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Draw the major product for the oxidation reaction below. Then, draw the proper full...

Question:

Draw the major product for the oxidation reaction below. Then, draw the proper full electron-pushing mechanism for the reaction, including all intermediates (with formal charges) and electron pushing arrows. Label the Electrophile and Nucleophile in each step.

REMEMBER: NaOCl (bleach) + CH{eq}^{3} {/eq}COOH (acetic acid) create the reactive species HOCl.

Oxidation of alcohol with HOCl generated from Sodium hypochlorite

Sodium hypochlorite is commonly known as bleaching powder and is used as a disinfectant in the maintenance of swimming pools. This apart, it is also an useful oxidant which can oxidize a variety of compounds. A common oxidation reaction that is carried out using this reagents is the oxidation of alcohols to aldehydes.

Answer and Explanation:

The effective oxidant in this reaction is {eq}HOCl {/eq} and this is generated insitu by the reaction between sodium hypochlorite and acetic acid. After the generation of the oxidant the remaining reaction follows the following mechanism:-

The reaction begins with the protonation of the alcohol and the genration of the hypochlorite ion.

In the next step the hypochlorite ion displaces the alcoholic -OH group as a water molecule.

Following this, there is an elimination of the {eq}\alpha {/eq}-H atom and the Cl-atom from the Oxygen resulting in the formation of the aldehyde and simultaneous removal of HCl.


Learn more about this topic:

Oxidation of Alcohols: Mechanism, Reaction & Conditions
Oxidation of Alcohols: Mechanism, Reaction & Conditions

from Organic & Inorganic Compounds Study Guide

Chapter 13 / Lesson 1
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