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Magazine Chapter 16: Q16-70E (page 524)
Propose a mechanism to account for the reaction of benzene with 2,2,5,5 tetramethyltetrahydrofuran.
Short Answer
Mechanism followed as:
a.
b.
c.
d.
Step by step solution
Reaction of benzene with 2,2,5,5-tetramethyltetrahydrofuran.
- Protonation of the cyclic ether occur which lead to the opening of the ring and the formation of carbocation takes place which is undergo Friedal craft alkylation as shown:
Reaction with 2,2,5,5-tetramethyltetrahydrofuran
Friedel craft alkylation
Benzene act as a nucleophile and attacks the carbocation and followed by the base which abstract the proton formation of the alcoholic product occurs follow:
Friedal craft alkylation
Protonation of alcohol
The hydroxyl proton of the alcohol is protonated and followed by the hydrolysis that the loss of water molecule leads to the generation of the secondary carbocation as shown below:
Protonation of alcohol
Internal alkylation
As the second carbocation is undergo internal alkylation that the shift of the alkyl group leads to the formation of the desired product occur:
Internal Alkylation
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