Cis 1 chloro 3 methylcyclohexane, a versatile and intriguing compound, takes center stage in this captivating exploration. Its unique structure and diverse applications make it a fascinating subject for scientific inquiry and practical use. Prepare to delve into the intricacies of this remarkable molecule as we unravel its properties, reactivity, and significance.
Cis 1 chloro 3 methylcyclohexane stands out as a versatile and widely applicable compound. Its unique structural features and chemical properties make it a valuable tool in various scientific disciplines and industrial processes. Join us as we delve deeper into its fascinating world, exploring its synthesis, reactivity, applications, and more.
Nomenclature and Structural Properties
Cis 1 chloro 3 methylcyclohexane is an organic compound with the molecular formula C 7H 13Cl. It is a cycloalkane with a chlorine atom and a methyl group attached to the same carbon atom. The IUPAC name of this compound is 1-chloro-3-methylcyclohexane.
The structural formula of cis 1 chloro 3 methylcyclohexane is:
Cis 1 chloro 3 methylcyclohexane has a molecular weight of 120.62 g/mol and is a colorless liquid at room temperature.
Synthesis and Reactivity: Cis 1 Chloro 3 Methylcyclohexane
Cis 1-chloro-3-methylcyclohexane can be synthesized through various methods, including:
- Hydrochlorination of 1-methylcyclohexene:This involves the addition of hydrogen chloride (HCl) to 1-methylcyclohexene in the presence of a Lewis acid catalyst, such as aluminum chloride (AlCl3), to form the desired product.
- Electrophilic addition of chlorine to 1-methylcyclohexene:Chlorine gas (Cl2) can be added to 1-methylcyclohexene in the presence of a radical initiator, such as benzoyl peroxide, to form cis 1-chloro-3-methylcyclohexane.
- Substitution reaction of 1-methylcyclohexanol with hydrogen chloride:1-Methylcyclohexanol can be reacted with hydrogen chloride in the presence of a strong acid catalyst, such as sulfuric acid (H2SO4), to form cis 1-chloro-3-methylcyclohexane.
Cis 1-chloro-3-methylcyclohexane is a reactive compound that can undergo various reactions, including:
- Nucleophilic substitution:The chlorine atom in cis 1-chloro-3-methylcyclohexane can be displaced by a nucleophile, such as hydroxide ion (OH-) or ammonia (NH3), to form the corresponding alcohol or amine.
- Electrophilic addition:Cis 1-chloro-3-methylcyclohexane can undergo electrophilic addition reactions with electrophiles, such as hydrogen bromide (HBr) or sulfuric acid (H2SO4), to form the corresponding alkyl halide or sulfonate ester.
- Elimination reactions:Cis 1-chloro-3-methylcyclohexane can undergo elimination reactions, such as dehydrohalogenation, to form 1-methylcyclohexene.
Here are some specific examples of reactions that illustrate the reactivity of cis 1-chloro-3-methylcyclohexane:
- Nucleophilic substitution:Cis 1-chloro-3-methylcyclohexane can be reacted with sodium hydroxide (NaOH) in water to form 1-methylcyclohexanol.
- Electrophilic addition:Cis 1-chloro-3-methylcyclohexane can be reacted with hydrogen bromide (HBr) in the presence of a radical initiator to form 1-bromo-3-methylcyclohexane.
- Elimination reactions:Cis 1-chloro-3-methylcyclohexane can be reacted with potassium tert-butoxide (t-BuOK) in dimethylformamide (DMF) to form 1-methylcyclohexene.
Applications and Uses
Cis 1 chloro 3 methylcyclohexane finds applications in various industries, including chemical manufacturing, pharmaceuticals, and personal care products.
In Organic Synthesis, Cis 1 chloro 3 methylcyclohexane
Cis 1 chloro 3 methylcyclohexane serves as an essential intermediate in the synthesis of various organic compounds. Its electrophilic chlorine atom undergoes nucleophilic substitution reactions, allowing for the introduction of different functional groups.
For example, it can be reacted with alcohols to form ethers or with amines to produce tertiary amines. This versatility makes it a valuable building block for complex organic molecules.
In Pharmaceutical Formulations
Cis 1 chloro 3 methylcyclohexane has limited direct pharmaceutical applications but is used as an intermediate in the synthesis of active pharmaceutical ingredients (APIs).
APIs are the biologically active components of drugs that interact with specific targets in the body. Cis 1 chloro 3 methylcyclohexane can contribute to the structural framework or functional groups of APIs, enhancing their therapeutic properties.
Environmental and Health Implications
The environmental and health implications of cis 1 chloro 3 methylcyclohexane must be considered during its use and disposal.
As a chlorinated hydrocarbon, it has the potential to persist in the environment and accumulate in living organisms. Its release into the environment should be minimized to prevent adverse effects on ecosystems and human health.
Exposure to cis 1 chloro 3 methylcyclohexane can cause skin irritation, eye damage, and respiratory problems. Proper handling and safety precautions are necessary to mitigate these risks.
Spectroscopy and Characterization
Spectroscopic techniques play a crucial role in identifying and characterizing organic compounds like cis 1 chloro 3 methylcyclohexane. These techniques provide valuable information about the molecular structure, functional groups, and bonding within the molecule.
Infrared (IR) Spectroscopy
The IR spectrum of cis 1 chloro 3 methylcyclohexane exhibits characteristic peaks that correspond to specific functional groups and molecular vibrations. The C-H stretching vibrations of the cyclohexane ring appear in the region of 2850-2950 cm -1. The C-Cl stretching vibration gives rise to a strong peak around 700-750 cm -1. Additionally, the presence of the methyl group is indicated by a peak around 1380 cm -1corresponding to the C-H bending vibration.
Nuclear Magnetic Resonance (NMR) Spectroscopy
1H NMR spectroscopy provides detailed information about the hydrogen atoms in the molecule. The spectrum of cis 1 chloro 3 methylcyclohexane shows distinct peaks corresponding to the different types of hydrogen atoms. The protons on the cyclohexane ring give rise to multiplets in the region of 1.0-2.0
ppm. The methyl protons appear as a singlet around 0.9 ppm. The proton adjacent to the chlorine atom resonates at a slightly higher field, typically around 3.5-4.0 ppm.
Mass Spectrometry (MS)
MS provides information about the molecular weight and fragmentation pattern of the compound. The mass spectrum of cis 1 chloro 3 methylcyclohexane shows a molecular ion peak at m/z = 120.5, corresponding to the molecular weight of the compound. Fragmentation of the molecule results in characteristic peaks that can be used to deduce the structure.
Related Compounds and Derivatives
Cis 1 chloro 3 methylcyclohexane shares structural and chemical similarities with other cyclohexane derivatives, particularly those containing halogen and alkyl substituents. The presence of the chlorine and methyl groups significantly influences its properties, leading to unique applications and reactivity patterns.
Structural Similarities
Cis 1 chloro 3 methylcyclohexane belongs to the class of cyclohexane derivatives, characterized by a six-membered carbon ring with various substituents. The presence of a chlorine atom and a methyl group distinguishes it from other cyclohexane derivatives, such as cyclohexane, methylcyclohexane, and chlorocyclohexane.
Chemical Similarities
The chlorine and methyl groups in cis 1 chloro 3 methylcyclohexane influence its chemical reactivity. The chlorine atom is electronegative, withdrawing electrons from the carbon-chlorine bond, making the carbon atom electrophilic. This electrophilicity enhances the reactivity of the compound towards nucleophilic substitution reactions.
Derivatives and Applications
Cis 1 chloro 3 methylcyclohexane can undergo various reactions to form derivatives with diverse applications. For example, reaction with alcohols in the presence of a base yields ethers, which are used as solvents and fragrances. Reaction with amines produces tertiary amines, which are employed as catalysts and surfactants.
Frequently Asked Questions
What is the IUPAC name of cis 1 chloro 3 methylcyclohexane?
1-Chloro-3-methylcyclohexane
How is cis 1 chloro 3 methylcyclohexane commonly synthesized?
Via the hydrochlorination of 3-methylcyclohexene
What are some applications of cis 1 chloro 3 methylcyclohexane?
As an intermediate in the synthesis of other organic compounds, in the production of pharmaceuticals, and as a solvent
