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E1 and E2 reactions

  • E1 and E2 reactions are two types of elimination reactions that occur in organic chemistry, where elements of a molecule are removed, leading to the formation of a double bond.

  • The key difference between them lies in the mechanism by which this elimination occurs.

E1 Reaction (Unimolecular Elimination)

The E1 reaction is a two-step process involving the formation of a carbocation intermediate.

Mechanism

Formation of Carbocation (Step 1):

  • The leaving group departs, forming a carbocation.

  • Equation: R-LG → R⁺ + LG⁻

Proton Abstraction and Double Bond Formation (Step 2):

  • A base abstracts a proton from a carbon adjacent to the carbocation, forming a double bond and generating the alkene.

  • Equation: R⁺ + B → R=CR₂ + BH⁺

Example:

Dehydration of 2-Methyl-2-Butanol

  • Step 1: Protonation of the alcohol (-OH) turns it into a good leaving group (water).

  • tep 2: The loss of water forms a tertiary carbocation.

  • Step 3: A base abstracts a proton, forming 2-methyl-2-butene.Factors Influencing E1 Reactions

Factors Influencing E1 Reactions:

  1. Carbocation Stability: Tertiary, allylic, or benzylic carbocations are more stable and favor E1 reactions.

  2. Leaving Group: A good leaving group facilitates carbocation formation.

  3. Solvent: Polar solvents stabilize the carbocation and leaving group.

  4. Temperature: Higher temperatures favor E1 reactions by providing energy for carbocation formation.

E2 Reaction (Bimolecular Elimination)

  • The E2 reaction is a one-step process where the leaving group is eliminated, and a proton is abstracted simultaneously.

Mechanism:

  • In an E2 reaction, a strong base attacks a β-hydrogen, and the electrons from the C-H bond are used to form a double bond between the α and β carbons, while simultaneously ejecting the leaving group.

  • This process is bimolecular, with the rate of reaction depending on the concentration of both the substrate and the base.

  • The stereochemistry of the E2 reaction is often important, with the most common outcome being anti-periplanar geometry, where the hydrogen and the leaving group are on opposite sides of the molecule.

Example:

  • 1-Bromopropane and Hydroxide Ion Reaction:

  • Equation: CH₃CH₂CH₂Br + OH⁻ → CH₃CH=CH₂ + Br⁻ + H₂O

  • Here, hydroxide abstracts a β-hydrogen, forming propene, bromide, and water.


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