An efficient synthesis for the given transformations has to be proposed. Concept Introduction : Friedel-Crafts Alkylation: The Friedel-Crafts alkylation involves the electrophilic substitution of alkyl groups on aromatic rings when arenes are treated with alkyl halides in presence of Lewis acids. This reaction is catalyzed by Lewis acids like anhydrous AlCl 3 , FeX 3, ZnCl 2 , BF 3 etc. Sandmeyer reaction : Sandmeyer reactions use copper salts as the reagents. Here, aryldiazonium salt is converted into aryl halides or aryl cyanides by using copper halides or copper cyanides. A compound containing an amino group is treated with sodium nitrite and HCl leading to the formation of diazonium salt . To find: Propose an efficient synthesis for the given transformation (a) Decide the transformation

Question

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Answer 1

Question

Chapter 22.11, Problem 26CC

(a)

Interpretation Introduction

Interpretation: An efficient synthesis for the given transformations has to be proposed.

Concept Introduction:

Friedel-Crafts Alkylation: The Friedel-Crafts alkylation involves the electrophilic substitution of alkyl groups on aromatic rings when arenes are treated with alkyl halides in presence of Lewis acids. This reaction is catalyzed by Lewis acids like anhydrous AlCl₃, FeX_3,ZnCl₂, BF₃ etc.

Sandmeyer reaction: Sandmeyer reactions use copper salts as the reagents. Here, aryldiazonium salt is converted into aryl halides or aryl cyanides by using copper halides or copper cyanides.

A compound containing an amino group is treated with sodium nitrite and HCl leading to the formation of diazonium salt.

To find: Propose an efficient synthesis for the given transformation (a)

Decide the transformation

(b)

Interpretation Introduction

Interpretation: An efficient synthesis for the given transformations has to be proposed.

Concept Introduction:

Electrophilic aromatic substitution: Electrophilic aromatic substitution is a reaction in which the hydrogen atom of an aromatic ring is replaced as a result of an electrophilic attack on the aromatic ring. Here are three general steps to an electrophilic aromatic substitution.

1) Generation of an electrophile

2) Attack of the electrophile on the aromatic ring, creating a resonance-stabilized carbocation called an arenium ion. It loses aromaticity in this step, so the energy of activation is high. Furthermore, this is the rate-determining step of the reaction because of the disruption of aromaticity. The arenium ion is a hybrid resonance structure. There are three general resonance contributors of an arenium ion.

3) Deprotonation of the arenium ion by a weak base to regain aromaticity.

Sandmeyer reaction: Sandmeyer reactions use copper salts as the reagents. Here, aryldiazonium salt is converted into aryl halides or aryl cyanides by using copper halides or copper cyanides.

A compound containing an amino group is treated with sodium nitrite and HCl leading to the formation of diazonium salt.

To find: Propose an efficient synthesis for the given transformation (b)

Apply a retrosynthetic analysis

(c)

Interpretation Introduction

Interpretation: An efficient synthesis for the given transformations has to be proposed.

Concept Introduction:

Friedel–Crafts Acylation: The Friedel–Crafts acylation is the reaction of an arene with acyl chlorides or anhydrides using a strong Lewis acid catalyst. This reaction proceeds via electrophilic aromatic substitution to form monoacylated products.

A compound containing an amino group is treated with sodium nitrite and HCl leading to the formation of diazonium salt.

To find: Propose an efficient synthesis for the given transformation (c)

Apply a retrosynthetic analysis

(d)

Interpretation Introduction

Interpretation: An efficient synthesis for the given transformations has to be proposed.

Concept Introduction:

Friedel-Crafts Alkylation: The Friedel-Crafts alkylation involves the electrophilic substitution of alkyl groups on aromatic rings when arenes are treated with alkyl halides in presence of Lewis acids. This reaction is catalyzed by Lewis acids like anhydrous AlCl₃, FeX_3,ZnCl₂, BF₃ etc.

Sandmeyer reaction: Sandmeyer reactions use copper salts as the reagents. Here, aryldiazonium salt is converted into aryl halides or aryl cyanides by using copper halides or copper cyanides.

A compound containing an amino group is treated with sodium nitrite and HCl leading to the formation of diazonium salt.

To find: Propose an efficient synthesis for the given transformation (d)

Apply a retrosynthetic analysis

(e)

Interpretation Introduction

Interpretation: An efficient synthesis for the given transformations has to be proposed.

Concept Introduction:

Electrophilic aromatic substitution: Electrophilic aromatic substitution is a reaction in which the hydrogen atom of an aromatic ring is replaced as a result of an electrophilic attack on the aromatic ring. Here are three general steps to an electrophilic aromatic substitution.

1) Generation of an electrophile

2) Attack of the electrophile on the aromatic ring, creating a resonance-stabilized carbocation called an arenium ion. It loses aromaticity in this step, so the energy of activation is high. Furthermore, this is the rate-determining step of the reaction because of the disruption of aromaticity. The arenium ion is a hybrid resonance structure. There are three general resonance contributors of an arenium ion.

3) Deprotonation of the arenium ion by a weak base to regain aromaticity.

Schiemann reaction: It is the reaction in which diazonium salt is converted into fluoro group using fluoroboric acid (HBF₄).

A compound containing an amino group is treated with sodium nitrite and HCl leading to the formation of diazonium salt.

To find: Propose an efficient synthesis for the given transformation (e)

Apply a retrosynthetic analysis

(f)

Interpretation Introduction

Interpretation: An efficient synthesis for the given transformations has to be proposed.

Concept Introduction:

Sandmeyer reaction: Sandmeyer reactions use copper salts as the reagents. Here, aryldiazonium salt is converted into aryl halides or aryl cyanides by using copper halides or copper cyanides.

A compound containing an amino group is treated with sodium nitrite and HCl leading to the formation of diazonium salt.

To find: Propose an efficient synthesis for the given transformation (f)

Perform elimination-addition process

Expert Solution & Answer

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See solution

Students have asked these similar questions

Please help with number 6 I got a negative number could that be right?

1,4-Dimethyl-1,3-cyclohexadiene can undergo 1,2- or 1,4-addition with hydrogen halides. (a) 1,2-Addition i. Draw the carbocation intermediate(s) formed during the 1,2-addition of hydrobromic acid to 1,4-dimethyl-1,3-cyclohexadiene. ii. What is the major 1,2-addition product formed during the reaction in (i)? (b) 1,4-Addition i. Draw the carbocation intermediate(s) formed during the 1,4-addition of hydrobromic acid to 1,4-dimethyl-1,3-cyclohexadiene. ii. What is the major 1,4-addition product formed from the reaction in (i)? (c) What is the kinetic product from the reaction of one mole of hydrobromic acid with 1,4-dimethyl-1,3-cyclohexadiene? Explain your reasoning. (d) What is the thermodynamic product from the reaction of one mole of hydrobro-mic acid with 1,4-dimethyl-1,3-cyclohexadiene? Explain your reasoning. (e) What major product will result when 1,4-dimethyl-1,3-cyclohexadiene is treated with one mole of hydrobromic acid at - 78 deg * C ? Explain your reasoning.

Give the product of the bimolecular elimination from each of the isomeric halogenated compounds. Reaction A Reaction B. КОВ CH₂ HotBu +B+ ко HOIBU +Br+ Templates More QQQ Select Cv Templates More Cras QQQ One of these compounds undergoes elimination 50x faster than the other. Which one and why? Reaction A because the conformation needed for elimination places the phenyl groups and to each other Reaction A because the conformation needed for elimination places the phenyl groups gauche to each other. ◇ Reaction B because the conformation needed for elimination places the phenyl groups gach to each other. Reaction B because the conformation needed for elimination places the phenyl groups anti to each other.

Answer 2

Question

Chapter 22.11, Problem 26CC

(a)

Interpretation Introduction

Interpretation: An efficient synthesis for the given transformations has to be proposed.

Concept Introduction:

Friedel-Crafts Alkylation: The Friedel-Crafts alkylation involves the electrophilic substitution of alkyl groups on aromatic rings when arenes are treated with alkyl halides in presence of Lewis acids. This reaction is catalyzed by Lewis acids like anhydrous AlCl₃, FeX_3,ZnCl₂, BF₃ etc.

Sandmeyer reaction: Sandmeyer reactions use copper salts as the reagents. Here, aryldiazonium salt is converted into aryl halides or aryl cyanides by using copper halides or copper cyanides.

A compound containing an amino group is treated with sodium nitrite and HCl leading to the formation of diazonium salt.

To find: Propose an efficient synthesis for the given transformation (a)

Decide the transformation

(b)

Interpretation Introduction

Interpretation: An efficient synthesis for the given transformations has to be proposed.

Concept Introduction:

Electrophilic aromatic substitution: Electrophilic aromatic substitution is a reaction in which the hydrogen atom of an aromatic ring is replaced as a result of an electrophilic attack on the aromatic ring. Here are three general steps to an electrophilic aromatic substitution.

1) Generation of an electrophile

2) Attack of the electrophile on the aromatic ring, creating a resonance-stabilized carbocation called an arenium ion. It loses aromaticity in this step, so the energy of activation is high. Furthermore, this is the rate-determining step of the reaction because of the disruption of aromaticity. The arenium ion is a hybrid resonance structure. There are three general resonance contributors of an arenium ion.

3) Deprotonation of the arenium ion by a weak base to regain aromaticity.

Sandmeyer reaction: Sandmeyer reactions use copper salts as the reagents. Here, aryldiazonium salt is converted into aryl halides or aryl cyanides by using copper halides or copper cyanides.

A compound containing an amino group is treated with sodium nitrite and HCl leading to the formation of diazonium salt.

To find: Propose an efficient synthesis for the given transformation (b)

Apply a retrosynthetic analysis

(c)

Interpretation Introduction

Interpretation: An efficient synthesis for the given transformations has to be proposed.

Concept Introduction:

Friedel–Crafts Acylation: The Friedel–Crafts acylation is the reaction of an arene with acyl chlorides or anhydrides using a strong Lewis acid catalyst. This reaction proceeds via electrophilic aromatic substitution to form monoacylated products.

A compound containing an amino group is treated with sodium nitrite and HCl leading to the formation of diazonium salt.

To find: Propose an efficient synthesis for the given transformation (c)

Apply a retrosynthetic analysis

(d)

Interpretation Introduction

Interpretation: An efficient synthesis for the given transformations has to be proposed.

Concept Introduction:

Friedel-Crafts Alkylation: The Friedel-Crafts alkylation involves the electrophilic substitution of alkyl groups on aromatic rings when arenes are treated with alkyl halides in presence of Lewis acids. This reaction is catalyzed by Lewis acids like anhydrous AlCl₃, FeX_3,ZnCl₂, BF₃ etc.

Sandmeyer reaction: Sandmeyer reactions use copper salts as the reagents. Here, aryldiazonium salt is converted into aryl halides or aryl cyanides by using copper halides or copper cyanides.

A compound containing an amino group is treated with sodium nitrite and HCl leading to the formation of diazonium salt.

To find: Propose an efficient synthesis for the given transformation (d)

Apply a retrosynthetic analysis

(e)

Interpretation Introduction

Interpretation: An efficient synthesis for the given transformations has to be proposed.

Concept Introduction:

Electrophilic aromatic substitution: Electrophilic aromatic substitution is a reaction in which the hydrogen atom of an aromatic ring is replaced as a result of an electrophilic attack on the aromatic ring. Here are three general steps to an electrophilic aromatic substitution.

1) Generation of an electrophile

2) Attack of the electrophile on the aromatic ring, creating a resonance-stabilized carbocation called an arenium ion. It loses aromaticity in this step, so the energy of activation is high. Furthermore, this is the rate-determining step of the reaction because of the disruption of aromaticity. The arenium ion is a hybrid resonance structure. There are three general resonance contributors of an arenium ion.

3) Deprotonation of the arenium ion by a weak base to regain aromaticity.

Schiemann reaction: It is the reaction in which diazonium salt is converted into fluoro group using fluoroboric acid (HBF₄).

A compound containing an amino group is treated with sodium nitrite and HCl leading to the formation of diazonium salt.

To find: Propose an efficient synthesis for the given transformation (e)

Apply a retrosynthetic analysis

(f)

Interpretation Introduction

Interpretation: An efficient synthesis for the given transformations has to be proposed.

Concept Introduction:

Sandmeyer reaction: Sandmeyer reactions use copper salts as the reagents. Here, aryldiazonium salt is converted into aryl halides or aryl cyanides by using copper halides or copper cyanides.

A compound containing an amino group is treated with sodium nitrite and HCl leading to the formation of diazonium salt.

To find: Propose an efficient synthesis for the given transformation (f)

Perform elimination-addition process

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

Answer 3

Question

Chapter 22.11, Problem 26CC

(a)

Interpretation Introduction

Interpretation: An efficient synthesis for the given transformations has to be proposed.

Concept Introduction:

Friedel-Crafts Alkylation: The Friedel-Crafts alkylation involves the electrophilic substitution of alkyl groups on aromatic rings when arenes are treated with alkyl halides in presence of Lewis acids. This reaction is catalyzed by Lewis acids like anhydrous AlCl₃, FeX_3,ZnCl₂, BF₃ etc.

Sandmeyer reaction: Sandmeyer reactions use copper salts as the reagents. Here, aryldiazonium salt is converted into aryl halides or aryl cyanides by using copper halides or copper cyanides.

A compound containing an amino group is treated with sodium nitrite and HCl leading to the formation of diazonium salt.

To find: Propose an efficient synthesis for the given transformation (a)

Decide the transformation

(b)

Interpretation Introduction

Interpretation: An efficient synthesis for the given transformations has to be proposed.

Concept Introduction:

Electrophilic aromatic substitution: Electrophilic aromatic substitution is a reaction in which the hydrogen atom of an aromatic ring is replaced as a result of an electrophilic attack on the aromatic ring. Here are three general steps to an electrophilic aromatic substitution.

1) Generation of an electrophile

2) Attack of the electrophile on the aromatic ring, creating a resonance-stabilized carbocation called an arenium ion. It loses aromaticity in this step, so the energy of activation is high. Furthermore, this is the rate-determining step of the reaction because of the disruption of aromaticity. The arenium ion is a hybrid resonance structure. There are three general resonance contributors of an arenium ion.

3) Deprotonation of the arenium ion by a weak base to regain aromaticity.

Sandmeyer reaction: Sandmeyer reactions use copper salts as the reagents. Here, aryldiazonium salt is converted into aryl halides or aryl cyanides by using copper halides or copper cyanides.

A compound containing an amino group is treated with sodium nitrite and HCl leading to the formation of diazonium salt.

To find: Propose an efficient synthesis for the given transformation (b)

Apply a retrosynthetic analysis

(c)

Interpretation Introduction

Interpretation: An efficient synthesis for the given transformations has to be proposed.

Concept Introduction:

Friedel–Crafts Acylation: The Friedel–Crafts acylation is the reaction of an arene with acyl chlorides or anhydrides using a strong Lewis acid catalyst. This reaction proceeds via electrophilic aromatic substitution to form monoacylated products.

A compound containing an amino group is treated with sodium nitrite and HCl leading to the formation of diazonium salt.

To find: Propose an efficient synthesis for the given transformation (c)

Apply a retrosynthetic analysis

(d)

Interpretation Introduction

Interpretation: An efficient synthesis for the given transformations has to be proposed.

Concept Introduction:

Friedel-Crafts Alkylation: The Friedel-Crafts alkylation involves the electrophilic substitution of alkyl groups on aromatic rings when arenes are treated with alkyl halides in presence of Lewis acids. This reaction is catalyzed by Lewis acids like anhydrous AlCl₃, FeX_3,ZnCl₂, BF₃ etc.

Sandmeyer reaction: Sandmeyer reactions use copper salts as the reagents. Here, aryldiazonium salt is converted into aryl halides or aryl cyanides by using copper halides or copper cyanides.

A compound containing an amino group is treated with sodium nitrite and HCl leading to the formation of diazonium salt.

To find: Propose an efficient synthesis for the given transformation (d)

Apply a retrosynthetic analysis

(e)

Interpretation Introduction

Interpretation: An efficient synthesis for the given transformations has to be proposed.

Concept Introduction:

Electrophilic aromatic substitution: Electrophilic aromatic substitution is a reaction in which the hydrogen atom of an aromatic ring is replaced as a result of an electrophilic attack on the aromatic ring. Here are three general steps to an electrophilic aromatic substitution.

1) Generation of an electrophile

2) Attack of the electrophile on the aromatic ring, creating a resonance-stabilized carbocation called an arenium ion. It loses aromaticity in this step, so the energy of activation is high. Furthermore, this is the rate-determining step of the reaction because of the disruption of aromaticity. The arenium ion is a hybrid resonance structure. There are three general resonance contributors of an arenium ion.

3) Deprotonation of the arenium ion by a weak base to regain aromaticity.

Schiemann reaction: It is the reaction in which diazonium salt is converted into fluoro group using fluoroboric acid (HBF₄).

A compound containing an amino group is treated with sodium nitrite and HCl leading to the formation of diazonium salt.

To find: Propose an efficient synthesis for the given transformation (e)

Apply a retrosynthetic analysis

(f)

Interpretation Introduction

Interpretation: An efficient synthesis for the given transformations has to be proposed.

Concept Introduction:

Sandmeyer reaction: Sandmeyer reactions use copper salts as the reagents. Here, aryldiazonium salt is converted into aryl halides or aryl cyanides by using copper halides or copper cyanides.

A compound containing an amino group is treated with sodium nitrite and HCl leading to the formation of diazonium salt.

To find: Propose an efficient synthesis for the given transformation (f)

Perform elimination-addition process

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

Answer 4

Question

Chapter 22.11, Problem 26CC

(a)

Interpretation Introduction

Interpretation: An efficient synthesis for the given transformations has to be proposed.

Concept Introduction:

Friedel-Crafts Alkylation: The Friedel-Crafts alkylation involves the electrophilic substitution of alkyl groups on aromatic rings when arenes are treated with alkyl halides in presence of Lewis acids. This reaction is catalyzed by Lewis acids like anhydrous AlCl₃, FeX_3,ZnCl₂, BF₃ etc.

Sandmeyer reaction: Sandmeyer reactions use copper salts as the reagents. Here, aryldiazonium salt is converted into aryl halides or aryl cyanides by using copper halides or copper cyanides.

A compound containing an amino group is treated with sodium nitrite and HCl leading to the formation of diazonium salt.

To find: Propose an efficient synthesis for the given transformation (a)

Decide the transformation

(b)

Interpretation Introduction

Interpretation: An efficient synthesis for the given transformations has to be proposed.

Concept Introduction:

Electrophilic aromatic substitution: Electrophilic aromatic substitution is a reaction in which the hydrogen atom of an aromatic ring is replaced as a result of an electrophilic attack on the aromatic ring. Here are three general steps to an electrophilic aromatic substitution.

1) Generation of an electrophile

2) Attack of the electrophile on the aromatic ring, creating a resonance-stabilized carbocation called an arenium ion. It loses aromaticity in this step, so the energy of activation is high. Furthermore, this is the rate-determining step of the reaction because of the disruption of aromaticity. The arenium ion is a hybrid resonance structure. There are three general resonance contributors of an arenium ion.

3) Deprotonation of the arenium ion by a weak base to regain aromaticity.

Sandmeyer reaction: Sandmeyer reactions use copper salts as the reagents. Here, aryldiazonium salt is converted into aryl halides or aryl cyanides by using copper halides or copper cyanides.

A compound containing an amino group is treated with sodium nitrite and HCl leading to the formation of diazonium salt.

To find: Propose an efficient synthesis for the given transformation (b)

Apply a retrosynthetic analysis

(c)

Interpretation Introduction

Interpretation: An efficient synthesis for the given transformations has to be proposed.

Concept Introduction:

Friedel–Crafts Acylation: The Friedel–Crafts acylation is the reaction of an arene with acyl chlorides or anhydrides using a strong Lewis acid catalyst. This reaction proceeds via electrophilic aromatic substitution to form monoacylated products.

A compound containing an amino group is treated with sodium nitrite and HCl leading to the formation of diazonium salt.

To find: Propose an efficient synthesis for the given transformation (c)

Apply a retrosynthetic analysis

(d)

Interpretation Introduction

Interpretation: An efficient synthesis for the given transformations has to be proposed.

Concept Introduction:

Friedel-Crafts Alkylation: The Friedel-Crafts alkylation involves the electrophilic substitution of alkyl groups on aromatic rings when arenes are treated with alkyl halides in presence of Lewis acids. This reaction is catalyzed by Lewis acids like anhydrous AlCl₃, FeX_3,ZnCl₂, BF₃ etc.

Sandmeyer reaction: Sandmeyer reactions use copper salts as the reagents. Here, aryldiazonium salt is converted into aryl halides or aryl cyanides by using copper halides or copper cyanides.

A compound containing an amino group is treated with sodium nitrite and HCl leading to the formation of diazonium salt.

To find: Propose an efficient synthesis for the given transformation (d)

Apply a retrosynthetic analysis

(e)

Interpretation Introduction

Interpretation: An efficient synthesis for the given transformations has to be proposed.

Concept Introduction:

Electrophilic aromatic substitution: Electrophilic aromatic substitution is a reaction in which the hydrogen atom of an aromatic ring is replaced as a result of an electrophilic attack on the aromatic ring. Here are three general steps to an electrophilic aromatic substitution.

1) Generation of an electrophile

2) Attack of the electrophile on the aromatic ring, creating a resonance-stabilized carbocation called an arenium ion. It loses aromaticity in this step, so the energy of activation is high. Furthermore, this is the rate-determining step of the reaction because of the disruption of aromaticity. The arenium ion is a hybrid resonance structure. There are three general resonance contributors of an arenium ion.

3) Deprotonation of the arenium ion by a weak base to regain aromaticity.

Schiemann reaction: It is the reaction in which diazonium salt is converted into fluoro group using fluoroboric acid (HBF₄).

A compound containing an amino group is treated with sodium nitrite and HCl leading to the formation of diazonium salt.

To find: Propose an efficient synthesis for the given transformation (e)

Apply a retrosynthetic analysis

(f)

Interpretation Introduction

Interpretation: An efficient synthesis for the given transformations has to be proposed.

Concept Introduction:

Sandmeyer reaction: Sandmeyer reactions use copper salts as the reagents. Here, aryldiazonium salt is converted into aryl halides or aryl cyanides by using copper halides or copper cyanides.

A compound containing an amino group is treated with sodium nitrite and HCl leading to the formation of diazonium salt.

To find: Propose an efficient synthesis for the given transformation (f)

Perform elimination-addition process

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

Answer 5

Chapter 22.11, Problem 26CC

(a)

Interpretation Introduction

Interpretation: An efficient synthesis for the given transformations has to be proposed.

Concept Introduction:

Friedel-Crafts Alkylation: The Friedel-Crafts alkylation involves the electrophilic substitution of alkyl groups on aromatic rings when arenes are treated with alkyl halides in presence of Lewis acids. This reaction is catalyzed by Lewis acids like anhydrous AlCl₃, FeX_3,ZnCl₂, BF₃ etc.

Sandmeyer reaction: Sandmeyer reactions use copper salts as the reagents. Here, aryldiazonium salt is converted into aryl halides or aryl cyanides by using copper halides or copper cyanides.

A compound containing an amino group is treated with sodium nitrite and HCl leading to the formation of diazonium salt.

To find: Propose an efficient synthesis for the given transformation (a)

Decide the transformation

(b)

Interpretation Introduction

Interpretation: An efficient synthesis for the given transformations has to be proposed.

Concept Introduction:

Electrophilic aromatic substitution: Electrophilic aromatic substitution is a reaction in which the hydrogen atom of an aromatic ring is replaced as a result of an electrophilic attack on the aromatic ring. Here are three general steps to an electrophilic aromatic substitution.

1) Generation of an electrophile

2) Attack of the electrophile on the aromatic ring, creating a resonance-stabilized carbocation called an arenium ion. It loses aromaticity in this step, so the energy of activation is high. Furthermore, this is the rate-determining step of the reaction because of the disruption of aromaticity. The arenium ion is a hybrid resonance structure. There are three general resonance contributors of an arenium ion.

3) Deprotonation of the arenium ion by a weak base to regain aromaticity.

Sandmeyer reaction: Sandmeyer reactions use copper salts as the reagents. Here, aryldiazonium salt is converted into aryl halides or aryl cyanides by using copper halides or copper cyanides.

A compound containing an amino group is treated with sodium nitrite and HCl leading to the formation of diazonium salt.

To find: Propose an efficient synthesis for the given transformation (b)

Apply a retrosynthetic analysis

(c)

Interpretation Introduction

Interpretation: An efficient synthesis for the given transformations has to be proposed.

Concept Introduction:

Friedel–Crafts Acylation: The Friedel–Crafts acylation is the reaction of an arene with acyl chlorides or anhydrides using a strong Lewis acid catalyst. This reaction proceeds via electrophilic aromatic substitution to form monoacylated products.

A compound containing an amino group is treated with sodium nitrite and HCl leading to the formation of diazonium salt.

To find: Propose an efficient synthesis for the given transformation (c)

Apply a retrosynthetic analysis

(d)

Interpretation Introduction

Interpretation: An efficient synthesis for the given transformations has to be proposed.

Concept Introduction:

Friedel-Crafts Alkylation: The Friedel-Crafts alkylation involves the electrophilic substitution of alkyl groups on aromatic rings when arenes are treated with alkyl halides in presence of Lewis acids. This reaction is catalyzed by Lewis acids like anhydrous AlCl₃, FeX_3,ZnCl₂, BF₃ etc.

Sandmeyer reaction: Sandmeyer reactions use copper salts as the reagents. Here, aryldiazonium salt is converted into aryl halides or aryl cyanides by using copper halides or copper cyanides.

A compound containing an amino group is treated with sodium nitrite and HCl leading to the formation of diazonium salt.

To find: Propose an efficient synthesis for the given transformation (d)

Apply a retrosynthetic analysis

(e)

Interpretation Introduction

Interpretation: An efficient synthesis for the given transformations has to be proposed.

Concept Introduction:

Electrophilic aromatic substitution: Electrophilic aromatic substitution is a reaction in which the hydrogen atom of an aromatic ring is replaced as a result of an electrophilic attack on the aromatic ring. Here are three general steps to an electrophilic aromatic substitution.

1) Generation of an electrophile

2) Attack of the electrophile on the aromatic ring, creating a resonance-stabilized carbocation called an arenium ion. It loses aromaticity in this step, so the energy of activation is high. Furthermore, this is the rate-determining step of the reaction because of the disruption of aromaticity. The arenium ion is a hybrid resonance structure. There are three general resonance contributors of an arenium ion.

3) Deprotonation of the arenium ion by a weak base to regain aromaticity.

Schiemann reaction: It is the reaction in which diazonium salt is converted into fluoro group using fluoroboric acid (HBF₄).

A compound containing an amino group is treated with sodium nitrite and HCl leading to the formation of diazonium salt.

To find: Propose an efficient synthesis for the given transformation (e)

Apply a retrosynthetic analysis

(f)

Interpretation Introduction

Interpretation: An efficient synthesis for the given transformations has to be proposed.

Concept Introduction:

Sandmeyer reaction: Sandmeyer reactions use copper salts as the reagents. Here, aryldiazonium salt is converted into aryl halides or aryl cyanides by using copper halides or copper cyanides.

A compound containing an amino group is treated with sodium nitrite and HCl leading to the formation of diazonium salt.

To find: Propose an efficient synthesis for the given transformation (f)

Perform elimination-addition process

Answer 6

Chapter 22.11, Problem 26CC

(a)

Interpretation Introduction

Interpretation: An efficient synthesis for the given transformations has to be proposed.

Concept Introduction:

Friedel-Crafts Alkylation: The Friedel-Crafts alkylation involves the electrophilic substitution of alkyl groups on aromatic rings when arenes are treated with alkyl halides in presence of Lewis acids. This reaction is catalyzed by Lewis acids like anhydrous AlCl₃, FeX_3,ZnCl₂, BF₃ etc.

Sandmeyer reaction: Sandmeyer reactions use copper salts as the reagents. Here, aryldiazonium salt is converted into aryl halides or aryl cyanides by using copper halides or copper cyanides.

A compound containing an amino group is treated with sodium nitrite and HCl leading to the formation of diazonium salt.

To find: Propose an efficient synthesis for the given transformation (a)

Decide the transformation

Answer 7

Chapter 22.11, Problem 26CC

(a)

Interpretation Introduction

Interpretation: An efficient synthesis for the given transformations has to be proposed.

Concept Introduction:

Friedel-Crafts Alkylation: The Friedel-Crafts alkylation involves the electrophilic substitution of alkyl groups on aromatic rings when arenes are treated with alkyl halides in presence of Lewis acids. This reaction is catalyzed by Lewis acids like anhydrous AlCl₃, FeX_3,ZnCl₂, BF₃ etc.

Sandmeyer reaction: Sandmeyer reactions use copper salts as the reagents. Here, aryldiazonium salt is converted into aryl halides or aryl cyanides by using copper halides or copper cyanides.

A compound containing an amino group is treated with sodium nitrite and HCl leading to the formation of diazonium salt.

To find: Propose an efficient synthesis for the given transformation (a)

Decide the transformation

Answer 8

(b)

Interpretation Introduction

Interpretation: An efficient synthesis for the given transformations has to be proposed.

Concept Introduction:

Electrophilic aromatic substitution: Electrophilic aromatic substitution is a reaction in which the hydrogen atom of an aromatic ring is replaced as a result of an electrophilic attack on the aromatic ring. Here are three general steps to an electrophilic aromatic substitution.

1) Generation of an electrophile

2) Attack of the electrophile on the aromatic ring, creating a resonance-stabilized carbocation called an arenium ion. It loses aromaticity in this step, so the energy of activation is high. Furthermore, this is the rate-determining step of the reaction because of the disruption of aromaticity. The arenium ion is a hybrid resonance structure. There are three general resonance contributors of an arenium ion.

3) Deprotonation of the arenium ion by a weak base to regain aromaticity.

Sandmeyer reaction: Sandmeyer reactions use copper salts as the reagents. Here, aryldiazonium salt is converted into aryl halides or aryl cyanides by using copper halides or copper cyanides.

A compound containing an amino group is treated with sodium nitrite and HCl leading to the formation of diazonium salt.

To find: Propose an efficient synthesis for the given transformation (b)

Apply a retrosynthetic analysis

Answer 9

(b)

Interpretation Introduction

Interpretation: An efficient synthesis for the given transformations has to be proposed.

Concept Introduction:

Electrophilic aromatic substitution: Electrophilic aromatic substitution is a reaction in which the hydrogen atom of an aromatic ring is replaced as a result of an electrophilic attack on the aromatic ring. Here are three general steps to an electrophilic aromatic substitution.

1) Generation of an electrophile

2) Attack of the electrophile on the aromatic ring, creating a resonance-stabilized carbocation called an arenium ion. It loses aromaticity in this step, so the energy of activation is high. Furthermore, this is the rate-determining step of the reaction because of the disruption of aromaticity. The arenium ion is a hybrid resonance structure. There are three general resonance contributors of an arenium ion.

3) Deprotonation of the arenium ion by a weak base to regain aromaticity.

Sandmeyer reaction: Sandmeyer reactions use copper salts as the reagents. Here, aryldiazonium salt is converted into aryl halides or aryl cyanides by using copper halides or copper cyanides.

A compound containing an amino group is treated with sodium nitrite and HCl leading to the formation of diazonium salt.

To find: Propose an efficient synthesis for the given transformation (b)

Apply a retrosynthetic analysis

Answer 10

(c)

Interpretation Introduction

Interpretation: An efficient synthesis for the given transformations has to be proposed.

Concept Introduction:

Friedel–Crafts Acylation: The Friedel–Crafts acylation is the reaction of an arene with acyl chlorides or anhydrides using a strong Lewis acid catalyst. This reaction proceeds via electrophilic aromatic substitution to form monoacylated products.

A compound containing an amino group is treated with sodium nitrite and HCl leading to the formation of diazonium salt.

To find: Propose an efficient synthesis for the given transformation (c)

Apply a retrosynthetic analysis

Answer 11

(c)

Interpretation Introduction

Interpretation: An efficient synthesis for the given transformations has to be proposed.

Concept Introduction:

Friedel–Crafts Acylation: The Friedel–Crafts acylation is the reaction of an arene with acyl chlorides or anhydrides using a strong Lewis acid catalyst. This reaction proceeds via electrophilic aromatic substitution to form monoacylated products.

A compound containing an amino group is treated with sodium nitrite and HCl leading to the formation of diazonium salt.

To find: Propose an efficient synthesis for the given transformation (c)

Apply a retrosynthetic analysis

Answer 12

(d)

Interpretation Introduction

Interpretation: An efficient synthesis for the given transformations has to be proposed.

Concept Introduction:

Friedel-Crafts Alkylation: The Friedel-Crafts alkylation involves the electrophilic substitution of alkyl groups on aromatic rings when arenes are treated with alkyl halides in presence of Lewis acids. This reaction is catalyzed by Lewis acids like anhydrous AlCl₃, FeX_3,ZnCl₂, BF₃ etc.

Sandmeyer reaction: Sandmeyer reactions use copper salts as the reagents. Here, aryldiazonium salt is converted into aryl halides or aryl cyanides by using copper halides or copper cyanides.

A compound containing an amino group is treated with sodium nitrite and HCl leading to the formation of diazonium salt.

To find: Propose an efficient synthesis for the given transformation (d)

Apply a retrosynthetic analysis

Answer 13

(d)

Interpretation Introduction

Interpretation: An efficient synthesis for the given transformations has to be proposed.

Concept Introduction:

Friedel-Crafts Alkylation: The Friedel-Crafts alkylation involves the electrophilic substitution of alkyl groups on aromatic rings when arenes are treated with alkyl halides in presence of Lewis acids. This reaction is catalyzed by Lewis acids like anhydrous AlCl₃, FeX_3,ZnCl₂, BF₃ etc.

Sandmeyer reaction: Sandmeyer reactions use copper salts as the reagents. Here, aryldiazonium salt is converted into aryl halides or aryl cyanides by using copper halides or copper cyanides.

A compound containing an amino group is treated with sodium nitrite and HCl leading to the formation of diazonium salt.

To find: Propose an efficient synthesis for the given transformation (d)

Apply a retrosynthetic analysis

Answer 14

(e)

Interpretation Introduction

Interpretation: An efficient synthesis for the given transformations has to be proposed.

Concept Introduction:

Electrophilic aromatic substitution: Electrophilic aromatic substitution is a reaction in which the hydrogen atom of an aromatic ring is replaced as a result of an electrophilic attack on the aromatic ring. Here are three general steps to an electrophilic aromatic substitution.

1) Generation of an electrophile

2) Attack of the electrophile on the aromatic ring, creating a resonance-stabilized carbocation called an arenium ion. It loses aromaticity in this step, so the energy of activation is high. Furthermore, this is the rate-determining step of the reaction because of the disruption of aromaticity. The arenium ion is a hybrid resonance structure. There are three general resonance contributors of an arenium ion.

3) Deprotonation of the arenium ion by a weak base to regain aromaticity.

Schiemann reaction: It is the reaction in which diazonium salt is converted into fluoro group using fluoroboric acid (HBF₄).

A compound containing an amino group is treated with sodium nitrite and HCl leading to the formation of diazonium salt.

To find: Propose an efficient synthesis for the given transformation (e)

Apply a retrosynthetic analysis

Answer 15

(e)

Interpretation Introduction

Interpretation: An efficient synthesis for the given transformations has to be proposed.

Concept Introduction:

Electrophilic aromatic substitution: Electrophilic aromatic substitution is a reaction in which the hydrogen atom of an aromatic ring is replaced as a result of an electrophilic attack on the aromatic ring. Here are three general steps to an electrophilic aromatic substitution.

1) Generation of an electrophile

2) Attack of the electrophile on the aromatic ring, creating a resonance-stabilized carbocation called an arenium ion. It loses aromaticity in this step, so the energy of activation is high. Furthermore, this is the rate-determining step of the reaction because of the disruption of aromaticity. The arenium ion is a hybrid resonance structure. There are three general resonance contributors of an arenium ion.

3) Deprotonation of the arenium ion by a weak base to regain aromaticity.

Schiemann reaction: It is the reaction in which diazonium salt is converted into fluoro group using fluoroboric acid (HBF₄).

A compound containing an amino group is treated with sodium nitrite and HCl leading to the formation of diazonium salt.

To find: Propose an efficient synthesis for the given transformation (e)

Apply a retrosynthetic analysis

Answer 16

(f)

Interpretation Introduction

Interpretation: An efficient synthesis for the given transformations has to be proposed.

Concept Introduction:

Sandmeyer reaction: Sandmeyer reactions use copper salts as the reagents. Here, aryldiazonium salt is converted into aryl halides or aryl cyanides by using copper halides or copper cyanides.

A compound containing an amino group is treated with sodium nitrite and HCl leading to the formation of diazonium salt.

To find: Propose an efficient synthesis for the given transformation (f)

Perform elimination-addition process

Answer 17

(f)

Interpretation Introduction

Interpretation: An efficient synthesis for the given transformations has to be proposed.

Concept Introduction:

Sandmeyer reaction: Sandmeyer reactions use copper salts as the reagents. Here, aryldiazonium salt is converted into aryl halides or aryl cyanides by using copper halides or copper cyanides.

A compound containing an amino group is treated with sodium nitrite and HCl leading to the formation of diazonium salt.

To find: Propose an efficient synthesis for the given transformation (f)

Perform elimination-addition process

Answer 18

Expert Solution & Answer

Answer 19

Expert Solution & Answer

Answer 20

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Answer 21

Ch. 22.2 - Prob. 1LTS Ch. 22.2 - Prob. 1PTS Ch. 22.2 - Prob. 2PTS Ch. 22.3 - Prob. 4CC Ch. 22.3 - Prob. 5CC Ch. 22.3 - Prob. 6CC Ch. 22.3 - Prob. 7CC Ch. 22.3 - Prob. 8CC Ch. 22.3 - Prob. 9CC Ch. 22.4 - Prob. 10CC

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Chapter 22 Solutions