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- Resveratrol is an antioxidant found in the skin of red grapes. Itsanticancer, anti-inflammatory, and various cardiovascular effects areunder active investigation. (a) Draw all resonance structures for theradical that results from homolysis of the OH bond shown in red. (b)Explain why homolysis of this OH bond is preferred to homolysis ofeither OH bond in the other benzene ring.(i) Explain why a high reaction temperature favours elimination reactions, instead of substitution reactions. (ii) Explain why polar aprotic solvents favour Sn2 reaction but not favour SN1 reaction.(a) Rank A, B, and C in order of increasing SN2 reactivity. (b) Rank A, B, and C in order of increasing SN1 reactivity.
- 2 Draw the retro Diels-Alder mechanism and product for each of the compounds shown here. Which retro Diels-Alder reaction do you think would require the lower temperature? Why? (a) (b) .CO2H Aco,H CO2H ČO,HResveratrol is an antioxidant found in the skin of red grapes. Its anticancer, anti-inammatory, and various cardiovascular effects are under active investigation. (a) Draw all resonance structures for the radical that results from homolysis of the OH bond shown in red. (b) Explain why homolysis of this OH bond is preferred to homolysis of either OH bond in the other benzene ring.Draw the complete, detailed E1 mechanism for each of the following reactions. (a) (b) I -Br CH3OH H20
- For each pair of compounds determine which will undergo electrophilic substitution faster. (a) (b) (c) (d) CF3 HO Он NO2 () (g) SCH, (e) SO,H OH (h) CI CI HODraw the structure of each molecule. (a) (E)-4-carbamoylbut-3-enoic acid; (b) 3-carbamoylpentanediamide; (c) 4,6-dioxohexanenitrile; (d) (1S,2S)-2-methoxycyclopent-3-ene-1-carbonitrile; (e) cyclohexa-3,6-diene-1,3-dicarboxylic acidWhich of the following carbons is the most electrophilic? (A) (B) 'N O (C) (D)
- (c) Nitrobenzene will undergo electrophilic aromatic substitution at meta position, but not at the ortho and para positions. Explain by showing all the resonance structures involved.Which of the following accurately shows the curved arrows for an SN2 reaction? (A) (C) 0.. CI CI (B) (D) 59: CIb) Explain in detail what characteristics of the alkyl halide influence whether a mechanism will be SN1 or SN2. c) Explain in detail what characteristics of a nucleophile influence whether a reaction will be SN1 or SN2.