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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 鈥榗hlorination reaction鈥�.

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 鈥楩riedel-Craft Acylation鈥�.

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

Tertiary ( 3掳) aromatic amines react with NaNO2 and HCl to afford products of electrophilic aromatic substitution. Draw a stepwise mechanism for this nitrosation reaction and explain why it occurs only on benzene rings with strong ortho, para activating groups.

Question: Rank the following compounds in order of increasing basicity and explain the order you chose.

What amine is formed by reduction of each amide?

a.

b.

c.

Decide which N atom in each molecule is most basic and draw the product formed when each compound is treated with CH3CO2H. Zolpidem (trade name Ambien) is used to treat insomnia, whereas aripiprazole (trade name Abilify) is used to treat depression, schizophrenia, and bipolar disorders.

(a)

(b)

Question: Draw鈥倀he鈥俻roduct鈥俧ormed鈥倃hen鈥俥ach鈥俢ompound鈥俰s鈥倀reated鈥倃ith鈥侼aNO2鈥俛苍诲鈥侣颁濒.

a.

b.

c.

d.
See all solutions

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