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Chapter 17: Q12P (page 543)

How would you carry out the following transformation, a step used in the commercial synthesis of (S)-ibuprofen?

Short Answer

Expert verified

The transformation occurs in the commercial synthesis of (S)-ibuprofen is,

Step by step solution

01

Conversion of alcohols into Tosylates

The SN2 reaction of alcohol via a tosylate occurs with only one inversion, and the stereochemistry of the product has the opposite stereochemistry to the starting alcohol compound.

02

The commercial synthesis of (S)-ibuprofen

We know that the reactions which run under SN2conditions have OH as a poor leaving group. The p-TosCl is an excellent leaving group, and the reaction of toluenesulfonate of alcohol with CN-occurs rapidly under SN2conditions. This gives the desired product with the inversion of configuration at the chiral carbon.

Synthesis of (S)-ibuprofen

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Most popular questions from this chapter

Name and assign R or S stereochemistry to the product (s) you would obtain by reaction of the following substance with ethylmagnesium bromide. Is the product chiral? Is it optically active? Explain.

How would you prepare the following substances from cyclopentanol?

More than one step may be required.

(a) Cyclopentanone

(b) Cyclopentene

(c) 1-Methylcyclopentanol

(d) trans-2-Methylcyclopentanol

What products would you obtain from reaction of 1-pentanol with the

following reagents?

(a) PBr3

(b)SOCl2

(c) CrO3, H2O,H2SO4

(d) Dess–Martin periodinane

Predict the product from reaction of the following substance (reddish brown=Br) with:

(a)PBr3

(b) AqueousH2SO4

(c)SOCl2

(d)Dess-Martin periodinane

(e)Br2 ,FeBr3

Assume that you need to prepare 5-Cholesten-3-one from Cholesterol. How could you use IR spectroscopy to tell whether the reaction was successful? What differences would you look for in the IR spectra of starting material and product?
See all solutions

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