Discovery of Benzaldehyde

Mar. 02, 2022

Benzaldehyde occurs in a variety of natural items such as almonds or cherries. The isolation of benzaldehyde from bitter almonds goes back to 1803 and is credited to a French pharmacist Martrès. It was later studied by the German chemists Justus von Liebig and Friedrich Wöhler, who first synthesized it successfully in the 1830s. This led to the establishment of the structural theory of organic chemistry.


What are Benzaldehyde and its Properties?

The simplest aromatic aldehyde, which consists of a benzene ring with a formyl (-CHO) substituent, is termed benzaldehyde (C6H5CHO). This organic chemical compound has several industrial applications, including dyes, flavoring agents, perfumes, and the manufacturing of several other organic compounds. Found naturally in glycoside amygdalin, this aromatic aldehyde is known for its distinct, almond oil-like taste and odor.


Benzaldehyde

 Benzaldehyde     

The molecular formula of this compound is C7H6O, and its IUPAC name is benzenecarbaldehyde. It is also referred to as several other names, including benzenedicarboxaldehyde, phenyl methanol, or benzoic aldehyde. It appears as a clear liquid with a smell like almonds. It is miscible with volatile oils, ether, and alcohol. It is denser than and thus only slightly soluble in water and has a solubility of 3 g/L.


Structure of Benzaldehyde

The structure of benzaldehyde consists of a benzene ring substituted with an aldehyde unit. This formyl unit has one atom of carbon, hydrogen, and oxygen. The number of benzaldehyde sigma bonds is 14, formed by the head-to-head overlapping of atomic orbitals.

 

Preparation of Benzaldehyde

This simple aromatic aldehyde can be derived from a variety of natural sources.

It can also be manufactured synthetically from toluene which is found in crude oil, for industrial usage. This is done by a series of chemical reactions in which toluene reacts with chlorine. This leads to the formation of benzyl chloride, which can be further treated with water to form benzaldehyde.

 

Benzaldehyde can also be synthesized by the oxidation of benzyl alcohol and carbonylation of benzene. Alkaline hydrolysis of benzal chloride also yields benzaldehyde.


What are the different types of chemical reactions that benzaldehyde can undergo?

Benzaldehyde undergoes all the chemical reactions that aromatic aldehydes undergo, such as electrophilic substitution and the Cannizzaro reaction.

It can also undergo an oxidation reaction to yield benzoic acid. Benzaldehyde can undergo additional reactions with hydrocyanic acid and sodium bisulfite. It reacts with alcoholic potassium cyanide to form benzoin. The hydrogenation of benzaldehyde produced benzyl alcohol.


Benzaldehyde CAS: 100-52-7

 Benzaldehyde CAS: 100-52-7         

The reaction between benzaldehyde, anhydrous sodium acetate, and acetic anhydride yields a compound called cinnamic acid. The reaction of benzaldehyde with potassium hydroxide produces an oxidation and reduction reaction known as the Cannizzaro reaction. This reaction yields products including potassium benzoate and benzyl alcohol.

 

Storage of Benzaldehyde

Benzaldehyde is usually stable but should be stored as per the recommended conditions. It should be properly stored in a sealed container away from heat and light. It should be kept away from reactive substances such as acids and reducing agents. It is also recommended to store this compound under nitrogen.


What are the different types of chemical reactions that benzaldehyde can undergo?

Benzaldehyde undergoes all the chemical reactions that aromatic aldehydes undergo, such as electrophilic substitution and the Cannizzaro reaction.

It can also undergo an oxidation reaction to yield benzoic acid. Benzaldehyde can undergo additional reactions with hydrocyanic acid and sodium bisulfite. It reacts with alcoholic potassium cyanide to form benzoin. The hydrogenation of benzaldehyde produced benzyl alcohol.


The reaction between benzaldehyde, anhydrous sodium acetate, and acetic anhydride yields a compound called cinnamic acid. The reaction of benzaldehyde with potassium hydroxide produces an oxidation and reduction reaction known as the Cannizzaro reaction. This reaction yields products including potassium benzoate and benzyl alcohol.


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