Question

If 1 -hexanol was treated with pyridinium chlorochromate, what would the end product be? (A) 2-hexanol (B) 2-hexanone (C) Hexanal (D) Hexanoic acid

Short answer

C) Hexanal

Step-by-step solution

Identify the Reactant

The reactant in the problem is 1-hexanol, which is a primary alcohol with the structure CH3-(CH2)4-CH2OH.

Identify the Reagent

The reagent used in this reaction is pyridinium chlorochromate (PCC). PCC is commonly used to oxidize primary alcohols to aldehydes.

Determine the Product

When a primary alcohol, such as 1-hexanol, is oxidized by PCC, the product is an aldehyde. Therefore, 1-hexanol will be oxidized to hexanal (an aldehyde).

Write Out the Reaction

The chemical equation for this reaction is: CH3-(CH2)4-CH2OH + PCC → CH3-(CH2)4-CHO. The product is hexanal.

Choose the Correct Option

Among the given options, (C) Hexanal is the correct product formed when 1-hexanol is treated with PCC.

Key concepts

pyridinium chlorochromate

Pyridinium chlorochromate (PCC) is a commonly used chemical reagent in organic chemistry. It is used primarily to oxidize primary alcohols to aldehydes. PCC is preferred in many laboratory settings because it is milder than other oxidizing agents like chromic acid. This means that PCC can perform oxidation without over-oxidizing the alcohol to a carboxylic acid. For example, treating 1-hexanol, which is a primary alcohol, with PCC produces hexanal (an aldehyde) rather than hexanoic acid (a carboxylic acid), due to this selective oxidation process. The reaction mechanism involves the formation of an intermediate chromate ester, which decomposes to yield the aldehyde.

1-hexanol

1-Hexanol is an organic compound that belongs to the alcohol family. It is also known as hexyl alcohol and has the chemical formula CH3-(CH2)4-CH2OH. The structure consists of a six-carbon chain with a hydroxyl group (-OH) attached to the first carbon atom. In its pure form, 1-hexanol is a colorless liquid with a slight aroma. It is often used in the manufacturing of perfumes and as a solvent. As a primary alcohol, it is reactive with oxidizing agents such as pyridinium chlorochromate (PCC) to form aldehydes. When 1-hexanol is treated with PCC, it undergoes oxidation to yield hexanal, highlighting its reactivity and transformations in synthetic organic chemistry.

hexanal

Hexanal is an aldehyde with the chemical formula CH3-(CH2)4-CHO. It is derived from the oxidation of primary alcohols like 1-hexanol. Aldehydes are characterized by the presence of a carbonyl group (C=O) attached to a hydrogen atom and an alkyl or aryl group. In the case of hexanal, the carbonyl group is bonded to a six-carbon chain. Hexanal is a significant compound in the flavor and fragrance industries, imparting a grassy odor. It is worth noting that when working with PCC, the selective oxidation of 1-hexanol to hexanal exemplifies the efficiency and specificity of PCC as an oxidizing agent. This product formation showcases the tailored chemical reactions that can be achieved in an organic synthesis setting.