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.

Question

Want to see the full answer?

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.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

Students have asked these similar questions

Draw the complete, detailed mechanism for the reaction shown here. Will the product be optically active? Explain.

Draw the complete, detailed mechanism for the reaction shown here and predict the major product. CH3ONA Explain. DMSO

The crossed aldol reaction shown here can be carried out using a weak base such as pyridine. (a) Draw the complete, detailed mechanism for this reaction. (b) Explain why a relatively weak base can be used. EtO OEt H EtO OEt H. Diethyl malonate

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.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

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.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

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.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

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

Expert Solution & Answer

Answer 9

Expert Solution & Answer

Answer 10

Want to see the full answer?

Check out a sample textbook solution

See solution

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.

Want to see the full answer?

Chapter 10 Solutions