The mechanism for the formation of compound A has to be proposed. Concept Introduction: Diels-Alder reaction: It is the reaction of conjugated dienes with double or triple bonded compounds which are known as “dienophiles” . The reaction is a 4 + 2 cycloaddition reaction that results in the formation of a six membered cyclic product which is known as “adduct” . Example: This mechanism shown that three π -bonds are broken to form two new σ -bonds and a new π -bond. Formation of Benzyne: The elimination of two halogens from the halobenzene forms the most reactive neutral intermediate with triple bond which is known as Benzyne intermediate. Diels-Alder reaction with Benzyne intermediate: The reaction of Benzyne with furan serves as an example for this reaction: Benzyne is an extremely reactive species because of the presence of triple bond in it. It undergoes Diels-Alder reaction in which it acts as dienophile and reacts with furan which acts a diene. The resulted product will be a tricyclic product which is known as Diels-Alder adduct.

Question

Want to see the full answer?

Answer 1

Question

Chapter 20, Problem 20.47P

(a)

Interpretation Introduction

Interpretation: The mechanism for the formation of compound A has to be proposed.

Concept Introduction:

Diels-Alder reaction:

It is the reaction of conjugated dienes with double or triple bonded compounds which are known as “dienophiles”. The reaction is a 4+2 cycloaddition reaction that results in the formation of a six membered cyclic product which is known as “adduct”.

Example:

This mechanism shown that three π-bonds are broken to form two new σ -bonds and a new π-bond.

Formation of Benzyne:

The elimination of two halogens from the halobenzene forms the most reactive neutral intermediate with triple bond which is known as Benzyne intermediate.

Diels-Alder reaction with Benzyne intermediate:

The reaction of Benzyne with furan serves as an example for this reaction:

Benzyne is an extremely reactive species because of the presence of triple bond in it. It undergoes Diels-Alder reaction in which it acts as dienophile and reacts with furan which acts a diene. The resulted product will be a tricyclic product which is known as Diels-Alder adduct.

(b)

Interpretation Introduction

Interpretation: Using the given sources, the conversion of compound (A) into Tolciclate has to be shown.

Concept Introduction:

Acidic hydrolysis of ether:

Ether on hydrolysis gets converted into two moles of alcohols of same type in the case of symmetrical ether and of different types in the case of unsymmetrical ether. .

General scheme for symmetrical ether:

General scheme for unsymmetrical ether:

Tosylation reaction:

When an alcohol is treated with any tosyl chloride (methane sulfonyl chloride) it gets converted into tosylated product and this reaction is called as Tosylation reaction which is shown below:

The reaction of acetyl chloride with amine:

The acyl group of acetyl chloride is very reactive and the chloride group attached to it is a good leaving group. The nucleophile from amine attacks the carbonyl carbon of the acetylchloride to form N- methylacetamide. The chloride group leaves and gets attached to hydrogen of the amine and leaves as hydrochloric acid.

The reaction is:

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

Students have asked these similar questions

How could you convert butanenitrile into the following compounds? Write each step showing the reagents needed.(a) 1-Butanol(b) Butylamine(c) 2-Methyl-3-hexanone

Reaction of p-nitroaniline with sodium nitrite and hydrochloric acid at 0 °C, followed by treatment with N,N-diethylaniline.

How could you convert butanenitrile into the following compounds? Write each step showing the reagents needed. (a) 1-Butanol (b) Butylamine

Answer 2

Question

Chapter 20, Problem 20.47P

(a)

Interpretation Introduction

Interpretation: The mechanism for the formation of compound A has to be proposed.

Concept Introduction:

Diels-Alder reaction:

It is the reaction of conjugated dienes with double or triple bonded compounds which are known as “dienophiles”. The reaction is a 4+2 cycloaddition reaction that results in the formation of a six membered cyclic product which is known as “adduct”.

Example:

This mechanism shown that three π-bonds are broken to form two new σ -bonds and a new π-bond.

Formation of Benzyne:

The elimination of two halogens from the halobenzene forms the most reactive neutral intermediate with triple bond which is known as Benzyne intermediate.

Diels-Alder reaction with Benzyne intermediate:

The reaction of Benzyne with furan serves as an example for this reaction:

Benzyne is an extremely reactive species because of the presence of triple bond in it. It undergoes Diels-Alder reaction in which it acts as dienophile and reacts with furan which acts a diene. The resulted product will be a tricyclic product which is known as Diels-Alder adduct.

(b)

Interpretation Introduction

Interpretation: Using the given sources, the conversion of compound (A) into Tolciclate has to be shown.

Concept Introduction:

Acidic hydrolysis of ether:

Ether on hydrolysis gets converted into two moles of alcohols of same type in the case of symmetrical ether and of different types in the case of unsymmetrical ether. .

General scheme for symmetrical ether:

General scheme for unsymmetrical ether:

Tosylation reaction:

When an alcohol is treated with any tosyl chloride (methane sulfonyl chloride) it gets converted into tosylated product and this reaction is called as Tosylation reaction which is shown below:

The reaction of acetyl chloride with amine:

The acyl group of acetyl chloride is very reactive and the chloride group attached to it is a good leaving group. The nucleophile from amine attacks the carbonyl carbon of the acetylchloride to form N- methylacetamide. The chloride group leaves and gets attached to hydrogen of the amine and leaves as hydrochloric acid.

The reaction is:

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

Answer 3

Question

Chapter 20, Problem 20.47P

(a)

Interpretation Introduction

Interpretation: The mechanism for the formation of compound A has to be proposed.

Concept Introduction:

Diels-Alder reaction:

It is the reaction of conjugated dienes with double or triple bonded compounds which are known as “dienophiles”. The reaction is a 4+2 cycloaddition reaction that results in the formation of a six membered cyclic product which is known as “adduct”.

Example:

This mechanism shown that three π-bonds are broken to form two new σ -bonds and a new π-bond.

Formation of Benzyne:

The elimination of two halogens from the halobenzene forms the most reactive neutral intermediate with triple bond which is known as Benzyne intermediate.

Diels-Alder reaction with Benzyne intermediate:

The reaction of Benzyne with furan serves as an example for this reaction:

Benzyne is an extremely reactive species because of the presence of triple bond in it. It undergoes Diels-Alder reaction in which it acts as dienophile and reacts with furan which acts a diene. The resulted product will be a tricyclic product which is known as Diels-Alder adduct.

(b)

Interpretation Introduction

Interpretation: Using the given sources, the conversion of compound (A) into Tolciclate has to be shown.

Concept Introduction:

Acidic hydrolysis of ether:

Ether on hydrolysis gets converted into two moles of alcohols of same type in the case of symmetrical ether and of different types in the case of unsymmetrical ether. .

General scheme for symmetrical ether:

General scheme for unsymmetrical ether:

Tosylation reaction:

When an alcohol is treated with any tosyl chloride (methane sulfonyl chloride) it gets converted into tosylated product and this reaction is called as Tosylation reaction which is shown below:

The reaction of acetyl chloride with amine:

The acyl group of acetyl chloride is very reactive and the chloride group attached to it is a good leaving group. The nucleophile from amine attacks the carbonyl carbon of the acetylchloride to form N- methylacetamide. The chloride group leaves and gets attached to hydrogen of the amine and leaves as hydrochloric acid.

The reaction is:

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

Answer 4

Question

Chapter 20, Problem 20.47P

(a)

Interpretation Introduction

Interpretation: The mechanism for the formation of compound A has to be proposed.

Concept Introduction:

Diels-Alder reaction:

It is the reaction of conjugated dienes with double or triple bonded compounds which are known as “dienophiles”. The reaction is a 4+2 cycloaddition reaction that results in the formation of a six membered cyclic product which is known as “adduct”.

Example:

This mechanism shown that three π-bonds are broken to form two new σ -bonds and a new π-bond.

Formation of Benzyne:

The elimination of two halogens from the halobenzene forms the most reactive neutral intermediate with triple bond which is known as Benzyne intermediate.

Diels-Alder reaction with Benzyne intermediate:

The reaction of Benzyne with furan serves as an example for this reaction:

Benzyne is an extremely reactive species because of the presence of triple bond in it. It undergoes Diels-Alder reaction in which it acts as dienophile and reacts with furan which acts a diene. The resulted product will be a tricyclic product which is known as Diels-Alder adduct.

(b)

Interpretation Introduction

Interpretation: Using the given sources, the conversion of compound (A) into Tolciclate has to be shown.

Concept Introduction:

Acidic hydrolysis of ether:

Ether on hydrolysis gets converted into two moles of alcohols of same type in the case of symmetrical ether and of different types in the case of unsymmetrical ether. .

General scheme for symmetrical ether:

General scheme for unsymmetrical ether:

Tosylation reaction:

When an alcohol is treated with any tosyl chloride (methane sulfonyl chloride) it gets converted into tosylated product and this reaction is called as Tosylation reaction which is shown below:

The reaction of acetyl chloride with amine:

The acyl group of acetyl chloride is very reactive and the chloride group attached to it is a good leaving group. The nucleophile from amine attacks the carbonyl carbon of the acetylchloride to form N- methylacetamide. The chloride group leaves and gets attached to hydrogen of the amine and leaves as hydrochloric acid.

The reaction is:

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

Answer 5

Chapter 20, Problem 20.47P

(a)

Interpretation Introduction

Interpretation: The mechanism for the formation of compound A has to be proposed.

Concept Introduction:

Diels-Alder reaction:

It is the reaction of conjugated dienes with double or triple bonded compounds which are known as “dienophiles”. The reaction is a 4+2 cycloaddition reaction that results in the formation of a six membered cyclic product which is known as “adduct”.

Example:

This mechanism shown that three π-bonds are broken to form two new σ -bonds and a new π-bond.

Formation of Benzyne:

The elimination of two halogens from the halobenzene forms the most reactive neutral intermediate with triple bond which is known as Benzyne intermediate.

Diels-Alder reaction with Benzyne intermediate:

The reaction of Benzyne with furan serves as an example for this reaction:

Benzyne is an extremely reactive species because of the presence of triple bond in it. It undergoes Diels-Alder reaction in which it acts as dienophile and reacts with furan which acts a diene. The resulted product will be a tricyclic product which is known as Diels-Alder adduct.

(b)

Interpretation Introduction

Interpretation: Using the given sources, the conversion of compound (A) into Tolciclate has to be shown.

Concept Introduction:

Acidic hydrolysis of ether:

Ether on hydrolysis gets converted into two moles of alcohols of same type in the case of symmetrical ether and of different types in the case of unsymmetrical ether. .

General scheme for symmetrical ether:

General scheme for unsymmetrical ether:

Tosylation reaction:

When an alcohol is treated with any tosyl chloride (methane sulfonyl chloride) it gets converted into tosylated product and this reaction is called as Tosylation reaction which is shown below:

The reaction of acetyl chloride with amine:

The acyl group of acetyl chloride is very reactive and the chloride group attached to it is a good leaving group. The nucleophile from amine attacks the carbonyl carbon of the acetylchloride to form N- methylacetamide. The chloride group leaves and gets attached to hydrogen of the amine and leaves as hydrochloric acid.

The reaction is:

Answer 6

Chapter 20, Problem 20.47P

(a)

Interpretation Introduction

Interpretation: The mechanism for the formation of compound A has to be proposed.

Concept Introduction:

Diels-Alder reaction:

It is the reaction of conjugated dienes with double or triple bonded compounds which are known as “dienophiles”. The reaction is a 4+2 cycloaddition reaction that results in the formation of a six membered cyclic product which is known as “adduct”.

Example:

This mechanism shown that three π-bonds are broken to form two new σ -bonds and a new π-bond.

Formation of Benzyne:

The elimination of two halogens from the halobenzene forms the most reactive neutral intermediate with triple bond which is known as Benzyne intermediate.

Diels-Alder reaction with Benzyne intermediate:

The reaction of Benzyne with furan serves as an example for this reaction:

Benzyne is an extremely reactive species because of the presence of triple bond in it. It undergoes Diels-Alder reaction in which it acts as dienophile and reacts with furan which acts a diene. The resulted product will be a tricyclic product which is known as Diels-Alder adduct.

Answer 7

Chapter 20, Problem 20.47P

(a)

Interpretation Introduction

Interpretation: The mechanism for the formation of compound A has to be proposed.

Concept Introduction:

Diels-Alder reaction:

It is the reaction of conjugated dienes with double or triple bonded compounds which are known as “dienophiles”. The reaction is a 4+2 cycloaddition reaction that results in the formation of a six membered cyclic product which is known as “adduct”.

Example:

This mechanism shown that three π-bonds are broken to form two new σ -bonds and a new π-bond.

Formation of Benzyne:

The elimination of two halogens from the halobenzene forms the most reactive neutral intermediate with triple bond which is known as Benzyne intermediate.

Diels-Alder reaction with Benzyne intermediate:

The reaction of Benzyne with furan serves as an example for this reaction:

Benzyne is an extremely reactive species because of the presence of triple bond in it. It undergoes Diels-Alder reaction in which it acts as dienophile and reacts with furan which acts a diene. The resulted product will be a tricyclic product which is known as Diels-Alder adduct.

Answer 8

(b)

Interpretation Introduction

Interpretation: Using the given sources, the conversion of compound (A) into Tolciclate has to be shown.

Concept Introduction:

Acidic hydrolysis of ether:

Ether on hydrolysis gets converted into two moles of alcohols of same type in the case of symmetrical ether and of different types in the case of unsymmetrical ether. .

General scheme for symmetrical ether:

General scheme for unsymmetrical ether:

Tosylation reaction:

When an alcohol is treated with any tosyl chloride (methane sulfonyl chloride) it gets converted into tosylated product and this reaction is called as Tosylation reaction which is shown below:

The reaction of acetyl chloride with amine:

The acyl group of acetyl chloride is very reactive and the chloride group attached to it is a good leaving group. The nucleophile from amine attacks the carbonyl carbon of the acetylchloride to form N- methylacetamide. The chloride group leaves and gets attached to hydrogen of the amine and leaves as hydrochloric acid.

The reaction is:

Answer 9

(b)

Interpretation Introduction

Interpretation: Using the given sources, the conversion of compound (A) into Tolciclate has to be shown.

Concept Introduction:

Acidic hydrolysis of ether:

Ether on hydrolysis gets converted into two moles of alcohols of same type in the case of symmetrical ether and of different types in the case of unsymmetrical ether. .

General scheme for symmetrical ether:

General scheme for unsymmetrical ether:

Tosylation reaction:

When an alcohol is treated with any tosyl chloride (methane sulfonyl chloride) it gets converted into tosylated product and this reaction is called as Tosylation reaction which is shown below:

The reaction of acetyl chloride with amine:

The acyl group of acetyl chloride is very reactive and the chloride group attached to it is a good leaving group. The nucleophile from amine attacks the carbonyl carbon of the acetylchloride to form N- methylacetamide. The chloride group leaves and gets attached to hydrogen of the amine and leaves as hydrochloric acid.

The reaction is:

Answer 10

Expert Solution & Answer

Answer 11

Expert Solution & Answer

Answer 12

Want to see the full answer?

Check out a sample textbook solution

See solution

Answer 13

Ch. 20.1 - Prob. 20.1P Ch. 20.1 - Estimate the stabilization gained as a result of...Ch. 20.2 - Predict the product(s) formed by addition of one...Ch. 20.3 - Prob. 20.4P Ch. 20.3 - Prob. 20.5P Ch. 20.4 - Prob. 20.6P Ch. 20.5 - Prob. 20.7P Ch. 20.5 - Prob. 20.8P Ch. 20.5 - Prob. 20.9P Ch. 20.6 - Prob. 20.10P

Solution Summary: The author explains how the reaction of conjugated dienes with double or triple bonded compounds produces a six-membered cyclic product known as "adduct".

Concept explainers

Videos

Want to see the full answer?

Chapter 20 Solutions