The complete mechanism for the given reactions is to be drawn, and the major product is to be predicted. Concept introduction: Under neutral or basic conditions, a nucleophile attacks an epoxide at the less highly alkyl-substituted C atom of the ring, from the side opposite the O atom. Under acidic conditions, a nucleophile attacks an epoxide at the more highly alkyl-substituted carbon. The C-O bonds in an epoxide partially break as a result of protonation, lengthening the C-O bonds. As a result, more positive charge develops at the more hindered side. The S N 2 reaction proceeds faster at carbon with less steric hindrance. The strong nucleophile attacks from backside, and the substituents remain bonded to the carbon atom.

Question

Want to see the full answer?

Answer 1

Question

Chapter 10, Problem 10.25P

Interpretation Introduction

Interpretation:

The complete mechanism for the given reactions is to be drawn, and the major product is to be predicted.

Concept introduction:

Under neutral or basic conditions, a nucleophile attacks an epoxide at the less highly alkyl-substituted C atom of the ring, from the side opposite the O atom.

Under acidic conditions, a nucleophile attacks an epoxide at the more highly alkyl-substituted carbon. The C-O bonds in an epoxide partially break as a result of protonation, lengthening the C-O bonds. As a result, more positive charge develops at the more hindered side.

The SN2 reaction proceeds faster at carbon with less steric hindrance. The strong nucleophile attacks from backside, and the substituents remain bonded to the carbon atom.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

Students have asked these similar questions

None

Answer 2

Question

Chapter 10, Problem 10.25P

Interpretation Introduction

Interpretation:

The complete mechanism for the given reactions is to be drawn, and the major product is to be predicted.

Concept introduction:

Under neutral or basic conditions, a nucleophile attacks an epoxide at the less highly alkyl-substituted C atom of the ring, from the side opposite the O atom.

Under acidic conditions, a nucleophile attacks an epoxide at the more highly alkyl-substituted carbon. The C-O bonds in an epoxide partially break as a result of protonation, lengthening the C-O bonds. As a result, more positive charge develops at the more hindered side.

The SN2 reaction proceeds faster at carbon with less steric hindrance. The strong nucleophile attacks from backside, and the substituents remain bonded to the carbon atom.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

Answer 3

Question

Chapter 10, Problem 10.25P

Interpretation Introduction

Interpretation:

The complete mechanism for the given reactions is to be drawn, and the major product is to be predicted.

Concept introduction:

Under neutral or basic conditions, a nucleophile attacks an epoxide at the less highly alkyl-substituted C atom of the ring, from the side opposite the O atom.

Under acidic conditions, a nucleophile attacks an epoxide at the more highly alkyl-substituted carbon. The C-O bonds in an epoxide partially break as a result of protonation, lengthening the C-O bonds. As a result, more positive charge develops at the more hindered side.

The SN2 reaction proceeds faster at carbon with less steric hindrance. The strong nucleophile attacks from backside, and the substituents remain bonded to the carbon atom.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

Answer 4

Question

Chapter 10, Problem 10.25P

Interpretation Introduction

Interpretation:

The complete mechanism for the given reactions is to be drawn, and the major product is to be predicted.

Concept introduction:

Under neutral or basic conditions, a nucleophile attacks an epoxide at the less highly alkyl-substituted C atom of the ring, from the side opposite the O atom.

Under acidic conditions, a nucleophile attacks an epoxide at the more highly alkyl-substituted carbon. The C-O bonds in an epoxide partially break as a result of protonation, lengthening the C-O bonds. As a result, more positive charge develops at the more hindered side.

The SN2 reaction proceeds faster at carbon with less steric hindrance. The strong nucleophile attacks from backside, and the substituents remain bonded to the carbon atom.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

Answer 5

Chapter 10, Problem 10.25P

Interpretation Introduction

Interpretation:

The complete mechanism for the given reactions is to be drawn, and the major product is to be predicted.

Concept introduction:

Under neutral or basic conditions, a nucleophile attacks an epoxide at the less highly alkyl-substituted C atom of the ring, from the side opposite the O atom.

Under acidic conditions, a nucleophile attacks an epoxide at the more highly alkyl-substituted carbon. The C-O bonds in an epoxide partially break as a result of protonation, lengthening the C-O bonds. As a result, more positive charge develops at the more hindered side.

The SN2 reaction proceeds faster at carbon with less steric hindrance. The strong nucleophile attacks from backside, and the substituents remain bonded to the carbon atom.

Answer 6

Chapter 10, Problem 10.25P

Interpretation Introduction

Interpretation:

The complete mechanism for the given reactions is to be drawn, and the major product is to be predicted.

Concept introduction:

Under neutral or basic conditions, a nucleophile attacks an epoxide at the less highly alkyl-substituted C atom of the ring, from the side opposite the O atom.

Under acidic conditions, a nucleophile attacks an epoxide at the more highly alkyl-substituted carbon. The C-O bonds in an epoxide partially break as a result of protonation, lengthening the C-O bonds. As a result, more positive charge develops at the more hindered side.

The SN2 reaction proceeds faster at carbon with less steric hindrance. The strong nucleophile attacks from backside, and the substituents remain bonded to the carbon atom.

Answer 7

Chapter 10, Problem 10.25P

Interpretation Introduction

Interpretation:

The complete mechanism for the given reactions is to be drawn, and the major product is to be predicted.

Concept introduction:

Under neutral or basic conditions, a nucleophile attacks an epoxide at the less highly alkyl-substituted C atom of the ring, from the side opposite the O atom.

Under acidic conditions, a nucleophile attacks an epoxide at the more highly alkyl-substituted carbon. The C-O bonds in an epoxide partially break as a result of protonation, lengthening the C-O bonds. As a result, more positive charge develops at the more hindered side.

The SN2 reaction proceeds faster at carbon with less steric hindrance. The strong nucleophile attacks from backside, and the substituents remain bonded to the carbon 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 how the nucleophile attacks an epoxide at the less alkyl-substituted C atom of the ring, from the side opposite the O

Concept explainers

Videos

Want to see the full answer?

Chapter 10 Solutions