Question
Question: What are the differences between \(E_1\) and \(E_2\) reaction?...
What are the differences between E1 and E2 reaction?
Solution
Elimination reactions are organic reactions in which two substituents from a molecule are separated in a one- or two-step mechanism. The reactivity of halogens influences the reaction rate, with iodide and bromide being preferred. Fluoride is a poor leaving group, but fluoride-based eliminations are slower than those involving other halogens.
Complete answer:
Reaction Parameter | E1 | E2 |
---|---|---|
Alkyl halide structure | Tertiary > secondary >>> primary | Tertiary > secondary > primary |
Mechanism | 2 – step | 1 – step |
Rate limiting step | Carbocation formation | Anti – coplanar bimolecular transition state |
Rate law | Rate = k[R-X] | Rate = k[R-X] [Base] |
Solvent | Polar aprotic (Good ionising) | Not important |
Stereochemistry | Mixed configuration | Retained configuration |
Nucleophile | Weak base | High concentration of a strong base |
E1 is a model that explains one kind of chemical removal reaction in particular. The following are the criteria for E1, which stands for unimolecular removal. Ionization and deprotonation are the two steps in the removal process. Ionization occurs as the carbon-halogen bond breaks, resulting in the formation of a carbocation intermediate. The carbocation is deprotonated.
Bimolecular reduction is abbreviated as E2. The reaction occurs in a single step, with the carbon-hydrogen and carbon-halogen bonds breaking to form a double bond (C=C Pi bond). With just one transition state, E2 is a single-step elimination.
Note:
The E2 reaction is the one-step mechanism, while the E1 reaction is the two-step mechanism. The numbers correspond to the kinetics of the reaction, not the number of steps in the mechanism: E2 is bimolecular (second-order), while E1 is unimolecular (first-order). A third form of reaction, E1CB, occurs where a molecule is able to stabilise an anion but has a weak leaving group. Finally, pyrolysis of xanthate and acetate esters occurs through the Ei mechanism, which is a "internal" removal mechanism.