An efficient synthesis for the given transformation has to be predicted. The given reaction is shown as, Concept Introduction: Deactivators are electron withdrawing groups attached to the benzenes that have either positive charge or an atom with high electronegativity. They are meta directors. Activators are electron donating groups attached to the benzenes that have either electron density that is able to push into benzene ring or a lone pair of electrons. They are ortho-para directing. Halogens are deactivators that are ortho-para directing. In a reaction, fuming sulfuric acid is used to introduce sulfonic groups in a compound (sulfonation) or sometimes used as blocking groups. Chlorination: A reaction in which a chlorine atom is introduced to the compound. In a reaction, sulfonic acid group can be removed from a compound by treating it with dilute sulfuric acid (desulfonation). Friedel-Crafts Alkylation: This Lewis acid-catalyzed electrophilic aromatic replacement that allows the synthesis of alkylated products by means of the reaction of arenes through alkyl halides or alkenes.

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Answer 1

Question

Chapter 4.9, Problem 4.94P

Interpretation Introduction

Interpretation:

An efficient synthesis for the given transformation has to be predicted. The given reaction is shown as,

Concept Introduction:

Deactivators are electron withdrawing groups attached to the benzenes that have either positive charge or an atom with high electronegativity. They are meta directors.

Activators are electron donating groups attached to the benzenes that have either electron density that is able to push into benzene ring or a lone pair of electrons. They are ortho-para directing.

Halogens are deactivators that are ortho-para directing.

In a reaction, fuming sulfuric acid is used to introduce sulfonic groups in a compound (sulfonation) or sometimes used as blocking groups.

Chlorination: A reaction in which a chlorine atom is introduced to the compound.

In a reaction, sulfonic acid group can be removed from a compound by treating it with dilute sulfuric acid (desulfonation).

Friedel-Crafts Alkylation: This Lewis acid-catalyzed electrophilic aromatic replacement that allows the synthesis of alkylated products by means of the reaction of arenes through alkyl halides or alkenes.

Expert Solution & Answer

Explanation of Solution

The given reaction is shown as,

Organic Chemistry As a Second Language: Second Semester Topics, Chapter 4.9, Problem 4.94P , additional homework tip 4

In the given reaction, a 2-propyl (alkyl) and chloro group has to be introduced to the benzene ring.

The 2-propyl group can be introduced to benzene ring by Friedel-Crafts Alkylation.
Since alkyl group is an activator and it is ortho-para directing. Due to steric effect, chloro group is expected to get substituted at para position on chlorination. For avoiding this, the para position is blocked by performing sulfonation.
The SO3H− substituted compound further undergoes chlorination where a chloro group gets introduced in the ortho position of alkyl group.
The sulfonic acid group present in the compound is then removed by treating it with dilute sulfuric acid.

Therefore, synthesis can be given as follows,

Organic Chemistry As a Second Language: Second Semester Topics, Chapter 4.9, Problem 4.94P , additional homework tip 5

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Complete the following synthesis by selecting from the list of 10 reagents below. Each reagent (or set of reagents) is labeled as a letter. In the answer box, simply place the order of reagents used as uppercase letters. For example, if your synthesis involves using reagent A followed by B,followed by C, and then D, your answer would be: ABCD.

The synthesis shown above can be accomplished in three steps. Select the reagents for each step from the dropdown lists below.

Propose a multi-step synthesis of the target molecule shown at the right, using the starting materials on the left and any other reagents you need. Show the reagents needed for each step and the product of each step. You will need 4 reaction arrows. Remember: Aldehyde + terminal alkyne anion in acid = alcohol

Answer 2

Question

Chapter 4.9, Problem 4.94P

Interpretation Introduction

Interpretation:

An efficient synthesis for the given transformation has to be predicted. The given reaction is shown as,

Concept Introduction:

Deactivators are electron withdrawing groups attached to the benzenes that have either positive charge or an atom with high electronegativity. They are meta directors.

Activators are electron donating groups attached to the benzenes that have either electron density that is able to push into benzene ring or a lone pair of electrons. They are ortho-para directing.

Halogens are deactivators that are ortho-para directing.

In a reaction, fuming sulfuric acid is used to introduce sulfonic groups in a compound (sulfonation) or sometimes used as blocking groups.

Chlorination: A reaction in which a chlorine atom is introduced to the compound.

In a reaction, sulfonic acid group can be removed from a compound by treating it with dilute sulfuric acid (desulfonation).

Friedel-Crafts Alkylation: This Lewis acid-catalyzed electrophilic aromatic replacement that allows the synthesis of alkylated products by means of the reaction of arenes through alkyl halides or alkenes.

Expert Solution & Answer

Explanation of Solution

The given reaction is shown as,

Organic Chemistry As a Second Language: Second Semester Topics, Chapter 4.9, Problem 4.94P , additional homework tip 4

In the given reaction, a 2-propyl (alkyl) and chloro group has to be introduced to the benzene ring.

The 2-propyl group can be introduced to benzene ring by Friedel-Crafts Alkylation.
Since alkyl group is an activator and it is ortho-para directing. Due to steric effect, chloro group is expected to get substituted at para position on chlorination. For avoiding this, the para position is blocked by performing sulfonation.
The SO3H− substituted compound further undergoes chlorination where a chloro group gets introduced in the ortho position of alkyl group.
The sulfonic acid group present in the compound is then removed by treating it with dilute sulfuric acid.

Therefore, synthesis can be given as follows,

Organic Chemistry As a Second Language: Second Semester Topics, Chapter 4.9, Problem 4.94P , additional homework tip 5

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Answer 3

Question

Chapter 4.9, Problem 4.94P

Interpretation Introduction

Interpretation:

An efficient synthesis for the given transformation has to be predicted. The given reaction is shown as,

Concept Introduction:

Deactivators are electron withdrawing groups attached to the benzenes that have either positive charge or an atom with high electronegativity. They are meta directors.

Activators are electron donating groups attached to the benzenes that have either electron density that is able to push into benzene ring or a lone pair of electrons. They are ortho-para directing.

Halogens are deactivators that are ortho-para directing.

In a reaction, fuming sulfuric acid is used to introduce sulfonic groups in a compound (sulfonation) or sometimes used as blocking groups.

Chlorination: A reaction in which a chlorine atom is introduced to the compound.

In a reaction, sulfonic acid group can be removed from a compound by treating it with dilute sulfuric acid (desulfonation).

Friedel-Crafts Alkylation: This Lewis acid-catalyzed electrophilic aromatic replacement that allows the synthesis of alkylated products by means of the reaction of arenes through alkyl halides or alkenes.

Expert Solution & Answer

Explanation of Solution

The given reaction is shown as,

Organic Chemistry As a Second Language: Second Semester Topics, Chapter 4.9, Problem 4.94P , additional homework tip 4

In the given reaction, a 2-propyl (alkyl) and chloro group has to be introduced to the benzene ring.

The 2-propyl group can be introduced to benzene ring by Friedel-Crafts Alkylation.
Since alkyl group is an activator and it is ortho-para directing. Due to steric effect, chloro group is expected to get substituted at para position on chlorination. For avoiding this, the para position is blocked by performing sulfonation.
The SO3H− substituted compound further undergoes chlorination where a chloro group gets introduced in the ortho position of alkyl group.
The sulfonic acid group present in the compound is then removed by treating it with dilute sulfuric acid.

Therefore, synthesis can be given as follows,

Organic Chemistry As a Second Language: Second Semester Topics, Chapter 4.9, Problem 4.94P , additional homework tip 5

Want to see more full solutions like this?

Subscribe now to access step-by-step solutions to millions of textbook problems written by subject matter experts!

Answer 4

Question

Chapter 4.9, Problem 4.94P

Interpretation Introduction

Interpretation:

An efficient synthesis for the given transformation has to be predicted. The given reaction is shown as,

Concept Introduction:

Deactivators are electron withdrawing groups attached to the benzenes that have either positive charge or an atom with high electronegativity. They are meta directors.

Activators are electron donating groups attached to the benzenes that have either electron density that is able to push into benzene ring or a lone pair of electrons. They are ortho-para directing.

Halogens are deactivators that are ortho-para directing.

In a reaction, fuming sulfuric acid is used to introduce sulfonic groups in a compound (sulfonation) or sometimes used as blocking groups.

Chlorination: A reaction in which a chlorine atom is introduced to the compound.

In a reaction, sulfonic acid group can be removed from a compound by treating it with dilute sulfuric acid (desulfonation).

Friedel-Crafts Alkylation: This Lewis acid-catalyzed electrophilic aromatic replacement that allows the synthesis of alkylated products by means of the reaction of arenes through alkyl halides or alkenes.

Expert Solution & Answer

Explanation of Solution

The given reaction is shown as,

Organic Chemistry As a Second Language: Second Semester Topics, Chapter 4.9, Problem 4.94P , additional homework tip 4

In the given reaction, a 2-propyl (alkyl) and chloro group has to be introduced to the benzene ring.

The 2-propyl group can be introduced to benzene ring by Friedel-Crafts Alkylation.
Since alkyl group is an activator and it is ortho-para directing. Due to steric effect, chloro group is expected to get substituted at para position on chlorination. For avoiding this, the para position is blocked by performing sulfonation.
The SO3H− substituted compound further undergoes chlorination where a chloro group gets introduced in the ortho position of alkyl group.
The sulfonic acid group present in the compound is then removed by treating it with dilute sulfuric acid.

Therefore, synthesis can be given as follows,

Organic Chemistry As a Second Language: Second Semester Topics, Chapter 4.9, Problem 4.94P , additional homework tip 5

Want to see more full solutions like this?

Subscribe now to access step-by-step solutions to millions of textbook problems written by subject matter experts!

Answer 5

Chapter 4.9, Problem 4.94P

Interpretation Introduction

Interpretation:

An efficient synthesis for the given transformation has to be predicted. The given reaction is shown as,

Concept Introduction:

Deactivators are electron withdrawing groups attached to the benzenes that have either positive charge or an atom with high electronegativity. They are meta directors.

Activators are electron donating groups attached to the benzenes that have either electron density that is able to push into benzene ring or a lone pair of electrons. They are ortho-para directing.

Halogens are deactivators that are ortho-para directing.

In a reaction, fuming sulfuric acid is used to introduce sulfonic groups in a compound (sulfonation) or sometimes used as blocking groups.

Chlorination: A reaction in which a chlorine atom is introduced to the compound.

In a reaction, sulfonic acid group can be removed from a compound by treating it with dilute sulfuric acid (desulfonation).

Friedel-Crafts Alkylation: This Lewis acid-catalyzed electrophilic aromatic replacement that allows the synthesis of alkylated products by means of the reaction of arenes through alkyl halides or alkenes.

Expert Solution & Answer

Explanation of Solution

The given reaction is shown as,

Organic Chemistry As a Second Language: Second Semester Topics, Chapter 4.9, Problem 4.94P , additional homework tip 4

In the given reaction, a 2-propyl (alkyl) and chloro group has to be introduced to the benzene ring.

The 2-propyl group can be introduced to benzene ring by Friedel-Crafts Alkylation.
Since alkyl group is an activator and it is ortho-para directing. Due to steric effect, chloro group is expected to get substituted at para position on chlorination. For avoiding this, the para position is blocked by performing sulfonation.
The SO3H− substituted compound further undergoes chlorination where a chloro group gets introduced in the ortho position of alkyl group.
The sulfonic acid group present in the compound is then removed by treating it with dilute sulfuric acid.

Therefore, synthesis can be given as follows,

Organic Chemistry As a Second Language: Second Semester Topics, Chapter 4.9, Problem 4.94P , additional homework tip 5

Answer 6

Chapter 4.9, Problem 4.94P

Interpretation Introduction

Interpretation:

An efficient synthesis for the given transformation has to be predicted. The given reaction is shown as,

Concept Introduction:

Deactivators are electron withdrawing groups attached to the benzenes that have either positive charge or an atom with high electronegativity. They are meta directors.

Activators are electron donating groups attached to the benzenes that have either electron density that is able to push into benzene ring or a lone pair of electrons. They are ortho-para directing.

Halogens are deactivators that are ortho-para directing.

In a reaction, fuming sulfuric acid is used to introduce sulfonic groups in a compound (sulfonation) or sometimes used as blocking groups.

Chlorination: A reaction in which a chlorine atom is introduced to the compound.

In a reaction, sulfonic acid group can be removed from a compound by treating it with dilute sulfuric acid (desulfonation).

Friedel-Crafts Alkylation: This Lewis acid-catalyzed electrophilic aromatic replacement that allows the synthesis of alkylated products by means of the reaction of arenes through alkyl halides or alkenes.

Expert Solution & Answer

Explanation of Solution

The given reaction is shown as,

Organic Chemistry As a Second Language: Second Semester Topics, Chapter 4.9, Problem 4.94P , additional homework tip 4

In the given reaction, a 2-propyl (alkyl) and chloro group has to be introduced to the benzene ring.

The 2-propyl group can be introduced to benzene ring by Friedel-Crafts Alkylation.
Since alkyl group is an activator and it is ortho-para directing. Due to steric effect, chloro group is expected to get substituted at para position on chlorination. For avoiding this, the para position is blocked by performing sulfonation.
The SO3H− substituted compound further undergoes chlorination where a chloro group gets introduced in the ortho position of alkyl group.
The sulfonic acid group present in the compound is then removed by treating it with dilute sulfuric acid.

Therefore, synthesis can be given as follows,

Organic Chemistry As a Second Language: Second Semester Topics, Chapter 4.9, Problem 4.94P , additional homework tip 5

Answer 7

Chapter 4.9, Problem 4.94P

Interpretation Introduction

Interpretation:

An efficient synthesis for the given transformation has to be predicted. The given reaction is shown as,

Concept Introduction:

Deactivators are electron withdrawing groups attached to the benzenes that have either positive charge or an atom with high electronegativity. They are meta directors.

Activators are electron donating groups attached to the benzenes that have either electron density that is able to push into benzene ring or a lone pair of electrons. They are ortho-para directing.

Halogens are deactivators that are ortho-para directing.

In a reaction, fuming sulfuric acid is used to introduce sulfonic groups in a compound (sulfonation) or sometimes used as blocking groups.

Chlorination: A reaction in which a chlorine atom is introduced to the compound.

In a reaction, sulfonic acid group can be removed from a compound by treating it with dilute sulfuric acid (desulfonation).

Friedel-Crafts Alkylation: This Lewis acid-catalyzed electrophilic aromatic replacement that allows the synthesis of alkylated products by means of the reaction of arenes through alkyl halides or alkenes.

Answer 8

Expert Solution & Answer

Explanation of Solution

The given reaction is shown as,

Organic Chemistry As a Second Language: Second Semester Topics, Chapter 4.9, Problem 4.94P , additional homework tip 4

In the given reaction, a 2-propyl (alkyl) and chloro group has to be introduced to the benzene ring.

The 2-propyl group can be introduced to benzene ring by Friedel-Crafts Alkylation.
Since alkyl group is an activator and it is ortho-para directing. Due to steric effect, chloro group is expected to get substituted at para position on chlorination. For avoiding this, the para position is blocked by performing sulfonation.
The SO3H− substituted compound further undergoes chlorination where a chloro group gets introduced in the ortho position of alkyl group.
The sulfonic acid group present in the compound is then removed by treating it with dilute sulfuric acid.

Therefore, synthesis can be given as follows,

Organic Chemistry As a Second Language: Second Semester Topics, Chapter 4.9, Problem 4.94P , additional homework tip 5