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Chapter 14: Q22P (page 733)

Propose mechanisms for the epoxidation and ring-opening steps of the epoxidation and hydrolysis of shown above. Predict the product of the same reaction with.

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01

Peroxyacid epoxidation

Peroxyacids can be used to convert alkenes to epoxides. The epoxides are known to open to a glycol if the reaction occur in an aqueous medium. For this reason, strong acids are avoided for the synthesis of epoxides.

02

Acid-catalyzed ring opening of epoxides

Epoxides react under both acidic and basic conditions. The products of the acid-catalyzed ring opening depend primarily on the solvent used.

03

Mechanisms 

In water as a solvent, the acid-catalyzed hydrolysis of epoxides forms glycols with anit-stereochemistry. The mechanism involves protonation of oxygen followed by attack by water. The back-side attack of water on the protonated epoxide results in anti-stereochemistry. Lastly, hydrolysis of epoxide occurs to give the glycol.



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Most popular questions from this chapter

Show how the following ethers might be synthesized using (1) alkoxymercuration-demercuration and (2) the Williamson synthesis. (When one of these methods cannot be used for the given ether, point out why it will not work.)

  1. 2-methoxybutane
  2. Ethyl cyclohexyl ether
  3. 1-methoxy-2-methylcyclopentane
  4. 1-methoxy-1-methylcyclopentane
  5. 1-isopropoxy-1-methylcyclopentane
  6. Tert-butyl phenyl ether

Propose a Williamson synthesis of 3-butoxy-1,1-dimethylcyclohexane from 3,3-dimethyl-cyclohexanol and butan-1-ol.

Question: Show how you would convert pent-1-eneto each of the following compounds. You may use any additional reagents and solvents you need.

(a) 2-methoxypentane

(b) 1-methoxypentane

(c) 1-methoxypentan-2-ol

(d) 2-methoxypentan-1-ol

(e) 1-phenylpentan-2-ol

(f) 2-methoxy-1-phenylpentane

Show how you would use the Williamson ether synthesis to prepare the following ethers. You may use any alcohols or phenols as your organic starting materials.

  1. Cyclohexyl propyl ether
  2. Isopropyl methyl ether
  3. 1-methoxy-4-nitrobenzene
  4. Ethyl n-propyl ether (two ways)
  5. Benzyl tert-butyl ether (benzyl =Ph-CH2-)

Show the rest of the mechanism for formation of cyclized intermediate in figure 14-6.

Role of squalene in the biosynthesis of steroids. The biosynthesis of steroids starts with epoxidation of squalene to squalene-2,3-epoxide. The opening of this epoxide promotes cyclization of the carbon skeleton under the control of an enzyme. The cyclized intermediate is converted to lanosterol and then to other steroids.
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