a)
Interpretation: The diene and dienophile from the given compounds has to be predicted.
Concept Introduction:
Diels-Alder reaction:
A conjugated diene reacts with a compound containing a carbon-carbon double bond. It is a cycloaddition reaction, where two reactants form a cyclic product.
Conformation of Diene:
S-Cis Conformer: The double bonds are cis about the single bond (s stands for single), in an s-cis conformer.
S-trans Conformer: The double bonds are trans- about the single bond (s stands for single) in an s-trans conformer.
Condition for Diels-Alder reaction:
The conjugate diene must be in an s-cis conformation because when it is in an S-trans conformation, C-1 and C-4 are too far apart to react with the dienophile in a concerted reaction.
b)
Interpretation: The diene and dienophile from the given compounds has to be predicted.
Concept Introduction:
Diels-Alder reaction:
A conjugated diene reacts with a compound containing a carbon-carbon double bond. It is a cycloaddition reaction, where two reactants form a cyclic product.
Conformation of Diene:
S-Cis Conformer: The double bonds are cis about the single bond (s stands for single), in an s-cis conformer.
S-trans Conformer: The double bonds are trans- about the single bond (s stands for single) in an s-trans conformer.
Condition for Diels-Alder reaction:
The conjugate diene must be in an s-cis conformation because when it is in an S-trans conformation, C-1 and C-4 are too far apart to react with the dienophile in a concerted reaction.
c)
Interpretation: The diene and dienophile from the given compounds has to be predicted.
Concept Introduction:
Diels-Alder reaction:
A conjugated diene reacts with a compound containing a carbon-carbon double bond. It is a cycloaddition reaction, where two reactants form a cyclic product.
Conformation of Diene:
S-Cis Conformer: The double bonds are cis about the single bond (s stands for single), in an s-cis conformer.
S-trans Conformer: The double bonds are trans- about the single bond (s stands for single) in an s-trans conformer.
Condition for Diels-Alder reaction:
The conjugate diene must be in an s-cis conformation because when it is in an S-trans conformation, C-1 and C-4 are too far apart to react with the dienophile in a concerted reaction.
d)
Interpretation: The diene and dienophile from the given compounds to be predicted.
Concept Introduction:
Diels-Alder reaction:
A conjugated diene reacts with a compound containing a carbon-carbon double bond. It is a cycloaddition reaction, where two reactants form a cyclic product.
Conformation of Diene:
S-Cis Conformer: The double bonds are cis about the single bond (s stands for single), in an s-cis conformer.
S-trans Conformer: The double bonds are trans- about the single bond (s stands for single) in an s-trans conformer.
Condition for Diels-Alder reaction:
The conjugate diene must be in an s-cis conformation because when it is in an S-trans conformation, C-1 and C-4 are too far apart to react with the dienophile in a concerted reaction.
e)
Interpretation: The diene and dienophile from the given compounds has to be predicted.
Concept Introduction:
Diels-Alder reaction:
A conjugated diene reacts with a compound containing a carbon-carbon double bond. It is a cycloaddition reaction, where two reactants form a cyclic product.
Conformation of Diene:
S-Cis Conformer: The double bonds are cis about the single bond (s stands for single), in an s-cis conformer.
S-trans Conformer: The double bonds are trans- about the single bond (s stands for single) in an s-trans conformer.
Condition for Diels-Alder reaction:
The conjugate diene must be in an s-cis conformation because when it is in an S-trans conformation, C-1 and C-4 are too far apart to react with the dienophile in a concerted reaction.
f)
Interpretation: The diene and dienophile from the given compounds has to be predicted.
Concept Introduction:
Diels-Alder reaction:
A conjugated diene reacts with a compound containing a carbon-carbon double bond. It is a cycloaddition reaction, where two reactants form a cyclic product.
Conformation of Diene:
S-Cis Conformer: The double bonds are cis about the single bond (s stands for single), in an s-cis conformer.
S-trans Conformer: The double bonds are trans- about the single bond (s stands for single) in an s-trans conformer.
Condition for Diels-Alder reaction:
The conjugate diene must be in an s-cis conformation because when it is in an S-trans conformation, C-1 and C-4 are too far apart to react with the dienophile in a concerted reaction.
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CHEM 262 ORG CHEM EBOOK DIGITAL DELIVERY
- Determine what conjugated diene and what dienophile wereused to make starting materials from a given Diels–Alder adduct ?arrow_forwardConsider the following dienes in a Diels–Alder reaction with ethene. Which will react the fastest? Which will react the slowest? Explainarrow_forwardProvide mechanistic pathway for each step and the products based on the reagents selected. Diels Alders reactions to consider the formation of the products stated below. Product in step 1 is used for step 2. Product instep 2 is used for step 3. Indicate any required stereochemistry (E, Z, R, S).Step 1: 3-bromo-3-methylbut-1-ene with sodium ethoxideStep 2: addition of maleic anhydride and heatStep 3: hydrogen gas bubbling with palladium metalarrow_forward
- Which of the following compounds can arise directly from a Diels-Alder reaction? Circle any structures that can. Then, identify the appropriate diene(s) and dienophile(s) that would lead to the compound. Pay attention to E-/Z- stereochemistry in all of the reactants. For those that cannot undergo a Diels-Alder reaction, please explain why.arrow_forwardGive detailed Solution with explanation needed..arrow_forwardPropose a pericyclic mechanism to account for the following transformation:arrow_forward
- 3 6. Identify the diene and dienophile which would give the following product. H NO₂ not A) B) D) + H₂C=CHNO2 sibixoiiclava Iorc8 to outle + CH₂CH=CHNO₂ noo vile + H₂C-CHNO₂ + H₂C-CH₂ NO₂ boinbbs B. Lors 0744 PRIS #arrow_forwardTreatment of the diene shown with excess ozone followed by a reductive work-up produces.arrow_forward3. Using the carbon sources provided and any other necessary reagents needed, propose a viable synthesis for the product shown. Your synthesis must include a Diels-Alder reaction. For each step in your synthesis be sure to show the reagents/conditions necessary for that step and also draw the major product expected for each step leading to the product. You will also need to use reactions discussed in previous chapters as well. Carbon Sources Available H₂C=CH2 CH3Br steps wirt or oy holted and Doubiquiti o toubong pimarybormanarrow_forward