A complete mechanism for the given reaction is to be provided. Concept introduction: Under acidic conditions, an ether is protonated, converting the oxygen into a better leaving group and the adjacent carbon into an electrophile. The oxygen is bonded to a primary carbon. Therefore, its substitution will occur via the S N 2 mechanism. Once the ether oxygen is protonated and converted to a better leaving group, the nucleophile ethanol will attack the adjacent carbon, opening the ring. A second substitution can take place, replacing the − OH group at the other end of the opened chain by a second ethoxide to give a disubstituted product.

Question

Want to see the full answer?

Answer 1

Question

Chapter 9, Problem 9.62P

Interpretation Introduction

Interpretation:

A complete mechanism for the given reaction is to be provided.

Concept introduction:

Under acidic conditions, an ether is protonated, converting the oxygen into a better leaving group and the adjacent carbon into an electrophile. The oxygen is bonded to a primary carbon. Therefore, its substitution will occur via the SN2 mechanism. Once the ether oxygen is protonated and converted to a better leaving group, the nucleophile ethanol will attack the adjacent carbon, opening the ring. A second substitution can take place, replacing the −OH group at the other end of the opened chain by a second ethoxide to give a disubstituted product.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

Students have asked these similar questions

Draw a complete, detailed mechanism for the reaction shown here.

Draw the complete, detailed mechanism for the reaction shown here and give the major product. CH3I (excess) ? NH2

Draw the complete, detailed mechanism for each of the following reactions ( (b) NaOH ? U NaOH ?

Answer 2

Question

Chapter 9, Problem 9.62P

Interpretation Introduction

Interpretation:

A complete mechanism for the given reaction is to be provided.

Concept introduction:

Under acidic conditions, an ether is protonated, converting the oxygen into a better leaving group and the adjacent carbon into an electrophile. The oxygen is bonded to a primary carbon. Therefore, its substitution will occur via the SN2 mechanism. Once the ether oxygen is protonated and converted to a better leaving group, the nucleophile ethanol will attack the adjacent carbon, opening the ring. A second substitution can take place, replacing the −OH group at the other end of the opened chain by a second ethoxide to give a disubstituted product.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

Answer 3

Question

Chapter 9, Problem 9.62P

Interpretation Introduction

Interpretation:

A complete mechanism for the given reaction is to be provided.

Concept introduction:

Under acidic conditions, an ether is protonated, converting the oxygen into a better leaving group and the adjacent carbon into an electrophile. The oxygen is bonded to a primary carbon. Therefore, its substitution will occur via the SN2 mechanism. Once the ether oxygen is protonated and converted to a better leaving group, the nucleophile ethanol will attack the adjacent carbon, opening the ring. A second substitution can take place, replacing the −OH group at the other end of the opened chain by a second ethoxide to give a disubstituted product.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

Answer 4

Question

Chapter 9, Problem 9.62P

Interpretation Introduction

Interpretation:

A complete mechanism for the given reaction is to be provided.

Concept introduction:

Under acidic conditions, an ether is protonated, converting the oxygen into a better leaving group and the adjacent carbon into an electrophile. The oxygen is bonded to a primary carbon. Therefore, its substitution will occur via the SN2 mechanism. Once the ether oxygen is protonated and converted to a better leaving group, the nucleophile ethanol will attack the adjacent carbon, opening the ring. A second substitution can take place, replacing the −OH group at the other end of the opened chain by a second ethoxide to give a disubstituted product.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

Answer 5

Chapter 9, Problem 9.62P

Interpretation Introduction

Interpretation:

A complete mechanism for the given reaction is to be provided.

Concept introduction:

Under acidic conditions, an ether is protonated, converting the oxygen into a better leaving group and the adjacent carbon into an electrophile. The oxygen is bonded to a primary carbon. Therefore, its substitution will occur via the SN2 mechanism. Once the ether oxygen is protonated and converted to a better leaving group, the nucleophile ethanol will attack the adjacent carbon, opening the ring. A second substitution can take place, replacing the −OH group at the other end of the opened chain by a second ethoxide to give a disubstituted product.

Answer 6

Chapter 9, Problem 9.62P

Interpretation Introduction

Interpretation:

A complete mechanism for the given reaction is to be provided.

Concept introduction:

Under acidic conditions, an ether is protonated, converting the oxygen into a better leaving group and the adjacent carbon into an electrophile. The oxygen is bonded to a primary carbon. Therefore, its substitution will occur via the SN2 mechanism. Once the ether oxygen is protonated and converted to a better leaving group, the nucleophile ethanol will attack the adjacent carbon, opening the ring. A second substitution can take place, replacing the −OH group at the other end of the opened chain by a second ethoxide to give a disubstituted product.

Answer 7

Chapter 9, Problem 9.62P

Interpretation Introduction

Interpretation:

A complete mechanism for the given reaction is to be provided.

Concept introduction:

Under acidic conditions, an ether is protonated, converting the oxygen into a better leaving group and the adjacent carbon into an electrophile. The oxygen is bonded to a primary carbon. Therefore, its substitution will occur via the SN2 mechanism. Once the ether oxygen is protonated and converted to a better leaving group, the nucleophile ethanol will attack the adjacent carbon, opening the ring. A second substitution can take place, replacing the −OH group at the other end of the opened chain by a second ethoxide to give a disubstituted product.

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. 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 the complete mechanism for the given reaction. Under acidic conditions, an ether is protonated, converting the oxygen into a better leaving group and the adjacent carbon into an electrophile.

Concept explainers

Videos

Want to see the full answer?

Chapter 9 Solutions