We have covered several oxidants that use a multi-valent atom (Cr, Cl, S, or I) as their active species, going from a higher oxidation state before the oxidation to a lower oxidation state after oxidizing the alcohol. Draw the structure of the following atoms, before and after the oxidation of an alcohol to a ketone or aldehyde. How many bonds to oxygen does each atom have before and after the oxidation?

(a) the Cr in chromic acid

(b) the Cl in sodium hypochlorite

(c) the S in the Swern oxidation

(d) the I in the DMP reagent

(e)the carbinol C in the alcohol that is oxidized.

Oxidants, also termed oxidizing agents constitute species that takes out one or several electrons from a reactant in a particular reaction. Some familiar oxidizing agents are hydrogen peroxide and potassium permanganate.

Oxidizing agents like potassium permanganate and nitric acid transforms primary alcohols to carboxylic acids and secondary alcohols to ketones. Alcohols can be transformed into ketones and aldehydes using dimethyl sulfoxide, and this process is termed Swern oxidation.

(a)Chromium in chromic acid begins with bonds to four oxygen atoms and ends with bonds to three oxygen atoms. It can be represented as:

Bonds of Cr in chromic acid before and after oxidation

(b)The Cl in sodium hypochlorite begins with one bond to oxygen and ends with no bonds to oxygen. The representation can be given as:

Bonds of Cl in sodium hypochlorite before and after oxidation

(c)The S in the Swern oxidation begins bonded to one oxygen atom and ends with no bonds to oxygen. It can be represented as:

Bonds of S in the Swern oxidation

(d) The I in the DMP reagent begins with four bonds to oxygen and ends with two bonds to oxygen. It can be represented as:

Bonds of I in the DMP reagent

(e) The carbon begins with one bond to oxygen and at least one bond to hydrogen. It ends with two bonds to oxygen and one lesser bond to hydrogen. It can be represented as:

Bonds of carbinol C in the alcohol that is oxidized