For each of the following reactions, draw the major elimination product; if the product can exist as stereoisomers, indicate which stereoisomer is obtained in greater yield.
c. trans-1-chloro-2-methylcyclohexane+high concentration of CH3O−
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1
Identify the type of elimination reaction: Since a strong base (CH3O−) is used, this is likely an E2 elimination reaction.
Determine the structure of the starting material: trans-1-chloro-2-methylcyclohexane is a cyclohexane ring with a chlorine atom and a methyl group on adjacent carbons, in a trans configuration.
Consider the stereochemistry: In an E2 reaction, the leaving group (Cl) and the hydrogen to be removed must be antiperiplanar. Identify the hydrogen atom on the adjacent carbon that is antiperiplanar to the chlorine.
Draw the transition state: Show the base (CH3O−) abstracting the antiperiplanar hydrogen, the formation of a double bond, and the departure of the chloride ion.
Determine the major product: The major product will be the more stable alkene, which is typically the one with the more substituted double bond (Zaitsev's rule). Consider the stereochemistry of the resulting alkene.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Elimination Reactions
Elimination reactions involve the removal of atoms or groups from a molecule, resulting in the formation of a double bond. In organic chemistry, the most common types are E1 and E2 mechanisms, which differ in their reaction pathways. Understanding the conditions that favor each mechanism is crucial for predicting the major product of the reaction.
Stereochemistry is the study of the spatial arrangement of atoms in molecules and how this affects their chemical behavior. In elimination reactions, the stereochemistry of the starting material can influence the stereochemical outcome of the product. Recognizing the potential for stereoisomers, such as cis and trans configurations, is essential for determining which isomer is formed in greater yield.
Regioselectivity refers to the preference of a chemical reaction to yield one structural isomer over others when multiple products are possible. In elimination reactions, the stability of the resulting alkene can dictate which product is favored. For cyclohexane derivatives, the formation of more substituted alkenes is often favored due to greater stability, which is a key consideration in predicting the major elimination product.