a) Methyl 1-phenylethyl ether Interpretation: How to prepare methyl 1-phenylethyl ether from 1-phenylethanol is to be shown. Concept introduction: Ether can be obtained by the Williamson synthesis reaction between the alkoxide of an alcohol with alkyl bromides. The alkoxide can be prepared by treating the alcohol with NaH. To give: How to prepare methyl 1-phenylethyl ether from 1-phenylethanol.

Question

Unshared, or lone, electron pairs play an important role in determining the chemical and physical properties of organic compounds. Thus, it is important to know which atoms carry unshared pairs. Use the structural formulas below to determine the number of unshared pairs at each designated atom. Be sure your answers are consistent with the formal charges on the formulas. CH. H₂ fo H2 H The number of unshared pairs at atom a is The number of unshared pairs at atom b is The number of unshared pairs at atom c is HC HC HC CH The number of unshared pairs at atom a is The number of unshared pairs at atom b is The number of unshared pairs at atom c is

Answer 1

Question

Chapter 18.SE, Problem 41AP

Interpretation Introduction

a) Methyl 1-phenylethyl ether

Interpretation:

How to prepare methyl 1-phenylethyl ether from 1-phenylethanol is to be shown.

Concept introduction:

Ether can be obtained by the Williamson synthesis reaction between the alkoxide of an alcohol with alkyl bromides. The alkoxide can be prepared by treating the alcohol with NaH.

To give:

How to prepare methyl 1-phenylethyl ether from 1-phenylethanol.

Interpretation Introduction

b) Phenylepoxyethane

Interpretation:

How to prepare methyl phenylepoxyethane from 1-phenylethanol is to be shown.

Concept introduction:

Alcohols dehydrate when treated with POCl₃ to yield alkenes. Alkenes can be converted into epoxides by oxidizing with peracids.

To give:

How to prepare methyl phenylepoxyethane from 1-phenylethanol.

Interpretation Introduction

c) tert-Butyl 1-phenylethyl ether

Interpretation:

How to prepare tert-butyl 1-phenylethyl ether from 1-phenylethanol is to be shown.

Concept introduction:

In the alkoxy-mercuration process, the addition of alcohols to double bonds in alkenes takes place following Markovnikov's regiochemistry. Variety of alcohols and alkenes can be used in this process. Primary, secondary and tertiary alcohols react well.

To show:

How to prepare tert-butyl 1-phenylethyl ether from 1-phenylethanol.

Interpretation Introduction

d) 1-Phenylethanethiol

Interpretation:

How to prepare 1-phenylthiol from 1-phenylethanol is to be shown.

Concept introduction:

Treatment of an alkyl halide with thiourea gives an alkyl thiourea salt. The salt when hydrolyzed with aqueous bases yields the thiol. The alkyl bromide can be prepared by treating an alcohol with PBr₃.

To show:

How to prepare 1-phenylthiol from 1-phenylethanol.

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Unshared, or lone, electron pairs play an important role in determining the chemical and physical properties of organic compounds. Thus, it is important to know which atoms carry unshared pairs. Use the structural formulas below to determine the number of unshared pairs at each designated atom. Be sure your answers are consistent with the formal charges on the formulas. CH. H₂ fo H2 H The number of unshared pairs at atom a is The number of unshared pairs at atom b is The number of unshared pairs at atom c is HC HC HC CH The number of unshared pairs at atom a is The number of unshared pairs at atom b is The number of unshared pairs at atom c is

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Answer 2

Question

Chapter 18.SE, Problem 41AP

Interpretation Introduction

a) Methyl 1-phenylethyl ether

Interpretation:

How to prepare methyl 1-phenylethyl ether from 1-phenylethanol is to be shown.

Concept introduction:

Ether can be obtained by the Williamson synthesis reaction between the alkoxide of an alcohol with alkyl bromides. The alkoxide can be prepared by treating the alcohol with NaH.

To give:

How to prepare methyl 1-phenylethyl ether from 1-phenylethanol.

Interpretation Introduction

b) Phenylepoxyethane

Interpretation:

How to prepare methyl phenylepoxyethane from 1-phenylethanol is to be shown.

Concept introduction:

Alcohols dehydrate when treated with POCl₃ to yield alkenes. Alkenes can be converted into epoxides by oxidizing with peracids.

To give:

How to prepare methyl phenylepoxyethane from 1-phenylethanol.

Interpretation Introduction

c) tert-Butyl 1-phenylethyl ether

Interpretation:

How to prepare tert-butyl 1-phenylethyl ether from 1-phenylethanol is to be shown.

Concept introduction:

In the alkoxy-mercuration process, the addition of alcohols to double bonds in alkenes takes place following Markovnikov's regiochemistry. Variety of alcohols and alkenes can be used in this process. Primary, secondary and tertiary alcohols react well.

To show:

How to prepare tert-butyl 1-phenylethyl ether from 1-phenylethanol.

Interpretation Introduction

d) 1-Phenylethanethiol

Interpretation:

How to prepare 1-phenylthiol from 1-phenylethanol is to be shown.

Concept introduction:

Treatment of an alkyl halide with thiourea gives an alkyl thiourea salt. The salt when hydrolyzed with aqueous bases yields the thiol. The alkyl bromide can be prepared by treating an alcohol with PBr₃.

To show:

How to prepare 1-phenylthiol from 1-phenylethanol.

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Answer 3

Question

Chapter 18.SE, Problem 41AP

Interpretation Introduction

a) Methyl 1-phenylethyl ether

Interpretation:

How to prepare methyl 1-phenylethyl ether from 1-phenylethanol is to be shown.

Concept introduction:

Ether can be obtained by the Williamson synthesis reaction between the alkoxide of an alcohol with alkyl bromides. The alkoxide can be prepared by treating the alcohol with NaH.

To give:

How to prepare methyl 1-phenylethyl ether from 1-phenylethanol.

Interpretation Introduction

b) Phenylepoxyethane

Interpretation:

How to prepare methyl phenylepoxyethane from 1-phenylethanol is to be shown.

Concept introduction:

Alcohols dehydrate when treated with POCl₃ to yield alkenes. Alkenes can be converted into epoxides by oxidizing with peracids.

To give:

How to prepare methyl phenylepoxyethane from 1-phenylethanol.

Interpretation Introduction

c) tert-Butyl 1-phenylethyl ether

Interpretation:

How to prepare tert-butyl 1-phenylethyl ether from 1-phenylethanol is to be shown.

Concept introduction:

In the alkoxy-mercuration process, the addition of alcohols to double bonds in alkenes takes place following Markovnikov's regiochemistry. Variety of alcohols and alkenes can be used in this process. Primary, secondary and tertiary alcohols react well.

To show:

How to prepare tert-butyl 1-phenylethyl ether from 1-phenylethanol.

Interpretation Introduction

d) 1-Phenylethanethiol

Interpretation:

How to prepare 1-phenylthiol from 1-phenylethanol is to be shown.

Concept introduction:

Treatment of an alkyl halide with thiourea gives an alkyl thiourea salt. The salt when hydrolyzed with aqueous bases yields the thiol. The alkyl bromide can be prepared by treating an alcohol with PBr₃.

To show:

How to prepare 1-phenylthiol from 1-phenylethanol.

Expert Solution & Answer

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Answer 4

Question

Chapter 18.SE, Problem 41AP

Interpretation Introduction

a) Methyl 1-phenylethyl ether

Interpretation:

How to prepare methyl 1-phenylethyl ether from 1-phenylethanol is to be shown.

Concept introduction:

Ether can be obtained by the Williamson synthesis reaction between the alkoxide of an alcohol with alkyl bromides. The alkoxide can be prepared by treating the alcohol with NaH.

To give:

How to prepare methyl 1-phenylethyl ether from 1-phenylethanol.

Interpretation Introduction

b) Phenylepoxyethane

Interpretation:

How to prepare methyl phenylepoxyethane from 1-phenylethanol is to be shown.

Concept introduction:

Alcohols dehydrate when treated with POCl₃ to yield alkenes. Alkenes can be converted into epoxides by oxidizing with peracids.

To give:

How to prepare methyl phenylepoxyethane from 1-phenylethanol.

Interpretation Introduction

c) tert-Butyl 1-phenylethyl ether

Interpretation:

How to prepare tert-butyl 1-phenylethyl ether from 1-phenylethanol is to be shown.

Concept introduction:

In the alkoxy-mercuration process, the addition of alcohols to double bonds in alkenes takes place following Markovnikov's regiochemistry. Variety of alcohols and alkenes can be used in this process. Primary, secondary and tertiary alcohols react well.

To show:

How to prepare tert-butyl 1-phenylethyl ether from 1-phenylethanol.

Interpretation Introduction

d) 1-Phenylethanethiol

Interpretation:

How to prepare 1-phenylthiol from 1-phenylethanol is to be shown.

Concept introduction:

Treatment of an alkyl halide with thiourea gives an alkyl thiourea salt. The salt when hydrolyzed with aqueous bases yields the thiol. The alkyl bromide can be prepared by treating an alcohol with PBr₃.

To show:

How to prepare 1-phenylthiol from 1-phenylethanol.

Expert Solution & Answer

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Answer 5

Chapter 18.SE, Problem 41AP

Interpretation Introduction

a) Methyl 1-phenylethyl ether

Interpretation:

How to prepare methyl 1-phenylethyl ether from 1-phenylethanol is to be shown.

Concept introduction:

Ether can be obtained by the Williamson synthesis reaction between the alkoxide of an alcohol with alkyl bromides. The alkoxide can be prepared by treating the alcohol with NaH.

To give:

How to prepare methyl 1-phenylethyl ether from 1-phenylethanol.

Interpretation Introduction

b) Phenylepoxyethane

Interpretation:

How to prepare methyl phenylepoxyethane from 1-phenylethanol is to be shown.

Concept introduction:

Alcohols dehydrate when treated with POCl₃ to yield alkenes. Alkenes can be converted into epoxides by oxidizing with peracids.

To give:

How to prepare methyl phenylepoxyethane from 1-phenylethanol.

Interpretation Introduction

c) tert-Butyl 1-phenylethyl ether

Interpretation:

How to prepare tert-butyl 1-phenylethyl ether from 1-phenylethanol is to be shown.

Concept introduction:

In the alkoxy-mercuration process, the addition of alcohols to double bonds in alkenes takes place following Markovnikov's regiochemistry. Variety of alcohols and alkenes can be used in this process. Primary, secondary and tertiary alcohols react well.

To show:

How to prepare tert-butyl 1-phenylethyl ether from 1-phenylethanol.

Interpretation Introduction

d) 1-Phenylethanethiol

Interpretation:

How to prepare 1-phenylthiol from 1-phenylethanol is to be shown.

Concept introduction:

Treatment of an alkyl halide with thiourea gives an alkyl thiourea salt. The salt when hydrolyzed with aqueous bases yields the thiol. The alkyl bromide can be prepared by treating an alcohol with PBr₃.

To show:

How to prepare 1-phenylthiol from 1-phenylethanol.

Answer 6

Chapter 18.SE, Problem 41AP

Interpretation Introduction

a) Methyl 1-phenylethyl ether

Interpretation:

How to prepare methyl 1-phenylethyl ether from 1-phenylethanol is to be shown.

Concept introduction:

Ether can be obtained by the Williamson synthesis reaction between the alkoxide of an alcohol with alkyl bromides. The alkoxide can be prepared by treating the alcohol with NaH.

To give:

How to prepare methyl 1-phenylethyl ether from 1-phenylethanol.

Answer 7

Chapter 18.SE, Problem 41AP

Interpretation Introduction

a) Methyl 1-phenylethyl ether

Interpretation:

How to prepare methyl 1-phenylethyl ether from 1-phenylethanol is to be shown.

Concept introduction:

Ether can be obtained by the Williamson synthesis reaction between the alkoxide of an alcohol with alkyl bromides. The alkoxide can be prepared by treating the alcohol with NaH.

To give:

How to prepare methyl 1-phenylethyl ether from 1-phenylethanol.

Answer 8

Interpretation Introduction

b) Phenylepoxyethane

Interpretation:

How to prepare methyl phenylepoxyethane from 1-phenylethanol is to be shown.

Concept introduction:

Alcohols dehydrate when treated with POCl₃ to yield alkenes. Alkenes can be converted into epoxides by oxidizing with peracids.

To give:

How to prepare methyl phenylepoxyethane from 1-phenylethanol.

Answer 9

Interpretation Introduction

b) Phenylepoxyethane

Interpretation:

How to prepare methyl phenylepoxyethane from 1-phenylethanol is to be shown.

Concept introduction:

Alcohols dehydrate when treated with POCl₃ to yield alkenes. Alkenes can be converted into epoxides by oxidizing with peracids.

To give:

How to prepare methyl phenylepoxyethane from 1-phenylethanol.

Answer 10

Interpretation Introduction

c) tert-Butyl 1-phenylethyl ether

Interpretation:

How to prepare tert-butyl 1-phenylethyl ether from 1-phenylethanol is to be shown.

Concept introduction:

In the alkoxy-mercuration process, the addition of alcohols to double bonds in alkenes takes place following Markovnikov's regiochemistry. Variety of alcohols and alkenes can be used in this process. Primary, secondary and tertiary alcohols react well.

To show:

How to prepare tert-butyl 1-phenylethyl ether from 1-phenylethanol.

Answer 11

Interpretation Introduction

c) tert-Butyl 1-phenylethyl ether

Interpretation:

How to prepare tert-butyl 1-phenylethyl ether from 1-phenylethanol is to be shown.

Concept introduction:

In the alkoxy-mercuration process, the addition of alcohols to double bonds in alkenes takes place following Markovnikov's regiochemistry. Variety of alcohols and alkenes can be used in this process. Primary, secondary and tertiary alcohols react well.

To show:

How to prepare tert-butyl 1-phenylethyl ether from 1-phenylethanol.

Answer 12

Interpretation Introduction

d) 1-Phenylethanethiol

Interpretation:

How to prepare 1-phenylthiol from 1-phenylethanol is to be shown.

Concept introduction:

Treatment of an alkyl halide with thiourea gives an alkyl thiourea salt. The salt when hydrolyzed with aqueous bases yields the thiol. The alkyl bromide can be prepared by treating an alcohol with PBr₃.

To show:

How to prepare 1-phenylthiol from 1-phenylethanol.

Answer 13

Interpretation Introduction

d) 1-Phenylethanethiol

Interpretation:

How to prepare 1-phenylthiol from 1-phenylethanol is to be shown.

Concept introduction:

Treatment of an alkyl halide with thiourea gives an alkyl thiourea salt. The salt when hydrolyzed with aqueous bases yields the thiol. The alkyl bromide can be prepared by treating an alcohol with PBr₃.

To show:

How to prepare 1-phenylthiol from 1-phenylethanol.

Answer 14

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Ch. 18.1 - Name the following ethers:Ch. 18.2 - Why do you suppose only symmetrical ethers are...Ch. 18.2 - How would you prepare the following ethers using a...Ch. 18.2 - Review the mechanism of oxymercuration shown in...Ch. 18.2 - How would you prepare the following ethers? Use...Ch. 18.2 - Prob. 6P Ch. 18.3 - Prob. 7P Ch. 18.3 - Write the mechanism of the acid-induced cleavage...Ch. 18.3 - Why are HI and HBr more effective than HCl in...Ch. 18.4 - What product would you expect from Claisen...

Chapter 18 Solutions