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- 4B1 Write the possible reactants that gave the following products in the Diels-Alder reaction osoUse bond-dissociation enthalpies (Table 4-2, p. 167) to calculate values of ∆H° for the following reactions. (a) CH3¬CH3 + I2 ¡ CH3CH2I + HI(b) CH3CH2Cl + HI ¡ CH3CH2I + HCl(c) (CH3)3C¬OH + HCl ¡ (CH3)3C¬Cl + H2O (d) CH3CH2CH3 + H2 ¡ CH3CH3 + CH4 (e) CH3CH2OH + HBr ¡ CH3CH2¬Br + H2O2) Predict the major product for each Diels-Alder reaction. Include stereochemistry where appropriate. H. C=N (a) H H. CH3 CH;O, (b) Ph (c) Ph
- 3. The following reactions are not technically the Diels-Alder reaction, but you should still be able to predict the product (with appropriate regio/stereochemistry). (a) (b) OMe OMe H3C N + NC H3C. CN CH310-11Draw curved arrows and identify the thermal and photochemical products of the electrocyclic reaction of (2Z,4Z,6E)-octa-2,4,6-triene. Step 2: An electrocyclic reaction will undergo a concerted electron shift to form a cyclic ring. A new sigma bond will be formed between carbons 2 and 7. The product will be neutral. (2ZAZ,6E)-octa-2,4,6-triene Draw the curved arrows to show the mechanism. Select Draw Rings More Erase
- 7-98. Propose a mechanism for the light-initlated free-radical monofluorination of ethane: CH;CH, + F2 → CH;CH,F + HF (a) Show both initiation and propagation steps. (b) Calculate AH° for each step in the reaction and characterize each as exothermic or endothermic. (c) Calculate the overall value of AH° for this reaction (omit the initiation step).A student adds NBS to a solution of 1-methylcyclohexene and irradiates the mixture with a sunlamp until all the NBS has reacted. After a careful distillation, the product mixture contains two major products of formula C7H11Br. (a) Draw the resonance forms of the three possible allylic free radical intermediates.
- (3) HI does not undergo free radical addition with 1-butene, even in the presence of a peroxide. Please provide an explanation by analyzing the propagation steps if the same radical reaction occurred with HI. Besides the bond dissociation enthalpies in the appendix, the following approximate bond dissociate enthalpies might be useful to you: ~310 kJ/mol The component of C=C CH3CH₂CH₂CH₂-Br CH3CH₂CH₂CH2-I -290 kJ/mol (C-Br bond) ~235 kJ/mol (C-I bond)Identify the diene and dienophile expected to produce the Diels-Alder product shown in the box below. SO 11 SO IV ον O. IV 4 ||| ||| ||The first step in a synthesis of dodecahedrane involves a Diels-Alder reaction between the cyclopentadiene derivative (1) and dimethyl acetylenedicarboxylate (2). Show how these two molecules react to form the dodecahedrane synthetic intermediate (3). + CH,0OCC=CCOOCH, COOCH ČOOCH3 Cyclopentadienyl- cyclopentadiene (1) Dimethyl acetylene- dicarboxylate (2) (3)