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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

There are two ways of making 2-ethoxyoctane from octan-2-ol using the Williamson ether synthesis. When pure (-) -octan-2-ol of specific rotation -8.240is treated with sodium metal and then ethyl iodide, the product is 2-ethoxyoctane with a specific rotation of -15.60. When pure (-) -octan-2-ol is treated with tosyl chloride and pyridine and then with sodium ethoxide, the product is also 2-ethoxyoctane. Predict the rotation of the 2-ethoxyoctane made using the tosylation/sodium ethoxide procedure, and propose a detailed mechanism to support your prediction.

Predict the major product when each reagent reacts with ethylene oxide.

(a) NaOCH2CH3(Sodium ethoxide)

(b) NaNH2(sodium amide)

(c) NaSPh (sodium thiophenoxide)

(d) PhNH2(aniline)

(e) KCN (potassium cyanide)

(f) NaN3(soidum azide)

Write structural formulas for the following compounds

  1. methyl isopropyl ether (b) di-iso-butyl ether (c) 2-methoxyoctane

(d) diallyl ether (e) allyl ethyl ether (f) cycloheptane oxide

(g) trans-2,3-epoxyheptane (h) (2R,3S)-2-ethoxypentan-3-ol (i) cis-2,3-dimethyloxirane

Question. Propose a mechanism for the following reaction.

Question. Glycerol (propane-1,2,3-triol) is a viscous syrup with molecular weight 92g/mol, boiling point 290oC, and density 1.24g/mol. Transforming the three hydroxy groups into their trimethylsilyl ethers (using chlorotrimethylsilane and a tertiary amine) produces a liquid that flows easily, has molecular weight 309g/mol, boiling point approximately 180oC, and density 0.88g/mol. Draw the structures of these two compounds and explain why glycerol has a lower molecular weight but a much higher boiling point and density.
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