Question

Give the structure and name of the following substance: Mesitylene

Answer 1

Hint: Before answering this question, we should first know a bit about mesitylene. A derivative of benzene which has three methyl substituents that are symmetrically positioned around the ring is known as Mesitylene. It is also called 1,3,4-trimethylbenzene.

Complete answer:
There are two isomers of Mesitylene; they are hemimellitene and pseudocumene. They have the formula.
Mesitylene has properties like it is a colorless liquid that has a sweet odor. Coal tar has mesitylene as one of its components. It is used as a precursor for many chemicals. Mesityl groups can be written as (mes).

It can be prepared-
By equilibration of Xylene or can be done by simple methyl alkylation of it with the help of a solid acid catalyst.
$2{{C}_{6}}{{H}_{3}}{{(C{{H}_{3}})}_{2}}\rightleftharpoons \,{{C}_{6}}{{H}_{3}}{{(C{{H}_{3}})}_{3}}+\,{{C}_{6}}{{H}_{5}}C{{H}_{3}}$
${{C}_{6}}{{H}_{4}}{{(C{{H}_{3}})}_{2}}+\,C{{H}_{3}}OH\to {{C}_{6}}{{H}_{3}}{{(C{{H}_{3}})}_{3}}$
With the help of aldol condensation, Trimerization of acetone is done which is catalyzed and dehydrated with the help of sulphuric acid gives a mixture of 1,3,5- and 1,2,4- trimethylbenzene.
The reaction of mesitylene with nitric acid gives trimesic acid, Its chemical formula is ${{C}_{6}}{{H}_{3}}{{(COOH)}_{3}}$. A mild oxidizing agent like manganese dioxide is used to form 3,5-dimethyl benzaldehyde. Mesitol is formed when mesitylene is oxidized by trifluoroacetic acid.

Note:
Mesitylene is a VOC- Volatile organic compound. It plays a major role in atmospheric chemistry It can be used as a specialty solvent. In organometallic chemistry it behaves like a ligand, for example- the organo molybdenum complex which can be prepared from molybdenum hexacarbonyl contains Mesitylene. Due to its solvent properties, It helps to develop photo patternable silicones in the electronic industry.