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.