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Chapter 18: Q31E (page 594)

Treatment of 1,1-diphenyl-1,2-epoxyethane with aqueous acid yields diphenylacetaldehyde as the major product. Propose a mechanism for the reaction.

Short Answer

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Mechanism followed as:

Step by step solution

01

Acid-catalyzed ether

Epoxide ring opening occurs on reaction with acid in mild condition due to the ring strain and nucleophilic substitution takes place from the backside followed by SN2mechanism and form trans 1,2 diol as a product.

02

Reaction of given epoxide with H3O+

The OH-is formed by the H3O+ which act as a nucleophile and attack on the epoxide and opening of the ring occur and formation of 1,2 diol occur but 1,2 diol with the phenyl group lead to high un stability due to the presence of high steric hindrance so that 1,2 diol is rearranged to the carbonyl form and the desired product is obtained.

03

Mechanism

  1. Formation of OH-
  2. Attack on the epoxide ring occur
  3. 1,2 diol formed鈥� rearranged to form carbonyl

Reaction of epoxide

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Most popular questions from this chapter

2-Butene-1-thiol is one component of skunk spray. How would you synthesize this substance from methyl 2-butenoate? From 1,3-butadiene?

How would you prepare the following ethers? Use whichever method you think is more appropriate, Williamson synthesis or the alkoxymercuration reaction.

  1. Butyl cyclohexyl ether
  2. Benzyl ethyl ether (C6H5CH2OCH2CH3)
  3. sec-Butyl tert-butyl ether
  4. Tetrahydrofuran

Imagine that you have created (2R, 3R)-2,3-epoxy-3-methylpentane with aqueous acid to carry out a ring opening reaction.

  1. Draw the epoxide showing stereochemistry.
  2. Draw and name the product showing stereochemistry.
  3. Is the product chiral? Explain.
  4. Is the product optically active? Explain.

Predict the product(s) and provide the mechanism for each reaction below. What does each mechanism have in common?

Why are HI and HBr more effective than HCl in cleaving ethers? (See Section 11-3).
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