a) Interpretation: A mechanism using curved arrows, for the conversion of alcohol given into the corresponding alkene by treating with POCl 3 , is to be proposed. The regiochemistry of the elimination is also to be explained. Concept introduction: The dehydration of alcohols to alkenes in the presence of POCl 3 follows E 2 mechanism. The –OH group is converted into a better leaving group dichlorophosphate, –OPOCl 2 , when treated with POCl 3 . Pyridine used as solvent is also a base and it removes a proton arranged anti to the leaving group from the β carbon (requirement for E 2 mechanism). The removal of the proton and –OPOCl 2 occurs simultaneously in a single step to yield the alkene as the product. To propose: A mechanism using curved arrows, for the conversion of alcohol given into the corresponding alkene by treating with POCl 3 is to be proposed. To explain: The regiochemistry of the elimination reaction.

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Answer 1

Question

Chapter 17.SE, Problem 33MP

Interpretation Introduction

a)

Interpretation:

A mechanism using curved arrows, for the conversion of alcohol given into the corresponding alkene by treating with POCl₃, is to be proposed. The regiochemistry of the elimination is also to be explained.

Concept introduction:

The dehydration of alcohols to alkenes in the presence of POCl₃ follows E² mechanism. The –OH group is converted into a better leaving group dichlorophosphate, –OPOCl₂, when treated with POCl₃. Pyridine used as solvent is also a base and it removes a proton arranged anti to the leaving group from the β carbon (requirement for E² mechanism). The removal of the proton and –OPOCl₂ occurs simultaneously in a single step to yield the alkene as the product.

To propose:

A mechanism using curved arrows, for the conversion of alcohol given into the corresponding alkene by treating with POCl₃ is to be proposed.

To explain:

The regiochemistry of the elimination reaction.

Interpretation Introduction

b)

Interpretation:

A mechanism using curved arrows, for the conversion of alcohol given into the corresponding alkene by treating with POCl₃, is to be proposed. The regiochemistry of the elimination is also to be explained.

Concept introduction:

The dehydration of alcohols to alkenes in the presence of POCl₃ follows E² mechanism. The –OH group is converted into a better leaving group dichlorophosphate, –OPOCl₂, when treated with POCl₃. Pyridine used as solvent is also a base and it removes a proton arranged anti to the leaving group from the β carbon (requirement for E² mechanism). The removal of the proton and –OPOCl₂ occurs simultaneously in a single step to yield the alkene as the product.

To propose:

A mechanism using curved arrows, for the conversion of alcohol given into the corresponding alkene by treating with POCl₃, is to be proposed.

To explain:

The regiochemistry of the elimination reaction.

Interpretation Introduction

c)

Interpretation:

A mechanism using curved arrows, for the conversion of alcohol given into the corresponding alkene by treating with POCl₃, is to be proposed. The regiochemistry of the elimination is also to be explained.

Concept introduction:

The dehydration of alcohols to alkenes in the presence of POCl₃ follows E² mechanism. The –OH group is converted into a better leaving group dichlorophosphate, –OPOCl₂, when treated with POCl₃. Pyridine used as solvent is also a base and it removes a proton arranged anti to the leaving group from the β carbon (requirement for E² mechanism). The removal of the proton and –OPOCl₂ occurs simultaneously in a single step to yield the alkene as the product.

To propose:

A mechanism using curved arrows, for the conversion of alcohol given into the corresponding alkene by treating with POCl₃, is to be proposed.

To explain:

The regiochemistry of the elimination reaction.

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Predict the major products of this reaction: ་ ་ + H NaOH ? Δ excess Note that the second reactant is used in excess, that is, there is much more of the second reactant than the first. If there won't be any products, just check the box under the drawing area instead.

Answer 2

Question

Chapter 17.SE, Problem 33MP

Interpretation Introduction

a)

Interpretation:

A mechanism using curved arrows, for the conversion of alcohol given into the corresponding alkene by treating with POCl₃, is to be proposed. The regiochemistry of the elimination is also to be explained.

Concept introduction:

The dehydration of alcohols to alkenes in the presence of POCl₃ follows E² mechanism. The –OH group is converted into a better leaving group dichlorophosphate, –OPOCl₂, when treated with POCl₃. Pyridine used as solvent is also a base and it removes a proton arranged anti to the leaving group from the β carbon (requirement for E² mechanism). The removal of the proton and –OPOCl₂ occurs simultaneously in a single step to yield the alkene as the product.

To propose:

A mechanism using curved arrows, for the conversion of alcohol given into the corresponding alkene by treating with POCl₃ is to be proposed.

To explain:

The regiochemistry of the elimination reaction.

Interpretation Introduction

b)

Interpretation:

A mechanism using curved arrows, for the conversion of alcohol given into the corresponding alkene by treating with POCl₃, is to be proposed. The regiochemistry of the elimination is also to be explained.

Concept introduction:

The dehydration of alcohols to alkenes in the presence of POCl₃ follows E² mechanism. The –OH group is converted into a better leaving group dichlorophosphate, –OPOCl₂, when treated with POCl₃. Pyridine used as solvent is also a base and it removes a proton arranged anti to the leaving group from the β carbon (requirement for E² mechanism). The removal of the proton and –OPOCl₂ occurs simultaneously in a single step to yield the alkene as the product.

To propose:

A mechanism using curved arrows, for the conversion of alcohol given into the corresponding alkene by treating with POCl₃, is to be proposed.

To explain:

The regiochemistry of the elimination reaction.

Interpretation Introduction

c)

Interpretation:

A mechanism using curved arrows, for the conversion of alcohol given into the corresponding alkene by treating with POCl₃, is to be proposed. The regiochemistry of the elimination is also to be explained.

Concept introduction:

The dehydration of alcohols to alkenes in the presence of POCl₃ follows E² mechanism. The –OH group is converted into a better leaving group dichlorophosphate, –OPOCl₂, when treated with POCl₃. Pyridine used as solvent is also a base and it removes a proton arranged anti to the leaving group from the β carbon (requirement for E² mechanism). The removal of the proton and –OPOCl₂ occurs simultaneously in a single step to yield the alkene as the product.

To propose:

A mechanism using curved arrows, for the conversion of alcohol given into the corresponding alkene by treating with POCl₃, is to be proposed.

To explain:

The regiochemistry of the elimination reaction.

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Answer 3

Question

Chapter 17.SE, Problem 33MP

Interpretation Introduction

a)

Interpretation:

A mechanism using curved arrows, for the conversion of alcohol given into the corresponding alkene by treating with POCl₃, is to be proposed. The regiochemistry of the elimination is also to be explained.

Concept introduction:

The dehydration of alcohols to alkenes in the presence of POCl₃ follows E² mechanism. The –OH group is converted into a better leaving group dichlorophosphate, –OPOCl₂, when treated with POCl₃. Pyridine used as solvent is also a base and it removes a proton arranged anti to the leaving group from the β carbon (requirement for E² mechanism). The removal of the proton and –OPOCl₂ occurs simultaneously in a single step to yield the alkene as the product.

To propose:

A mechanism using curved arrows, for the conversion of alcohol given into the corresponding alkene by treating with POCl₃ is to be proposed.

To explain:

The regiochemistry of the elimination reaction.

Interpretation Introduction

b)

Interpretation:

A mechanism using curved arrows, for the conversion of alcohol given into the corresponding alkene by treating with POCl₃, is to be proposed. The regiochemistry of the elimination is also to be explained.

Concept introduction:

The dehydration of alcohols to alkenes in the presence of POCl₃ follows E² mechanism. The –OH group is converted into a better leaving group dichlorophosphate, –OPOCl₂, when treated with POCl₃. Pyridine used as solvent is also a base and it removes a proton arranged anti to the leaving group from the β carbon (requirement for E² mechanism). The removal of the proton and –OPOCl₂ occurs simultaneously in a single step to yield the alkene as the product.

To propose:

A mechanism using curved arrows, for the conversion of alcohol given into the corresponding alkene by treating with POCl₃, is to be proposed.

To explain:

The regiochemistry of the elimination reaction.

Interpretation Introduction

c)

Interpretation:

A mechanism using curved arrows, for the conversion of alcohol given into the corresponding alkene by treating with POCl₃, is to be proposed. The regiochemistry of the elimination is also to be explained.

Concept introduction:

The dehydration of alcohols to alkenes in the presence of POCl₃ follows E² mechanism. The –OH group is converted into a better leaving group dichlorophosphate, –OPOCl₂, when treated with POCl₃. Pyridine used as solvent is also a base and it removes a proton arranged anti to the leaving group from the β carbon (requirement for E² mechanism). The removal of the proton and –OPOCl₂ occurs simultaneously in a single step to yield the alkene as the product.

To propose:

A mechanism using curved arrows, for the conversion of alcohol given into the corresponding alkene by treating with POCl₃, is to be proposed.

To explain:

The regiochemistry of the elimination reaction.

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Answer 4

Question

Chapter 17.SE, Problem 33MP

Interpretation Introduction

a)

Interpretation:

A mechanism using curved arrows, for the conversion of alcohol given into the corresponding alkene by treating with POCl₃, is to be proposed. The regiochemistry of the elimination is also to be explained.

Concept introduction:

The dehydration of alcohols to alkenes in the presence of POCl₃ follows E² mechanism. The –OH group is converted into a better leaving group dichlorophosphate, –OPOCl₂, when treated with POCl₃. Pyridine used as solvent is also a base and it removes a proton arranged anti to the leaving group from the β carbon (requirement for E² mechanism). The removal of the proton and –OPOCl₂ occurs simultaneously in a single step to yield the alkene as the product.

To propose:

A mechanism using curved arrows, for the conversion of alcohol given into the corresponding alkene by treating with POCl₃ is to be proposed.

To explain:

The regiochemistry of the elimination reaction.

Interpretation Introduction

b)

Interpretation:

A mechanism using curved arrows, for the conversion of alcohol given into the corresponding alkene by treating with POCl₃, is to be proposed. The regiochemistry of the elimination is also to be explained.

Concept introduction:

The dehydration of alcohols to alkenes in the presence of POCl₃ follows E² mechanism. The –OH group is converted into a better leaving group dichlorophosphate, –OPOCl₂, when treated with POCl₃. Pyridine used as solvent is also a base and it removes a proton arranged anti to the leaving group from the β carbon (requirement for E² mechanism). The removal of the proton and –OPOCl₂ occurs simultaneously in a single step to yield the alkene as the product.

To propose:

A mechanism using curved arrows, for the conversion of alcohol given into the corresponding alkene by treating with POCl₃, is to be proposed.

To explain:

The regiochemistry of the elimination reaction.

Interpretation Introduction

c)

Interpretation:

A mechanism using curved arrows, for the conversion of alcohol given into the corresponding alkene by treating with POCl₃, is to be proposed. The regiochemistry of the elimination is also to be explained.

Concept introduction:

The dehydration of alcohols to alkenes in the presence of POCl₃ follows E² mechanism. The –OH group is converted into a better leaving group dichlorophosphate, –OPOCl₂, when treated with POCl₃. Pyridine used as solvent is also a base and it removes a proton arranged anti to the leaving group from the β carbon (requirement for E² mechanism). The removal of the proton and –OPOCl₂ occurs simultaneously in a single step to yield the alkene as the product.

To propose:

A mechanism using curved arrows, for the conversion of alcohol given into the corresponding alkene by treating with POCl₃, is to be proposed.

To explain:

The regiochemistry of the elimination reaction.

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Answer 5

Chapter 17.SE, Problem 33MP

Interpretation Introduction

a)

Interpretation:

A mechanism using curved arrows, for the conversion of alcohol given into the corresponding alkene by treating with POCl₃, is to be proposed. The regiochemistry of the elimination is also to be explained.

Concept introduction:

The dehydration of alcohols to alkenes in the presence of POCl₃ follows E² mechanism. The –OH group is converted into a better leaving group dichlorophosphate, –OPOCl₂, when treated with POCl₃. Pyridine used as solvent is also a base and it removes a proton arranged anti to the leaving group from the β carbon (requirement for E² mechanism). The removal of the proton and –OPOCl₂ occurs simultaneously in a single step to yield the alkene as the product.

To propose:

A mechanism using curved arrows, for the conversion of alcohol given into the corresponding alkene by treating with POCl₃ is to be proposed.

To explain:

The regiochemistry of the elimination reaction.

Interpretation Introduction

b)

Interpretation:

A mechanism using curved arrows, for the conversion of alcohol given into the corresponding alkene by treating with POCl₃, is to be proposed. The regiochemistry of the elimination is also to be explained.

Concept introduction:

The dehydration of alcohols to alkenes in the presence of POCl₃ follows E² mechanism. The –OH group is converted into a better leaving group dichlorophosphate, –OPOCl₂, when treated with POCl₃. Pyridine used as solvent is also a base and it removes a proton arranged anti to the leaving group from the β carbon (requirement for E² mechanism). The removal of the proton and –OPOCl₂ occurs simultaneously in a single step to yield the alkene as the product.

To propose:

A mechanism using curved arrows, for the conversion of alcohol given into the corresponding alkene by treating with POCl₃, is to be proposed.

To explain:

The regiochemistry of the elimination reaction.

Interpretation Introduction

c)

Interpretation:

A mechanism using curved arrows, for the conversion of alcohol given into the corresponding alkene by treating with POCl₃, is to be proposed. The regiochemistry of the elimination is also to be explained.

Concept introduction:

The dehydration of alcohols to alkenes in the presence of POCl₃ follows E² mechanism. The –OH group is converted into a better leaving group dichlorophosphate, –OPOCl₂, when treated with POCl₃. Pyridine used as solvent is also a base and it removes a proton arranged anti to the leaving group from the β carbon (requirement for E² mechanism). The removal of the proton and –OPOCl₂ occurs simultaneously in a single step to yield the alkene as the product.

To propose:

A mechanism using curved arrows, for the conversion of alcohol given into the corresponding alkene by treating with POCl₃, is to be proposed.

To explain:

The regiochemistry of the elimination reaction.

Answer 6

Chapter 17.SE, Problem 33MP

Interpretation Introduction

a)

Interpretation:

A mechanism using curved arrows, for the conversion of alcohol given into the corresponding alkene by treating with POCl₃, is to be proposed. The regiochemistry of the elimination is also to be explained.

Concept introduction:

The dehydration of alcohols to alkenes in the presence of POCl₃ follows E² mechanism. The –OH group is converted into a better leaving group dichlorophosphate, –OPOCl₂, when treated with POCl₃. Pyridine used as solvent is also a base and it removes a proton arranged anti to the leaving group from the β carbon (requirement for E² mechanism). The removal of the proton and –OPOCl₂ occurs simultaneously in a single step to yield the alkene as the product.

To propose:

A mechanism using curved arrows, for the conversion of alcohol given into the corresponding alkene by treating with POCl₃ is to be proposed.

To explain:

The regiochemistry of the elimination reaction.

Answer 7

Chapter 17.SE, Problem 33MP

Interpretation Introduction

a)

Interpretation:

A mechanism using curved arrows, for the conversion of alcohol given into the corresponding alkene by treating with POCl₃, is to be proposed. The regiochemistry of the elimination is also to be explained.

Concept introduction:

The dehydration of alcohols to alkenes in the presence of POCl₃ follows E² mechanism. The –OH group is converted into a better leaving group dichlorophosphate, –OPOCl₂, when treated with POCl₃. Pyridine used as solvent is also a base and it removes a proton arranged anti to the leaving group from the β carbon (requirement for E² mechanism). The removal of the proton and –OPOCl₂ occurs simultaneously in a single step to yield the alkene as the product.

To propose:

A mechanism using curved arrows, for the conversion of alcohol given into the corresponding alkene by treating with POCl₃ is to be proposed.

To explain:

The regiochemistry of the elimination reaction.

Answer 8

Interpretation Introduction

b)

Interpretation:

A mechanism using curved arrows, for the conversion of alcohol given into the corresponding alkene by treating with POCl₃, is to be proposed. The regiochemistry of the elimination is also to be explained.

Concept introduction:

The dehydration of alcohols to alkenes in the presence of POCl₃ follows E² mechanism. The –OH group is converted into a better leaving group dichlorophosphate, –OPOCl₂, when treated with POCl₃. Pyridine used as solvent is also a base and it removes a proton arranged anti to the leaving group from the β carbon (requirement for E² mechanism). The removal of the proton and –OPOCl₂ occurs simultaneously in a single step to yield the alkene as the product.

To propose:

A mechanism using curved arrows, for the conversion of alcohol given into the corresponding alkene by treating with POCl₃, is to be proposed.

To explain:

The regiochemistry of the elimination reaction.

Answer 9

Interpretation Introduction

b)

Interpretation:

A mechanism using curved arrows, for the conversion of alcohol given into the corresponding alkene by treating with POCl₃, is to be proposed. The regiochemistry of the elimination is also to be explained.

Concept introduction:

The dehydration of alcohols to alkenes in the presence of POCl₃ follows E² mechanism. The –OH group is converted into a better leaving group dichlorophosphate, –OPOCl₂, when treated with POCl₃. Pyridine used as solvent is also a base and it removes a proton arranged anti to the leaving group from the β carbon (requirement for E² mechanism). The removal of the proton and –OPOCl₂ occurs simultaneously in a single step to yield the alkene as the product.

To propose:

A mechanism using curved arrows, for the conversion of alcohol given into the corresponding alkene by treating with POCl₃, is to be proposed.

To explain:

The regiochemistry of the elimination reaction.

Answer 10

Interpretation Introduction

c)

Interpretation:

A mechanism using curved arrows, for the conversion of alcohol given into the corresponding alkene by treating with POCl₃, is to be proposed. The regiochemistry of the elimination is also to be explained.

Concept introduction:

The dehydration of alcohols to alkenes in the presence of POCl₃ follows E² mechanism. The –OH group is converted into a better leaving group dichlorophosphate, –OPOCl₂, when treated with POCl₃. Pyridine used as solvent is also a base and it removes a proton arranged anti to the leaving group from the β carbon (requirement for E² mechanism). The removal of the proton and –OPOCl₂ occurs simultaneously in a single step to yield the alkene as the product.

To propose:

A mechanism using curved arrows, for the conversion of alcohol given into the corresponding alkene by treating with POCl₃, is to be proposed.

To explain:

The regiochemistry of the elimination reaction.

Answer 11

Interpretation Introduction

c)

Interpretation:

A mechanism using curved arrows, for the conversion of alcohol given into the corresponding alkene by treating with POCl₃, is to be proposed. The regiochemistry of the elimination is also to be explained.

Concept introduction:

The dehydration of alcohols to alkenes in the presence of POCl₃ follows E² mechanism. The –OH group is converted into a better leaving group dichlorophosphate, –OPOCl₂, when treated with POCl₃. Pyridine used as solvent is also a base and it removes a proton arranged anti to the leaving group from the β carbon (requirement for E² mechanism). The removal of the proton and –OPOCl₂ occurs simultaneously in a single step to yield the alkene as the product.

To propose:

A mechanism using curved arrows, for the conversion of alcohol given into the corresponding alkene by treating with POCl₃, is to be proposed.

To explain:

The regiochemistry of the elimination reaction.

Answer 12

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Answer 23

Ch. 17.1 - Give IUPAC names for the following compounds:Ch. 17.1 - Prob. 2P Ch. 17.2 - The following data for isomeric four-carbon...Ch. 17.2 - Rank the following substances in order of...Ch. 17.2 - Prob. 5P Ch. 17.3 - Prob. 6P Ch. 17.4 - What reagent would you use to accomplish each of...Ch. 17.4 - Prob. 8P Ch. 17.5 - Prob. 9P Ch. 17.5 - Prob. 10P

Solution Summary: The author proposes a mechanism using curved arrows, for the conversion of alcohol into the corresponding alkene by treating with POCl 3.

Chapter 17 Solutions