(a) Interpretation: The stepwise mechanism that illustrates the formation of E is to be drawn. Concept introduction: The treatment of an organic halide with an alkene in the presence of Pd catalyst to form an alkene that is highly substituted with a new C − C bond is known as Heck reaction. Generally, [ Pd ( OAc ) 2 ] in the presence of [ P ( o -tolyl ) 3 ] is utilized as a catalyst. The reaction is carried out in the presence of organic base, like Et 3 N .

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Answer 1

Question

Chapter 26, Problem 26.39P

Interpretation Introduction

(a)

Interpretation: The stepwise mechanism that illustrates the formation of E is to be drawn.

Concept introduction: The treatment of an organic halide with an alkene in the presence of Pd catalyst to form an alkene that is highly substituted with a new C−C bond is known as Heck reaction. Generally, [Pd(OAc)2] in the presence of [P(o-tolyl)3] is utilized as a catalyst. The reaction is carried out in the presence of organic base, like Et3N.

Interpretation Introduction

(b)

Interpretation: The suggestion made by the formation of E about the stereochemistry of elimination reaction is to be stated.

Concept introduction: The treatment of an organic halide with an alkene in the presence of Pd catalyst to form an alkene that is highly substituted with a new C−C bond is known as Heck reaction. Generally, [Pd(OAc)2] in the presence of [P(o-tolyl)3] is utilized as a catalyst. The reaction is carried out in the presence of organic base, like Et3N.

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What product is formed when A is treated with Grubbs catalyst underhigh-dilution conditions? This reaction was a key step in the synthesis ofstemoamide, the naturally occurring amide described in the opening paragraph.

When naphthalene undergoes an irreversible electrophilic aromatic substitution, such as a Friedel–Crafts acylation, the major product is the kinetic product,which proceeds through the most stable arenium ion intermediate. InSection 23.7, we mentioned that substitution is generally favored at the αposition over the β position, which means that the arenium ion is more stable when the electrophile attaches to the α position. Explain this difference in arenium ion stabilities. Hint: Draw out allresonance structures for each arenium ion intermediate. Does each one have the same number of resonancestructures? How many resonance structures of each intermediate preserve the aromaticity?

The reaction of cyclohexene with iodobenzene under Heck conditions forms E, a coupling product with the new phenyl group on the allylic carbon, but none of the “expected” coupling product F with the phenyl group bonded directly to the carbon–carbon double bond. Draw a stepwise mechanism that illustrates how E is formed.

Answer 2

Question

Chapter 26, Problem 26.39P

Interpretation Introduction

(a)

Interpretation: The stepwise mechanism that illustrates the formation of E is to be drawn.

Concept introduction: The treatment of an organic halide with an alkene in the presence of Pd catalyst to form an alkene that is highly substituted with a new C−C bond is known as Heck reaction. Generally, [Pd(OAc)2] in the presence of [P(o-tolyl)3] is utilized as a catalyst. The reaction is carried out in the presence of organic base, like Et3N.

Interpretation Introduction

(b)

Interpretation: The suggestion made by the formation of E about the stereochemistry of elimination reaction is to be stated.

Concept introduction: The treatment of an organic halide with an alkene in the presence of Pd catalyst to form an alkene that is highly substituted with a new C−C bond is known as Heck reaction. Generally, [Pd(OAc)2] in the presence of [P(o-tolyl)3] is utilized as a catalyst. The reaction is carried out in the presence of organic base, like Et3N.

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Answer 3

Question

Chapter 26, Problem 26.39P

Interpretation Introduction

(a)

Interpretation: The stepwise mechanism that illustrates the formation of E is to be drawn.

Concept introduction: The treatment of an organic halide with an alkene in the presence of Pd catalyst to form an alkene that is highly substituted with a new C−C bond is known as Heck reaction. Generally, [Pd(OAc)2] in the presence of [P(o-tolyl)3] is utilized as a catalyst. The reaction is carried out in the presence of organic base, like Et3N.

Interpretation Introduction

(b)

Interpretation: The suggestion made by the formation of E about the stereochemistry of elimination reaction is to be stated.

Concept introduction: The treatment of an organic halide with an alkene in the presence of Pd catalyst to form an alkene that is highly substituted with a new C−C bond is known as Heck reaction. Generally, [Pd(OAc)2] in the presence of [P(o-tolyl)3] is utilized as a catalyst. The reaction is carried out in the presence of organic base, like Et3N.

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Answer 4

Question

Chapter 26, Problem 26.39P

Interpretation Introduction

(a)

Interpretation: The stepwise mechanism that illustrates the formation of E is to be drawn.

Concept introduction: The treatment of an organic halide with an alkene in the presence of Pd catalyst to form an alkene that is highly substituted with a new C−C bond is known as Heck reaction. Generally, [Pd(OAc)2] in the presence of [P(o-tolyl)3] is utilized as a catalyst. The reaction is carried out in the presence of organic base, like Et3N.

Interpretation Introduction

(b)

Interpretation: The suggestion made by the formation of E about the stereochemistry of elimination reaction is to be stated.

Concept introduction: The treatment of an organic halide with an alkene in the presence of Pd catalyst to form an alkene that is highly substituted with a new C−C bond is known as Heck reaction. Generally, [Pd(OAc)2] in the presence of [P(o-tolyl)3] is utilized as a catalyst. The reaction is carried out in the presence of organic base, like Et3N.

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Answer 5

Chapter 26, Problem 26.39P

Interpretation Introduction

(a)

Interpretation: The stepwise mechanism that illustrates the formation of E is to be drawn.

Concept introduction: The treatment of an organic halide with an alkene in the presence of Pd catalyst to form an alkene that is highly substituted with a new C−C bond is known as Heck reaction. Generally, [Pd(OAc)2] in the presence of [P(o-tolyl)3] is utilized as a catalyst. The reaction is carried out in the presence of organic base, like Et3N.

Interpretation Introduction

(b)

Interpretation: The suggestion made by the formation of E about the stereochemistry of elimination reaction is to be stated.

Concept introduction: The treatment of an organic halide with an alkene in the presence of Pd catalyst to form an alkene that is highly substituted with a new C−C bond is known as Heck reaction. Generally, [Pd(OAc)2] in the presence of [P(o-tolyl)3] is utilized as a catalyst. The reaction is carried out in the presence of organic base, like Et3N.

Answer 6

Chapter 26, Problem 26.39P

Interpretation Introduction

(a)

Interpretation: The stepwise mechanism that illustrates the formation of E is to be drawn.

Concept introduction: The treatment of an organic halide with an alkene in the presence of Pd catalyst to form an alkene that is highly substituted with a new C−C bond is known as Heck reaction. Generally, [Pd(OAc)2] in the presence of [P(o-tolyl)3] is utilized as a catalyst. The reaction is carried out in the presence of organic base, like Et3N.

Answer 7

Chapter 26, Problem 26.39P

Interpretation Introduction

(a)

Interpretation: The stepwise mechanism that illustrates the formation of E is to be drawn.

Concept introduction: The treatment of an organic halide with an alkene in the presence of Pd catalyst to form an alkene that is highly substituted with a new C−C bond is known as Heck reaction. Generally, [Pd(OAc)2] in the presence of [P(o-tolyl)3] is utilized as a catalyst. The reaction is carried out in the presence of organic base, like Et3N.

Answer 8

Interpretation Introduction

(b)

Interpretation: The suggestion made by the formation of E about the stereochemistry of elimination reaction is to be stated.

Concept introduction: The treatment of an organic halide with an alkene in the presence of Pd catalyst to form an alkene that is highly substituted with a new C−C bond is known as Heck reaction. Generally, [Pd(OAc)2] in the presence of [P(o-tolyl)3] is utilized as a catalyst. The reaction is carried out in the presence of organic base, like Et3N.

Answer 9

Interpretation Introduction

(b)

Interpretation: The suggestion made by the formation of E about the stereochemistry of elimination reaction is to be stated.

Concept introduction: The treatment of an organic halide with an alkene in the presence of Pd catalyst to form an alkene that is highly substituted with a new C−C bond is known as Heck reaction. Generally, [Pd(OAc)2] in the presence of [P(o-tolyl)3] is utilized as a catalyst. The reaction is carried out in the presence of organic base, like Et3N.

Answer 10

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Answer 11

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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 - Problem 26.8 What starting materials are needed to...Ch. 26 - Prob. 26.9P Ch. 26 - Problem 26.10 What reagents are needed to convert...

Solution Summary: The author explains the stepwise mechanism that illustrates the formation of E in Figure 1.

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