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Chapter 20: 58E (page 678)

Show how you might prepare the anti-inflammatory agent ibuprofen starting from isobutyl benzene. More than one step is needed.

Short Answer

Expert verified

The synthesis of ibuprofen starting from isobutyl benzene can be shown.

Step by step solution

01

Steps for the synthesis of ibuprofen

The acylation of Friedel-Crafts with acetyl chloride in the presence of AlCl3 which introduces an acetyl group in p-position for the yield of p-isopropylacetophenone. The ketone will convert into secondary alcohol when it is reduced with NaBH4. There is a displacement of bromine to –OH in the alcohol when it is treated with PBr3 to yield bromide. The nitrile to bromide conversion when treated with NaCN and hydrolysis will yield ibuprofen.

02

Structure for the ibuprofen synthesis

The steps for the ibuprofen synthesis have shown below,

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Most popular questions from this chapter

1,6 Hexanediamine, a starting material needed for making nylon, can be made from 1,3 butadiene. How would you accomplish the synthesis?

H2C=CHCH=CH2→?H2NCH2CH2CH2CH2CH2CH2CH2NH2

The Kafor dichloroacetic acid is3.32×10-2. Approximately what percentage of the acid is dissociated in a 0.10 M aqueous solution?

How would you prepare the following carboxylic acids?

(a)(CH3)3CCO2Hfrom(CH3)3CCI

(b) CH3CH2CH2CO2HfromCH3CH2CH2Br

Propose a synthesis of the anti-inflammatory drug Fenclorac from phenyl cyclohexane.

Draw structures corresponding to the following IUPAC names:

  1. cis-1,2-Cyclohexanedicarboxylic acid

  2. Hepatanedioic acid

  3. 2-Hexen-4-ynoic acid

  4. 4-Ethyl-2-propyloctanoic acid

  5. 3-chlorophthalic acid

  6. Triphenylacetic acid


  7. 2-Cyclobutenecarbonitrile

  8. m-Benzoyl benzonitrile
See all solutions

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