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What products would you expect from oxidation of the following compounds with CrO3 in aqueous acid? With the Dess-Martin periodinane?

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

Short Answer

Expert verified


a.

b.

c.

Step by step solution

01

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.

02

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 CrO3 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 CrO3 in aqueous acid and with Dess-Martin Periodinane

03

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 CrO3 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 CrO3 in aqueous acid and with Dess-Martin Periodinane

04

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 CrO3 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 CrO3in aqueous acid and with Dess-Martin Periodinane

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Most popular questions from this chapter

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