Organic chemistry - Diels Alder reaction

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Discussion Overview

The discussion revolves around the Diels-Alder reaction involving p-methylbenzyn and 1,3-butadien. Participants explore the identity of the reactants and the expected product of the reaction.

Discussion Character

  • Homework-related, Technical explanation

Main Points Raised

  • One participant poses a homework question regarding the product of the reaction between p-methylbenzyn and 1,3-butadien.
  • Another participant questions the nomenclature of "p-methylbenzyn," suggesting it does not make sense.
  • A different participant proposes that "3-methylbenzyn" (3-methyldehydrobenzen) might be the intended compound.
  • One participant suggests that a benzyne intermediate is likely involved and asks for clarification on which compound serves as the diene and which as the dienophile.
  • There is agreement that the dienophile is methylbenzyn and the diene is 1,3-butadien, with one participant stating that determining the product is a straightforward application of the Diels-Alder mechanism.
  • Participants express positive reinforcement towards each other’s contributions.

Areas of Agreement / Disagreement

There is some confusion regarding the correct nomenclature of the reactants, and while participants agree on the roles of the diene and dienophile, the discussion does not reach a consensus on the identity of the starting materials.

Contextual Notes

Participants have not resolved the ambiguity surrounding the naming of "p-methylbenzyn," and the discussion relies on the assumption that the Diels-Alder mechanism applies to the proposed reaction.

Who May Find This Useful

Students studying organic chemistry, particularly those interested in reaction mechanisms and nomenclature in organic compounds.

charlie05
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Homework Statement


What is the product of this reaction: p-methylbenzyn + 1,3-butadien?

Homework Equations


C6H4CH3 + C4H6

The Attempt at a Solution


a bicyclic ring is formed?
 
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What is p-methylbenzyn? Name doesn't make sense.
 
3-methylbenzyn ( 3-methyldehydrobenzen)
 
I’m guessing you mean a benzyne intermediate. Which compound is your diene and which is your dienophile?
 
Yes...Dienophile is methylbenzyn, dien is dien - 1,3 - butadien :-)
 
charlie05 said:
Yes...Dienophile is methylbenzyn, dien is dien - 1,3 - butadien :-)
Given this info, figuring out the product is a straightforward application of the mechanism of the DA reaction.
 
upload_2017-10-23_12-34-32.png
 

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Good job.
 
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Thanks :-)
 

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