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Chapter 14: Q 46P (page 748)

Show how you would convert 2-bromocyclohexanol to the following diol. You may use any additional reagents you need.

Short Answer

Expert verified

Different steps involved in the conversion process are as given below.

(1) Protection of hydroxyl group by treating 3-bromocyclohexanol withtriisopropylsilyl chloride(TIPSCl) in presence of triethylamine.

(2) Making Grignard reagent by treating the initial product with magnesium and ether.

(3) Reaction of Grignard reagent with a ketone (butan-2-one).

(4) Hydrolysis ( becomes OH).

(5) Removing the protection by reacting with tetrabutylammonium fluoride (Bu4N+F-). This gives the final product as diol.

Step by step solution

01

Steps involved in conversion of 2-bromocyclohexanol to the given diol

Different steps involved in the conversion process are as given below.

(1) Protection of hydroxyl group by treating 3-bromocyclohexanol withtriisopropylsilyl chloride(TIPSCl) in presence of triethylamine.

(2) Making Grignard reagent by treating the initial product with magnesium and ether.

(3) Reaction of Grignard reagent with a ketone (butan-2-one).

(4) Hydrolysis ( becomes OH).

(5) Removing the protection by reacting with tetrabutylammonium fluoride (Bu4N+F-). This gives the final product as diol.

02

Synthesis

conversion of 3-bromocyclohexanol to diol

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Most popular questions from this chapter

Predict the products of the following reactants. An excess acid is available in each case.

(a) Ethoxycyclohexane + HBr (b) tetrahydropyran + HI

(c) anisole ( methoxybenzene) + HBr

(d)

(e)

Question. Give the structures of intermediates A through H in the following synthesis of trans-1-cyclohexyl-2-methoxycyclohexane.

(a) When ethylene oxide is treated with anhydrous HBr gas, the major product is 1,2-dibromoethane. When ethylene oxide is treated with concentrated aqueous HBr, the major product is ethylene glycol. Use mechanisms to explain these results.

(b) Under base-catalyzed conditions, several molecules of propylene oxide can react to give short polymers. Propose a mechanism for the base-catalyzed formation of the following trimer.

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?

Propose a fragmentation to account for each numbered peak in the mass spectrum of n-butyl isopropyl ether.
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