Elimination Reaction: OH & H Removal Explained

In summary, the elimination reaction of ethanol involves the removal of the OH and H atoms to form a double bond. This is achieved through an E1 mechanism, where the hydroxyl oxygen is protonated and then leaves to form a carbocation, followed by deprotonation and bond formation. It is not possible to remove one H from each carbon, as the hydroxyl group is a mandatory leaving group in this reaction. While there are other reactions that can convert ethanol to vinyl alcohol, this is not the case in this specific reaction.
  • #1
DespicableMe
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For the elimination reaction of ethanol:
elimination1.jpg


How come only the OH and H get taken out? I understand that you have to take out one atom from each carbon, so how come we can't take out, for example, one H from the left carbon and one H from the right carbon to get?

Or is it mandatory to take out the hydroxyl from an alcohol?
 
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  • #2
There's probably some reaction that can convert ethanol to vinyl alcohol (ethenol), which would subsequently tautomerize to acetaldehyde... BUT that's not what is happening here. The answer lies in the mechanism.

This is an E1 elimination. First step is the hydroxyl oxygen gets protonated by the rather strong acid present (sulfuric), which is then a pretty darn good leaving group and like a good leaving group does, it leaves (and forms a carbocation)! Next, a water molecule comes in and deprotonates the neighboring carbon, the electrons migrate between the two carbons, and whammo: double bond.
 

FAQ: Elimination Reaction: OH & H Removal Explained

What is an elimination reaction?

An elimination reaction is a type of chemical reaction where a molecule or functional group is removed from a larger molecule, resulting in the formation of a double bond or triple bond. This type of reaction is often used to form alkenes or alkynes from alkanes.

How does an elimination reaction occur?

An elimination reaction typically occurs in two steps: the first step involves the loss of a leaving group, such as OH or H, from the starting molecule. In the second step, a proton is removed from an adjacent carbon atom, resulting in the formation of a double bond or triple bond.

What is the difference between E1 and E2 reactions?

E1 and E2 reactions are two types of elimination reactions that differ in their reaction mechanisms. E1 reactions are unimolecular, meaning they only involve one molecule in the rate-determining step. E2 reactions are bimolecular, meaning they involve two molecules in the rate-determining step.

What is the role of OH and H in an elimination reaction?

OH and H are commonly found as leaving groups in elimination reactions. These groups are usually attached to a carbon atom that will form a double bond or triple bond during the reaction. By removing these groups, a double bond or triple bond can be formed in its place.

What are some common examples of elimination reactions?

Some common examples of elimination reactions include the dehydration of alcohols to form alkenes, the dehydrohalogenation of alkyl halides to form alkenes, and the dehalogenation of haloalkanes to form alkenes or alkynes. These reactions are commonly used in organic synthesis to form carbon-carbon double or triple bonds.

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