Question

What products would you expect from oxidation of the following compounds with ${\mathbf{CrO}}_3$ in aqueous acid? With the Dess-Martin periodinane?

1. 1-Hexanol
2. 2-Hexanol
3. Hexanal

Short answer

a.

b.

c.

Step-by-step solution

Oxidation of alcohol

Oxidation of alcohols can be done using reagents like aqueous acid and Dess-Martin Periodinane.Dess-Martin Periodinane is used to oxidize primary alcohols to aldehydes, whereas secondary alcohols are oxidized to ketones.

The product expected from the oxidation of 1-Hexanol with CrO3 in aqueous acid and with Dess-Martin Periodinane

a. The starting material is 1-Hexanol, and when it is treated with ${\text{CrO}}_{\text{3}}$ in an aqueous solution, 1-Hexanol gets oxidized and converted to Hexanoic acid. When 1-Hexanol is treated with Dess-Martin Periodinane, the primary alcohol is converted to aldehyde, and we get Hexanal as a product.

Oxidation of 1-Hexanol with ${\text{CrO}}_{\text{3}}$ in aqueous acid and with Dess-Martin Periodinane

The product expected from the oxidation of 2-Hexanol with CrO3 in aqueous acid and with Dess-Martin Periodinane

b.The starting material is 2-Hexanol, and when it is treated with ${\text{CrO}}_{\text{3}}$ in an aqueous solution, 2-Hexanol gets oxidized and converted to Hexan-2-one.

When 2-Hexanol is treated with Dess-Martin Periodinane, the product Hexan-2-one is formed. We know that the secondary alcohols are converted to a ketone by ketone using Dess-Martin Periodinane.

Oxidation of 2-Hexanol with ${\text{CrO}}_{\text{3}}$ in aqueous acid and with Dess-Martin Periodinane

The product expected from the oxidation of Hexanal with CrO3 in aqueous acid and with Dess-Martin Periodinane

c.The starting material is Hexanal, and when it is treated with ${\text{CrO}}_{\text{3}}$ in an aqueous solution, the aldehyde group gets oxidized to carboxylic acid.

When Hexanal is treated with Dess-Martin Periodinane, the aldehyde group does not oxidize further, and no reaction is possible.

Oxidation of Hexanal with ${\text{CrO}}_{\text{3}}$in aqueous acid and with Dess-Martin Periodinane