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Question:

Draw the structure and name the product formed if the following alcohols are oxidized. Assume that an excess of oxidizing agent is used: (i) CH3CH2CH2CH2OH (ii) 2-butenol (iii) 2-methyl-propanol

Solution:

The structure and name are:
(i) CH3CH2CH2COOH, butanoic acid
(ii) CH3−CH=CH−CHO, but-2-enal
(iii) CH3−CH(CH3)−COOH, 2-methyl propanoic acid
Primary alcohols on oxidation give carboxylic acids in the presence of an excess oxidizing agent. Secondary alcohols on oxidation give ketones in the presence of an excess oxidizing agent. However, in the case of 2-butenol, which is an unsaturated secondary alcohol, it will be oxidized to an aldehyde (but-2-enal).