The product of the reaction is to be predicted and the complete, detailed mechanism is to be drawn. Concept introduction: Epoxides react readily under neutral, basic, and acidic reaction conditions. The mechanism for the epoxides under neutral and basic conditions consists of an S N 2 step followed by a proton transfer reaction. Thus, epoxides can undergo S N 2 reactions in neutral or basic reaction conditions so as to relieve the ring strain, and this compensates for the poor leaving group ability of alkoxides ( R-HN − ). Under neutral or basic conditions, a nucleophile attacks an epoxide at the less substituted carbon atom (less sterically hindered) of the ring from the side opposite to the oxygen atom.

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Answer 1

Question

Chapter 10, Problem 10.56P

Interpretation Introduction

Interpretation:

The product of the reaction is to be predicted and the complete, detailed mechanism is to be drawn.

Concept introduction:

Epoxides react readily under neutral, basic, and acidic reaction conditions. The mechanism for the epoxides under neutral and basic conditions consists of an SN2 step followed by a proton transfer reaction. Thus, epoxides can undergo SN2 reactions in neutral or basic reaction conditions so as to relieve the ring strain, and this compensates for the poor leaving group ability of alkoxides (R-HN−). Under neutral or basic conditions, a nucleophile attacks an epoxide at the less substituted carbon atom (less sterically hindered) of the ring from the side opposite to the oxygen atom.

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A 2-step reaction has the following mechanism: | 1. (fast) R2 R+R 2. (slow) R+Q K₂ P k_1 What series does it have? (A). v= - = (k + k1 − k-1)[R2][Q] (B). v=-k₁[R₂] + k₁[R]² - k₂[R][Q] (C). v=k₂[R]²[Q]² (D). v = k[R₂]1/2[Q]

Steps and explanations. Also provide, if possible, ways to adress this kind of problems in general.

Answer 2

Question

Chapter 10, Problem 10.56P

Interpretation Introduction

Interpretation:

The product of the reaction is to be predicted and the complete, detailed mechanism is to be drawn.

Concept introduction:

Epoxides react readily under neutral, basic, and acidic reaction conditions. The mechanism for the epoxides under neutral and basic conditions consists of an SN2 step followed by a proton transfer reaction. Thus, epoxides can undergo SN2 reactions in neutral or basic reaction conditions so as to relieve the ring strain, and this compensates for the poor leaving group ability of alkoxides (R-HN−). Under neutral or basic conditions, a nucleophile attacks an epoxide at the less substituted carbon atom (less sterically hindered) of the ring from the side opposite to the oxygen atom.

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Answer 3

Question

Chapter 10, Problem 10.56P

Interpretation Introduction

Interpretation:

The product of the reaction is to be predicted and the complete, detailed mechanism is to be drawn.

Concept introduction:

Epoxides react readily under neutral, basic, and acidic reaction conditions. The mechanism for the epoxides under neutral and basic conditions consists of an SN2 step followed by a proton transfer reaction. Thus, epoxides can undergo SN2 reactions in neutral or basic reaction conditions so as to relieve the ring strain, and this compensates for the poor leaving group ability of alkoxides (R-HN−). Under neutral or basic conditions, a nucleophile attacks an epoxide at the less substituted carbon atom (less sterically hindered) of the ring from the side opposite to the oxygen atom.

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Answer 4

Question

Chapter 10, Problem 10.56P

Interpretation Introduction

Interpretation:

The product of the reaction is to be predicted and the complete, detailed mechanism is to be drawn.

Concept introduction:

Epoxides react readily under neutral, basic, and acidic reaction conditions. The mechanism for the epoxides under neutral and basic conditions consists of an SN2 step followed by a proton transfer reaction. Thus, epoxides can undergo SN2 reactions in neutral or basic reaction conditions so as to relieve the ring strain, and this compensates for the poor leaving group ability of alkoxides (R-HN−). Under neutral or basic conditions, a nucleophile attacks an epoxide at the less substituted carbon atom (less sterically hindered) of the ring from the side opposite to the oxygen atom.

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Answer 5

Chapter 10, Problem 10.56P

Interpretation Introduction

Interpretation:

The product of the reaction is to be predicted and the complete, detailed mechanism is to be drawn.

Concept introduction:

Epoxides react readily under neutral, basic, and acidic reaction conditions. The mechanism for the epoxides under neutral and basic conditions consists of an SN2 step followed by a proton transfer reaction. Thus, epoxides can undergo SN2 reactions in neutral or basic reaction conditions so as to relieve the ring strain, and this compensates for the poor leaving group ability of alkoxides (R-HN−). Under neutral or basic conditions, a nucleophile attacks an epoxide at the less substituted carbon atom (less sterically hindered) of the ring from the side opposite to the oxygen atom.

Answer 6

Chapter 10, Problem 10.56P

Interpretation Introduction

Interpretation:

The product of the reaction is to be predicted and the complete, detailed mechanism is to be drawn.

Concept introduction:

Epoxides react readily under neutral, basic, and acidic reaction conditions. The mechanism for the epoxides under neutral and basic conditions consists of an SN2 step followed by a proton transfer reaction. Thus, epoxides can undergo SN2 reactions in neutral or basic reaction conditions so as to relieve the ring strain, and this compensates for the poor leaving group ability of alkoxides (R-HN−). Under neutral or basic conditions, a nucleophile attacks an epoxide at the less substituted carbon atom (less sterically hindered) of the ring from the side opposite to the oxygen atom.

Answer 7

Chapter 10, Problem 10.56P

Interpretation Introduction

Interpretation:

The product of the reaction is to be predicted and the complete, detailed mechanism is to be drawn.

Concept introduction:

Epoxides react readily under neutral, basic, and acidic reaction conditions. The mechanism for the epoxides under neutral and basic conditions consists of an SN2 step followed by a proton transfer reaction. Thus, epoxides can undergo SN2 reactions in neutral or basic reaction conditions so as to relieve the ring strain, and this compensates for the poor leaving group ability of alkoxides (R-HN−). Under neutral or basic conditions, a nucleophile attacks an epoxide at the less substituted carbon atom (less sterically hindered) of the ring from the side opposite to the oxygen atom.

Answer 8

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Answer 9

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Answer 10

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Answer 11

Ch. 10 - Prob. 10.1P Ch. 10 - Prob. 10.2P Ch. 10 - Prob. 10.3P Ch. 10 - Prob. 10.4P Ch. 10 - Prob. 10.5P Ch. 10 - Prob. 10.6P Ch. 10 - Prob. 10.7P Ch. 10 - Prob. 10.8P Ch. 10 - Prob. 10.9P Ch. 10 - Prob. 10.10P

Solution Summary: The author explains that epoxides react readily under neutral, basic, and acidic reaction conditions.

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Chapter 10 Solutions