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Chapter 18: Q23P (page 898)

Show how the following compounds can be synthesized from benzene:

a)

b)

c)

Short Answer

Expert verified

a)

Formation of the desired product

b)

Formation of the desired product

c)

Formation of the desired product

Step by step solution

01

Step-by-step-solutionStep 1: Benzene

Benzene undergoes an electrophilic substitution reaction based on the substituent attached to the benzene ring. It can be ortho-para directing or meta directing.

02

Formation of the products

a)

Benzene reacts with ethanoyl chloride in the presence of Lewis acid to give acetophenone. Acetophenone reacts with nitric acid in the presence of sulfuric acid to give 3-nitroacetophenone.

Formation of the desired product (a)

b)

Benzene reacts with propionyl chloride in the presence of Lewis acid to give propiophenone. Propiophenone reacts with fuming sulfuric acid to give the desired product.

Formation of the desired product (b)

c)

Benzene reacts with methyl chloride in the presence of Lewis acid to give toluene. Toluene on oxidation gives benzoic acid, followed by a reaction with methanol in an acidic medium that produces the corresponding ester. This reacts with nitric acid in the presence of sulfuric acid giving 3-nitrobenzoic acid.

Formation of the desired product (c)

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Most popular questions from this chapter

Show how each of the following compounds can be synthesized from benzene:

a. o-bromopropylbenzene

b. m-nitrobenzoic acid

c. p-nitrobenzoic acid

d. p-chloroaniline

e. m-chloroaniline

f. m-xylene

g. 2-phenylpropene

h. m-bromopropylbenzene

i. 1-phenyl-2-propanol

Why isn鈥檛 FeBr3 used as a catalyst in the first step of the synthesis of 1,3,5-tribromobenzene?

Question:a. How can aspirin be synthesized from benzene?b. Ibuprofen is the active ingredient in pain relievers such as Advil, Motrin and Nuprin. How can ibuprofen be synthesized from benzene?c. Acetaminophen is the active ingredient in Tylenol. How can acetaminophen be synthesized from benzene?

aspirin ibuprofen acetaminophen

Explain why fluorobenzene is more reactive than chlorobenzene toward electrophilic aromatic substitution but chloromethyl benzene is more reactive than fluoromethylbenzene.

For each horizontal row of substituted benzenes, indicate

  1. the one that is the most reactive in an electrophilic aromatic substitution reaction.
  2. the one that is the least reactive in an electrophilic aromatic substitution reaction.
  3. the one that yields the highest percentage of meta product in an electrophilic aromatic substitution reaction

1.

2.

3.
See all solutions

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