Q6(g). Diels–Alder reaction: product and reactants
Given below are two examples of Diels–Alder reaction. Provide the product in the first reaction and the reactants in the second reaction: (i) [diene + dienophile, Δ → ?] (ii) A + B, Δ → [adduct]. [Structures given in the paper]
Answer in brief
(i) The cis-fused endo adduct C₁₃H₁₆O₃, all four new ring hydrogens cis. (ii) A = cyclopenta-1,3-diene, B = ethyl acrylate (ethyl prop-2-enoate).
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CoversDiels-Alder reactionendo rule[4+2] cycloadditioncyclopentadieneretro-synthesis of adduct
All parts of Question 6
- 6(a) Singlet and triplet carbenes; fluorenylidene with cis-but-2-ene4 marks
- 6(b) Bromine addition: styrene reacts faster than propene4 marks
- 6(c) Addition of HCl to an α,β-unsaturated acid4 marks
- 6(d) Michael addition of a cyclic 1,3-dione to cyclohex-2-enone4 marks
- 6(e) Hydroboration–oxidation of 1-methylcyclohexene4 marks
- 6(f) Cope rearrangement of a 1,5-diene4 marks
- 6(g) Diels–Alder reaction: product and reactants4 marks
- 6(h) IR distinction: hydrogen bonding and ring strain4 marks
- 6(i) McLafferty rearrangement: 2-pentanone and 3-pentanone4 marks
- 6(j) NMR assignment of 4-methylpent-1-yne4 marks