Question Details

The product obtained on heating 2-Bromopentane with potassium ethoxide in ethanol is

Options

A

1-pentene

B

2-cis-pentene

C

trans-2-pentene

D

2-ethoxy pentane

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 (C2H5O-K+) in ethanol (C2H5OH), 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:
C|HH2-C|CH3H-C|BrH-C|HH2-CH3
Here, carbon-2 (C2) is the alpha-carbon bearing the bromine group. The adjacent carbons are carbon-1 (C1) and carbon-3 (C3), which act as beta-carbons. Dehydrohalogenation can proceed in two ways depending on which beta-hydrogen is abstracted:

1. Abstraction of hydrogen from C1:
Elimination yields 1-pentene (a monosubstituted alkene):
CH3-CH2-CH2-CH=CH2

2. Abstraction of hydrogen from C3:
Elimination yields 2-pentene (a disubstituted alkene):
CH3-CH2-CH=CH-CH3

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 (-CH3) and ethyl (-C2H5) groups on opposite sides of the double bond. Therefore, trans-2-pentene is formed preferentially as the major product.

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