpretation:

Mechanism for the given reaction should be identified.

Concept introduction:

Carbonyl compound when treated with LDA (Lithium diisopropylamide) undergoes deprotonation at the α carbon to form enolate. The resulting enolate ion is resonance stabilized by carbon and oxygen atom. The resonance stabilized intermediate undergoes reaction with other molecule of carbonyl (same or different) to form the respective products. If LDA is used as a base the less substituted α carbon is deprotonated due to steric hindrance.

Deprotonation of α carbon to form enolate

Nucleophilic attach of enolate

Protonation of α carbon to final product

Expert Solution & Answer

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Answer 5

Chapter 21, Problem 82PP

Interpretation Introduction

Interpretation:

Mechanism for the given reaction should be identified.

Concept introduction:

Carbonyl compound when treated with LDA (Lithium diisopropylamide) undergoes deprotonation at the α carbon to form enolate. The resulting enolate ion is resonance stabilized by carbon and oxygen atom. The resonance stabilized intermediate undergoes reaction with other molecule of carbonyl (same or different) to form the respective products. If LDA is used as a base the less substituted α carbon is deprotonated due to steric hindrance.

Deprotonation of α carbon to form enolate

Nucleophilic attach of enolate

Protonation of α carbon to final product

Answer 6

Chapter 21, Problem 82PP

Interpretation Introduction

Interpretation:

Mechanism for the given reaction should be identified.

Concept introduction:

Carbonyl compound when treated with LDA (Lithium diisopropylamide) undergoes deprotonation at the α carbon to form enolate. The resulting enolate ion is resonance stabilized by carbon and oxygen atom. The resonance stabilized intermediate undergoes reaction with other molecule of carbonyl (same or different) to form the respective products. If LDA is used as a base the less substituted α carbon is deprotonated due to steric hindrance.

Deprotonation of α carbon to form enolate

Nucleophilic attach of enolate

Protonation of α carbon to final product

Answer 7

Chapter 21, Problem 82PP

Interpretation Introduction

Interpretation:

Mechanism for the given reaction should be identified.

Concept introduction:

Carbonyl compound when treated with LDA (Lithium diisopropylamide) undergoes deprotonation at the α carbon to form enolate. The resulting enolate ion is resonance stabilized by carbon and oxygen atom. The resonance stabilized intermediate undergoes reaction with other molecule of carbonyl (same or different) to form the respective products. If LDA is used as a base the less substituted α carbon is deprotonated due to steric hindrance.

Deprotonation of α carbon to form enolate

Nucleophilic attach of enolate

Protonation of α carbon to final product

Answer 8

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Answer 9

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Answer 10

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Answer 11

Ch. 21.1 - Prob. 1CC Ch. 21.1 - Prob. 2CC Ch. 21.1 - Prob. 3CC Ch. 21.1 - Prob. 1LTS Ch. 21.1 - Prob. 4PTS Ch. 21.1 - Prob. 5ATS Ch. 21.1 - Prob. 6CC Ch. 21.1 - Prob. 7CC Ch. 21.2 - Prob. 8CC Ch. 21.2 - Prob. 9CC

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Chapter 21 Solutions