Question Details

The major product formed in dehydrohalogenation reaction of 2-Bromo pentane is Pent-2-ene. This product formation is based on ?

Options

A

Saytzeff’s Rule

B

Hund’s Rule

C

Hofmann Rule

D

Huckel’s Rule

Correct Answer :

Saytzeff’s Rule

Solution :

The correct option is Saytzeff’s Rule.

Step-by-Step Explanation:

1. Understanding the Reaction:
The reaction described is the dehydrohalogenation of 2-bromopentane. Dehydrohalogenation is an elimination reaction (specifically an E2 or E1 mechanism) where a hydrogen halide (HBr) is removed from an alkyl halide to form an alkene.

2. Analyzing the Reactant (2-Bromopentane):
The structure of 2-bromopentane is:
CH3-CH(Br)-CH2-CH2-CH3
The carbon attached to the bromine atom (C-2) is the α-carbon. The adjacent carbons, C-1 and C-3, are β-carbons and have hydrogen atoms (called β-hydrogens) that can be eliminated:
- C-1 is a primary carbon with three β-hydrogens: -CH3
- C-3 is a secondary carbon with two β-hydrogens: -CH2-

3. Possible Elimination Products:
Depending on which β-hydrogen is removed along with the bromine atom, two different alkene products can be formed:
- Route A (elimination from C-1): Removal of a hydrogen from C-1 and bromine from C-2 yields Pent-1-ene:
CH2=CH-CH2-CH2-CH3 (a monosubstituted alkene).
- Route B (elimination from C-3): Removal of a hydrogen from C-3 and bromine from C-2 yields Pent-2-ene:
CH3-CH=CH-CH2-CH3 (a disubstituted alkene).

4. Applying Saytzeff’s (Zaitsev's) Rule:
Saytzeff's Rule states that in an elimination (dehydrohalogenation) reaction of an alkyl halide, the preferred major product is the more highly substituted alkene, which is thermodynamically more stable.
- Pent-2-ene is disubstituted (two alkyl groups attached to the double-bonded carbons).
- Pent-1-ene is monosubstituted (only one alkyl group attached to the double-bonded carbons).
Therefore, according to Saytzeff's Rule, Pent-2-ene is formed as the major product (about 81%) because it has more alkyl substituents attached to the double bond, making it more stable than Pent-1-ene.

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