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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

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

following reagents?

(a) PBr3

(b)SOCl2

(c) CrO3, H2O,H2SO4

(d) Dess鈥揗artin periodinane

Draw structures corresponding to the following IUPAC names:

  1. (Z)-2-Ethyl-2-buten-1-ol
  2. 3-Cyclohexen-1-ol
  3. trans-3-Chlorocycloheptanol
  4. 1,4-Pentanediol
  5. 2,6-Dimethylphenol
  6. o-(2-Hydroxyethyl)phenol

Question: Use a Grignard reaction to prepare the following alcohols.

  1. 2-Methyl-2-propanol
  2. 1-Methylcyclohexanol
  3. 3-Methyl-3-pentanol
  4. 2-Phenyl-2-butanol
  5. Benzyl alcohol
  6. 4-Methyl-1-pentanol

Named bombykol, the sex pheromone secreted by the female silkworm

moth has the formula C16H28O and the systematic name (10E,12Z)-

10,12-hexadecadien-1-ol. Draw bombykol, showing the correct geometry

for the two double bonds.

Show the products obtained from addition of methylmagnesium bromide to the following compounds:

  1. Cyclopentanone
  2. Benzophenone (diphenyl ketone)
  3. 3-Hexanone
See all solutions

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