Chapter 19, Problem 19.57P

Interpretation Introduction

(a)

Interpretation:

How to carry out the given transformation is to be shown.

Concept introduction:

There are several oxidizing agents which are used to oxidize primary alcohols into corresponding acids. Chromic acid will oxidize a primary alcohol to a carboxylic acid or a secondary alcohol to a ketone. Chromic acid is prepared by dissolving sodium dichromate in an acidic solution. Like chromic acid, potassium permanganate is also used as an oxidizing agent. When treated with a basic solution of potassium permanganate (${\text{KMnO}}_4$), followed by aqueous acid, primary alcohols and aldehydes are converted to carboxylic acids, while secondary alcohols are converted to ketones. However, tertiary alcohols do not undergo an oxidation reaction with ${\text{KMnO}}_4$. Chromic acid, potassium permanganate are the reagents that can be used in oxidizing a primary alcohol to corresponding acids.

Interpretation Introduction

(b)

Interpretation:

The product of the given reaction is to be predicted.

Concept introduction:

Pyridinium chlorochromate (PCC) is a partial oxidizing agent. Oxidation of a primary alcohol by pyridinium chlorochromate (PCC) stops at the aldehyde because the reaction takes place in a nonaqueous medium. Pyridinium chlorochromate (PCC) oxidizes a primary alcohol to an aldehyde and a secondary alcohol to a ketone.

Interpretation Introduction

(c)

Interpretation:

How to carry out the given transformation is to be shown.

Concept introduction:

There are several oxidizing agents which are used to oxidize secondary alcohols into ketones. Chromic acid will oxidize a primary alcohol to a carboxylic acid or a secondary alcohol to a ketone. Chromic acid is prepared by dissolving sodium dichromate in an acidic solution. Like chromic acid, potassium permanganate is also used as an oxidizing agent. When treated with a basic solution of potassium permanganate (${\text{KMnO}}_4$), followed by aqueous acid: Primary alcohols and aldehydes are converted to carboxylic acids, while secondary alcohols are converted to ketones. Pyridinium chlorochromate (PCC) oxidizes a primary alcohol to an aldehyde and a secondary alcohol to a ketone.

Interpretation Introduction

(d)

Interpretation:

The product of the given reaction is to be predicted.

Concept introduction:

Pyridinium chlorochromate (PCC) is a partial oxidizing agent. Oxidation of a primary alcohol by pyridinium chlorochromate (PCC) stops at the aldehyde because the reaction takes place in a nonaqueous medium. Pyridinium chlorochromate (PCC) oxidizes a primary alcohol to an aldehyde and a secondary alcohol to a ketone.