Chapter 19.12, Problem 9P

a)

Interpretation Introduction

Interpretation:

The product of the given reaction has to be stated.

Concept Introduction:

The chromic acid reagent is used to oxidize a benzylic hydrocarbon chain into carboxylic acid.  However, this reagent is not applicable to that benzylic hydrocarbon chain which has no benzylic hydrogen.

b)

Interpretation Introduction

Interpretation:

The product of the given reaction has to be stated.

Concept Introduction:

The chromic acid reagent is used to oxidize a benzylic hydrocarbon chain into carboxylic acid. However, this reagent is not applicable to that benzylic hydrocarbon chain which has no benzylic hydrogen.

c)

Interpretation Introduction

Interpretation:

The product of the given reaction has to be stated.

Concept Introduction:

The N-bromosuccinamide reagent is used to convert benzylic hydrogen into benzylic bromide in the presence of peroxide through radical substitution reaction. The benzylic bromide is replaced by $-{\text{OCH}}_{\text{3}}$ using strong base like sodium methoxide.

d)

Interpretation Introduction

Interpretation:

The product of the given reaction has to be stated.

Concept Introduction:

Bromine in the presence of $h\upsilon$ light is used to convert benzylic hydrogen into benzylic bromide in the presence of peroxide through radical substitution reaction. The benzylic bromide is replaced by $-\text{CN}$ group by nucleophilic attack of ${}^{-}\text{C}\equiv \text{N}$. The reduction of $-\text{CN}$ group by ${\text{H}}_{\text{2}}\text{,}\text{Raney}\text{Ni}$ leads to the conversion of $-\text{CN}$ group into amine group.