Chapter 10, Problem 24P

Interpretation Introduction

Interpretation:

The structures for the compounds A and B that are produced in the photochemical chlorination of the given alkane are to be deduced and the factors that influencing their distribution are to be discussed.

Concept introduction:

If the hydrogens in alkanes are not equivalent the chlorination produces a mixture of constitutionally isomeric products. In propagation step, a substituent may abstract a hydrogen atom either from a primary or secondary or tertiary positions in the propagation step.

Among alkanes, tertiary hydrogens are replaced faster than secondary, and secondary faster than primary.

The ratio of the monochlorination products depends on the type of hydrogen that is abstracted by the chlorine atom and the free radical that is formed.

In ${\text{S}}_{\text{N}}\text{1}$ hydrolysis reaction, the rate of hydrolysis depends on the position of the halogen group present. The order is $\text{tertiary halides}>\text{secondary halides}>\text{primary halides}$.