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

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Students have asked these similar questions

An expression for the root mean square velocity, vrms, of a gas was derived. Using Maxwell’s velocity distribution, one can also calculate the mean velocity and the most probable velocity (mp) of a collection of molecules. The equations used for these two quantities are vmean=(8RT/πM)1/2 and vmp=(2RT/M)1/2 These values have a fixed relationship to each other.(a) Arrange these three quantities in order of increasing magnitude.(b) Show that the relative magnitudes are independent of the molar mass of the gas.(c) Use the smallest velocity as a reference for establishing the order of magnitude and determine the relationship between the larger and smaller values.

The reaction of solid dimethylhydrazine, (CH3)2N2H2, and liquefied dinitrogen tetroxide, N2O4, has been investigated for use as rocket fuel. The reaction produces the gases carbon dioxide (CO2), nitrogen (N2), and water vapor (H2O), which are ejected in the exhaust gases. In a controlled experiment, solid dimethylhydrazine was reacted with excess dinitrogen tetroxide, and the gases were collected in a closed balloon until a pressure of 2.50 atm and a temperature of 400.0 K were reached.(a) What are the partial pressures of CO2, N2, and H2O?(b) When the CO2 is removed by chemical reaction, what are the partial pressures of the remaining gases?

One liter of chlorine gas at 1 atm and 298 K reacts completely with 1.00 L of nitrogen gas and 2.00 L of oxygen gas at the same temperature and pressure. A single gaseous product is formed, which fills a 2.00 L flask at 1.00 atm and 298 K. Use this information to determine the following characteristics of the product:(a) its empirical formula;(b) its molecular formula;(c) the most favorable Lewis formula based on formal charge arguments (the central atom is N);(d) the shape of the molecule.

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