Question

Give the structural formula and systematic name for the product, if any, from the reactions of each of the following pairs of compounds: (a) pentanal and \(\mathrm{KMnO}_{4}\) (b) pentanal and \(\mathrm{LiAlH}_{4}\) (c) 2-octanone and \(\mathrm{LiAlH}_{4}\) (d) 2 -octanone and \(\mathrm{KMnO}_{4}\)

Short answer

(a) Pentanoic acid, (b) 1-pentanol, (c) 2-octanol, (d) 2-octanone (no change).

Step-by-step solution

Understanding the Reactions

We are dealing with pairs of compounds reacting with either \(\text{KMnO}_4\) or \(\text{LiAlH}_4\). We'll address the chemical changes step by step.

Reaction (a) Pentanal with KMnO4

\( \text{KMnO}_4 \) is a strong oxidizing agent. When reacted with pentanal, it oxidizes the aldehyde to a carboxylic acid, forming pentanoic acid. The structural formula is \( \text{CH}_3(\text{CH}_2)_3\text{COOH} \).

Naming the Product (a)

The systematic name of the product is pentanoic acid.

Reaction (b) Pentanal with LiAlH4

\( \text{LiAlH}_4 \) is a strong reducing agent. When reacted with pentanal, it reduces the aldehyde to a primary alcohol, forming 1-pentanol. The structural formula is \( \text{CH}_3(\text{CH}_2)_3\text{CH}_2\text{OH} \).

Naming the Product (b)

The systematic name of the product is 1-pentanol.

Reaction (c) 2-Octanone with LiAlH4

\( \text{LiAlH}_4 \) reduces the ketone group to an alcohol. For 2-octanone, it forms 2-octanol. The structural formula is \( \text{CH}_3(\text{CH}_2)_4\text{CHOHCH}_3 \).

Naming the Product (c)

The systematic name of the product is 2-octanol.

Reaction (d) 2-Octanone with KMnO4

\( \text{KMnO}_4 \) usually oxidizes primary and secondary alcohols. Since 2-octanone is already oxidized, it remains unchanged by \( \text{KMnO}_4 \).

Naming the Product (d)

There is no change, so the name remains 2-octanone.

Key concepts

Aldehyde Oxidation

Aldehydes are organic compounds characterized by the presence of a carbonyl group bonded to at least one hydrogen atom. When an aldehyde is exposed to a strong oxidizing agent like potassium permanganate (\(\mathrm{KMnO}_4\)), it undergoes an oxidation reaction.
In this reaction, the aldehyde group is converted into a carboxylic acid.

• The carbonyl carbon gains an additional oxygen, leading to a new hydroxyl group, transforming the compound into a carboxylic acid.
• For example, when pentanal oxidizes, it turns into pentanoic acid with the structural formula \(\text{CH}_3(\text{CH}_2)_3\text{COOH}\)

This process is fundamental in organic chemistry because it transforms molecules into more reactive species or prepares them for further reactions.

Ketone Reduction

Ketones are a type of organic compound that feature a carbonyl group bonded to two carbon atoms. Unlike aldehydes, ketones cannot be oxidized to carboxylic acids under normal conditions but can be reduced to alcohols.
When a ketone reacts with a strong reducing agent like lithium aluminum hydride (\(\mathrm{LiAlH}_4\)), it undergoes a reduction process.

• This reaction converts the carbonyl group into a hydroxyl group, resulting in an alcohol.
• For example, the reduction of 2-octanone produces 2-octanol, with the structural formula \(\text{CH}_3(\text{CH}_2)_4\text{CHOHCH}_3\)

This type of reaction is useful because it transforms functional groups into others, allowing for the synthesis of complex molecules from simpler precursors.

Organic Reactions

Organic reactions involve the making and breaking of chemical bonds within organic molecules. They are essential to chemistry because they form the basis for creating nearly all organic compounds.
Key reactions include oxidation and reduction, where the functional groups of organic compounds are transformed.

• Oxidation typically involves increasing the oxygen content or removing hydrogen.
• Reduction involves increasing hydrogen content or removing oxygen.

These reactions enable chemists to modify molecules to enhance their properties or combine them to create new substances. In educational settings, understanding these reactions helps students grasp the complex processes involved in organic chemistry.

Systematic Nomenclature

Systematic nomenclature in chemistry refers to a set of rules used to generate a standard name for chemical compounds.
It allows chemists to precisely describe a molecule's composition and structure.

• For carbon compounds, this often involves identifying the length of the carbon chain and the type and position of functional groups.
• For example, in 'pentanoic acid', 'pent' indicates five carbons, and 'oic acid' signals a carboxylic acid group.
• Similarly, '1-pentanol' signifies a primary alcohol derived from pentane.

This system is crucial because it ensures consistent communication among chemists worldwide, reducing misunderstandings and improving clarity in scientific discourse.