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Chapter 18: 23 P (page 706)

Devise a synthesis of each compound from the indicated starting material.

Short Answer

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Sulphonation reaction involves the substitution of the sulphonic group for the aromatic group. It occurs in the presence of sulfur trioxide and sulfuric acid.

Step by step solution

01

Sulphonation

Sulphonation reaction involves the substitution of the sulphonic group for the aromatic group. It occurs in the presence of sulfur trioxide and sulfuric acid.

02

Nitration

Thenitration reaction involves the substitution of the nitrate group on the aromatic group. It occurs in the presence of nitric acid and sulfuric acid.

03

Explanation

a. The given product has sulphonic and chloride groups. Therefore, sulphonation and chlorination processes are used to obtain the product.


b. The given product has acyl and nitro groups. Therefore, Friedel-Crafts acylation and nitration processes are used to obtain the product.


c. The given product has alkyl and bromine groups. Therefore, Friedel-Crafts alkylation and bromination processes are used to obtain the product.

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Most popular questions from this chapter

Draw a stepwise mechanism for the sulfonation of an alkyl benzene such as A to form a substituted benzenesulfonic acid B. Treatment of B with base forms a sodium salt C that can be used as a synthetic detergent to clean away dirt (see Problem 3.22).

Question: Devise a stepwise mechanism for the following reaction. The reaction does not take place by direct electrophilic aromatic substitution at C2 . (Hint: The mechanism begins with addition of an electrophile at C3.)

Draw a detailed mechanism for the chlorination of benzene using Cl2andFeCl3 .

Draw the products formed when phenol ( C6H5OH) is treated with each set of reagents.

a. [1] HNO3, H2SO4; [2] Sn, HCl

b. [1] CH3CH22COCl,AlCl3; [2] Zn(Hg), HCl

c. [1] CH3CH2Cl,AlCl3; [2]Br2,hν

d. [1] CH32CHCl,AlCl3; [2] KMnO4

Draw all resonance structures for each compound and use the resonance structures to determine if the substituent has an electron-donating or electron-withdrawing resonance effect.
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