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

What are the IUPAC Names of all the compounds in the picture?

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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What are the IUPAC Names of all the compounds in the picture?

1) a) Give the dominant Intermolecular Force (IMF) in a sample of each of the following compounds. Please show your work. (8) SF2, CH,OH, C₂H₂ b) Based on your answers given above, list the compounds in order of their Boiling Point from low to high. (8)

19.78 Write the products of the following sequences of reactions. Refer to your reaction road- maps to see how the combined reactions allow you to "navigate" between the different functional groups. Note that you will need your old Chapters 6-11 and Chapters 15-18 roadmaps along with your new Chapter 19 roadmap for these. (a) 1. BHS 2. H₂O₂ 3. H₂CrO4 4. SOCI₂ (b) 1. Cl₂/hv 2. KOLBU 3. H₂O, catalytic H₂SO4 4. H₂CrO4 Reaction Roadmap An alkene 5. EtOH 6.0.5 Equiv. NaOEt/EtOH 7. Mild H₂O An alkane 1.0 2. (CH3)₂S 3. H₂CrO (d) (c) 4. Excess EtOH, catalytic H₂SO OH 4. Mild H₂O* 5.0.5 Equiv. NaOEt/EtOH An alkene 6. Mild H₂O* A carboxylic acid 7. Mild H₂O* 1. SOC₁₂ 2. EtOH 3.0.5 Equiv. NaOEt/E:OH 5.1.0 Equiv. NaOEt 6. NH₂ (e) 1. 0.5 Equiv. NaOEt/EtOH 2. Mild H₂O* Br (f) i H An aldehyde 1. Catalytic NaOE/EtOH 2. H₂O*, heat 3. (CH,CH₂)₂Culi 4. Mild H₂O* 5.1.0 Equiv. LDA Br An ester 4. NaOH, H₂O 5. Mild H₂O* 6. Heat 7. MgBr 8. Mild H₂O* 7. Mild H₂O+

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 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