Chapter 18, Problem 18.21P

Interpretation Introduction

(a)

Interpretation: The products formed by the Friedel-Craft alkylation of given compound with ${\text{CH}}_{\text{3}}\text{Cl}$ and ${\text{AlCl}}_{\text{3}}$ 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 ${\text{CH}}_{\text{3}}\text{Cl}$ and ${\text{AlCl}}_{\text{3}}$.

Explanation of Solution

The Friedel-craft alkylation of aromatic compound with ${\text{CH}}_{\text{3}}\text{Cl}$ in presence of ${\text{AlCl}}_{\text{3}}$ involves substitution of ${\text{CH}}_{\text{3}}$ 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 $-{\text{SO}}_{\text{3}}\text{H}$ group. This group is strong electron withdrawing group. Hence, the Friedel-craft alkylation reaction will not take place on reaction of given compound with ${\text{CH}}_{\text{3}}\text{Cl}$ and ${\text{AlCl}}_{\text{3}}$.

Figure 1

Conclusion

The given compound does not undergo Friedel-craft alkylation reaction on reaction with ${\text{CH}}_{\text{3}}\text{Cl}$ and ${\text{AlCl}}_{\text{3}}$.

Interpretation Introduction

(b)

Interpretation: The products formed by the Friedel-Craft alkylation of given compound with ${\text{CH}}_{\text{3}}\text{Cl}$ and ${\text{AlCl}}_{\text{3}}$ 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 ${\text{CH}}_{\text{3}}\text{Cl}$ and ${\text{AlCl}}_{\text{3}}$.

Explanation of Solution

The Friedel-craft alkylation of aromatic compound with ${\text{CH}}_{\text{3}}\text{Cl}$ in presence of ${\text{AlCl}}_{\text{3}}$ involves substitution of ${\text{CH}}_{\text{3}}$ 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 $-\text{Cl}$ group. This group is a strong deactivating group. Hence, the Friedel-craft alkylation reaction will not take place on reaction of given compound with ${\text{CH}}_{\text{3}}\text{Cl}$ and ${\text{AlCl}}_{\text{3}}$.

Figure 2

Conclusion

The given compound does not undergo Friedel-craft alkylation reaction on reaction with ${\text{CH}}_{\text{3}}\text{Cl}$ and ${\text{AlCl}}_{\text{3}}$.

Interpretation Introduction

(c)

Interpretation: The products formed by the Friedel-Craft alkylation of given compound with ${\text{CH}}_{\text{3}}\text{Cl}$ and ${\text{AlCl}}_{\text{3}}$ 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 ${\text{CH}}_{\text{3}}\text{Cl}$ and ${\text{AlCl}}_{\text{3}}$.

Explanation of Solution

The Friedel-craft alkylation of aromatic compound with ${\text{CH}}_{\text{3}}\text{Cl}$ in presence of ${\text{AlCl}}_{\text{3}}$ involves substitution of ${\text{CH}}_{\text{3}}$ 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 $-\text{N}{\left({\text{CH}}_3\right)}_2$ 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 ${\text{CH}}_{\text{3}}\text{Cl}$ and ${\text{AlCl}}_{\text{3}}$.

Figure 3

Conclusion

The given compound does not undergo Friedel-craft alkylation reaction on reaction with ${\text{CH}}_{\text{3}}\text{Cl}$ and ${\text{AlCl}}_{\text{3}}$.

Interpretation Introduction

(d)

Interpretation: The products formed by the Friedel-Craft alkylation of given compound with ${\text{CH}}_{\text{3}}\text{Cl}$ and ${\text{AlCl}}_{\text{3}}$ 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 ${\text{CH}}_{\text{3}}\text{Cl}$ and ${\text{AlCl}}_{\text{3}}$ are drawn below.

Explanation of Solution

The Friedel-craft alkylation of aromatic compound with ${\text{CH}}_{\text{3}}\text{Cl}$ in presence of ${\text{AlCl}}_{\text{3}}$ involves substitution of ${\text{CH}}_{\text{3}}$ 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 $-{\text{NHCOCH}}_{\text{3}}$ group. This group is moderately electron releasing group. Hence, the given compound undergoes Friedel-craft alkylation reaction with ${\text{CH}}_{\text{3}}\text{Cl}$ and ${\text{AlCl}}_{\text{3}}$ as shown in Figure 4.

Figure 4

Conclusion

The products formed by the Friedel-Craft alkylation of given compound with ${\text{CH}}_{\text{3}}\text{Cl}$ and ${\text{AlCl}}_{\text{3}}$ are shown in Figure 4.