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

34. Give the expected major product of each of the following reactions. Conc. HI a. CH3CH2CH2OH b. (CH3)2CHCH2CH2OH Conc. HBr H Conc. HI C. OH Conc.HCI d. (CH3CH2)3COH

42. Which of the following halogenated compounds can be used successfully to prepare a Grignard reagent for alcohol synthesis by subsequent reaction with an aldehyde or ketone? Which ones cannot and why? H3C CH3 a. Br H OH b. Cl C. I H H d. Cl e. H OCH3 Br H

For each reaction below, decide if the first stable organic product that forms in solution will create a new CC bond, and check the appropriate box. Next, for each reaction to which you answered "Yes" to in the table, draw this product in the drawing area below. Note for advanced students: for this problem, don't worry if you think this product will continue to react under the current conditions - just focus on the first stable product you expect to form in solution. ? Will the first MgBr product that forms in this reaction create a new CC bond? olo ? OH جمله O Yes Ⓒ No MgCl ? Will the first product that forms in this reaction create a new CC bond? Click and drag to start drawing a structure. Yes No X ☐ : ☐ टे PH