As the name indicates, small molecule eliminates during these types of reactions. This small molecule is generally water (-H2O) in the case of dehydration or HX in the case of dehydrohalogenation. A 1, 2-elimination suggests that the atoms that are eliminated
come from adjacent or neighbor carbon atoms. In the organic chemistry, Elimination reactions are the important method for alkenes synthesis.
- Dehydration: Elimination of water i.e.-H2O from the Alcohol.
- Dehydrohalogenation: Elimination of HX from alkyl halides. ( where X = Cl, F, Br or I)
Let’s see what happens during elimination process. There are three steps through which these reactions proceeds –
- Removal of a hydrogen or proton.
- Formation of the new Carbon-Carbon double bond i.e. pi bond.
- Breaking of Carbon -leaving group bond.
Now depending on facts, which step happen first, these reactions can be classified into two categories-
- Removal of leaving the group to form a carbocation, then removal of a proton and formation of the C=C bond. Reactions proceeds via this pathway are referred as E1 reactions.
- Another pathway, simultaneous proton removal and loss of the leaving group to form C=C bond. These types of reactions are referred as E2 reactions.
Now we will see the difference between these two mechanisms-
E1 mechanism
E1 means elimination and reaction.
Following two events happens during E1 reactions (shown in figure)-
E2 mechanism
E2 means elimination, bimolecular reaction.
This is a concerted pathway with the following mechanism (Shown in figure)-
So the factors which decide the pathway of reaction, means whether it would follow E1 pathway or E2 pathway are:
- Stability of Carbocation.
- Nature of leaving the group.
- Base: Strong or weak base.
On this basis, we can now differentiate E1 and E2 reactions-
E1 | E2 | |
Unimolecular/Bimolecular | Unimolecular | Bimolecular |
Rate depends on | The concentration of Substrate. | The concentration of Substrate and concentration of Base as well. |
Base | Strong base not needed. | Strong base needed |
Stereochemistry requirement | Not needed. | Leaving group should be anti to hydrogen that has to remove. |
Steps | Two step reactions | One step reaction. |
Carbocation | Should form a stable carbocation. | Not needed. |