Chapter 23, Problem 23.69P

(a)

Interpretation Introduction

Interpretation:

The synthesis has to be shown for the 2,4-dichloro benzoic acid from toluene.

Concept introduction:

Chromic Acid:

Chromic Acid (${\text{H}}_{\text{2}}{\text{CrO}}_{\text{4}}$) is used as an oxidizing agent, primary alcohol oxidized in to aldehyde or acid depends on the condition, secondary alcohol oxidized in to ketone.

(b)

Interpretation Introduction

Interpretation:

The mechanism for the chlorosulfonation is to be proposed.

(c)

Interpretation Introduction

Interpretation:

The mechanism is to be proposed for step 3.

Concept introduction:

Ipso substitution reaction: It is the one of the aromatic substitution reaction in which both the substituent (nucleophile and the parent substituent) present in the same ring position in an intermediate compound. Finally the parent substituent leave from the intermediate leads to the formation of product. The mechanism of desulfonation curved arrow pattern is given below.

(d)

Interpretation Introduction

Interpretation:

The possible stereoisomer’s has to be shown if the product is chiral.

Concept introduction:

Isomer: A molecule having the same molecular formula but with different chemical structure is called isomer.

Enantiomers: A compound which is non-superimposable mirror image is called enantiomers.

Diastereomers: A compound which is non-superimposable and non-mirror image is called diastereomers.

Racemic mixture: A racemic mixture is simply a mixture containing an equal amount of each enantiomer.

Achiral:

A molecule is superimposable on its mirror image is called achiral molecule.