The following reaction shows the nucleophilic ring opening of an epoxide. CH3CH₂CH-CH₂ + CH3OH *denotes chiral center Draw curved arrows to show the movement of electrons in the step of the mechanism shown below. Arrow-pushing Instructions 03 XM CH₂O'Na CH₂CH₂CHCH₂OCH3 SN2 OH CH3CH₂CH-CH₂ + CH3O: Na+ :0:- * denotes chiral center SN2 CH3CH₂2CHCH₂OCH3 |_ :O:Na+ X
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.
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