(a) Interpretation: The reaction that occur instead of the reaction, indole + NaNH 2 → 2 - aminoindole , on the basis of the variation on the Chichibabin reaction is to be stated. Concept introduction: The Chichibabin reaction is a reaction in which pyridine reacts with sodium amide to yield 2 − aminopyridine . The Chichibabin reaction follows the addition-elimination mechanism.

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Answer 1

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Chapter 26, Problem 26.35AP

Interpretation Introduction

(a)

Interpretation:

The reaction that occur instead of the reaction, indole + NaNH2→2-aminoindole, on the basis of the variation on the Chichibabin reaction is to be stated.

Concept introduction:

The Chichibabin reaction is a reaction in which pyridine reacts with sodium amide to yield 2−aminopyridine. The Chichibabin reaction follows the addition-elimination mechanism.

Interpretation Introduction

(b)

Interpretation:

The reaction that occur instead of the reaction, 2−chloropyridine + NaNH2→2 amino−6− chloropyridine, on the basis of the variation on the Chichibabin reaction is to be stated.

Concept introduction:

The Chichibabin reaction is a reaction in which pyridine reacts with sodium amide to yield 2−aminopyridine. The Chichibabin reaction follows the addition-elimination mechanism.

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b) Draw the amine product of this reaction sequence. + Br Na 1) 2) HCI, heat 3) AcOH, NaBH3CN

H NH₂ ཡིནྣཾ ༥ ཨ ཨནྡྷ༥ ༠ ཨི་ཝཱ, ཙ ཨ་ར༩ H NH3+ the acidity of the amine ion drives the reaction to shift toward the conjugate base of the carboxylic acid product. the resulting carboxylic acid ion is a weaker base than an acetate ion. O aldehydes are more reactive toward nucleophiles than ketones. Onucleophilic attack occurs preferentially at the less hindered carbon of the formyl group.

The following three derivatives of succinimide are anticonvulsants and have found use in the treatment of epilepsy, particularly petit mal seizures. Ph Ph `N' `N' ČH3 ČH3 Methsuximide Ethosuximide Phensuximide Following is a synthesis of phensuximide. CN Ph CN Ph CN 1. NaOH, H2O 2. HC, Н20 NaOEt KCN Ph-CHO cOOEt H cOOEt NC COOEt 3. Нeat Ethyl cyanoacetate (A) (B) Benzaldehyde Ph Ph Ph CH;NH2 НООС СООН Et0oC COOEt `N' (C) (D) ČH3 Phensuximide Methsuximide is formed by a similar pathway to that shown for phensuximide. Draw the structure of the compound that reacts with ethyl cyanoacetate in the synthesis of methsuximide.

Answer 2

Question

Chapter 26, Problem 26.35AP

Interpretation Introduction

(a)

Interpretation:

The reaction that occur instead of the reaction, indole + NaNH2→2-aminoindole, on the basis of the variation on the Chichibabin reaction is to be stated.

Concept introduction:

The Chichibabin reaction is a reaction in which pyridine reacts with sodium amide to yield 2−aminopyridine. The Chichibabin reaction follows the addition-elimination mechanism.

Interpretation Introduction

(b)

Interpretation:

The reaction that occur instead of the reaction, 2−chloropyridine + NaNH2→2 amino−6− chloropyridine, on the basis of the variation on the Chichibabin reaction is to be stated.

Concept introduction:

The Chichibabin reaction is a reaction in which pyridine reacts with sodium amide to yield 2−aminopyridine. The Chichibabin reaction follows the addition-elimination mechanism.

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Answer 3

Question

Chapter 26, Problem 26.35AP

Interpretation Introduction

(a)

Interpretation:

The reaction that occur instead of the reaction, indole + NaNH2→2-aminoindole, on the basis of the variation on the Chichibabin reaction is to be stated.

Concept introduction:

The Chichibabin reaction is a reaction in which pyridine reacts with sodium amide to yield 2−aminopyridine. The Chichibabin reaction follows the addition-elimination mechanism.

Interpretation Introduction

(b)

Interpretation:

The reaction that occur instead of the reaction, 2−chloropyridine + NaNH2→2 amino−6− chloropyridine, on the basis of the variation on the Chichibabin reaction is to be stated.

Concept introduction:

The Chichibabin reaction is a reaction in which pyridine reacts with sodium amide to yield 2−aminopyridine. The Chichibabin reaction follows the addition-elimination mechanism.

Expert Solution & Answer

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Answer 4

Question

Chapter 26, Problem 26.35AP

Interpretation Introduction

(a)

Interpretation:

The reaction that occur instead of the reaction, indole + NaNH2→2-aminoindole, on the basis of the variation on the Chichibabin reaction is to be stated.

Concept introduction:

The Chichibabin reaction is a reaction in which pyridine reacts with sodium amide to yield 2−aminopyridine. The Chichibabin reaction follows the addition-elimination mechanism.

Interpretation Introduction

(b)

Interpretation:

The reaction that occur instead of the reaction, 2−chloropyridine + NaNH2→2 amino−6− chloropyridine, on the basis of the variation on the Chichibabin reaction is to be stated.

Concept introduction:

The Chichibabin reaction is a reaction in which pyridine reacts with sodium amide to yield 2−aminopyridine. The Chichibabin reaction follows the addition-elimination mechanism.

Expert Solution & Answer

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Answer 5

Chapter 26, Problem 26.35AP

Interpretation Introduction

(a)

Interpretation:

The reaction that occur instead of the reaction, indole + NaNH2→2-aminoindole, on the basis of the variation on the Chichibabin reaction is to be stated.

Concept introduction:

The Chichibabin reaction is a reaction in which pyridine reacts with sodium amide to yield 2−aminopyridine. The Chichibabin reaction follows the addition-elimination mechanism.

Interpretation Introduction

(b)

Interpretation:

The reaction that occur instead of the reaction, 2−chloropyridine + NaNH2→2 amino−6− chloropyridine, on the basis of the variation on the Chichibabin reaction is to be stated.

Concept introduction:

The Chichibabin reaction is a reaction in which pyridine reacts with sodium amide to yield 2−aminopyridine. The Chichibabin reaction follows the addition-elimination mechanism.

Answer 6

Chapter 26, Problem 26.35AP

Interpretation Introduction

(a)

Interpretation:

The reaction that occur instead of the reaction, indole + NaNH2→2-aminoindole, on the basis of the variation on the Chichibabin reaction is to be stated.

Concept introduction:

The Chichibabin reaction is a reaction in which pyridine reacts with sodium amide to yield 2−aminopyridine. The Chichibabin reaction follows the addition-elimination mechanism.

Answer 7

Chapter 26, Problem 26.35AP

Interpretation Introduction

(a)

Interpretation:

The reaction that occur instead of the reaction, indole + NaNH2→2-aminoindole, on the basis of the variation on the Chichibabin reaction is to be stated.

Concept introduction:

The Chichibabin reaction is a reaction in which pyridine reacts with sodium amide to yield 2−aminopyridine. The Chichibabin reaction follows the addition-elimination mechanism.

Answer 8

Interpretation Introduction

(b)

Interpretation:

The reaction that occur instead of the reaction, 2−chloropyridine + NaNH2→2 amino−6− chloropyridine, on the basis of the variation on the Chichibabin reaction is to be stated.

Concept introduction:

The Chichibabin reaction is a reaction in which pyridine reacts with sodium amide to yield 2−aminopyridine. The Chichibabin reaction follows the addition-elimination mechanism.

Answer 9

Interpretation Introduction

(b)

Interpretation:

The reaction that occur instead of the reaction, 2−chloropyridine + NaNH2→2 amino−6− chloropyridine, on the basis of the variation on the Chichibabin reaction is to be stated.

Concept introduction:

The Chichibabin reaction is a reaction in which pyridine reacts with sodium amide to yield 2−aminopyridine. The Chichibabin reaction follows the addition-elimination mechanism.

Answer 10

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Answer 12

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Answer 13

Ch. 26 - Prob. 26.1P Ch. 26 - Prob. 26.2P Ch. 26 - Prob. 26.3P Ch. 26 - Prob. 26.4P Ch. 26 - Prob. 26.5P Ch. 26 - Prob. 26.6P Ch. 26 - Prob. 26.7P Ch. 26 - Prob. 26.8P Ch. 26 - Prob. 26.9P Ch. 26 - Prob. 26.10P

Solution Summary: The author explains the Chichibabin reaction, which is a reaction in which pyridine reacts with sodium amide and follows the addition-elimination mechanism.

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Chapter 26 Solutions