(a) Interpretation: The alkene from which the derivative of cyclopropane is prepared by using the Simmons-Smith reaction is to be predicted. Concept introduction: Alkenes on reaction with diiodomethane in the presence of zinc-copper couple give norcarane. The C = C bond of alkene breaks and a single three membered cyclic ring is formed. Methylene ( :CH 2 ) is formed as a reactive intermediate during this reaction.

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Answer 1

Question

Chapter 9, Problem 9.38P

Interpretation Introduction

(a)

Interpretation:

The alkene from which the derivative of cyclopropane is prepared by using the Simmons-Smith reaction is to be predicted.

Concept introduction:

Alkenes on reaction with diiodomethane in the presence of zinc-copper couple give norcarane. The C=C bond of alkene breaks and a single three membered cyclic ring is formed. Methylene (:CH2) is formed as a reactive intermediate during this reaction.

Interpretation Introduction

(b)

Interpretation:

The alkene from which the derivative of cyclopropane is prepared by using the Simmons-Smith reaction is to be predicted.

Concept introduction:

Alkenes on reaction with diiodomethane in the presence of zinc-copper couple give norcarane. The C=C bond of alkene breaks and a single three membered cyclic ring is formed. Methylene (:CH2) is formed as a reactive intermediate during this reaction.

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Rank the compounds in each group below according to their reactivity toward electrophilic aromatic substitution (most reactive = 1; least reactive = 3). Place the number corresponding to the compounds' relative reactivity in the blank below the compound. a. CH₂F CH3 F b. At what position, and on what ring, is bromination of phenyl benzoate expected to occur? Explain your answer. :0: C-O phenyl benzoate 6.Consider the reaction below to answer the following questions. A B C NO₂ FeBr3 + Br₂ D a. The nucleophile in the reaction is: BODADES b. The Lewis acid catalyst in the reaction is: C. This reaction proceeds d. Draw the structure of product D. (faster or slower) than benzene.

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Answer 2

Question

Chapter 9, Problem 9.38P

Interpretation Introduction

(a)

Interpretation:

The alkene from which the derivative of cyclopropane is prepared by using the Simmons-Smith reaction is to be predicted.

Concept introduction:

Alkenes on reaction with diiodomethane in the presence of zinc-copper couple give norcarane. The C=C bond of alkene breaks and a single three membered cyclic ring is formed. Methylene (:CH2) is formed as a reactive intermediate during this reaction.

Interpretation Introduction

(b)

Interpretation:

The alkene from which the derivative of cyclopropane is prepared by using the Simmons-Smith reaction is to be predicted.

Concept introduction:

Alkenes on reaction with diiodomethane in the presence of zinc-copper couple give norcarane. The C=C bond of alkene breaks and a single three membered cyclic ring is formed. Methylene (:CH2) is formed as a reactive intermediate during this reaction.

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Answer 3

Question

Chapter 9, Problem 9.38P

Interpretation Introduction

(a)

Interpretation:

The alkene from which the derivative of cyclopropane is prepared by using the Simmons-Smith reaction is to be predicted.

Concept introduction:

Alkenes on reaction with diiodomethane in the presence of zinc-copper couple give norcarane. The C=C bond of alkene breaks and a single three membered cyclic ring is formed. Methylene (:CH2) is formed as a reactive intermediate during this reaction.

Interpretation Introduction

(b)

Interpretation:

The alkene from which the derivative of cyclopropane is prepared by using the Simmons-Smith reaction is to be predicted.

Concept introduction:

Alkenes on reaction with diiodomethane in the presence of zinc-copper couple give norcarane. The C=C bond of alkene breaks and a single three membered cyclic ring is formed. Methylene (:CH2) is formed as a reactive intermediate during this reaction.

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Answer 4

Question

Chapter 9, Problem 9.38P

Interpretation Introduction

(a)

Interpretation:

The alkene from which the derivative of cyclopropane is prepared by using the Simmons-Smith reaction is to be predicted.

Concept introduction:

Alkenes on reaction with diiodomethane in the presence of zinc-copper couple give norcarane. The C=C bond of alkene breaks and a single three membered cyclic ring is formed. Methylene (:CH2) is formed as a reactive intermediate during this reaction.

Interpretation Introduction

(b)

Interpretation:

The alkene from which the derivative of cyclopropane is prepared by using the Simmons-Smith reaction is to be predicted.

Concept introduction:

Alkenes on reaction with diiodomethane in the presence of zinc-copper couple give norcarane. The C=C bond of alkene breaks and a single three membered cyclic ring is formed. Methylene (:CH2) is formed as a reactive intermediate during this reaction.

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Answer 5

Chapter 9, Problem 9.38P

Interpretation Introduction

(a)

Interpretation:

The alkene from which the derivative of cyclopropane is prepared by using the Simmons-Smith reaction is to be predicted.

Concept introduction:

Alkenes on reaction with diiodomethane in the presence of zinc-copper couple give norcarane. The C=C bond of alkene breaks and a single three membered cyclic ring is formed. Methylene (:CH2) is formed as a reactive intermediate during this reaction.

Interpretation Introduction

(b)

Interpretation:

The alkene from which the derivative of cyclopropane is prepared by using the Simmons-Smith reaction is to be predicted.

Concept introduction:

Alkenes on reaction with diiodomethane in the presence of zinc-copper couple give norcarane. The C=C bond of alkene breaks and a single three membered cyclic ring is formed. Methylene (:CH2) is formed as a reactive intermediate during this reaction.

Answer 6

Chapter 9, Problem 9.38P

Interpretation Introduction

(a)

Interpretation:

The alkene from which the derivative of cyclopropane is prepared by using the Simmons-Smith reaction is to be predicted.

Concept introduction:

Alkenes on reaction with diiodomethane in the presence of zinc-copper couple give norcarane. The C=C bond of alkene breaks and a single three membered cyclic ring is formed. Methylene (:CH2) is formed as a reactive intermediate during this reaction.

Answer 7

Chapter 9, Problem 9.38P

Interpretation Introduction

(a)

Interpretation:

The alkene from which the derivative of cyclopropane is prepared by using the Simmons-Smith reaction is to be predicted.

Concept introduction:

Alkenes on reaction with diiodomethane in the presence of zinc-copper couple give norcarane. The C=C bond of alkene breaks and a single three membered cyclic ring is formed. Methylene (:CH2) is formed as a reactive intermediate during this reaction.

Answer 8

Interpretation Introduction

(b)

Interpretation:

The alkene from which the derivative of cyclopropane is prepared by using the Simmons-Smith reaction is to be predicted.

Concept introduction:

Alkenes on reaction with diiodomethane in the presence of zinc-copper couple give norcarane. The C=C bond of alkene breaks and a single three membered cyclic ring is formed. Methylene (:CH2) is formed as a reactive intermediate during this reaction.

Answer 9

Interpretation Introduction

(b)

Interpretation:

The alkene from which the derivative of cyclopropane is prepared by using the Simmons-Smith reaction is to be predicted.

Concept introduction:

Alkenes on reaction with diiodomethane in the presence of zinc-copper couple give norcarane. The C=C bond of alkene breaks and a single three membered cyclic ring is formed. Methylene (:CH2) is formed as a reactive intermediate during this reaction.

Answer 10

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Answer 12

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Answer 13

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 how the alkene from which the derivative of cyclopropane is prepared by using the Simmons-Smith reaction is shown.

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