(a) Interpretation: The stereochemistry of compound B is to be predicted with information about the stereochemistry of bromine addition. Concept introduction: The addition of one or more than one halogen atom in alkene is known as halogenation reaction. The pathway of the halogenation reaction depends on the structure of the substrate. In this the halogen is added to C=C bond of the alkene to form haloalkane.

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Answer 1

Question

Chapter 9, Problem 9.86AP

Interpretation Introduction

(a)

Interpretation:

The stereochemistry of compound B is to be predicted with information about the stereochemistry of bromine addition.

Concept introduction:

The addition of one or more than one halogen atom in alkene is known as halogenation reaction. The pathway of the halogenation reaction depends on the structure of the substrate. In this the halogen is added to C=C bond of the alkene to form haloalkane.

Interpretation Introduction

(b)

Interpretation:

Whether B→C reaction is a syn- or an anti-elimination is to be stated.

Concept introduction:

Alkyl halides undergo elimination reaction in the presence of a base to form alkenes. The mechanism of the reaction followed depends on the base used. The most substituted alkene is formed as the major product according to Zaitsev rule.

Interpretation Introduction

(c)

Interpretation:

The change in the stereochemistry of products that would occur if E stereoisomer of compound A were carried through the corresponding sequence of reactions is to be stated. The explanation for the corresponding answer is to be stated.

Concept introduction:

The addition of one or more than one halogen atom in alkene is known as halogenation reaction. The pathway of the halogenation reaction depends on the structure of the substrate. In this the halogen is added to C=C bond of the alkene to form haloalkane.

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Part II. xiao isolated a compound TAD (Ca H 10 N₂) from tobacco and obtained its IR spectrum. Xiao proposed a chemical structure shown below: % Transmittance 4000 3500 3000 2500 2000 Wavenumber (cm-1) 1500 1000 (a) Explain why her proposed structure is inconsistent with the IR spectrum obtained (b) TAD exists as a tautomer of the structure xiao proposed. Draw the structure and explain why it is more compatible with the obtained spectrum. (C) what is the possible source for the fairly intense signal at 1621cm1

AE>AE₁ (Y/N) AE=AE₁ (Y/N) AE

Treatment of 2-phenylpropan-2-amine with methyl 2,4-dibromobutanoate in the presence of a nonnucleophilic base, R3N, involves two successive SN2 reactions and gives compound A. ? NH2 Br Br Propose a structural formula for compound A. You do not have to explicitly draw H atoms. You do not have to consider stereochemistry. In cases where there is more than one answer, just draw one. R3N C14H19NO2 + 2 R3NH*Br A

Answer 2

Question

Chapter 9, Problem 9.86AP

Interpretation Introduction

(a)

Interpretation:

The stereochemistry of compound B is to be predicted with information about the stereochemistry of bromine addition.

Concept introduction:

The addition of one or more than one halogen atom in alkene is known as halogenation reaction. The pathway of the halogenation reaction depends on the structure of the substrate. In this the halogen is added to C=C bond of the alkene to form haloalkane.

Interpretation Introduction

(b)

Interpretation:

Whether B→C reaction is a syn- or an anti-elimination is to be stated.

Concept introduction:

Alkyl halides undergo elimination reaction in the presence of a base to form alkenes. The mechanism of the reaction followed depends on the base used. The most substituted alkene is formed as the major product according to Zaitsev rule.

Interpretation Introduction

(c)

Interpretation:

The change in the stereochemistry of products that would occur if E stereoisomer of compound A were carried through the corresponding sequence of reactions is to be stated. The explanation for the corresponding answer is to be stated.

Concept introduction:

The addition of one or more than one halogen atom in alkene is known as halogenation reaction. The pathway of the halogenation reaction depends on the structure of the substrate. In this the halogen is added to C=C bond of the alkene to form haloalkane.

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Answer 3

Question

Chapter 9, Problem 9.86AP

Interpretation Introduction

(a)

Interpretation:

The stereochemistry of compound B is to be predicted with information about the stereochemistry of bromine addition.

Concept introduction:

The addition of one or more than one halogen atom in alkene is known as halogenation reaction. The pathway of the halogenation reaction depends on the structure of the substrate. In this the halogen is added to C=C bond of the alkene to form haloalkane.

Interpretation Introduction

(b)

Interpretation:

Whether B→C reaction is a syn- or an anti-elimination is to be stated.

Concept introduction:

Alkyl halides undergo elimination reaction in the presence of a base to form alkenes. The mechanism of the reaction followed depends on the base used. The most substituted alkene is formed as the major product according to Zaitsev rule.

Interpretation Introduction

(c)

Interpretation:

The change in the stereochemistry of products that would occur if E stereoisomer of compound A were carried through the corresponding sequence of reactions is to be stated. The explanation for the corresponding answer is to be stated.

Concept introduction:

The addition of one or more than one halogen atom in alkene is known as halogenation reaction. The pathway of the halogenation reaction depends on the structure of the substrate. In this the halogen is added to C=C bond of the alkene to form haloalkane.

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Answer 4

Question

Chapter 9, Problem 9.86AP

Interpretation Introduction

(a)

Interpretation:

The stereochemistry of compound B is to be predicted with information about the stereochemistry of bromine addition.

Concept introduction:

The addition of one or more than one halogen atom in alkene is known as halogenation reaction. The pathway of the halogenation reaction depends on the structure of the substrate. In this the halogen is added to C=C bond of the alkene to form haloalkane.

Interpretation Introduction

(b)

Interpretation:

Whether B→C reaction is a syn- or an anti-elimination is to be stated.

Concept introduction:

Alkyl halides undergo elimination reaction in the presence of a base to form alkenes. The mechanism of the reaction followed depends on the base used. The most substituted alkene is formed as the major product according to Zaitsev rule.

Interpretation Introduction

(c)

Interpretation:

The change in the stereochemistry of products that would occur if E stereoisomer of compound A were carried through the corresponding sequence of reactions is to be stated. The explanation for the corresponding answer is to be stated.

Concept introduction:

The addition of one or more than one halogen atom in alkene is known as halogenation reaction. The pathway of the halogenation reaction depends on the structure of the substrate. In this the halogen is added to C=C bond of the alkene to form haloalkane.

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Answer 5

Chapter 9, Problem 9.86AP

Interpretation Introduction

(a)

Interpretation:

The stereochemistry of compound B is to be predicted with information about the stereochemistry of bromine addition.

Concept introduction:

The addition of one or more than one halogen atom in alkene is known as halogenation reaction. The pathway of the halogenation reaction depends on the structure of the substrate. In this the halogen is added to C=C bond of the alkene to form haloalkane.

Interpretation Introduction

(b)

Interpretation:

Whether B→C reaction is a syn- or an anti-elimination is to be stated.

Concept introduction:

Alkyl halides undergo elimination reaction in the presence of a base to form alkenes. The mechanism of the reaction followed depends on the base used. The most substituted alkene is formed as the major product according to Zaitsev rule.

Interpretation Introduction

(c)

Interpretation:

The change in the stereochemistry of products that would occur if E stereoisomer of compound A were carried through the corresponding sequence of reactions is to be stated. The explanation for the corresponding answer is to be stated.

Concept introduction:

The addition of one or more than one halogen atom in alkene is known as halogenation reaction. The pathway of the halogenation reaction depends on the structure of the substrate. In this the halogen is added to C=C bond of the alkene to form haloalkane.

Answer 6

Chapter 9, Problem 9.86AP

Interpretation Introduction

(a)

Interpretation:

The stereochemistry of compound B is to be predicted with information about the stereochemistry of bromine addition.

Concept introduction:

The addition of one or more than one halogen atom in alkene is known as halogenation reaction. The pathway of the halogenation reaction depends on the structure of the substrate. In this the halogen is added to C=C bond of the alkene to form haloalkane.

Answer 7

Chapter 9, Problem 9.86AP

Interpretation Introduction

(a)

Interpretation:

The stereochemistry of compound B is to be predicted with information about the stereochemistry of bromine addition.

Concept introduction:

The addition of one or more than one halogen atom in alkene is known as halogenation reaction. The pathway of the halogenation reaction depends on the structure of the substrate. In this the halogen is added to C=C bond of the alkene to form haloalkane.

Answer 8

Interpretation Introduction

(b)

Interpretation:

Whether B→C reaction is a syn- or an anti-elimination is to be stated.

Concept introduction:

Alkyl halides undergo elimination reaction in the presence of a base to form alkenes. The mechanism of the reaction followed depends on the base used. The most substituted alkene is formed as the major product according to Zaitsev rule.

Answer 9

Interpretation Introduction

(b)

Interpretation:

Whether B→C reaction is a syn- or an anti-elimination is to be stated.

Concept introduction:

Alkyl halides undergo elimination reaction in the presence of a base to form alkenes. The mechanism of the reaction followed depends on the base used. The most substituted alkene is formed as the major product according to Zaitsev rule.

Answer 10

Interpretation Introduction

(c)

Interpretation:

The change in the stereochemistry of products that would occur if E stereoisomer of compound A were carried through the corresponding sequence of reactions is to be stated. The explanation for the corresponding answer is to be stated.

Concept introduction:

The addition of one or more than one halogen atom in alkene is known as halogenation reaction. The pathway of the halogenation reaction depends on the structure of the substrate. In this the halogen is added to C=C bond of the alkene to form haloalkane.

Answer 11

Interpretation Introduction

(c)

Interpretation:

The change in the stereochemistry of products that would occur if E stereoisomer of compound A were carried through the corresponding sequence of reactions is to be stated. The explanation for the corresponding answer is to be stated.

Concept introduction:

The addition of one or more than one halogen atom in alkene is known as halogenation reaction. The pathway of the halogenation reaction depends on the structure of the substrate. In this the halogen is added to C=C bond of the alkene to form haloalkane.

Answer 12

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Answer 15

Ch. 9 - Prob. 9.1P Ch. 9 - Prob. 9.2P Ch. 9 - Prob. 9.3P Ch. 9 - Prob. 9.4P Ch. 9 - Prob. 9.5P Ch. 9 - Prob. 9.6P Ch. 9 - Prob. 9.7P Ch. 9 - Prob. 9.8P Ch. 9 - Prob. 9.9P Ch. 9 - Prob. 9.10P

Solution Summary: The author explains that the stereochemistry of compound B is to be predicted with information about bromine addition.

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Chapter 9 Solutions