(a)
To determine: The product that is formed when given diene reacts with methyl acetylenecarboxylate, a strong dienophile.
Interpretation: The product that is formed when given diene reacts with methyl acetylenecarboxylate, a strong dienophile is to be stated.
Concept introduction: Diels-alder reaction is a cycloaddition reaction in which two molecules combine to form a new ring. In this type of reaction, syn addition takes place. It is a reaction between diene with a dienophile to yield a cyclohexene. The dienophile adds to one side of the diene, and the diene adds to the one side of the dienophile. Thus, they have syn stereochemistry. In Diels-Alder reaction, the diene behaves like an electron rich species, whereas the dienophile behaves like an electron poor species.
(b)
To determine: The path by which the strongly exothermic decarboxylation takes place.
Interpretation: The path by which the strongly exothermic decarboxylation takes place is to be stated.
Concept introduction: Diels-alder reaction is a cycloaddition reaction in which two molecules combine to form a new ring. In this type of reaction, syn addition takes place. It is a reaction between diene with a dienophile to yield a cyclohexene. The dienophile adds to one side of the diene, and the diene adds to the one side of the dienophile. Thus, they have syn stereochemistry.
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EP ORGANIC CHEMISTRY -MOD.MASTERING 18W
- 10. The following compound was produced in a Diels-Alder reaction. COOH a) How many sp³ hybridized carbons are in this molecule? b) Is this molecule chiral? c) Are the carboxylic acid substituents electron donating group or electron withdrawing group? d) Draw the diene and dienophile which would react together to give this product.arrow_forwardThe diene shown below will NOT react in a Diels-Alder reaction. Why not? Select one: DA. The compound is not a conjugated diene. OB. This compound cannot adopt the s-cis conformation. C. The compound is lacking in electron donating groups. ⒸD. The compound is lacking in electron withdrawing groups.arrow_forwardThe diene shown below will NOT react in a Diels-Alder reaction. Why not? Select one: A. The compound is not a conjugated diene. B. The compound is lacking in electron withdrawing groups. O C. This compound cannot adopt the s-cis conformation. D. The compound is lacking in electron donating groups.arrow_forward
- Rank the following dienes in their rate of reaction with the same dienophile in a Diels-Alder reaction. For example, 1 = fastest or most reactive diene, 4 = slowest or least reactive diene.arrow_forward6.) For the following reactions, please draw the structures of both the diene and dienophile that would afford the depicted Diels Alder adducts. 1. Cl ? ? cl Diene Dienophile cl Cl 2. CH3 O CH3 ? CH3 Diene Dienophile CH3 3. ? + ? Diene Dienophile 4. CH3 ? + Diene Dienophile CH3arrow_forwardDraw the structures of the diene and dienophile that yield the following enantiomeric products in the Diels-Alder reaction below: Diene: Dienophile: Do the products represent an endo or an exo addition of dienophile to diene? left product is endo, right product is exo left product is exo, right product is endo both products are endo both products are exoarrow_forward
- True or False: Acetylene is a naturally occurring conjugated diene True or False: The Diels-Alder reaction has the stereochemistry of the dienophile is retained in the product. True or False: When looking at kinetic vs. thermodynamic products the kinetic product predominates at low temperature. True or False: the mechanism of the Diels-Alder reaction is three π bonds break; one σ bond and two π bonds form.arrow_forwardDraw the structures of the diene and dienophile that would be used in the diels alder reaction to synthesize the following compounds. Label each structure as diene or dienophile.arrow_forwardDraw the diene and dienophile that are needed to prepare the following Diels-Alder product. Diene: draw structure. Dienophile: draw structure ..arrow_forward
- For the Diels-Alder reaction, identify the diene, the dienophile, and the Diels-Alder adduct. H3CO. R OCH3 LOCH3 R H3CO R compound A compound B compound C Compound A is a: Compound B is a: Compound C is a:arrow_forward2. Please rank the following dienophiles in their rate of reaction with the same diene in a Diels-Alder reaction (i.e. 1= fastest or most reactive dienophile, 4 = slowest or least reactive dienophile). Put your answer on the line below each structure. 3. Please rank the following dienes in their rate of reaction with the same dienophile in a Diels-Alder reaction (i.e. 1= fastest or most reactive diene, 4 = slowest or least reactive diene). Put your answer on the line below each structure. OMe OMe OMe |arrow_forward6) The Diels-Alder reaction of anthracene (which is achiral) and maleic anhydride (also achiral) results in the formation of an achiral product. This is not always the case (where two achiral reactants form an achiral product). a) Propose a Diels-Alder reaction where two achiral starting materials result in the formation of a chiral product. b) Would this chiral product be a single enantiomer or a racemic mixture?arrow_forward