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

Feedback (4/10) 30% Retry Curved arrows are used to illustrate the flow of electrons. Use the reaction conditions provided and follow the arrows to draw the reactant and missing intermediates involved in this reaction. Include all lone pairs and charges as appropriate. Ignore inorganic byproducts. Incorrect, 6 attempts remaining :0: Draw the Reactant H H3CO H- HIO: Ö-CH3 CH3OH2* protonation H. a H (+) H Ο CH3OH2 O: H3C protonation CH3OH deprotonation > CH3OH nucleophilic addition H. HO 0:0 Draw Intermediate a X

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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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Feedback (4/10) 30% Retry Curved arrows are used to illustrate the flow of electrons. Use the reaction conditions provided and follow the arrows to draw the reactant and missing intermediates involved in this reaction. Include all lone pairs and charges as appropriate. Ignore inorganic byproducts. Incorrect, 6 attempts remaining :0: Draw the Reactant H H3CO H- HIO: Ö-CH3 CH3OH2* protonation H. a H (+) H Ο CH3OH2 O: H3C protonation CH3OH deprotonation > CH3OH nucleophilic addition H. HO 0:0 Draw Intermediate a X

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