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Magazine Chapter 11: Q5P (page 549)
Predict the products you expect when the following starting material undergoes oxidation with an excess of each of the reagents shown below.
(a)chromic acid
(b)PCC(pyridinium chlorochromate)
(c)sodium hypochlorite/ acetic acid
(d)DMSO and oxalyl chloride
(e)DMP(periodinane)reagent
Short Answer
Step by step solution
Oxidation
The number of C-O bonds can be counted to understand whether an oxidation or reduction reaction has happened. The C-H bonds are transformed into C-O bonds in reduction reactions.
Oxidation of alcohols
Oxidation of primary alcohols generates an aldehyde. Ketones are generated when secondary alcohols are subjected to oxidation. NaOCl and chromic acid can be used to perform this kind of reaction.
Products formed when the given starting material undergoes oxidation with the given reagents
(a)The primary alcohol is oxidized to carboxylic acid when the starting material is treated with chromic acid (H2CrO4). The reaction can be given as:
The treatment of the starting material with chromic acid
(b)The primary alcohol is oxidized into an aldehyde when the starting material is treated with PCC. The reaction can be given as:
The treatment of the starting material with PCC
(c)The treatment of the starting material with NaOCl oxidizes the primary alcohol into a carboxylic acid. The reaction can be given as:
The treatment of the starting material with NaOCl
(d)The treatment of the starting material with DMSO or oxalyl chloride oxidizes the primary alcohol into an aldehyde. The reaction can be given as:
The treatment of the starting material with DMSO or oxalyl chloride
(e)The treatment of the starting material with DMP oxidizes the primary alcohol into an aldehyde. The reaction can be given as:
The treatment of the starting material with DMP
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