
Concept explainers
(a)
Interpretation: The products formed by the Friedel-Craft alkylation of given compound with CH3Cl and AlCl3 are to be drawn.
Concept introduction: The replacement or substitution of one

Answer to Problem 18.21P
The given compound does not undergo Friedel-craft alkylation reaction on reaction with CH3Cl and AlCl3.
Explanation of Solution
The Friedel-craft alkylation of
The structure of given compound shows that benzene ring is substituted by −SO3H group. This group is strong electron withdrawing group. Hence, the Friedel-craft alkylation reaction will not take place on reaction of given compound with CH3Cl and AlCl3.
Figure 1
The given compound does not undergo Friedel-craft alkylation reaction on reaction with CH3Cl and AlCl3.
(b)
Interpretation: The products formed by the Friedel-Craft alkylation of given compound with CH3Cl and AlCl3 are to be drawn.
Concept introduction: The replacement or substitution of one functional group with another different functional group in any chemical reaction is termed as substitution reaction. The electron deficient chemical species that contains positive charge are known as electrophile. In electrophilic aromatic substitution reaction, electrophile takes the position of hydrogen atom by attacking the electron rich carbon atom of benzene.

Answer to Problem 18.21P
The given compound does not undergo Friedel-craft alkylation reaction on reaction with CH3Cl and AlCl3.
Explanation of Solution
The Friedel-craft alkylation of aromatic compound with CH3Cl in presence of AlCl3 involves substitution of CH3 group. Friedel-craft alkylation reaction does not take place when an aromatic ring is substituted by a strong electron releasing or strong electron withdrawing group.
The structure of given compound shows that benzene ring is substituted by −Cl group. This group is a strong deactivating group. Hence, the Friedel-craft alkylation reaction will not take place on reaction of given compound with CH3Cl and AlCl3.
Figure 2
The given compound does not undergo Friedel-craft alkylation reaction on reaction with CH3Cl and AlCl3.
(c)
Interpretation: The products formed by the Friedel-Craft alkylation of given compound with CH3Cl and AlCl3 are to be drawn.
Concept introduction: The replacement or substitution of one functional group with another different functional group in any chemical reaction is termed as substitution reaction. The electron deficient chemical species that contains positive charge are known as electrophile. In electrophilic aromatic substitution reaction, electrophile takes the position of hydrogen atom by attacking the electron rich carbon atom of benzene.

Answer to Problem 18.21P
The given compound does not undergo Friedel-craft alkylation reaction on reaction with CH3Cl and AlCl3.
Explanation of Solution
The Friedel-craft alkylation of aromatic compound with CH3Cl in presence of AlCl3 involves substitution of CH3 group. Friedel-craft alkylation reaction does not take place when an aromatic ring is substituted by a strong electron releasing or strong electron withdrawing group.
The structure of given compound shows that benzene ring is substituted by −N(CH3)2 group. This group is a strong electron releasing group. Hence, the Friedel-craft alkylation reaction will not take place on reaction of given compound with CH3Cl and AlCl3.
Figure 3
The given compound does not undergo Friedel-craft alkylation reaction on reaction with CH3Cl and AlCl3.
(d)
Interpretation: The products formed by the Friedel-Craft alkylation of given compound with CH3Cl and AlCl3 are to be drawn.
Concept introduction: The replacement or substitution of one functional group with another different functional group in any chemical reaction is termed as substitution reaction. The electron deficient chemical species that contains positive charge are known as electrophile. In electrophilic aromatic substitution reaction, electrophile takes the position of hydrogen atom by attacking the electron rich carbon atom of benzene.

Answer to Problem 18.21P
The products formed by the Friedel-Craft alkylation of given compound with CH3Cl and AlCl3 are drawn below.
Explanation of Solution
The Friedel-craft alkylation of aromatic compound with CH3Cl in presence of AlCl3 involves substitution of CH3 group. Friedel-craft alkylation reaction does not take place when an aromatic ring is substituted by a strong electron releasing or strong electron withdrawing group.
The structure of given compound shows that benzene ring is substituted by −NHCOCH3 group. This group is moderately electron releasing group. Hence, the given compound undergoes Friedel-craft alkylation reaction with CH3Cl and AlCl3 as shown in Figure 4.
Figure 4
The products formed by the Friedel-Craft alkylation of given compound with CH3Cl and AlCl3 are shown in Figure 4.
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Chapter 18 Solutions
Package: Loose Leaf for Organic Chemistry with Biological Topics with Connect Access Card
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- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning
