Cis 1 chloro 3 methylcyclohexane, an intriguing organic compound, invites exploration into its remarkable properties, versatile synthesis methods, diverse reactions, and practical applications. Delve into this comprehensive guide to unravel the complexities of this fascinating chemical entity.
Unveiling the molecular structure of cis 1 chloro 3 methylcyclohexane reveals a six-membered cyclohexane ring adorned with a chlorine atom and a methyl group. This unique arrangement imparts distinct physical and chemical characteristics that shape its behavior and reactivity.
Properties of cis-1-Chloro-3-methylcyclohexane
Cis-1-chloro-3-methylcyclohexane is a colorless liquid with a strong, pungent odor. It is slightly soluble in water and has a boiling point of 162-164 °C and a melting point of -59.3 °C. The molecular structure of cis-1-chloro-3-methylcyclohexane is a six-membered ring with a chlorine atom and a methyl group attached to the same carbon atom.
The bond lengths and angles in the molecule are as follows:
- C-Cl bond length: 1.76 Å
- C-C bond lengths: 1.54 Å
- C-H bond lengths: 1.09 Å
- C-C-C bond angles: 109.5°
- C-C-Cl bond angle: 111.0°
Synthesis of cis-1-Chloro-3-methylcyclohexane
Cis-1-chloro-3-methylcyclohexane can be synthesized by several methods, including:
- Hydrochlorination of 1-methylcyclohexene:This method involves the addition of hydrogen chloride to 1-methylcyclohexene in the presence of a Lewis acid catalyst, such as aluminum chloride. The reaction proceeds via a carbocation intermediate, which is then attacked by the chloride ion to form the product.
- Addition of chlorine to 1-methylcyclohexene:This method involves the addition of chlorine gas to 1-methylcyclohexene in the presence of a radical initiator, such as benzoyl peroxide. The reaction proceeds via a free radical mechanism, which results in the formation of a mixture of cis- and trans-1-chloro-3-methylcyclohexane.
- Dehydrochlorination of 1-chloro-2-methylcyclohexane:This method involves the removal of hydrogen chloride from 1-chloro-2-methylcyclohexane in the presence of a base, such as sodium hydroxide. The reaction proceeds via an E2 elimination mechanism, which results in the formation of cis-1-chloro-3-methylcyclohexane.
It is important to note that the synthesis of cis-1-chloro-3-methylcyclohexane should be carried out in a well-ventilated area and with appropriate safety precautions, as the chemicals involved are toxic and corrosive.
Reactions of cis-1-Chloro-3-methylcyclohexane, Cis 1 chloro 3 methylcyclohexane
Cis-1-chloro-3-methylcyclohexane can undergo a variety of reactions, including:
- Nucleophilic substitution:This reaction involves the replacement of the chlorine atom by a nucleophile, such as hydroxide ion or ammonia. The reaction proceeds via an SN2 mechanism, which results in the formation of a substituted cyclohexane derivative.
- Elimination:This reaction involves the removal of hydrogen chloride from cis-1-chloro-3-methylcyclohexane in the presence of a base, such as sodium hydroxide. The reaction proceeds via an E2 elimination mechanism, which results in the formation of 1-methylcyclohexene.
- Addition:This reaction involves the addition of a nucleophile, such as water or alcohol, to the double bond of 1-methylcyclohexene. The reaction proceeds via a Markovnikov addition mechanism, which results in the formation of a substituted cyclohexane derivative.
The regio- and stereoselectivity of these reactions depend on the reaction conditions and the nature of the nucleophile.
Applications of cis-1-Chloro-3-methylcyclohexane
Cis-1-chloro-3-methylcyclohexane is used in a variety of industrial and laboratory applications, including:
- Solvent:Cis-1-chloro-3-methylcyclohexane is used as a solvent for a variety of organic compounds, including oils, fats, and waxes.
- Intermediate:Cis-1-chloro-3-methylcyclohexane is used as an intermediate in the synthesis of a variety of other organic compounds, including pharmaceuticals and fragrances.
- Laboratory reagent:Cis-1-chloro-3-methylcyclohexane is used as a laboratory reagent in a variety of reactions, including nucleophilic substitution and elimination reactions.
Safety and Handling of cis-1-Chloro-3-methylcyclohexane
Cis-1-chloro-3-methylcyclohexane is a toxic and corrosive chemical. It is important to take appropriate safety precautions when handling this chemical, including:
- Wear gloves, eye protection, and a lab coat when handling cis-1-chloro-3-methylcyclohexane.
- Work in a well-ventilated area.
- Avoid contact with skin and eyes.
- In case of contact with skin or eyes, flush with plenty of water and seek medical attention.
- Dispose of cis-1-chloro-3-methylcyclohexane properly according to local regulations.
Q&A: Cis 1 Chloro 3 Methylcyclohexane
What is the molecular formula of cis 1 chloro 3 methylcyclohexane?
C6H11Cl
What is the boiling point of cis 1 chloro 3 methylcyclohexane?
142-144 °C
What is the density of cis 1 chloro 3 methylcyclohexane?
0.97 g/mL
