The complete, detailed mechanism to account for the incorporation of 18 O twice in the acetate ion in the given reaction is to be drawn. Concept introduction: Under basic conditions, only weak acids can exist in the reaction mixture. A carboxylate ion can be reversibly protonated by the solvent, water. This removes the negative charge on the carboxylate ion, making it more accessible to a nucleophile. The hydroxide ion from the base can then add to the carbonyl carbon to initiate a nucleophilic addition-elimination reaction. The reaction can occur twice, effectively replacing both oxygen atoms in the carboxylate by the oxygen atoms from the base and solvent water.

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Answer 1

Question

Chapter 20, Problem 20.34P

Interpretation Introduction

Interpretation:

The complete, detailed mechanism to account for the incorporation of 18O twice in the acetate ion in the given reaction is to be drawn.

Concept introduction:

Under basic conditions, only weak acids can exist in the reaction mixture. A carboxylate ion can be reversibly protonated by the solvent, water. This removes the negative charge on the carboxylate ion, making it more accessible to a nucleophile. The hydroxide ion from the base can then add to the carbonyl carbon to initiate a nucleophilic addition-elimination reaction. The reaction can occur twice, effectively replacing both oxygen atoms in the carboxylate by the oxygen atoms from the base and solvent water.

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Answer 2

Question

Chapter 20, Problem 20.34P

Interpretation Introduction

Interpretation:

The complete, detailed mechanism to account for the incorporation of 18O twice in the acetate ion in the given reaction is to be drawn.

Concept introduction:

Under basic conditions, only weak acids can exist in the reaction mixture. A carboxylate ion can be reversibly protonated by the solvent, water. This removes the negative charge on the carboxylate ion, making it more accessible to a nucleophile. The hydroxide ion from the base can then add to the carbonyl carbon to initiate a nucleophilic addition-elimination reaction. The reaction can occur twice, effectively replacing both oxygen atoms in the carboxylate by the oxygen atoms from the base and solvent water.

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Answer 3

Question

Chapter 20, Problem 20.34P

Interpretation Introduction

Interpretation:

The complete, detailed mechanism to account for the incorporation of 18O twice in the acetate ion in the given reaction is to be drawn.

Concept introduction:

Under basic conditions, only weak acids can exist in the reaction mixture. A carboxylate ion can be reversibly protonated by the solvent, water. This removes the negative charge on the carboxylate ion, making it more accessible to a nucleophile. The hydroxide ion from the base can then add to the carbonyl carbon to initiate a nucleophilic addition-elimination reaction. The reaction can occur twice, effectively replacing both oxygen atoms in the carboxylate by the oxygen atoms from the base and solvent water.

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Answer 4

Question

Chapter 20, Problem 20.34P

Interpretation Introduction

Interpretation:

The complete, detailed mechanism to account for the incorporation of 18O twice in the acetate ion in the given reaction is to be drawn.

Concept introduction:

Under basic conditions, only weak acids can exist in the reaction mixture. A carboxylate ion can be reversibly protonated by the solvent, water. This removes the negative charge on the carboxylate ion, making it more accessible to a nucleophile. The hydroxide ion from the base can then add to the carbonyl carbon to initiate a nucleophilic addition-elimination reaction. The reaction can occur twice, effectively replacing both oxygen atoms in the carboxylate by the oxygen atoms from the base and solvent water.

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Answer 5

Chapter 20, Problem 20.34P

Interpretation Introduction

Interpretation:

The complete, detailed mechanism to account for the incorporation of 18O twice in the acetate ion in the given reaction is to be drawn.

Concept introduction:

Under basic conditions, only weak acids can exist in the reaction mixture. A carboxylate ion can be reversibly protonated by the solvent, water. This removes the negative charge on the carboxylate ion, making it more accessible to a nucleophile. The hydroxide ion from the base can then add to the carbonyl carbon to initiate a nucleophilic addition-elimination reaction. The reaction can occur twice, effectively replacing both oxygen atoms in the carboxylate by the oxygen atoms from the base and solvent water.

Answer 6

Chapter 20, Problem 20.34P

Interpretation Introduction

Interpretation:

The complete, detailed mechanism to account for the incorporation of 18O twice in the acetate ion in the given reaction is to be drawn.

Concept introduction:

Under basic conditions, only weak acids can exist in the reaction mixture. A carboxylate ion can be reversibly protonated by the solvent, water. This removes the negative charge on the carboxylate ion, making it more accessible to a nucleophile. The hydroxide ion from the base can then add to the carbonyl carbon to initiate a nucleophilic addition-elimination reaction. The reaction can occur twice, effectively replacing both oxygen atoms in the carboxylate by the oxygen atoms from the base and solvent water.

Answer 7

Chapter 20, Problem 20.34P

Interpretation Introduction

Interpretation:

The complete, detailed mechanism to account for the incorporation of 18O twice in the acetate ion in the given reaction is to be drawn.

Concept introduction:

Under basic conditions, only weak acids can exist in the reaction mixture. A carboxylate ion can be reversibly protonated by the solvent, water. This removes the negative charge on the carboxylate ion, making it more accessible to a nucleophile. The hydroxide ion from the base can then add to the carbonyl carbon to initiate a nucleophilic addition-elimination reaction. The reaction can occur twice, effectively replacing both oxygen atoms in the carboxylate by the oxygen atoms from the base and solvent water.

Answer 8

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Answer 9

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Answer 10

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Answer 11

Ch. 20 - Prob. 20.1P Ch. 20 - Prob. 20.2P Ch. 20 - Prob. 20.3P Ch. 20 - Prob. 20.4P Ch. 20 - Prob. 20.5P Ch. 20 - Prob. 20.6P Ch. 20 - Prob. 20.7P Ch. 20 - Prob. 20.8P Ch. 20 - Prob. 20.9P Ch. 20 - Prob. 20.10P

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Chapter 20 Solutions