Aldehydes Ketones and Carboxylic Acids

Bookmark added to your notes.
View Notes
×

What are Aldehydes Ketones and Carboxylic Acids?

Aldehyde Ketone and Carboxylic Acids are the carbonyl compounds containing a double bond or carbon-oxygen. These are very important organic compounds in the field of organic chemistry, and they also have many industrial applications. The common carbonyl group presence in the two classes of compounds makes them display the same chemical properties. However, aldehydes are more reactive compared to ketones due to the presence of free hydrogen atoms.

Organic compounds that contain a carbon-oxygen double bond is called the carboxyl group, which is one of the essential functional groups in organic chemistry. At the same time, the carbonyl group is also one of the important groups present in the living system compounds.


What are Aldehydes?

Aldehydes are organic compounds that contain the functional group -CHO.

These carbonyl compounds contain the central carbonyl-carbon, which is single bonded to the R group (any of the alkyl group) and a hydrogen atom and doubly bonded to oxygen.

[Image will be Uploaded Soon]

Here, R stands for the aryl or alkyl group.


Preparation of Aldehydes

The acid chlorides are reduced to aldehydes with hydrogen molecules in the palladium catalyst, which is spread on barium sulfate.

[Image will be Uploaded Soon]

This reaction is called Rosenmund reduction, and it is mostly used in the preparation of aromatic aldehydes. But, the same reaction cannot be used for the preparation of formaldehyde and ketones.


Properties of Aldehydes

  • Aldehydes' structure represents an sp2 hybridized central carbon that is connected double to oxygen and has a single bond with hydrogen.

  • Small aldehydes are the one that are quite soluble in water.

  • Acetaldehyde and formaldehyde are great examples of this. Also, industrially, these two aldehydes are quite important.

  • In general, aldehydes tend to undergo either polymerization or oligomerization.

  • The carbonyl center of the aldehyde contains an electron-withdrawing nature. Thus, the aldehyde group is considered somewhat polar.

What are Ketones?

Ketones are organic compounds with the functional group C=O and the structure R-(C=O)-R'.

These are the carbonyl compounds that have carbon-containing substituents on both sides of the double bond of the carbon-oxygen. The ketone group's carbonyl carbon is of sp2 hybridized, and the structure of ketones is a trigonal planar, which is centered around the carbonyl carbon. The bond angles of this structure fall at approximately 120°. Because the carbon-oxygen bond makes the carbonyl group polar (the oxygen is more electron-withdrawing to that of carbon), ketones tend to be electrophilic at the carbon atom and nucleophilic at the oxygen atom.

[Image will be Uploaded Soon]

Industrially, ketones are mass-produced for their use as pharmaceuticals, solvents, and s precursors for polymers. Some of the important ketones are methyl ethyl ketone (also known as butanone), acetone, and cyclohexanone.


Preparation of Ketones

Acid chlorides on reaction with dialkyl cadmium form ketones. Dialkyl cadmium themselves are prepared from the Grignard reagents.

2R-Mg-X + CdCl2 → R2Cd + 2 Mg(X)Cl

2RCOCl + R2Cd → 2R-CO-R + CdCl2

This method is useful in a manner; the mixed ketones are prepared very conveniently.


Properties of Ketones

  • Ketones always are polar in nature because of the presence of a polar carbonyl group. Thus, they have higher boiling points compared to the non-polar compounds.

  • It cannot form alcohols of any intermolecular hydrogen bond-like since no hydrogen is attached to an oxygen atom.

  • Ketones contain the large dipole moments to that of ethers or alcohols because of pi electrons' shifting.

  • Ketones also react with hydrogen cyanide to produce cyanohydrins. Normally, the reaction is carried out in the presence of a base, which acts as a catalyst. The reaction proceeds slowly in the absence of a base.

  • The majority of the ketones form bisulphite addition products when added to sodium bisulfite.

What is Carboxylic Acid?

They are the organic compounds, containing a (C=O)OH group, which is attached to an R group (here, R refers to the molecule's remaining part).

Commonly, the COOH group is called a carboxyl group. Generally, the carboxylic acids can be expressed via the formula R-COOH and have a polar nature. They can also participate in hydrogen bonding due to their hydrogen bond donating nature of the O-H bond and the hydrogen bond accepting nature of the C=O group. Generally, these have higher boiling points compared to water and tend to form stable dimers.

Carboxylic acids play an essential role in producing food additives, pharmaceuticals, polymers, and solvents. Adipic acid, acetic acid, and citric acid are some carboxylic acids that are useful extremely industrially.


Preparation of Carboxylic Acids

Primary alcohols are oxidized readily to the carboxylic acids with the common oxidizing agents such as potassium permanganate in the alkaline media or neutral, acidic, or potassium dichromate chromium trioxide in the acidic media.

RCH2OH → RCOOH

CH3(CH2)8CH2OH → CH3(CH3)3COOH


Properties of Carboxylic Acids

  • Carboxylic acids are polar compounds and can enter extensively into the hydrogen bonding.

  • The aromatic carboxylic acids are practically insoluble in cold water, whereas all the carboxylic acids are soluble in the organic solvents like ether, alcohol, benzene, and more.

  • Carboxylic acids are the most acidic among the organic acids, but they are less acidic than mineral acids, namely sulphuric acid and nitric acid.

FAQ (Frequently Asked Questions)

1. Explain the Uses of Aldehydes and Ketones?

Let us look at the important uses of both aldehydes and ketones individually as follows.


Uses of Aldehydes

  • Formaldehyde can be used as a preservative for biological specimens and as a disinfectant.

  • Aldehyde is used in mirrors silvering.

  • Formaldehyde is also used for the production of a variety of resins and plastic.

  • Benzaldehyde is used in the dye industry and perfumery.

Uses of Ketones

  • Propanone is used in the preparation of polymers as an example, perspex.

  • Ketones are used as a starting material and as solvents for the synthesis of many organic compounds.

  • Ethyl methyl ketone and acetone are primarily used as industrial solvents.

2. Explain the Nomenclature of Carboxylic Acids?

Carboxylic acids are organic compounds, containing a (C=O)OH group attached to an R group.

  • Carboxylic acids can be named by adding a suffix, "-oic acid" to their parent chain. For example, C₃H₇COOH is known as butanoic acid.

  • Even if any other substituents present, the carboxylic acid is considered at the parent chain's first position, which is seen in the name for 3-Chloropropanoic acid.

  • The COOH group is also called "carboxy" and can be used as a substituent in the name of the parent structure. For example, commonly, a 2-Furoic acid is called 2-carboxy furan.