When it comes to the acidic cleavage of ether with a 2° alkyl group, the mechanism involved is quite different from the ones seen in ethers with 3° alkyl group and 1° alkyl group or two 1° alkyl groups.
Reaction Mechanism
The acidic cleavage of ether with a 2° alkyl group involves the use of a halogen acid (HX), typically hydrochloric acid (HCl) or hydrobromic acid (HBr), which acts as a proton source. The mechanism is slightly similar to the acidic hydrolysis of esters.
Here’s how the reaction mechanism works:
1. The halogen acid protonates the ether to form an oxonium ion.
2. The oxygen atom in the oxonium ion acts as a nucleophile and attacks the 2° carbon.
3. This results in the formation of a carbocation intermediate and an alcohol molecule.
4. The halide ion (X-) acts as a nucleophile and attacks the carbocation, leading to the formation of a 2° alkyl halide and a protonated alcohol.
It’s worth noting that this reaction mechanism involves both and reactions, which means that the product will depend on the reaction conditions.
Products Obtained
When an ether with a 2° alkyl group and a 1° alkyl group is cleaved with a halogen acid, two products are obtained:
A 2° alkyl halide
A protonated alcohol
The protonated alcohol that’s obtained can undergo further dehydration to form an alkene. However, this step is reversible and depends on the reaction conditions.
Examples
Let’s take a look at some examples to better understand the acidic cleavage of ether with a 2° alkyl group:
Example 1:
CH3CH2CH(OCH2CH3)CH3 + HBr → CH3CH2CHBrCH3 + HOCH2CH3
Example 2:
CH3(CH2)3CH(OCH3)CH3 + HCl → CH3(CH2)3CHClCH3 + HOCH3
In example 1, the ether is propyl ethyl ether, and the product that’s obtained is 2-bromopropane and ethanol. In example 2, the ether is butyl methyl ether, and the product that’s obtained is 1-chlorobutane and methanol.
Conclusion
So there you have it, the acidic cleavage of ether with a 2° alkyl group involves the use of a halogen acid, which results in the formation of a 2° alkyl halide and a protonated alcohol. This reaction mechanism involves both and reactions and is reversible depending on the reaction conditions.
Acidic Cleavage of Ether With a 2° Alkyl Group
When it comes to the acidic cleavage of ether with a 2° alkyl group, the mechanism involved is quite different from the ones seen in ethers with 3° alkyl group and 1° alkyl group or two 1° alkyl groups.
Reaction Mechanism
The acidic cleavage of ether with a 2° alkyl group involves the use of a halogen acid (HX), typically hydrochloric acid (HCl) or hydrobromic acid (HBr), which acts as a proton source. The mechanism is slightly similar to the acidic hydrolysis of esters.
Here’s how the reaction mechanism works:
It’s worth noting that this reaction mechanism involves both
and 
reactions, which means that the product will depend on the reaction conditions.
Products Obtained
When an ether with a 2° alkyl group and a 1° alkyl group is cleaved with a halogen acid, two products are obtained:
The protonated alcohol that’s obtained can undergo further dehydration to form an alkene. However, this step is reversible and depends on the reaction conditions.
Examples
Let’s take a look at some examples to better understand the acidic cleavage of ether with a 2° alkyl group:
In example 1, the ether is propyl ethyl ether, and the product that’s obtained is 2-bromopropane and ethanol. In example 2, the ether is butyl methyl ether, and the product that’s obtained is 1-chlorobutane and methanol.
Conclusion
So there you have it, the acidic cleavage of ether with a 2° alkyl group involves the use of a halogen acid, which results in the formation of a 2° alkyl halide and a protonated alcohol. This reaction mechanism involves both
and 
reactions and is reversible depending on the reaction conditions.