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Chapter 14: Q28P (page 741)

Give the expected products of the following reactions. Include a protonation step where necessary.

  1. 1,2-dimethyloxirane + isopropylmagnesium bromide
  2. ethyl oxide + n-butyllithium
  3. cyclohexyloxirane + ethyllithium

Short Answer

Expert verified

Answer

(c)

Step by step solution

01

isopropyl magnesium bromide

We can use Grignard reagents to convert epoxide to alcohol. At first the epoxide is converted bto organo magnesium bromide compound. And then it will converted to alcohol by the addition of base or water.

02

n- Butyllithium

As Grignard reagent it will convert the epoxide to alcohol. At first it will convert it to organo lithium compound and then it will convert to alcohol.

03

Ethyllithium

This is used to convert the epoxide to organolithium and to alcohol. But here is a possibility to give one minor product when the organo lithium compound is attack to the carbon which is attached to the cyclohexane. This will be the less stable product in this

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Most popular questions from this chapter

Question. The 2001 Nobel Prize in Chemistry was awarded to three organic chemists who have developed methods for catalytic asymmetric synthesis. An asymmetric (or enantioselective) synthesis is one that converts an achiral starting material into mostly one enantiomer of a chiral product. K. Barry Sharpless (The Scripps Research Institute) developed an asymmetric epoxidation of allylic alcohols that gives excellent chemical yields and greater than 90% enantiomeric excess.

The Sharpless epoxidation uses tert-butyl hydroperoxide, titanium(IV) isopropoxide, and a dialkyl tartarate ester as the reagents. The following epoxidation of geraniol is typical.

  1. Which of these reagents is most likely to be the actual oxidizing agent? That is, which reagent is reduced in the reaction? What is the likely function of the other reagents?
  2. When achiral reagents react to give a chiral product, that product is normally formed as a racemic mixture of enantiomers. How can the Sharpless epoxidation give just one nearly pure enantiomer of the product?
  3. Draw the other enantiomer of the product. What reagents would you use if you wanted to epoxidize geraniol to give this other enantiomer?

Show how you would synthesize the following ethers in good yields from the indicated starting materials and any additional reagents needed.

(a) Cyclopentyl n propyl etherfromcyclopentanolandpropan-1-ol.

(b) n-butyl phenyl etherfromphenolandbutan-1-ol.

(c) 2-ethoxyoctanefrom anoctene

(d) 1-methoxydecanefrom adecene

(e) 1-ethoxy-1-methylcyclohexanefrom 2-methylcyclohexanol.

(f) trans-2,3-epoxyoctane from octane-2-ol.

Propylene oxide is a chiral molecule. Hydrolysis of propylene oxide gives propylene glycol, another chiral molecule.

(a) Draw the enantiomers of propylene oxide.

(b) Propose a mechanism for the acid-catalyzed hydrolysis of pure (R)-propyleneoxide.

(c) Propose a mechanism for the base-catalyzed hydrolysis of pure (R)-propyleneoxide.

(d) Explain why the acid-catalyzed hydrolysis of optically active propylene oxide gives a product with lower enantiomeric excess and a rotation opposite that of the product of the base- catalyzed hydrolysis.

Question. The following reaction resembles the acid-catalyzed cyclization of squalene oxide. Propose a mechanism for this reaction.

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-)
See all solutions

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