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Chapter 11 – Aldehydes, Ketones and Carboxylic Acids

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Aldehydes, ketones, and carboxylic acids are commonly found in plant and animal species. They form an important part of the biochemical processes of living organisms. For better conceptual knowledge of their role in organic chemistry, you need to be aware of their structure, nomenclature, and preparation methods.

Aldehydes, ketones, and carboxylic acids are organic compounds containing carbonyl groups, i.e., carbon-oxygen double bond (C=O). The carbonyl group is considered crucial in the study of organic compounds. In the case of aldehydes, the carbonyl group has bonds with hydrogen and carbon, whereas it is attached to two carbon atoms in ketones. On the other hand, in carboxylic acids, the carbonyl group is bonded with oxygen.

Aldehydes and Ketones

Aldehydes and ketones are regarded as the simplest of all carbonyl compounds. The functional group of aldehydes is ‘-CHO,’ and that of ketones is ‘C=O.’

Generally, these compounds are named in two different ways:

  1. Common Names

Most aldehydes are named after their corresponding carboxylic acid group. Here, the ending ‘-ic’ part of carboxylic acid’s common name is replaced with the word ‘aldehyde.’ For example, the name of ‘acetaldehyde’ is derived from ‘acetic acid.’ These names indicate the Greek or Latin term used for the original source of that aldehyde or acid.

Similarly, the ketones are named after their aryl or alkyl groups that are attached to the carbonyl group. For example, ketone with a propyl group is named propiophenone. Some of the ketones also have historical names.

  1. IUPAC Names

While the common name ‘benzaldehydes’ is included by IUPAC as such only, other aldehydes and ketones are named by the following rules:

  • The open-chain aliphatic ketones and aldehydes have names derived from their corresponding alkanes where the ending part ‘-e’ is replaced with ‘-one’ and ‘al’ respectively.
  • In ketones, the longest carbon chain is assigned numbers from the end nearest to the carbonyl group, but in aldehydes, the numbering is done from the starting carbon of the group.
  • If the aldehyde group is bonded with a ring, the complete name of cycloalkane is prefixed with the word ‘carbaldehyde.’

The carbon atoms of the carbonyl group are sp2 hybridized and create three sigma (σ) bonds. So, the valence electron that remains in the p-orbital orbital of carbon creates a π-bond by overlapping with the p-orbital of oxygen. Further, the oxygen atom has two non-bonded electron pairs. Therefore, the carbon atom of carbonyl and other three atoms bonded to it are in the same plane form a trigonal planar structure while the π-electron cloud lies above and below the plane. The carbon-oxygen double bond has polarity due to the relatively higher electronegativity of oxygen.

Aldehydes and ketones are mostly prepared by oxidizing primary and secondary alcohols respectively. For example, when ethanol is used as the primary alcohol, treating it with an oxidizing agent will produce ethanal (acetaldehyde). However, excessive oxidation can turn the aldehyde into carboxylic acid.

This kind of further reaction does not occur in the case of secondary alcohol. For instance, when propan-2-ol is heated with acidified potassium dichromate (VI) solution, propanone is formed. Here, using an excess amount of oxidising agent or alcohol makes no difference to the final product.

Apart from the methods mentioned above, there are several other ways of preparing aldehydes and ketones; like hydrogenation of alcohols, hydration of alkynes, ozonolysis of alkenes, etc.

Carboxylic acids are one of the oldest known organic compounds found in nature. They carry carboxyl functional groups (-COOH) containing the carbonyl and hydroxyl groups. Carboxylic acids have many derivatives in the form of amides, esters, etc.

Most carboxylic acids are known by their common names that end with the suffix ‘-ic acid.’ These names are based on the Greek or Latin terms used for their natural resources. For example, formic acid, acetic acid, etc.

In IUPAC, the names of aliphatic carboxylic acids are kept by replacing the last ‘-e’ of the corresponding alkane with ‘-oic acid.’ For example, ethanoic acid.

Structure of Carboxyl Group

Like the carbonyl group, the hydroxyl oxygen is sp2 hybridised resulting in the conjugation of an unbonded electron pair and the π structure of carbonyl. So, the bonds of carboxyl carbon are in one plane separated by 120°. The resonant structure of carboxylic carbon makes it less electrophilic compared to the carbonyl carbon.

Similar to aldehydes, carboxylic acids are prepared by oxidation of primary with common oxidants like potassium permanganate. Alternatively, carboxylic acids can also be prepared from aldehydes using mild oxidants.

Other methods of preparing carboxylic acids include hydrolysis of esters or nitriles, oxidation of alkylbenzenes, etc.

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