During dehydration of alcohols to alkenes by heating with conc. H2SO4 ...
Answer
Dehydration of alcohol to alkene in presence of concentrated H2SO4 involves the –OH group in the alcohol that donates two electrons to H+ from the acid reagent, forming an alkyloxonium ion. The deprotonated acid (the nucleophile) then attacks the hydrogen adjacent to the carbocation and form a double bond.
Thus, the initiation step is protonation of alcohol.
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During dehydration of alcohols to alkenes by heating with conc. H2SO4 ...
Protonation of Alcohol Molecule
In the dehydration of alcohols to alkenes, the initiation step involves the protonation of the alcohol molecule. Protonation refers to the addition of a proton (H+) to a molecule. This step is facilitated by the presence of concentrated sulfuric acid (H2SO4), which acts as a catalyst in the reaction.
Explanation:
1. Role of Concentrated H2SO4:
- Concentrated sulfuric acid serves as a catalyst in the dehydration of alcohols to alkenes.
- It provides protons (H+) that can react with the alcohol molecule, initiating the reaction.
- The presence of sulfuric acid helps in the removal of water, which is formed as a byproduct during the reaction.
2. Protonation of Alcohol:
- In the initiation step, a proton from the sulfuric acid is transferred to the oxygen atom of the alcohol molecule.
- This results in the formation of a positively charged intermediate known as a carbocation.
- The protonation of the alcohol molecule increases the electrophilic character of the oxygen atom, making it more prone to nucleophilic attack.
3. Formation of Carbocation:
- The formation of a carbocation is a key step in the dehydration of alcohols.
- A carbocation is a highly reactive species with a positively charged carbon atom.
- The positively charged carbon atom is surrounded by three bonds and lacks a complete octet of electrons.
- The formation of a carbocation is energetically unfavorable and highly endothermic.
4. Rearrangement:
- In some cases, the carbocation formed may undergo rearrangement to form a more stable carbocation through a hydride shift or a methyl shift.
- This rearrangement occurs to achieve a more stable electron configuration and lower the overall energy of the system.
5. Formation of Alkene:
- The carbocation formed in the initiation step can undergo elimination of a proton (H+) from an adjacent carbon atom.
- This elimination reaction leads to the formation of a double bond (alkene) and regenerates the sulfuric acid catalyst.
- The alkene formed is the desired product of the dehydration reaction.
In conclusion, the initiation step in the dehydration of alcohols to alkenes involves the protonation of the alcohol molecule by concentrated sulfuric acid. This proton transfer leads to the formation of a carbocation, which is a reactive intermediate that undergoes subsequent elimination to form the alkene product.
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