The product obtained on heating 2-Bromopentane with potassium ethoxide in ethanol is
Correct Answer :
trans-2-pentene
Solution :
The correct option is trans-2-pentene.
Reaction Mechanism and Explanation:
When 2-bromopentane is heated with a strong base like potassium ethoxide () in ethanol (), it undergoes an elimination reaction, specifically a dehydrohalogenation via the E2 mechanism.
In this E2 elimination, a hydrogen atom from a beta-carbon (adjacent to the carbon containing the bromine atom) and the bromine atom are removed to form a double bond. Let's analyze the structure of 2-bromopentane:
Here, carbon-2 () is the alpha-carbon bearing the bromine group. The adjacent carbons are carbon-1 () and carbon-3 (), which act as beta-carbons. Dehydrohalogenation can proceed in two ways depending on which beta-hydrogen is abstracted:
1. Abstraction of hydrogen from :
Elimination yields 1-pentene (a monosubstituted alkene):
2. Abstraction of hydrogen from :
Elimination yields 2-pentene (a disubstituted alkene):
According to Saytzeff's Rule (or Zaitsev's Rule), the major product of an elimination reaction is the more highly substituted, and therefore more stable, alkene. A disubstituted alkene (2-pentene) is more thermodynamically stable than a monosubstituted alkene (1-pentene). Hence, 2-pentene is the major product.
Furthermore, 2-pentene exists as diastereomers: cis-2-pentene and trans-2-pentene. The trans-isomer is more stable than the cis-isomer because it has less steric hindrance between the bulkier methyl (-) and ethyl (-) groups on opposite sides of the double bond. Therefore, trans-2-pentene is formed preferentially as the major product.
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