Solution Found!
Show how the following ethers might be synthesized using
Chapter 24, Problem 10P(choose chapter or problem)
Problem 10P
Show how the following ethers might be synthesized using (1) alkoxymercuration–demercuration and (2) the Williamson synthesis. (When one of these methods cannot be used for the given ether, point out why it will not work.)
(a) 2-methoxybutane
(b) ethyl cyclohexyl ether
(c) 1-methoxy-2-methylcyclopentane
(d) 1-methoxy-1-methylcyclopentane
(e) 1-isopropoxy-1-methylcyclopentane
(f) tert-butyl phenyl ether
Questions & Answers
QUESTION:
Problem 10P
Show how the following ethers might be synthesized using (1) alkoxymercuration–demercuration and (2) the Williamson synthesis. (When one of these methods cannot be used for the given ether, point out why it will not work.)
(a) 2-methoxybutane
(b) ethyl cyclohexyl ether
(c) 1-methoxy-2-methylcyclopentane
(d) 1-methoxy-1-methylcyclopentane
(e) 1-isopropoxy-1-methylcyclopentane
(f) tert-butyl phenyl ether
ANSWER:
Solution 10P
- 2-Methoxybutane :
Alkoxymercuration–demercuration reaction to form 2-methoyxbutane. The methoxy group is bonded to more substituted carbon and the H is bonded to less substituted carbon.
Williamson synthesis the sodium 2-butanolate is treated with methyl iodide by mechanism to form 2-methoxybutane.
b. Ethyl cyclohexyl ether:
Alkoxymercuration–demercuration reaction to form ethyl cyclohexyl ether. The ethoxy group is bonded to more substituted carbon and the H is bonded to less substituted carbon.
Williamson synthesis the sodium cyclohexanolate is treated with ethyl iodide by mechanism to form ethyl cyclohexyl ether.
c. 1-Methoxy-2-methylcyclopentane
Alkoxymercuration–demercuration reaction to form 1-methoxy-1-methylcyclopentane by Markovnikov v rule.This method is not used for the synthesis of 1-methoxy-2-methylcyclopentane.
Williamson synthesis the sodium 2-methylcyclopentanolate is treated with methyl iodide by