
(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 have 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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Chapter 8 Solutions
Organic Chemistry
- A mixture of C7H12O2, C9H9OCl, biphenyl and acetone was put together in a gas chromatography tube. Please decide from the GC resutls which correspond to the peak for C7,C9 and biphenyl and explain the reasoning based on GC results. Eliminate unnecessary peaks from Gas Chromatography results.arrow_forwardIs the molecule chiral, meso, or achiral? CI .CH3 H₂C CIarrow_forwardPLEASE HELP ! URGENT!arrow_forward
- Identify priority of the substituents: CH3arrow_forwardHow many chiral carbons are in the molecule? OH F CI Brarrow_forwardA mixture of three compounds Phen-A, Acet-B and Rin-C was analyzed using TLC with 1:9 ethanol: hexane as the mobile phase. The TLC plate showed three spots of R, 0.1 and 0.2 and 0.3. Which of the three compounds (Phen-A; Acet-B or Rin-C) would have the highest (Blank 1), middle (Blank 2) and lowest (Blank 3) spot respectively? 0 CH: 0 CH, 0 H.C OH H.CN OH Acet-B Rin-C phen-A A A <arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning

