Chapter 23, Problem 23.34P

Interpretation Introduction

(a)

Interpretation:

The major product with detailed mechanism for the given reaction is to be drawn.

Concept introduction:

The nitration is the electrophilic aromatic substitution reaction. The aromatic ring on reaction with nitric acid or with a mixture of concentrated nitric acid and sulfuric acid undergoes substitution of one of the ring hydrogen by nitro group and forms nitrobenzene, this is called nitration. The electron withdrawing groups deactivates the aromatic ring and decreases the electron density at ortho-para position comparatively than meta position. Thus they are meta directors. That means electrophilic aromatic substitution preferably occurs at meta position.

Answer to Problem 23.34P

The major product with detailed mechanism for the given reaction is:

Explanation of Solution

The given equation is:

In this aromatic compound, the benzene ring has sulfonyl group attached. The sulfonyl group is electron withdrawing and deactivates the ring at ortho-para positions. Thus it is meta director, on nitration using ${\text{HNO}}_{\text{3}}{\text{/H}}_{\text{2}}{\text{SO}}_{\text{4}}$ introduced the nitro group at meta position. The reaction proceeds with formation of nitronium ion ${\text{NO}}_{\text{2}}{}^{+}$. The detailed mechanism for the reaction is as follows:

Conclusion

The product with detailed mechanism is drawn by identifying the substituent at ring is meta director and on nitration introduced nitro group to ring.

Interpretation Introduction

(b)

Interpretation:

The products with detailed mechanisms for the formation of each product are to be drawn.

Concept introduction:

The chlorination of aromatic ring can be carried out by reacting with $\text{Cl}$ in presence of ${\text{FeCl}}_{\text{3}}$. The electron donating groups activates the aromatic ring and increases the electron density at ortho-para position comparatively than meta position. That means electrophilic aromatic substitution preferably occurs at ortho-para position.

Answer to Problem 23.34P

The products with detailed mechanisms for the formation of each product are:

Explanation of Solution

The given equation is:

In this aromatic compound, the benzene ring has ethyl group attached. The ethyl group is electron donating inductively and activates the ring at ortho-para positions. Thus it is ortho-para director, on chlorination with $\text{Cl}$ in presence of ${\text{FeCl}}_{\text{3}}$. introduced the chlorine atom at ortho-para positions and forms two products. The reaction proceeds with formation of ${\text{Cl}}^{+}$ ion. The detailed mechanisms for the formation of ortho and para products are as follows:

Conclusion

The products with detailed mechanisms are drawn by identifying the substituent at ring is ortho-para director and on chlorination introduced chlorine atom to ring.

Interpretation Introduction

(c)

Interpretation:

The products with detailed mechanisms for the formation of each product are to be drawn.

Concept introduction:

The aromatic ring on reaction with acyl chloride in ${\text{AlCl}}_{\text{3}}$ undergoes Friedel-Craft acylation. The electron donating groups activates the aromatic ring and increases the electron density at ortho-para position comparatively than meta position. That means electrophilic aromatic substitution preferably occurs at ortho-para position.

Answer to Problem 23.34P

The products with detailed mechanisms for the formation of each product are:

Explanation of Solution

The given equation is:

In this aromatic compound, the benzene ring has methoxy group attached. The methoxy group is electron donating and activates the ring at ortho-para positions. Thus it is ortho-para director, on Friedel-Craft acylation in presence of ${\text{AlCl}}_{\text{3}}$ introduced the acyl group at ortho-para positions and forms two products. The reaction proceeds with formation of $\text{O=}\stackrel{\text{+}}{\text{C}}\text{-Ph}$ ion. The detailed mechanisms for the formation of ortho and para products are as follows:

Conclusion

The products with detailed mechanisms are drawn by identifying the substituent at ring is ortho-para director and on F.C. acylation introduced acyl group to ring.

Interpretation Introduction

(d)

Interpretation:

The major product with detailed mechanism for the given reaction is to be drawn.

Concept introduction:

The bromination of aromatic ring can be carried out by reacting with $\text{Br}$ in presence of ${\text{FeBr}}_{\text{3}}$. The electron withdrawing groups deactivates the aromatic ring and decreases the electron density at ortho-para position comparatively than meta position. Thus they are meta directors. That means electrophilic aromatic substitution preferably occurs at meta position.

Answer to Problem 23.34P

The major product with detailed mechanism for the given reaction is:

Explanation of Solution

The given equation is:

In this aromatic compound, the benzene ring has carbonyl group attached. The carbonyl group is electron withdrawing and deactivates the ring at ortho-para positions. Thus it is meta director, on bromination with $\text{Br}$ in presence of ${\text{FeBr}}_{\text{3}}$ introduced the bromine atom at meta position. The reaction proceeds with formation of ${\text{Br}}^{+}$ ion. The detailed mechanism for the reaction is as follows:

Conclusion

The product with detailed mechanism is drawn by identifying the substituent at ring is meta director and on bromination introduced bromine atom to ring.

Interpretation Introduction

(e)

Interpretation:

The products with detailed mechanisms for the formation of each product are to be drawn.

Concept introduction:

The nitration is the electrophilic aromatic substitution reaction. The aromatic ring on reaction with nitric acid or with a mixture of concentrated nitric acid and sulfuric acid undergoes substitution of one of the ring hydrogen by nitro group and forms nitrobenzene, this is called nitration. The electron donating groups activates the aromatic ring and increases the electron density at ortho-para position comparatively than meta position. That means electrophilic aromatic substitution preferably occurs at ortho-para position.

Answer to Problem 23.34P

The products with detailed mechanisms for the formation of each product are:

Explanation of Solution

The given equation is:

In this aromatic compound, the benzene ring has methoxy group attached. The methoxy group is electron donating and activates the ring at ortho-para positions. Thus it is ortho-para director, on nitration using $\text{conc}{\text{.HNO}}_{\text{3}}$ introduced the nitro group at meta position. The reaction proceeds with formation of nitronium ion ${\text{NO}}_{\text{2}}{}^{+}$. The detailed mechanisms for the formation of ortho and para products are as follows:

Conclusion

The products with detailed mechanisms are drawn by identifying the substituent at ring is ortho-para director and on nitration introduced nitro group to ring.