The Sharpless epoxidation is used when a single enantiomer product is required. Predict the structure of the predominant product of the following transformation. Oll... (S) (E) OH (-)-diethyl tartrate Ti(O'Pr)4 cumene hydroperoxide
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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The Sharpless epoxidation is used when a single enantiomer product is required. Predict the structure of the predominant product of the following transformation.
O
(S)
(E)
OH
(-)-diethyl tartrate
Ti(O'Pr)4
cumene hydroperoxide
• Use the wedge/hash bond tools to indicate stereochemistry where it exists.
• For your convenience, the starting material has been drawn for you in the sketchpad.
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![Draw the structural formula of the product of the reaction shown below.
H3C.
CH3CH₂
+ CH3CH₂OH
**VIL
• You do not have to consider stereochemistry.
Na OCH₂CH3
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?
O
ChemDoodle
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First reaction involves the asymmetric epoxidation of alkene bond () bond.
second reaction is opening of epoxide ring by nucleophilic attack of from less hindered side of epoxide.
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