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Chapter 12: Q.57. (page 491)

Question: Draw the product of each asymmetric epoxidation reaction.

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01

Asymmetric epoxidation

  • Asymmetric epoxidation is also known as Sharpless epoxidation.
  • Allyl alcohols participate in this reaction.
  • DET affects the stereochemistry of the product.If it is of (+)-DET, then the epoxide is formed below the plane, and if it is (-)-DET, then the epoxide is formed above the plane.
02

Products of the given reaction

The double bond of the alkene reacts with the sharpless reagent and forms the epoxide.

The specialty of the reaction is that it forms one of the stereoisomers in excess. Hence, the selective product can be obtained by using a suitable reagent.

The formation of products for the given reactions is shown below.

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Most popular questions from this chapter

Question: Epoxidation of the following allylic alcohol using the Sharpess reagent (-)-DET gives two epoxy alcohols in a ratio of 87:13.

  1. Assign structures to the major and minor product.
  2. What is the enantiomeric excess in this reaction?

Question: Classify each reaction as oxidation, reduction, or neither

a.

b.

c.

d.

Question: Draw the products formed when each alkyne is treated with O3 followed by H2O .

a.

b.

c.

Question: Draw the products formed when each diene is treated with O3 followed by CH3SCH3.

a.

b.

c.

Question: A chiral alkyne A with molecular formula C6H10 is reduced with and Lindlar catalyst to B having the R configuration at its stereogeniccentre. What are the structures of A and B?
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