a) Draw the most stable conformation of the starting material 8 and explain why this is the most stable conformation. b) Draw the reaction mechanism for how 9 is formed from 8 and explain why 10 and 11 are not formed if one assumes the E2 mechanism.
Reactions of Ethers
Ethers (R-O-R’) are compounds formed by replacing hydrogen atoms of an alcohol (R-OH compound) or a phenol (C6H5OH) by an aryl/ acyl group (functional group after removing single hydrogen from an aromatic ring). In this section, reaction, preparation and behavior of ethers are discussed in the context of organic chemistry.
Epoxides
Epoxides are a special class of cyclic ethers which are an important functional group in organic chemistry and generate reactive centers due to their unusual high reactivity. Due to their high reactivity, epoxides are considered to be toxic and mutagenic.
Williamson Ether Synthesis
An organic reaction in which an organohalide and a deprotonated alcohol forms ether is known as Williamson ether synthesis. Alexander Williamson developed the Williamson ether synthesis in 1850. The formation of ether in this synthesis is an SN2 reaction.
During the further development of other prostaglandin-like molecules, it is necessary to replace the cyclopentane ring with the cyclohexene as shown in the reaction scheme below. (Deuterium (D) is a heavier isotope of hydrogen)
a) Draw the most stable conformation of the starting material 8 and explain why this is the most stable conformation.
b) Draw the reaction mechanism for how 9 is formed from 8 and explain why 10 and 11 are not formed if one assumes the E2 mechanism.
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