Cis 1 ethyl 3 methylcyclopentane, a versatile organic compound, stands out with its unique physical and chemical properties, diverse synthesis methods, and wide-ranging applications. This comprehensive overview delves into the intricacies of this fascinating molecule, exploring its molecular structure, synthesis pathways, practical uses, and safety considerations.
Physical and Chemical Properties
Cis 1 ethyl 3 methylcyclopentane, also known as 1-ethyl-3-methylcyclopentane, is an organic compound with the molecular formula C8H16. It is a colorless liquid with a characteristic odor.The physical and chemical properties of cis 1 ethyl 3 methylcyclopentane are as follows:
Molecular Formula and Molecular Weight
The molecular formula of cis 1 ethyl 3 methylcyclopentane is C8H16. Its molecular weight is 112.21 g/mol.
Boiling Point
The boiling point of cis 1 ethyl 3 methylcyclopentane is 131.7 °C (269.1 °F).
Melting Point
The melting point of cis 1 ethyl 3 methylcyclopentane is
126.5 °C (-195.7 °F).
Density
The density of cis 1 ethyl 3 methylcyclopentane is 0.79 g/cm3 at 25 °C (77 °F).
Solubility
Cis 1 ethyl 3 methylcyclopentane is insoluble in water. It is soluble in organic solvents such as ethanol, ether, and benzene.
Refractive Index
The refractive index of cis 1 ethyl 3 methylcyclopentane is 1.434 at 25 °C (77 °F).The physical and chemical properties of cis 1 ethyl 3 methylcyclopentane are influenced by its molecular structure. The cyclopentane ring is a rigid structure that restricts the rotation of the ethyl and methyl groups.
This results in two isomers of cis 1 ethyl 3 methylcyclopentane: the cis isomer and the trans isomer. The cis isomer is the more stable isomer and has a lower boiling point than the trans isomer.
Synthesis Methods
Cis 1-ethyl-3-methylcyclopentane can be synthesized through various methods, each offering unique advantages and disadvantages. These methods include:
Hydrogenation of Cyclopentadiene
This method involves the hydrogenation of cyclopentadiene in the presence of a catalyst, such as palladium or nickel. The reaction proceeds via a stepwise addition of hydrogen atoms to the double bond of cyclopentadiene, resulting in the formation of cis 1-ethyl-3-methylcyclopentane.
- Advantages:Simple and straightforward procedure, high yield.
- Disadvantages:Requires specialized equipment for hydrogenation, potential for side reactions.
Diels-Alder Reaction
This method utilizes a Diels-Alder reaction between cyclopentadiene and an appropriate dienophile, such as ethyl vinyl ether. The reaction proceeds through a concerted cycloaddition mechanism, leading to the formation of a cyclohexene intermediate. Subsequent hydrogenation of the cyclohexene intermediate affords cis 1-ethyl-3-methylcyclopentane.
- Advantages:Versatile method that allows for the incorporation of various substituents.
- Disadvantages:Can be sensitive to reaction conditions, may require multiple steps.
Ring-Closing Metathesis
This method involves the ring-closing metathesis of a suitable diene precursor, such as 1,5-hexadiene. The reaction is catalyzed by a Grubbs or Schrock catalyst and proceeds via a stepwise metathesis mechanism, leading to the formation of cis 1-ethyl-3-methylcyclopentane.
- Advantages:Efficient and atom-economical, mild reaction conditions.
- Disadvantages:Requires specialized catalysts, may be sensitive to functional groups.
Applications: Cis 1 Ethyl 3 Methylcyclopentane
Cis 1 ethyl 3 methylcyclopentane finds diverse applications in various industries. Its unique properties make it a valuable solvent, intermediate in chemical synthesis, and fuel additive.
As a solvent, cis 1 ethyl 3 methylcyclopentane exhibits excellent solvating power for nonpolar and slightly polar compounds. It is commonly used in the paint and coatings industry as a diluent for paints, lacquers, and varnishes. Additionally, it is employed in the extraction of essential oils from plant materials.
Intermediate in Chemical Synthesis
Cis 1 ethyl 3 methylcyclopentane serves as an important intermediate in the synthesis of various chemicals. It is a versatile building block for the production of pharmaceuticals, fragrances, and flavors. Its reactivity allows for the introduction of different functional groups, enabling the synthesis of complex organic molecules.
Fuel Additive
In the fuel industry, cis 1 ethyl 3 methylcyclopentane is utilized as a fuel additive to improve the octane rating of gasoline. By increasing the octane number, it reduces engine knocking and enhances fuel efficiency. Furthermore, it possesses anti-knock properties, making it a valuable component in high-performance fuels.
However, the use of cis 1 ethyl 3 methylcyclopentane also has certain limitations. Its high volatility can lead to evaporation losses during storage and handling. Additionally, its reactivity may require specific storage conditions to prevent unwanted reactions.
Safety and Handling
Cis 1 ethyl 3 methylcyclopentane is a flammable liquid that can pose potential hazards if not handled and stored properly.
Flammability
Cis 1 ethyl 3 methylcyclopentane has a flash point of26°C (-15°F) and an autoignition temperature of 363°C (685°F). It is therefore highly flammable and can easily ignite in the presence of an ignition source, such as a spark or flame.
Appropriate precautions should be taken to prevent fires and explosions.
Toxicity, Cis 1 ethyl 3 methylcyclopentane
Cis 1 ethyl 3 methylcyclopentane is considered moderately toxic. Inhalation of its vapors can cause irritation to the respiratory tract, while skin contact can lead to dermatitis. Ingestion of the liquid can cause gastrointestinal distress. Adequate ventilation and personal protective equipment (PPE) should be used to minimize exposure.
Environmental Impact
Cis 1 ethyl 3 methylcyclopentane is harmful to aquatic organisms and can contaminate water sources. It is important to dispose of waste and spills in accordance with local environmental regulations.
Personal Protective Equipment (PPE) and Safety Precautions
When working with cis 1 ethyl 3 methylcyclopentane, it is essential to wear appropriate PPE, including:
- Respirator or face mask to prevent inhalation of vapors
- Gloves made of chemically resistant material to protect skin from contact
- Protective clothing to prevent skin exposure
- Safety goggles or face shield to protect eyes from splashes
Other safety precautions include:
- Store cis 1 ethyl 3 methylcyclopentane in a cool, well-ventilated area away from heat and ignition sources
- Keep containers tightly closed when not in use
- Avoid contact with skin, eyes, and clothing
- Handle spills promptly and dispose of waste properly
- Follow all applicable safety regulations and guidelines
Detailed FAQs
What is the molecular formula of cis 1 ethyl 3 methylcyclopentane?
C8H16
What is the boiling point of cis 1 ethyl 3 methylcyclopentane?
132-133 °C
What are the common applications of cis 1 ethyl 3 methylcyclopentane?
Solvent, intermediate in chemical synthesis, fuel additive
