The product of the given reaction to be predicted. Concept Introduction : Ring-opening reactions of epoxide: Generally, Epoxides have significant ring strain (high in energy), thus it undergoes reaction in which the ring is opened and alleviates the strain. Ring-opening occurs under conditions involving a strong nucleophile or under acid-catalyzed conditions. The reaction transformation involves two mechanistic step: I. Nucleophilic attack via S N 2 process. II. Proton transfer. Regiochemistry: if the epoxide is unsymmetrical, the nucleophile attacks at the less hindered position (less substituted). Stereochemistry: when the attack takes place at the chiral center, inversion of configuration is observed. Only the center being attacked undergoes an inversion of configuration. To Identify: The product of the given reaction to be identified.

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Answer 1

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Chapter 13, Problem 64IP

Interpretation Introduction

Interpretation: The product of the given reaction to be predicted.

Concept Introduction:

Ring-opening reactions of epoxide:

Generally, Epoxides have significant ring strain (high in energy), thus it undergoes reaction in which the ring is opened and alleviates the strain. Ring-opening occurs under conditions involving a strong nucleophile or under acid-catalyzed conditions.

The reaction transformation involves two mechanistic step:

I. Nucleophilic attack via SN2 process.

II. Proton transfer.

Regiochemistry: if the epoxide is unsymmetrical, the nucleophile attacks at the less hindered position (less substituted).

Stereochemistry: when the attack takes place at the chiral center, inversion of configuration is observed. Only the center being attacked undergoes an inversion of configuration.

To Identify: The product of the given reaction to be identified.

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Answer 2

Question

Chapter 13, Problem 64IP

Interpretation Introduction

Interpretation: The product of the given reaction to be predicted.

Concept Introduction:

Ring-opening reactions of epoxide:

Generally, Epoxides have significant ring strain (high in energy), thus it undergoes reaction in which the ring is opened and alleviates the strain. Ring-opening occurs under conditions involving a strong nucleophile or under acid-catalyzed conditions.

The reaction transformation involves two mechanistic step:

I. Nucleophilic attack via SN2 process.

II. Proton transfer.

Regiochemistry: if the epoxide is unsymmetrical, the nucleophile attacks at the less hindered position (less substituted).

Stereochemistry: when the attack takes place at the chiral center, inversion of configuration is observed. Only the center being attacked undergoes an inversion of configuration.

To Identify: The product of the given reaction to be identified.

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Answer 3

Question

Chapter 13, Problem 64IP

Interpretation Introduction

Interpretation: The product of the given reaction to be predicted.

Concept Introduction:

Ring-opening reactions of epoxide:

Generally, Epoxides have significant ring strain (high in energy), thus it undergoes reaction in which the ring is opened and alleviates the strain. Ring-opening occurs under conditions involving a strong nucleophile or under acid-catalyzed conditions.

The reaction transformation involves two mechanistic step:

I. Nucleophilic attack via SN2 process.

II. Proton transfer.

Regiochemistry: if the epoxide is unsymmetrical, the nucleophile attacks at the less hindered position (less substituted).

Stereochemistry: when the attack takes place at the chiral center, inversion of configuration is observed. Only the center being attacked undergoes an inversion of configuration.

To Identify: The product of the given reaction to be identified.

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Answer 4

Question

Chapter 13, Problem 64IP

Interpretation Introduction

Interpretation: The product of the given reaction to be predicted.

Concept Introduction:

Ring-opening reactions of epoxide:

Generally, Epoxides have significant ring strain (high in energy), thus it undergoes reaction in which the ring is opened and alleviates the strain. Ring-opening occurs under conditions involving a strong nucleophile or under acid-catalyzed conditions.

The reaction transformation involves two mechanistic step:

I. Nucleophilic attack via SN2 process.

II. Proton transfer.

Regiochemistry: if the epoxide is unsymmetrical, the nucleophile attacks at the less hindered position (less substituted).

Stereochemistry: when the attack takes place at the chiral center, inversion of configuration is observed. Only the center being attacked undergoes an inversion of configuration.

To Identify: The product of the given reaction to be identified.

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Answer 5

Chapter 13, Problem 64IP

Interpretation Introduction

Interpretation: The product of the given reaction to be predicted.

Concept Introduction:

Ring-opening reactions of epoxide:

Generally, Epoxides have significant ring strain (high in energy), thus it undergoes reaction in which the ring is opened and alleviates the strain. Ring-opening occurs under conditions involving a strong nucleophile or under acid-catalyzed conditions.

The reaction transformation involves two mechanistic step:

I. Nucleophilic attack via SN2 process.

II. Proton transfer.

Regiochemistry: if the epoxide is unsymmetrical, the nucleophile attacks at the less hindered position (less substituted).

Stereochemistry: when the attack takes place at the chiral center, inversion of configuration is observed. Only the center being attacked undergoes an inversion of configuration.

To Identify: The product of the given reaction to be identified.

Answer 6

Chapter 13, Problem 64IP

Interpretation Introduction

Interpretation: The product of the given reaction to be predicted.

Concept Introduction:

Ring-opening reactions of epoxide:

Generally, Epoxides have significant ring strain (high in energy), thus it undergoes reaction in which the ring is opened and alleviates the strain. Ring-opening occurs under conditions involving a strong nucleophile or under acid-catalyzed conditions.

The reaction transformation involves two mechanistic step:

I. Nucleophilic attack via SN2 process.

II. Proton transfer.

Regiochemistry: if the epoxide is unsymmetrical, the nucleophile attacks at the less hindered position (less substituted).

Stereochemistry: when the attack takes place at the chiral center, inversion of configuration is observed. Only the center being attacked undergoes an inversion of configuration.

To Identify: The product of the given reaction to be identified.

Answer 7

Chapter 13, Problem 64IP

Interpretation Introduction

Interpretation: The product of the given reaction to be predicted.

Concept Introduction:

Ring-opening reactions of epoxide:

Generally, Epoxides have significant ring strain (high in energy), thus it undergoes reaction in which the ring is opened and alleviates the strain. Ring-opening occurs under conditions involving a strong nucleophile or under acid-catalyzed conditions.

The reaction transformation involves two mechanistic step:

I. Nucleophilic attack via SN2 process.

II. Proton transfer.

Regiochemistry: if the epoxide is unsymmetrical, the nucleophile attacks at the less hindered position (less substituted).

Stereochemistry: when the attack takes place at the chiral center, inversion of configuration is observed. Only the center being attacked undergoes an inversion of configuration.

To Identify: The product of the given reaction to be identified.

Answer 8

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Answer 9

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Answer 10

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Answer 11

Ch. 13.2 - Prob. 1LTS Ch. 13.2 - Prob. 1PTS Ch. 13.2 - Prob. 2PTS Ch. 13.2 - Prob. 3ATS Ch. 13.4 - Prob. 4CC Ch. 13.5 - Prob. 2LTS Ch. 13.5 - Prob. 5PTS Ch. 13.5 - Prob. 6ATS Ch. 13.5 - Prob. 7CC Ch. 13.5 - Prob. 8CC

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Chapter 13 Solutions