The structural formula for the given compound A has to be proposed along with the mechanism for the formation of the given tricyclic product. Concept Introduction: Diazotisation: It is the formation of diazonium salt from the reaction between a secondary amine such as aniline and sodium nitrite in acidic medium. 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: Diels-Alder reaction to form bicyclic system: The Diels-Alder adduct formed in the Diels-Alder reaction can also be a bicyclic system which will be obtained when cylopentadiene is used as the diene as shown here: In this reaction, the cylopentadiene acts as both diene and dienophile and formed a bicyclic system. When it is heated to 170 o C , a reverse Diels-Alder reaction takes place in which the bicyclic system will be decomposed and gives back the cylopentadiene.

Question

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. ? NH2 MgBr Will the first product that forms in this reaction create a new CC bond? ○ Yes ○ No MgBr ? Will the first product that forms in this reaction create a new CC bond? O Yes O No Click and drag to start drawing a structure. :☐ G x c olo Ar HE

Answer 1

Question

Chapter 20, Problem 20.43P

Interpretation Introduction

Interpretation:

The structural formula for the given compound A has to be proposed along with the mechanism for the formation of the given tricyclic product.

Concept Introduction:

Diazotisation:

It is the formation of diazonium salt from the reaction between a secondary amine such as aniline and sodium nitrite in acidic medium.

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:

Diels-Alder reaction to form bicyclic system:

The Diels-Alder adduct formed in the Diels-Alder reaction can also be a bicyclic system which will be obtained when cylopentadiene is used as the diene as shown here:

In this reaction, the cylopentadiene acts as both diene and dienophile and formed a bicyclic system. When it is heated to 170o C, a reverse Diels-Alder reaction takes place in which the bicyclic system will be decomposed and gives back the cylopentadiene.

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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. ? NH2 MgBr Will the first product that forms in this reaction create a new CC bond? ○ Yes ○ No MgBr ? Will the first product that forms in this reaction create a new CC bond? O Yes O No Click and drag to start drawing a structure. :☐ G x c olo Ar HE

Predicting As the lead product manager at OrganometALEKS Industries, you are trying to decide if the following reaction will make a molecule with a new C - C bond as its major product: H₂N O H 1. ? 2. H3O+ If this reaction will work, draw the major organic product or products you would expect in the drawing area below. If there's more than one major product, you can draw them in any arrangement you like. Be sure you use wedge and dash bonds if necessary, for example to distinguish between major products with different stereochemistry. 0 If the major products of this reaction won't have a new CC bond, just check the box under the drawing area and leave it blank. فا Explanation Check Click and drag to start drawing a structure.

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