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Chapter 25: 70 (page 1046)

Devise a synthesis of each biologically active compound from benzene.

Short Answer

Expert verified

a

b

Step by step solution

01

Chlorination

The organic reaction involving the replacement of hydrogen atom(s) by chloride ion in the presence of ferric chloride in an aromatic compound is known as the ‘chlorination reaction’.

a. Benzene is chlorinated to form the chlorobenzene which is treated with a strong base such as sodium hydroxide to form phenol. Phenol is nitrated to form ortho-nitro phenol which is reduced to form the corresponding p-amino phenol.

Formation of -amino phenol

02

Friedel-Craft Acylation

The reaction involving the introduction of an acyl group into an aromatic compound is known as the ‘Friedel-Craft Acylation’.

a. The p-aminophenol is treated with acetyl chloride in the presence of anhydrous aluminum chloride to undergo dehalogenation to form the required compound.

Formation of acetaminophen

b. Benzene is treated with 2-chloropropanoyl chloride followed by reduction of the carbonyl group. The compound is further treated with ethylamine in presence of hydrogen and any liquified solvent to form the required compound.

Formation of pseudo ephedrine

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Most popular questions from this chapter

Heating compound X with aqueous formaldehyde forms Y C17H23NO, which has been converted to a mixture of lupinine and epilupinine, alkaloids isolated from lupin, a perennial ornamental plant commonly seen on the roadside in parts of Alaska (Section 25.10). Identify Y and explain how it is formed.

Question: Write out steps to show how each of the following pairs of compounds can be separated by an extraction procedure.

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Treatment of compound D with LiAlH4 followed by H2O forms compound E. D shows a molecular ion in its mass spectrum at m/z= 71 and IR absorptions at 3600-3200cm-1 and . E shows a molecular ion in its mass spectrum at m/z= 75 and IR absorptions at 3636cm-1 and 3600-3200cm-1 . Propose structures for D and E from these data and the given 1H NMR spectra.

Question: Label the stereogenic centers in each compound.

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b.

Question: Draw the products formed when each carbonyl compound reacts with the following amines:

1. CH3CH2CH2NH2

2.(CH3CH2)2NH

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