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

An unknown weak acid with a concentration of 0.410 M has a pH of 5.600. What is the Ka of the weak acid?

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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An unknown weak acid with a concentration of 0.410 M has a pH of 5.600. What is the Ka of the weak acid?

(racemic) 19.84 Using your reaction roadmaps as a guide, show how to convert 2-oxepanone and ethanol into 1-cyclopentenecarbaldehyde. You must use 2-oxepanone as the source of all carbon atoms in the target molecule. Show all reagents and all molecules synthesized along the way. & + EtOH H 2-Oxepanone 1-Cyclopentenecarbaldehyde

R₂ R₁ R₁ a R Rg Nu R₂ Rg R₁ R R₁₂ R3 R R Nu enolate forming R₁ R B-Alkylated carbonyl species or amines Cyclic B-Ketoester R₁₁ HOB R R₁B R R₁₂ B-Hydroxy carbonyl R diester R2 R3 R₁ RB OR R₂ 0 aB-Unsaturated carbonyl NaOR Aldol HOR reaction 1) LDA 2) R-X 3) H₂O/H₂O ketone, aldehyde 1) 2°-amine 2) acid chloride 3) H₂O'/H₂O 0 O R₁ R₁ R R₁ R₁₂ Alkylated a-carbon R₁ H.C R₁ H.C Alkylated methyl ketone acetoacetic ester B-Ketoester ester R₁ HO R₂ R B-Dicarbonyl HO Alkylated carboxylic acid malonic ester Write the reagents required to bring about each reaction next to the arrows shown. Next, record any regiochemistry or stereochemistry considerations relevant to the reaction. You should also record any key aspects of the mechanism, such as forma- tion of an important intermediate, as a helpful reminder. You may want to keep track of all reactions that make carbon-carbon bonds, because these help you build large molecules from smaller fragments. This especially applies to the reactions in…

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.

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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.

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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