Cis 1 isopropyl 4 methylcyclohexane, an organic compound with a captivating molecular structure, takes center stage in this discourse. This comprehensive overview delves into the intricacies of its nomenclature, physical and chemical properties, synthesis methods, and diverse applications, providing a thorough understanding of this versatile substance.
Prepare to embark on a journey of scientific exploration as we unravel the secrets of cis 1 isopropyl 4 methylcyclohexane, deciphering its IUPAC nomenclature, examining its physical attributes, and uncovering its reactivity toward electrophiles, nucleophiles, and free radicals. We will delve into the methods employed for its synthesis, weighing the advantages and disadvantages of each approach, and finally, we will explore the practical applications of this compound across various industries.
Nomenclature
The IUPAC nomenclature for cis 1 isopropyl 4 methylcyclohexane is as follows:
1-isopropyl-4-methylcyclohexane
The structural formula of the compound is:
CH3
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/ \
CH3-C-CH2-CH2-CH2-CH-CH3
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\ /
CH3
Stereochemistry
The stereochemistry of the compound is cis. This means that the two methyl groups are on the same side of the cyclohexane ring.
Physical Properties
Cis 1 isopropyl 4 methylcyclohexane possesses distinct physical properties that are closely intertwined with its molecular structure. Understanding these properties is crucial for comprehending the compound’s behavior and applications.
The physical properties of cis 1 isopropyl 4 methylcyclohexane include:
Boiling Point
The boiling point of cis 1 isopropyl 4 methylcyclohexane is 162.5 °C. This relatively high boiling point is attributed to the presence of the bulky isopropyl and methyl groups, which hinder intermolecular interactions and increase the energy required for the compound to vaporize.
Melting Point
Cis 1 isopropyl 4 methylcyclohexane has a melting point of -60.3 °C. The presence of the isopropyl and methyl groups disrupts the close packing of the molecules, leading to a lower melting point compared to cyclohexane.
Density
The density of cis 1 isopropyl 4 methylcyclohexane is 0.786 g/cm 3at 25 °C. The bulky substituents increase the molecular volume, resulting in a lower density than cyclohexane.
Refractive Index
The refractive index of cis 1 isopropyl 4 methylcyclohexane is 1.424 at 25 °C. The presence of the isopropyl and methyl groups alters the electron distribution in the molecule, leading to a higher refractive index than cyclohexane.
Chemical Properties
Cis 1 isopropyl 4 methylcyclohexane exhibits characteristic chemical reactivity due to the presence of its cyclohexane ring and alkyl substituents.
The cyclohexane ring undergoes electrophilic addition reactions, where electrophiles add across the double bond. For example, it reacts with hydrogen bromide (HBr) to form 1-bromo-1-isopropyl-4-methylcyclohexane.
Reactions with Nucleophiles
The alkyl substituents, isopropyl and methyl groups, can undergo nucleophilic substitution reactions. For instance, the isopropyl group can react with a strong nucleophile like sodium hydroxide (NaOH) to form the corresponding alcohol, 1-isopropyl-4-methylcyclohexanol.
Reactions with Free Radicals
Cis 1 isopropyl 4 methylcyclohexane also participates in free radical reactions. Free radicals are highly reactive species with unpaired electrons. In the presence of a free radical initiator, such as benzoyl peroxide, the cyclohexane ring can undergo radical addition reactions, leading to the formation of various products, including alkyl radicals and cyclohexyl radicals.
Synthesis: Cis 1 Isopropyl 4 Methylcyclohexane
Cis 1 isopropyl 4 methylcyclohexane can be synthesized through various methods, each with its own advantages and disadvantages. The choice of method depends on factors such as availability of starting materials, desired purity, and scale of production.
One common method for synthesizing cis 1 isopropyl 4 methylcyclohexane is the catalytic hydrogenation of 1-isopropyl-4-methylbenzene. This reaction involves the addition of hydrogen gas to the double bond of the benzene ring in the presence of a catalyst, such as palladium on carbon.
The reaction proceeds with high selectivity for the cis isomer due to the steric hindrance provided by the isopropyl group.
Advantages:
- High yield of the desired product
- Relatively mild reaction conditions
- Widely available starting materials
Disadvantages:
- Requires the use of a catalyst, which can be expensive
- Can be sensitive to reaction conditions, such as temperature and pressure
- May require multiple reaction steps to achieve the desired purity
Another method for synthesizing cis 1 isopropyl 4 methylcyclohexane is the Diels-Alder reaction between isoprene and methyl acrylate. This reaction involves the cycloaddition of the isoprene diene to the methyl acrylate dienophile, forming a six-membered ring. The reaction proceeds with high regio- and stereoselectivity for the cis isomer due to the steric hindrance provided by the methyl group on the dienophile.
Advantages:
- High yield of the desired product
- Relatively mild reaction conditions
- Widely available starting materials
Disadvantages:
- Requires the use of a Lewis acid catalyst, which can be corrosive
- Can be sensitive to reaction conditions, such as temperature and solvent
- May require multiple reaction steps to achieve the desired purity
The choice of synthesis method for cis 1 isopropyl 4 methylcyclohexane depends on the specific requirements of the application. For large-scale production, the catalytic hydrogenation method may be preferred due to its high yield and relatively mild reaction conditions. For smaller-scale production or for applications requiring high purity, the Diels-Alder reaction may be preferred.
Applications
Cis 1 isopropyl 4 methylcyclohexane finds diverse applications in various industries, primarily as a solvent, intermediate, or additive.
Its unique properties make it a valuable component in the manufacturing of a wide range of products and processes.
Solvent
Cis 1 isopropyl 4 methylcyclohexane’s non-polar nature and high solvency power make it an effective solvent for various organic compounds, including oils, greases, and waxes.
It is commonly used in the paint and coating industry as a solvent for thinning paints and cleaning equipment.
Intermediate
Cis 1 isopropyl 4 methylcyclohexane serves as an intermediate in the synthesis of more complex organic compounds.
It is a key starting material for the production of fragrances, pharmaceuticals, and other specialty chemicals.
Additive, Cis 1 isopropyl 4 methylcyclohexane
The addition of cis 1 isopropyl 4 methylcyclohexane to certain products enhances their properties.
For instance, it is used as an additive in fuels to improve their combustion efficiency and reduce emissions.
FAQ Explained
What is the IUPAC nomenclature of cis 1 isopropyl 4 methylcyclohexane?
Cis 1 isopropyl 4 methylcyclohexane, according to IUPAC nomenclature, is 1-isopropyl-4-methylcyclohexane.
What is the boiling point of cis 1 isopropyl 4 methylcyclohexane?
Cis 1 isopropyl 4 methylcyclohexane has a boiling point of 162-164 °C.
How is cis 1 isopropyl 4 methylcyclohexane synthesized?
Cis 1 isopropyl 4 methylcyclohexane can be synthesized through various methods, including the Diels-Alder reaction, hydrogenation of 1-isopropyl-4-methylbenzene, and isomerization of trans 1-isopropyl-4-methylcyclohexane.
What are the applications of cis 1 isopropyl 4 methylcyclohexane?
Cis 1 isopropyl 4 methylcyclohexane finds applications as a solvent, intermediate, and additive in various industries, including pharmaceuticals, fragrances, and petroleum refining.
