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.

Question

Draw all of the substitution and elimination products formed from the given alkyl halide with each reagent: (a) CH3OH; (b) KOH. Indicate the stereochemistry around the stereogenic centers present in the products, as well as the mechanism by which each product is formed.

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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Draw all of the substitution and elimination products formed from the given alkyl halide with each reagent: (a) CH3OH; (b) KOH. Indicate the stereochemistry around the stereogenic centers present in the products, as well as the mechanism by which each product is formed.

Draw the products formed when both cis- and trans-but-2-ene are treated with OsO4, followed by hydrolysis with NaHSO3 + H2O. Explain how these reactions illustrate that syn dihydroxylation is stereospecific.

Draw all of the substitution and elimination products formed from thegiven alkyl halide with each reagent: (a) CH3OH; (b) KOH. Indicate thestereochemistry around the stereogenic centers present in the products,as well as the mechanism by which each product is formed.

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.

Expert Solution & Answer

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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 17

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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