Chapter 16.SE, Problem 71AP

Interpretation Introduction

a)

Interpretation:

Starting from benzene and assuming that the ortho and para isomers can be separated how the compound can be synthesized is to be shown.

Concept introduction:

The compound required is 2-bromo-4-nitrotoluene. Benzene can be converted into alkyl benzene by Friedal-Crafts alkylation. The alkylbenzene can be nitrated in the ortho and para positions as the alkyl groups are ortho and para directors. Nitro group is deactivating while alkyl group is activating in nature. Hence bromonation of the nitrotoluene will introduce the bromine in the ortho position to alkyl group.

To show:

Starting from benzene and assuming that the ortho and para isomers can be separated how 2-bromo-4-nitrotoluene can be synthesized.

Interpretation Introduction

b)

Interpretation:

Starting from benzene and assuming that the ortho and para isomers can be separated how the compound can be synthesized is to be shown.

Concept introduction:

The Friedal-Crafts acylation of benzene will yield an acyl benzene as the product. Chlorination of the acyl benzene will produce m-chloroacyl benzene as the acyl group is meta directing. Reduction of the acyl group to the corresponding alkyl group and sulfonation of the product will result in the product required.

To show:

Starting from benzene and assuming that the ortho and para isomers can be separated how the compound can be synthesized.