The reaction of PBr 3 with the given diol gives a dibromide molecule of which, the structure is to be determined. Concept Introduction: Bromination of a diol usually results in the formation of bromide compounds due to nucleophilic substitution reactions. Reactions like these usually follow a mechanism, which usually results in a change in the configuration of the molecule.

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Answer 1

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Chapter 12.9, Problem 20ATS

(a)

Interpretation Introduction

Interpretation:

The reaction of PBr3 with the given diol gives a dibromide molecule of which, the structure is to be determined.

Concept Introduction:

Bromination of a diol usually results in the formation of bromide compounds due to nucleophilic substitution reactions. Reactions like these usually follow a mechanism, which usually results in a change in the configuration of the molecule.

(b)

Interpretation Introduction

Interpretation:

A plausible mechanism for the formation of the cyclic ether by-product has to be determined along with the stereochemical justification of the molecule.

Concept Introduction:

Diols when undergoing nucleophilic substitution reactions, sometimes tend to undergo cyclization via intramolecular bonding to form a cyclic ether, under appropriate conditions. Depending upon the type of alcoholic group involved in the formation of the nucleophile, the stereochemical configuration of the product molecule varies.

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Answer 2

Question

Chapter 12.9, Problem 20ATS

(a)

Interpretation Introduction

Interpretation:

The reaction of PBr3 with the given diol gives a dibromide molecule of which, the structure is to be determined.

Concept Introduction:

Bromination of a diol usually results in the formation of bromide compounds due to nucleophilic substitution reactions. Reactions like these usually follow a mechanism, which usually results in a change in the configuration of the molecule.

(b)

Interpretation Introduction

Interpretation:

A plausible mechanism for the formation of the cyclic ether by-product has to be determined along with the stereochemical justification of the molecule.

Concept Introduction:

Diols when undergoing nucleophilic substitution reactions, sometimes tend to undergo cyclization via intramolecular bonding to form a cyclic ether, under appropriate conditions. Depending upon the type of alcoholic group involved in the formation of the nucleophile, the stereochemical configuration of the product molecule varies.

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Answer 3

Question

Chapter 12.9, Problem 20ATS

(a)

Interpretation Introduction

Interpretation:

The reaction of PBr3 with the given diol gives a dibromide molecule of which, the structure is to be determined.

Concept Introduction:

Bromination of a diol usually results in the formation of bromide compounds due to nucleophilic substitution reactions. Reactions like these usually follow a mechanism, which usually results in a change in the configuration of the molecule.

(b)

Interpretation Introduction

Interpretation:

A plausible mechanism for the formation of the cyclic ether by-product has to be determined along with the stereochemical justification of the molecule.

Concept Introduction:

Diols when undergoing nucleophilic substitution reactions, sometimes tend to undergo cyclization via intramolecular bonding to form a cyclic ether, under appropriate conditions. Depending upon the type of alcoholic group involved in the formation of the nucleophile, the stereochemical configuration of the product molecule varies.

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Answer 4

Question

Chapter 12.9, Problem 20ATS

(a)

Interpretation Introduction

Interpretation:

The reaction of PBr3 with the given diol gives a dibromide molecule of which, the structure is to be determined.

Concept Introduction:

Bromination of a diol usually results in the formation of bromide compounds due to nucleophilic substitution reactions. Reactions like these usually follow a mechanism, which usually results in a change in the configuration of the molecule.

(b)

Interpretation Introduction

Interpretation:

A plausible mechanism for the formation of the cyclic ether by-product has to be determined along with the stereochemical justification of the molecule.

Concept Introduction:

Diols when undergoing nucleophilic substitution reactions, sometimes tend to undergo cyclization via intramolecular bonding to form a cyclic ether, under appropriate conditions. Depending upon the type of alcoholic group involved in the formation of the nucleophile, the stereochemical configuration of the product molecule varies.

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Answer 5

Chapter 12.9, Problem 20ATS

(a)

Interpretation Introduction

Interpretation:

The reaction of PBr3 with the given diol gives a dibromide molecule of which, the structure is to be determined.

Concept Introduction:

Bromination of a diol usually results in the formation of bromide compounds due to nucleophilic substitution reactions. Reactions like these usually follow a mechanism, which usually results in a change in the configuration of the molecule.

(b)

Interpretation Introduction

Interpretation:

A plausible mechanism for the formation of the cyclic ether by-product has to be determined along with the stereochemical justification of the molecule.

Concept Introduction:

Diols when undergoing nucleophilic substitution reactions, sometimes tend to undergo cyclization via intramolecular bonding to form a cyclic ether, under appropriate conditions. Depending upon the type of alcoholic group involved in the formation of the nucleophile, the stereochemical configuration of the product molecule varies.

Answer 6

Chapter 12.9, Problem 20ATS

(a)

Interpretation Introduction

Interpretation:

The reaction of PBr3 with the given diol gives a dibromide molecule of which, the structure is to be determined.

Concept Introduction:

Bromination of a diol usually results in the formation of bromide compounds due to nucleophilic substitution reactions. Reactions like these usually follow a mechanism, which usually results in a change in the configuration of the molecule.

Answer 7

Chapter 12.9, Problem 20ATS

(a)

Interpretation Introduction

Interpretation:

The reaction of PBr3 with the given diol gives a dibromide molecule of which, the structure is to be determined.

Concept Introduction:

Bromination of a diol usually results in the formation of bromide compounds due to nucleophilic substitution reactions. Reactions like these usually follow a mechanism, which usually results in a change in the configuration of the molecule.

Answer 8

(b)

Interpretation Introduction

Interpretation:

A plausible mechanism for the formation of the cyclic ether by-product has to be determined along with the stereochemical justification of the molecule.

Concept Introduction:

Diols when undergoing nucleophilic substitution reactions, sometimes tend to undergo cyclization via intramolecular bonding to form a cyclic ether, under appropriate conditions. Depending upon the type of alcoholic group involved in the formation of the nucleophile, the stereochemical configuration of the product molecule varies.

Answer 9

(b)

Interpretation Introduction

Interpretation:

A plausible mechanism for the formation of the cyclic ether by-product has to be determined along with the stereochemical justification of the molecule.

Concept Introduction:

Diols when undergoing nucleophilic substitution reactions, sometimes tend to undergo cyclization via intramolecular bonding to form a cyclic ether, under appropriate conditions. Depending upon the type of alcoholic group involved in the formation of the nucleophile, the stereochemical configuration of the product molecule varies.

Answer 10

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Answer 11

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Answer 12

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Answer 13

Ch. 12.1 - Prob. 1LTS Ch. 12.1 - Prob. 1PTS Ch. 12.1 - Prob. 2ATS Ch. 12.1 - Prob. 3CC Ch. 12.2 - Prob. 4CC Ch. 12.3 - Prob. 8CC Ch. 12.3 - Prob. 9CC Ch. 12.4 - Prob. 3LTS Ch. 12.4 - Prob. 10PTS Ch. 12.4 - Prob. 11ATS

Solution Summary: The author explains the formation of the cyclic ether by-product by assuming that the primary alcoholic group is attacked by PBr_ 3, forming an intermediate.

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Chapter 12 Solutions